State the UUID-is-the-credential rule as a rule (closes #301)

The receiver has authenticated on the entrypoint UUID alone since
inbound signature verification was removed in #279. The README
described that as the current state; it did not say it is the
decision. Restate it as the rule, so a proposal to add HMAC, a shared
secret or a bearer token to the receiver is contradicted by the docs
rather than merely unimplemented.

The rule now appears in the intro, in its own section, and in the
Authentication and Security lists, and carries the two consequences an
operator has to act on: the URL is a capability to be kept out of logs
and tickets, and rotation means minting a new entrypoint rather than
changing a key.

Also corrects one stale comment: a redirect test said the inbound
signature was one "the receiver verifies", which in this repo's
vocabulary names webhooker's own receiver. The endpoint that verifies
it is the delivery target's.

Dockerfile

@@ -109,6 +109,18 @@ USER webhooker
 
 EXPOSE 8080
 
+# The binary defaults BIND_ADDRESS to 127.0.0.1, which is right for a
+# bare host: the cleartext listener serves the admin UI and the
+# unauthenticated receiver, so it must not appear on every interface
+# of a machine that configured nothing. A container is the other case.
+# Its network namespace is already the isolation boundary, so binding
+# every address inside it exposes nothing; what decides exposure is
+# the publish flag, and `-p 127.0.0.1:8080:8080` is the operator's
+# control there. Shipping the image on loopback would buy no security
+# and would make the process unreachable through its own published
+# port.
+ENV BIND_ADDRESS=0.0.0.0
+
 HEALTHCHECK --interval=30s --timeout=3s --start-period=5s --retries=3 \
     CMD wget --no-verbose --tries=1 --spider http://localhost:8080/.well-known/healthcheck || exit 1
 

README.md

@@ -7,6 +7,13 @@ services, durably stores them, and delivers them to configured targets
 with retry support, logging, and observability. Category: infrastructure
 / web service. License: MIT.
 
+Each entrypoint is a version 4 UUID served at `/webhook/{uuid}`, and
+that UUID is the entrypoint's only credential. webhooker does not use
+shared secrets, HMAC signatures or token headers on the receiver, and
+will not add them — read
+[The entrypoint URL is the authentication secret](#the-entrypoint-url-is-the-authentication-secret)
+before deploying one.
+
 ## Getting Started
 
 ### Prerequisites
@@ -71,8 +78,18 @@ make clean      # Remove bin/
 ### Configuration
 
 All configuration is via environment variables. For local development,
-you can place variables in a `.env` file in the project root (loaded
-automatically via `godotenv/autoload`).
+you can place variables in a `.env` file in the process working
+directory, read once at startup before anything else looks at the
+environment.
+
+The file is optional and having none is the normal case for a
+deployment. A file that is there but cannot be parsed aborts startup
+with a message naming it, because a single malformed line makes none
+of the file apply: every variable in it silently reverts to its
+default, which is exactly the failure [Invalid values abort
+startup](#invalid-values-abort-startup) exists to prevent, for all of
+them at once. A variable already present in the real environment wins
+over the file's value for the same name.
 
 The environment is selected by setting `WEBHOOKER_ENVIRONMENT` to `dev`
 or `prod` (default: `dev`). The setting controls exactly one behavior:
@@ -119,12 +136,13 @@ TTY detection, and security headers are always applied.
 | ----------------------- | ----------------------------------- | -------- |
 | `WEBHOOKER_ENVIRONMENT` | `dev` or `prod`                     | `dev`    |
 | `PORT`                  | HTTP listen port                    | `8080`   |
+| `BIND_ADDRESS`          | IP address the HTTP listener binds. Loopback by default, so the cleartext listener is not published on every interface. The Docker image ships `0.0.0.0` instead. See [Bind address](#bind-address) | `127.0.0.1` (image: `0.0.0.0`) |
 | `DATA_DIR`              | Directory for all SQLite databases  | `/var/lib/webhooker` |
 | `DEBUG`                 | Enable debug logging                | `false`  |
 | `MAINTENANCE_MODE`      | Report `maintenanceMode: true` in the healthcheck JSON. It does not change how any request is served — no maintenance page exists | `false`  |
 | `METRICS_USERNAME`      | Basic auth username for `/metrics`. Must be set together with `METRICS_PASSWORD`; one without the other fails startup | `""`     |
 | `METRICS_PASSWORD`      | Basic auth password for `/metrics`. Must be set together with `METRICS_USERNAME`; one without the other fails startup | `""`     |
-| `SENTRY_DSN`            | Sentry error reporting DSN          | `""`     |
+| `SENTRY_DSN`            | Sentry error reporting DSN. Unset leaves error reporting off; a value the Sentry SDK cannot parse fails startup rather than serving with reporting silently off | `""`     |
 | `RETENTION_SWEEP_INTERVAL` | How often the retention reaper and archive sweeper run (Go duration, must be positive) | `1h` |
 | `SESSION_IDLE_TIMEOUT`  | Idle session timeout (Go duration)  | `24h`    |
 | `RECEIVER_RATE_LIMIT`   | Receiver requests/minute per IP per entrypoint (10x that per IP across the route) | `120` |
@@ -240,6 +258,68 @@ A set but unparseable value aborts startup. When the list is non-empty
 webhooker logs it at startup, blocks and all, so the hole is visible in
 the log of any deployment that has one.
 
+#### Bind address
+
+`BIND_ADDRESS` is the IP address the HTTP listener binds. The binary
+defaults to `127.0.0.1`, so a bare webhooker is reachable only from the
+host it runs on. The Docker image ships `ENV BIND_ADDRESS=0.0.0.0`
+instead — see below for why the two differ.
+
+That listener speaks **cleartext**, and it serves both the admin UI and
+the unauthenticated webhook receiver. webhooker terminates no TLS
+itself; a production deployment puts a reverse proxy in front of it
+(see
+[Deployment behind a reverse proxy](#deployment-behind-a-reverse-proxy)),
+and the proxy reaches it over loopback. A default that bound every
+interface would leave that cleartext port answering the internet
+alongside the proxy — the admin login form and the receiver, in the
+clear, on a port nobody chose to publish. Reaching webhooker from
+another host is therefore something you configure, not something you
+get by default.
+
+**In a container the answer is `0.0.0.0`, which is why the image ships
+that.** A container's network namespace is already the boundary the
+loopback default is reaching for: nothing outside the container gets to
+`0.0.0.0:8080` because of the namespace, whatever the process bound.
+Exposure is decided at the publish flag instead — `-p
+127.0.0.1:8080:8080` rather than `-p 8080:8080` — which is the
+operator's to choose and is what
+[Running with Docker](#running-with-docker) shows. A loopback bind
+inside a container buys nothing and makes the process unreachable
+through its own published port.
+
+The value must be an IP address literal:
+
+- `127.0.0.1` — loopback only (the binary's default). Use this with a
+  reverse proxy on the same host.
+- `0.0.0.0` — every IPv4 address. The image's default; on a bare host,
+  only behind a firewall on the port.
+- `::` — every address, IPv6 and (on Linux, with the default
+  `net.ipv6.bindv6only=0`) IPv4 as well.
+- A specific address such as `10.0.0.5` — that interface only.
+
+An **empty** value is treated as unset, as everywhere else here, and
+takes the default. In a container that matters: `BIND_ADDRESS=` throws
+away the image's `0.0.0.0` and falls back to the binary's
+`127.0.0.1`, which is the one quiet failure this setting has — see
+[Running with Docker](#running-with-docker).
+
+Hostnames are **not** accepted. `localhost` aborts startup rather than
+being resolved: which of `127.0.0.1` and `::1` it means differs by
+host, a name can resolve to several addresses of which only one could
+be bound, and the answer can change under a running process. A value
+carrying a port (`127.0.0.1:8080`) is likewise rejected — the port is
+`PORT`'s business. Any unparseable value aborts startup; see
+[Invalid values abort startup](#invalid-values-abort-startup).
+
+An address that parses but is not assigned to this host — say
+`10.0.0.5` on a machine that has no such interface — is a valid
+literal, so it reaches the listener and fails there. The process logs
+the bind error and exits non-zero rather than staying up with nothing
+listening. The effective value is in the `bindAddress` field of the
+startup log line, which is the way to check what a running deployment
+actually bound.
+
 #### Metrics credentials
 
 `METRICS_USERNAME` and `METRICS_PASSWORD` are set together or not at
@@ -397,11 +477,24 @@ additionally be a number in the range 1–65535,
 `RECEIVER_RATE_LIMIT` must be at least 1,
 `RETENTION_SWEEP_INTERVAL` must be greater than zero (it is a ticker
 period, so `0s` or a negative value would crash the reaper after
-startup), and every entry in `TRUSTED_PROXIES` and
-`ALLOWED_EGRESS_CIDRS` must be a CIDR block or a bare IP address.
+startup), every entry in `TRUSTED_PROXIES` and
+`ALLOWED_EGRESS_CIDRS` must be a CIDR block or a bare IP address, and
+`BIND_ADDRESS` must be an IP address literal — `localhost`,
+`127.0.0.1:8080` and `10.0.0.0/8` are each rejected rather than
+resolved, split, or narrowed to something they do not say — and
+`SENTRY_DSN` must parse as a Sentry DSN.
 `SESSION_IDLE_TIMEOUT` is the exception: a
 non-positive value there means idle expiry is disabled, not invalid.
 
+`SENTRY_DSN` is checked with the Sentry SDK's own parser, the same call
+the SDK makes on the DSN it is later handed, so what configuration
+accepts is exactly what will initialise. A typo in it is the one
+configuration mistake nothing downstream can ever notice — the variable
+is still set, so every later signal reports error reporting as on while
+no report is being sent — which is why it aborts rather than starting
+with reporting off. Leaving it unset is not a mistake and not affected:
+error reporting is simply off and startup is normal.
+
 Boolean variables (`DEBUG`, `MAINTENANCE_MODE`) accept exactly the
 spellings Go's `strconv.ParseBool` accepts — `1`, `t`, `T`, `TRUE`,
 `true`, `True`, `0`, `f`, `F`, `FALSE`, `false`, `False` — and nothing
@@ -543,12 +636,54 @@ decision:
 
 ```bash
 docker run -d \
-  -p 8080:8080 \
+  -p 127.0.0.1:8080:8080 \
   -v /path/to/data:/var/lib/webhooker \
   -e WEBHOOKER_ENVIRONMENT=prod \
+  -e BIND_ADDRESS=0.0.0.0 \
   webhooker:latest
 ```
 
+**The image and the bare binary default `BIND_ADDRESS` differently, on
+purpose.** The binary defaults to `127.0.0.1`; the image ships
+`ENV BIND_ADDRESS=0.0.0.0`, so the `-e BIND_ADDRESS=0.0.0.0` above is
+belt-and-braces and the command works without it.
+
+The two cases are not the same question. On a bare host, `0.0.0.0`
+puts the cleartext admin UI and the unauthenticated receiver on every
+interface of the machine, which is what the loopback default exists to
+prevent. In a container, the network namespace is already that
+boundary: nothing outside reaches `0.0.0.0:8080` because of the
+namespace, not because of the bind. What decides exposure there is the
+**publish flag**, and that is the line to get right.
+
+So publish to `127.0.0.1:8080` rather than `8080`. A bare
+`-p 8080:8080` opens the port on every interface of the host — through
+firewall rules too, since Docker's forwarding rules are inserted ahead
+of most host firewalls. Publish to the host address your reverse proxy
+connects from, and nothing wider.
+
+**An empty `BIND_ADDRESS` is treated as unset**, like every other
+variable here, so `-e BIND_ADDRESS=` does not mean "keep the image
+default" — it discards the image's `0.0.0.0` and falls back to the
+_binary's_ `127.0.0.1`. In a container that is the failure below, and
+nothing in the logs names the variable. A templated Compose file or a
+`.env` line with an empty value is the usual way in. Either set a
+literal or leave the variable out entirely.
+
+Overriding `BIND_ADDRESS` to a loopback address in a container — by
+that route or deliberately — makes the container unreachable from
+outside its namespace even with `-p`. The published port answers
+nothing, and the health check fails too: it requests
+`http://localhost:8080`, `localhost` resolves to `::1` first, and a
+`127.0.0.1` bind is not listening there. The container then goes
+`unhealthy` about **65 seconds** after start — from `HEALTHCHECK
+--start-period=5s --interval=30s --retries=3`, so failing probes at
+5s, 35s and 65s, and `unhealthy` on the third. (Docker's probe cadence
+during the start period has changed between versions; re-derive from
+those three values rather than trusting the figure. Measured at 65s on
+Docker 29.7.2.) A container `unhealthy` with `connection refused` in
+its health log, or a published port that resets connections, is this.
+
 The container runs as a non-root user (`webhooker`, UID 1000), exposes
 port 8080, and includes a health check against
 `/.well-known/healthcheck`. The `/var/lib/webhooker` volume holds all
@@ -558,6 +693,189 @@ databases written by `database` targets (`archive-{uuid}.db`). Mount
 this as a persistent volume to preserve data across container
 restarts.
 
+**The bind-mounted directory must be owned by UID 1000, or the
+container does not start.** Docker creates a `-v` source path that
+does not exist yet as `root:root`, and the process runs as UID 1000,
+so it cannot take its `DATA_DIR` lock:
+
+```
+webhooker: locking data directory /var/lib/webhooker: open
+/var/lib/webhooker/webhooker.lock: permission denied
+```
+
+It exits non-zero at that point, before opening any database. Create
+the directory ahead of the first `docker run`:
+
+```bash
+mkdir -p /path/to/data
+chown 1000:1000 /path/to/data
+chmod 750 /path/to/data
+```
+
+The same `chown` is what a restore needs — see step 4 of
+[Restore](#restore). A **named volume** does not have this problem:
+Docker copies the image's ownership onto a volume it initializes, and
+the image creates `/var/lib/webhooker` owned by `webhooker`.
+
+**The file modes are not yours to set, and do not depend on the
+directory.** `webhooker.db` holds target configuration in plaintext —
+bearer tokens, API keys, Slack webhook URLs — along with the session
+encryption key, so webhooker creates every SQLite file it owns `0600`:
+each database and both of its `-wal` and `-shm` sidecars, across all
+three tiers. Files an earlier build left `0644` are tightened when
+they are opened. A `DATA_DIR` webhooker creates itself is `0750`, but
+a bind mount supplies its own directory and Docker's default for one
+it creates is `0755`; the `0600` files hold there regardless. The
+`chmod 750` above is defence in depth — it stops other local users
+listing the directory and learning your webhook UUIDs from the
+`events-{uuid}.db` filenames — not the barrier protecting the
+credentials.
+
+## Deployment behind a reverse proxy
+
+webhooker terminates no TLS of its own. It serves plaintext HTTP and
+expects a reverse proxy in front of it, which is the deployment it is
+built for: the proxy holds the certificate, and webhooker binds
+loopback where only the proxy can reach it.
+
+Five things have to be right. Each one is silent when it is wrong —
+the service comes up, serves pages, and is broken in a way nothing
+reports.
+
+1. **Bind or firewall the app port.** The binary binds `127.0.0.1` by
+   default, so the cleartext listener is not published beside the
+   proxy. The image binds `0.0.0.0` inside its own network namespace
+   and relies on the publish address instead —
+   `-p 127.0.0.1:8080:8080`. Either way the port must reach the proxy
+   and nothing else; widen it only with a firewall or a publish
+   address in front of it. A cleartext port answering the internet
+   serves the admin login form and the unauthenticated receiver with
+   no TLS at all, and the proxy in front of it changes nothing about
+   that.
+2. **Set `WEBHOOKER_ENVIRONMENT=prod`, and make sure the proxy sends
+   `X-Forwarded-Proto`.** These are two requirements, not one. The
+   environment setting decides CORS and nothing else: the default
+   `dev` answers every origin with `Access-Control-Allow-Origin: *`
+   (without credentials), which a server-rendered production
+   deployment has no use for. Cookie `Secure` and the strict
+   Origin/Referer mode are **not** tied to it — they are decided per
+   request from the transport, which behind a proxy means the
+   `X-Forwarded-Proto` header. The block below sets it; without it
+   every request is read as plaintext and cookies ship without
+   `Secure`. See [Configuration](#configuration).
+3. **Set `TRUSTED_PROXIES` to the proxy's address.** Unset, every rate
+   limiter keys on the connecting peer, which behind a proxy is the
+   proxy on every request: all clients collapse into one global bucket
+   per limit and the receiver's per-IP limits become service-wide
+   ceilings. See [Trusted proxies](#trusted-proxies). List the proxy
+   and nothing else.
+4. **Send `Host` as `$http_host`, not `$host`.** `$host` strips the
+   port. webhooker's Origin/Referer check compares against the host it
+   was given, so on any port other than 443 `$host` makes every form
+   POST — including login — fail with `403 origin invalid`, with
+   nothing in the error naming the cause.
+5. **Keep the proxy's access log.** webhooker's own access log records
+   the peer address, which behind a proxy is always the proxy. The
+   proxy's log is the only record of which client sent what. nginx's
+   default `combined` format already logs `$remote_addr`; do not
+   replace it with one that drops the client address, and retain those
+   logs as long as you would want to answer a question about traffic.
+
+### nginx
+
+Complete server block. Replace the `server_name` and the two
+certificate paths.
+
+```nginx
+server {
+    listen 443 ssl;
+    listen [::]:443 ssl;
+    http2 on;  # nginx 1.25.1+; older: listen 443 ssl http2;
+
+    server_name webhooker.example.com;
+
+    ssl_certificate     /etc/ssl/certs/webhooker.example.com.crt;
+    ssl_certificate_key /etc/ssl/private/webhooker.example.com.key;
+    ssl_protocols       TLSv1.2 TLSv1.3;
+
+    # webhooker caps form POST bodies at 1 MB. nginx's default happens
+    # to match, so leaving this out breaks nothing today — but if you
+    # ever raise webhooker's cap, this is the limit you will still be
+    # hitting, and the rejection is nginx's HTML page rather than
+    # webhooker's message.
+    client_max_body_size 1m;
+
+    # $remote_addr is the client. webhooker's own log records this
+    # proxy and nothing else, so this file is the only place the
+    # client's address is written down.
+    access_log /var/log/nginx/webhooker.access.log combined;
+
+    location / {
+        # A literal address, not localhost: with BIND_ADDRESS at its
+        # 127.0.0.1 default, a localhost that resolves to ::1 first
+        # gets connection refused.
+        proxy_pass http://127.0.0.1:8080;
+
+        # $http_host, NOT $host. $host drops the port and every form
+        # POST fails with 403 origin invalid on any port but 443.
+        proxy_set_header Host              $http_host;
+        proxy_set_header X-Forwarded-For   $proxy_add_x_forwarded_for;
+        proxy_set_header X-Forwarded-Proto $scheme;
+
+        # Above webhooker's own 60s request timeout, so its 503
+        # reaches the client instead of nginx cutting the connection
+        # first and answering 504.
+        proxy_read_timeout 70s;
+    }
+}
+
+server {
+    listen 80;
+    listen [::]:80;
+    server_name webhooker.example.com;
+    return 308 https://$host$request_uri;
+}
+```
+
+`X-Forwarded-For` must be **appended** to, which
+`$proxy_add_x_forwarded_for` does. webhooker reads no other forwarded
+client header: `X-Real-IP` and `True-Client-IP` are ignored from every
+peer, so setting them has no effect. See
+[Trusted proxies](#trusted-proxies) for how the chain is walked.
+
+`X-Forwarded-Proto: https` is what tells webhooker the request arrived
+over TLS, which decides the `Secure` flag on both the session and CSRF
+cookies and the strict Origin/Referer mode. Without it, requests are
+treated as plaintext and the cookies ship without `Secure`. Unlike
+`X-Forwarded-For`, this header is read from any peer and is not gated
+by `TRUSTED_PROXIES`, so the proxy must overwrite whatever a client
+sent — `$scheme` above does.
+
+With that block, webhooker's environment is:
+
+```sh
+WEBHOOKER_ENVIRONMENT=prod
+BIND_ADDRESS=127.0.0.1   # the default; stated here to be explicit
+TRUSTED_PROXIES=127.0.0.1
+```
+
+If nginx runs on another host, `BIND_ADDRESS` becomes the address it
+connects to, `TRUSTED_PROXIES` becomes nginx's address, and the port
+must be firewalled to that address — the traffic between them is
+cleartext.
+
+### HSTS is always sent, and is not configurable
+
+Every response carries
+`Strict-Transport-Security: max-age=63072000; includeSubDomains; preload`.
+Two years, every subdomain, and a `preload` token. There is no setting
+that changes or suppresses it.
+
+This is worth knowing before the first request reaches a browser: a
+client that sees it once will refuse plaintext HTTP to that hostname —
+and to every subdomain of it — for two years, whatever else is served
+there. Terminate TLS on a hostname you are prepared to keep on HTTPS.
+
 ## Backup, Restore, and Upgrades
 
 ### What to back up
@@ -581,9 +899,25 @@ is both the simplest and the only complete rule:
 `events-3f2a1c9e-....db`. The only other file is `webhooker.lock`, the
 always-empty [single-instance lock](#single-instance-lock); it holds no
 state and is not part of the backup set — a copied one is stale and
-blocks nothing. No `-wal` or `-shm` files are produced (see below); a
-transient `{name}.db-journal` may exist beside a database while a write
-is in flight and is not part of the backup set either.
+blocks nothing.
+
+**`-wal` and `-shm` sidecars.** Every database runs in WAL journal mode,
+so while the service is running each `{name}.db` has a `{name}.db-wal`
+and a `{name}.db-shm` beside it. **`-wal` is part of the database, not a
+scratch file**: it holds committed transactions that are not yet in the
+`.db`, so a copy of the `.db` without its `-wal` is missing data and may
+have no readable schema at all. `-shm` is regenerable, but there is no
+reason to separate the two — copy the directory and you have them.
+
+A clean shutdown closes `webhooker.db` and every `events-*.db`, which
+checkpoints and removes their sidecars; a killed or crashed instance
+leaves them, and they must be carried with the `.db`. **Archive
+databases are different**: their handle is not closed at shutdown, so
+`archive-*.db-wal` and `-shm` normally survive a clean stop and the
+`-wal` can hold every row the archive has. Measured on a stopped
+instance: `archive-….db` 4096 bytes with no table, its `-wal` 157 KB
+holding all 8 archived events. Copying `DATA_DIR` in full is what makes
+this a non-issue; copying `.db` files out of it by name is not.
 
 Configuration is **not** in `DATA_DIR` — it comes from the environment
 and from a `.env` file read out of the process working directory. Back
@@ -591,17 +925,19 @@ that up with your deployment config, separately.
 
 ### A hot copy is not safe
 
-No `journal_mode` pragma is ever issued on any database webhooker opens,
-so all of them run on SQLite's default rollback journal. There is no
-WAL. The main and event databases are also held open for the entire
-process lifetime — `WebhookDBManager` caches event database handles and
-closes them only on webhook deletion or shutdown — so "it looked idle"
-is not a guarantee that nothing was mid-transaction.
+Every database webhooker opens runs in WAL journal mode. The main and
+event databases are also held open for the entire process lifetime —
+`WebhookDBManager` caches event database handles and closes them only on
+webhook deletion or shutdown — so "it looked idle" is not a guarantee
+that nothing was mid-transaction.
 
 That means `cp`, `rsync`, `tar` or a filesystem snapshot taken against a
-running instance can capture a database mid-transaction and yield a file
-that is corrupt or missing state the journal would have rolled back. Use
-one of the two procedures below instead.
+running instance can capture a database and its `-wal` at two different
+instants and yield a file that is corrupt or missing state. Copying a
+`.db` on its own is worse and fails loudly: recently written pages,
+including the schema itself on a young database, live in the `-wal`, so
+the copy reads back as an empty or table-less database. Use one of the
+two procedures below instead.
 
 **Stop, copy, start.** The simplest, needs no extra tooling, and the
 only one that gives a single point in time across every file:
@@ -620,8 +956,9 @@ for db in /path/to/data/*.db; do
 done
 ```
 
-`.backup` takes the proper locks and writes a consistent file. Two
-caveats. First, the runtime image is `alpine:3.21` with only
+`.backup` reads through the WAL and writes a single consistent file with
+no sidecars of its own, so the destination is complete as it stands.
+Two caveats. First, the runtime image is `alpine:3.21` with only
 `ca-certificates` added — the `sqlite3` CLI is **not** in it, so run
 this on the host against the volume path, or from a throwaway container
 that mounts the volume. Second, each file is captured at its own
@@ -629,15 +966,37 @@ instant, so a webhook created or an event delivered between two files
 being copied lands in one and not the other. If you need the whole set
 coherent as of a single moment, stop the service.
 
+Note that `sqlite3 <db> .dump` is **not** one of these procedures: it is
+an export, it holds a read transaction open for as long as it runs, and
+it pins the WAL against checkpointing for that whole time. It is safe to
+run — it does not block ingestion — but back up with `.backup` or a
+stopped copy.
+
 Archive databases are the one exception the service is built for: the
-archive writer closes its handle after each write (debounced to at most
-one reopen per second), so an operator can move `archive-{uuid}.db`
-away for offline retention while the service runs, and it is recreated
-on the next write (see
-[Database Architecture](#database-architecture)). That is a
+archive writer closes and reopens its handle around writes (debounced
+to at most one reopen per second), so an operator can move
+`archive-{uuid}.db` away for offline retention while the service runs,
+and it is recreated on the next write. See
+[Database Architecture](#database-architecture). That is a
 move-the-file-away workflow, not a substitute for the backup procedures
 above.
 
+**Move the sidecars with it.** Under WAL that workflow is no longer a
+single file, and the common case is the dangerous one. The reopen
+happens on the *next* write after the debounce window elapses, so after
+the last write of a burst nothing checkpoints: measured, 20 s after ten
+events the `archive-….db` was 4096 bytes — a header, no table — with
+all ten rows sitting in a 189 KB `-wal`. Copying the `.db` alone at that
+moment yields a file that opens with `no such table: archived_events`.
+The file becomes self-contained again when the handle closes, which
+happens on the next write past the debounce window, when the connection
+pool retires the idle connection (about a minute after the last write),
+or at the idle archive sweep — measured, the same file was a complete
+20 KB `.db` with no sidecars about a minute after its last write.
+Shutdown is **not** on that list: the archive handle is not closed when
+the service stops. So either move `archive-{uuid}.db` together with any
+`-wal`/`-shm` beside it, or wait until there are none.
+
 ### Restore
 
 1. Stop the service.
@@ -651,14 +1010,22 @@ above.
    restored without `webhooker.db` are simply orphaned; nothing
    references their UUIDs.
 
-3. Do not carry `*.db-journal` files into the restore. Backups taken by
-   either procedure above are self-consistent and do not need one.
+3. Carry any `*.db-wal` and `*.db-shm` files that are in the backup.
+   They are part of the database, and dropping a `-wal` silently
+   discards every transaction it still holds. An `.backup` set will not
+   contain any: it writes a single consolidated file per database. A
+   stop-and-copy set has none for `webhooker.db` or the `events-*.db`,
+   because a clean stop closes those and checkpoints their sidecars
+   away — but it will normally have them for `archive-*.db`, whose
+   handle stays open across shutdown, and those carry the archive's
+   rows. A copy salvaged from a crashed instance has them for
+   everything, and needs all of them.
 
 4. **Fix ownership.** The container runs as the non-root `webhooker`
    user, UID 1000 / GID 1000. Restored files must be owned by (or
    writable by) that UID, and so must the directory itself — SQLite
-   creates the rollback journal beside the database, so a writable file
-   inside a directory it cannot write is not enough:
+   creates the `-wal` and `-shm` sidecars beside the database, so a
+   writable file inside a directory it cannot write is not enough:
 
     ```bash
     chown -R 1000:1000 /path/to/data
@@ -696,6 +1063,18 @@ Upgrade procedure:
    `curl -s http://host:8080/.well-known/healthcheck` reports the
    version it was stamped with (see [Version stamping](#version-stamping)).
 
+**Upgrading past the introduction of `BIND_ADDRESS`:** earlier versions
+always bound every interface. **Container deployments are unaffected**
+— the image ships `ENV BIND_ADDRESS=0.0.0.0`, so a `docker run` or
+Compose service that worked before still works with nothing changed.
+
+A **bare binary** is the case that changes: the listener now binds
+`127.0.0.1` unless `BIND_ADDRESS` says otherwise, so a deployment that
+relied on reaching it from another host becomes unreachable until it
+sets the address the proxy connects to. Check the `bindAddress` field
+of the startup log to see what a running process bound. See
+[Bind address](#bind-address).
+
 **Downgrade is unsupported.** Once a newer binary has migrated the files
 there is no way to move them back. `AutoMigrate` is additive — it adds
 tables, columns and indexes and never drops or rewrites them — so an
@@ -777,14 +1156,38 @@ backups at rest and restrict who can read them.
 
 ## The entrypoint URL is the authentication secret
 
-The receiver verifies nothing about an inbound request. The UUID in an
-entrypoint's URL is its credential: anyone who holds that URL can
-submit events to it, and the receiver checks nothing else about the
-sender. Treat an entrypoint URL the way you would treat an API token.
+**The entrypoint UUID is the credential, and it is the only one.**
+webhooker mints a version 4 UUID per entrypoint and serves it at
+`/webhook/{uuid}`. Possession of that URL is the authentication:
+anyone who holds it can submit events to the entrypoint, and the
+receiver verifies nothing else about the sender.
 
-There is no way to rotate the UUID in place. To retire one, delete the
-entrypoint (or deactivate it, which answers `410`) and create a new
-one, then point the sender at the new URL.
+There is no shared secret, no HMAC signature, no bearer token and no
+second factor on the receiver, and none will be added. This was
+considered and rejected; the implementation that existed was removed
+in [PR #279](https://git.eeqj.de/sneak/webhooker/pulls/279), closing
+[issue #67](https://git.eeqj.de/sneak/webhooker/issues/67) and
+[issue #241](https://git.eeqj.de/sneak/webhooker/issues/241). A
+proposal to reintroduce any of them — including as "defence in depth"
+alongside the UUID — is answered by this section. Inbound signature
+headers a sender sends anyway (`X-Hub-Signature` and its
+per-provider equivalents) are stored and forwarded as ordinary
+headers; nothing checks them.
+
+What that means for an operator:
+
+- **The URL is a capability, so treat it as a secret.** Keep it out of
+  logs, ticket bodies, chat messages and screenshots. Anyone who reads
+  it anywhere can post events as that sender.
+- **Rotating means minting a new entrypoint, not changing a key.**
+  There is no way to rotate the UUID in place. To retire one, delete
+  the entrypoint (or deactivate it, which answers `410`) and create a
+  new one, then point the sender at the new URL.
+- **A sender that cannot be given a secret URL is a constraint on that
+  integration, not a reason to change this.** If a service only
+  supports signed payloads to a well-known URL, raise it as its own
+  problem — pick a different integration path, or accept that it
+  cannot be used. It is not grounds to reintroduce shared secrets.
 
 ## Entrypoints
 
@@ -862,6 +1265,16 @@ webhooker solves this by acting as a durable intermediary:
    backoff. Every delivery attempt is logged with status codes, response
    bodies, and timing.
 
+   **That guarantee is at-least-once, not exactly-once.** When a send
+   reaches its target but the write recording that outcome fails, the
+   delivery is deliberately left in a recoverable state rather than
+   marked done — losing a delivery is the worse failure — so the
+   pending sweep picks it up about fifteen minutes later, or the next
+   restart does, and the target receives a payload it already got.
+   webhooker adds no delivery identifier of its own to an outbound
+   request, so **make your receiver idempotent** against whatever the
+   payload itself carries.
+
 3. **Observability** — Full request/response logging for every webhook
    received and every delivery attempted. Prometheus metrics expose
    volume, latency, and error rates. The web UI provides real-time
@@ -1308,6 +1721,11 @@ webhooker uses **separate SQLite database files**: a main application
 database for configuration data and per-webhook databases for event
 storage. All database files live in the `DATA_DIR` directory.
 
+Every one of them is created `0600`, and so is each `-wal` and `-shm`
+sidecar. See
+[Running with Docker](#running-with-docker) for what that does and
+does not protect.
+
 **Main Application Database** (`{DATA_DIR}/webhooker.db`) — stores
 configuration and application state:
 
@@ -1349,10 +1767,12 @@ This separation provides:
   only, or disables cleanup entirely when set to `0` (retain forever).
 - **Performance** — each webhook's database has its own page cache and
   its own lock, so concurrent event ingestion across webhooks won't
-  contend. No write-ahead log is involved: both DSNs are
-  `file:{path}?cache=shared&mode=rwc` and no `journal_mode` pragma is
-  ever issued, so every database runs on SQLite's default rollback
-  journal.
+  contend. Every database — main, per-webhook, and archive — is opened
+  through one code path (`internal/database/sqlite_open.go`) in WAL
+  journal mode, with a 10-second busy timeout, `BEGIN IMMEDIATE`
+  transactions, and a bounded connection pool. Under WAL a reader never
+  blocks a writer, so an operator reading a database does not stall
+  event ingestion into it.
 
 The **database target type** builds on this architecture to provide
 long-term archiving, separate from the per-webhook event database (which
@@ -2237,12 +2657,15 @@ abuse limit later; they are tracked as future work.
 | `POST` | `/source/{id}/edit`      | Edit webhook submission |
 | `POST` | `/source/{id}/delete`    | Delete webhook |
 | `GET`  | `/source/{id}/logs`      | Webhook event logs |
+| `GET`  | `/source/{id}/logs/{eventID}/body` | Download an event's full stored body. The log page renders each body only up to its cap, so this is the only route that serves a whole one; it is offered wherever a body is shown truncated |
 | `POST` | `/source/{id}/deliveries/{deliveryID}/replay` | Replay a finished delivery: creates a new delivery for the same event against the target's current configuration (30 per minute per bucket, then `429`) |
 | `POST` | `/source/{id}/events/{eventID}/resubmit` | Resubmit a stored event: creates a new event copying it and fans that out to every currently active target (30 per minute per bucket, then `429`) |
 | `POST` | `/source/{id}/entrypoints` | Add entrypoint to webhook |
 | `POST` | `/source/{id}/entrypoints/{entrypointID}/delete` | Delete an entrypoint |
 | `POST` | `/source/{id}/entrypoints/{entrypointID}/toggle` | Enable or disable an entrypoint |
 | `POST` | `/source/{id}/targets`   | Add target to webhook |
+| `GET`  | `/source/{id}/targets/{targetID}/edit` | Edit target form. The one page that renders a target's destination URL and header values in full, rather than masked |
+| `POST` | `/source/{id}/targets/{targetID}/edit` | Edit target submission |
 | `POST` | `/source/{id}/targets/{targetID}/delete` | Delete a target |
 | `POST` | `/source/{id}/targets/{targetID}/toggle` | Enable or disable a target |
 
@@ -2281,6 +2704,8 @@ webhooker/
 ├── internal/
 │   ├── banner/
 │   │   └── banner.go          # Ruled block for the one credential shown in the clear
+│   ├── ciscript/
+│   │   └── doc.go             # Tests for the CI shell scripts in script/; no runtime code
 │   ├── resetpw/
 │   │   └── resetpw.go         # `webhooker resetpw`: set an account's password, stopped deployments only
 │   ├── config/
@@ -2350,13 +2775,17 @@ webhooker/
 │   │   ├── ratelimit.go       # Per-IP rate limiting middleware (go-chi/httprate)
 │   │   ├── loginguard.go      # Login failure counters and the Argon2id verification semaphore
 │   │   └── testing.go         # NewForTest: Middleware without the fx lifecycle
+│   ├── reqtls/
+│   │   └── reqtls.go          # IsTLS: the one TLS predicate, r.TLS or X-Forwarded-Proto
 │   ├── server/
 │   │   ├── server.go          # Server struct, fx lifecycle, signal handling
 │   │   ├── http.go            # HTTP server setup with timeouts
 │   │   └── routes.go          # All route definitions
-│   └── session/
-│       ├── session.go         # Cookie-based session management
-│       └── testing.go         # NewForTest: Session without the fx lifecycle
+│   ├── session/
+│   │   ├── session.go         # Cookie-based session management
+│   │   └── testing.go         # NewForTest: Session without the fx lifecycle
+│   └── versionscript/
+│       └── doc.go             # Tests for script/version and the build files that use it
 ├── static/
 │   ├── static.go              # //go:embed directive
 │   ├── css/input.css          # Tailwind input, source for tailwind.css (make css)
@@ -2469,6 +2898,10 @@ check, see [The login endpoint](#the-login-endpoint).
 
 ### Authentication
 
+- **Webhook receiver:** the entrypoint UUID in the URL, and nothing
+  else. No shared secret, no HMAC signature, no token header, and none
+  will be added — see
+  [The entrypoint URL is the authentication secret](#the-entrypoint-url-is-the-authentication-secret).
 - **Web UI:** Cookie-based sessions using gorilla/sessions with
   encrypted cookies. Sessions are configured with HttpOnly, SameSite
   Lax, and Secure whenever the request is on TLS — the flag follows the
@@ -2508,7 +2941,8 @@ check, see [The login endpoint](#the-login-endpoint).
   mode
 - **The entrypoint URL is the receiver's only credential.** Nothing
   about an inbound request is verified; possession of the UUID
-  authorises submission (see
+  authorises submission, and no shared secret or signature check will
+  be added alongside it (see
   [The entrypoint URL is the authentication secret](#the-entrypoint-url-is-the-authentication-secret))
 - **SSRF prevention** for HTTP delivery targets: private/reserved IP
   ranges (RFC 1918, loopback, link-local, cloud metadata) are blocked

TODO.md

@@ -18,18 +18,27 @@ Issue branches do NOT touch this file — the manager maintains it on
 
 # Status
 
-1.0.0 is open, with work remaining. The milestone
-(https://git.eeqj.de/sneak/webhooker/milestone/9) is the authoritative
-list and the only place to read a count from; this file deliberately
-carries neither, because both drift between the commits that touch it.
-`next` is ahead of `main` and a strict fast-forward. No release has
-been tagged yet.
+The milestone (https://git.eeqj.de/sneak/webhooker/milestone/9) is the
+authoritative list, and the only place to read a count or a state of
+play from. This file records where the project is, not what is in
+flight: a sentence whose truth depends on a branch being unmerged is
+wrong the moment it merges, and this file has been wrong that way
+before.
 
-The tag is held on a durability defect
-(https://git.eeqj.de/sneak/webhooker/issues/256): a concurrent reader
-of a per-webhook event database strands delivered webhooks at
-`pending`, and the next restart re-delivers them. A fix is in review
-(https://git.eeqj.de/sneak/webhooker/pulls/263).
+The durability defect that held the tag has landed
+(https://git.eeqj.de/sneak/webhooker/issues/256, commit `8d64259`).
+Every SQLite handle opens with WAL journaling and a busy timeout, a
+bookkeeping write that fails leaves its delivery in a recoverable
+state rather than a lying one, and recovery skips a delivery that
+already has a successful result row. Final pre-tag verification
+exercised it and confirmed it holds. Whatever the milestone still
+shows open is what remains before `v1.0.0`.
+
+Delivery is at-least-once by design, not by accident: a send whose
+result row does not land is attempted again, so a receiver can see a
+duplicate. That is deliberate — the alternative is a silent lost
+delivery — and the README says so under Rationale. It is not a defect
+to re-file.
 
 One caveat on reading a green check: a docs-only commit deliberately
 replays from the layer cache
@@ -39,16 +48,25 @@ commit invalidates the `COPY` layer and genuinely executes.
 
 # Next Step
 
-Land https://git.eeqj.de/sneak/webhooker/issues/256, then clear the
-rest of the open 1.0.0 milestone and tag `v1.0.0`.
-
-The milestone PR (https://git.eeqj.de/sneak/webhooker/pulls/111) is
-`merge-ready` and assigned to sneak. Merging it is safe whenever sneak
-wants it — the durability defect predates the branch and exists on
-`main` too — but merging it is not the tag.
+Clear the rest of the open 1.0.0 milestone
+(https://git.eeqj.de/sneak/webhooker/milestone/9) and tag `v1.0.0`.
+Merging `next` into `main` is a separate act from tagging and waits on
+neither of those: `next` is kept mergeable at all times, which is the
+point of the branch.
 
 # Completed Steps
 
+- 2026-08-24 Bind the plaintext HTTP listener deliberately, via
+  `BIND_ADDRESS` defaulting to `127.0.0.1`, and document the
+  reverse-proxy deployment. A hostname, an empty value or a value
+  carrying a port is a startup error, and the `Dockerfile` sets
+  `0.0.0.0` because a loopback bind inside a container is unreachable
+  (https://git.eeqj.de/sneak/webhooker/issues/268). The same commit
+  removed the shutdown race: `httpServer` is built in the constructor
+  rather than assigned from the serving goroutine, which orders the
+  write before every fx hook and rules out the nil dereference a
+  SIGTERM arriving first would have caused, and `sentryEnabled` is an
+  `atomic.Bool` (https://git.eeqj.de/sneak/webhooker/issues/226)
 - 2026-08-24 Remove inbound request signature verification. The
   entrypoint UUID is the authentication secret, so the per-entrypoint
   shared secret, the `internal/signature` package, the receiver check,

cmd/webhooker/dotenv_test.go

@@ -0,0 +1,107 @@
+package main
+
+import (
+	"bytes"
+	"os"
+	"path/filepath"
+	"strings"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	"sneak.berlin/go/webhooker/internal/config"
+)
+
+// dotEnvKey is a throwaway variable name these tests write and read,
+// so they cannot disturb real configuration.
+const dotEnvKey = "WEBHOOKER_TEST_DISPATCH_VALUE"
+
+// writeDotEnvInWorkingDir puts contents in a .env file in a fresh
+// temporary directory and moves the process there.
+//
+// The callers are deliberately not parallel and must stay that way:
+// t.Chdir moves the whole process. Go releases parallel tests only
+// after every sequential test in the package has finished, so nothing
+// else runs while these do.
+func writeDotEnvInWorkingDir(t *testing.T, contents string) {
+	t.Helper()
+
+	dir := t.TempDir()
+	require.NoError(t, os.WriteFile(
+		filepath.Join(dir, config.DotEnvPath),
+		[]byte(contents), 0o600,
+	))
+	t.Chdir(dir)
+}
+
+// TestDispatch_MalformedDotEnvRefuses pins the second half of the
+// defect. godotenv applies nothing at all when a file will not parse,
+// so one mistyped line used to revert every variable in it to its
+// default and start the server anyway, with no log line naming the
+// file. The refusal has to arrive before any subcommand runs, which
+// is why `help` — the one subcommand that touches nothing — is still
+// refused here.
+//
+//nolint:paralleltest // t.Chdir moves the whole process.
+func TestDispatch_MalformedDotEnvRefuses(t *testing.T) {
+	writeDotEnvInWorkingDir(t, "PORT 19615\n")
+
+	var stdout, stderr bytes.Buffer
+
+	code := dispatch(
+		[]string{helpCommand}, strings.NewReader(""), &stdout, &stderr,
+	)
+
+	require.Equal(t, 1, code, "a broken .env must exit non-zero")
+	assert.Contains(
+		t, stderr.String(), config.DotEnvPath,
+		"the refusal must name the file",
+	)
+	assert.Empty(
+		t, stdout.String(),
+		"the subcommand must not have run",
+	)
+}
+
+// TestDispatch_LoadsDotEnvBeforeSubcommands pins the ordering the
+// godotenv/autoload import used to provide for free. It ran in an
+// init(), so .env was in the environment before anything read it —
+// including config.DataDir, which both the DATA_DIR lock and resetpw
+// call outside the fx graph. Loading any later would let a .env that
+// sets DATA_DIR lock one directory while the config opened databases
+// in another.
+func TestDispatch_LoadsDotEnvBeforeSubcommands(t *testing.T) {
+	t.Setenv(dotEnvKey, "placeholder")
+	require.NoError(t, os.Unsetenv(dotEnvKey))
+
+	writeDotEnvInWorkingDir(t, dotEnvKey+"=from-dot-env\n")
+
+	var stdout, stderr bytes.Buffer
+
+	code := dispatch(
+		[]string{helpCommand}, strings.NewReader(""), &stdout, &stderr,
+	)
+
+	require.Equal(t, 0, code)
+	assert.Equal(
+		t, "from-dot-env", os.Getenv(dotEnvKey),
+		"the file must be applied before the subcommand runs",
+	)
+}
+
+// TestDispatch_MissingDotEnvIsFine pins the case most deployments are
+// in: no .env at all, which must stay a normal start.
+//
+//nolint:paralleltest // t.Chdir moves the whole process.
+func TestDispatch_MissingDotEnvIsFine(t *testing.T) {
+	t.Chdir(t.TempDir())
+
+	var stdout, stderr bytes.Buffer
+
+	code := dispatch(
+		[]string{helpCommand}, strings.NewReader(""), &stdout, &stderr,
+	)
+
+	require.Equal(t, 0, code)
+	assert.Empty(t, stderr.String())
+}

cmd/webhooker/main.go

@@ -54,6 +54,11 @@ const stopTimeout = 5 * time.Second
 // caller can tell "called wrong" from "declined".
 const exitUsage = 2
 
+// helpCommand is the subcommand that prints usage. The flag spellings
+// beside it in the switch are aliases; this is the name the usage text
+// documents and the one tests invoke.
+const helpCommand = "help"
+
 // Build-time variables set via -ldflags.
 //
 //nolint:gochecknoglobals // Build-time variables injected by the linker.
@@ -75,11 +80,27 @@ func main() {
 // every existing deployment invoke; that path is unchanged, including
 // where the DATA_DIR lock is taken relative to building the fx graph
 // and how fx propagates a non-zero exit itself.
+//
+// The optional .env file is read here, before any subcommand and so
+// before anything reads the environment — config.DataDir, which both
+// the DATA_DIR lock and resetpw call outside the fx graph, above all.
+// It used to be read from an init() in internal/config, which put it
+// earlier still but threw the error away: a single malformed line
+// applied none of the file and said nothing about it. A file that is
+// not there stays fine, since .env is optional and most deployments
+// do not have one.
 func dispatch(
 	args []string,
 	stdin io.Reader,
 	stdout, stderr io.Writer,
 ) int {
+	err := config.LoadDotEnv()
+	if err != nil {
+		_, _ = fmt.Fprintf(stderr, "%s: %v\n", appname, err)
+
+		return 1
+	}
+
 	if len(args) == 0 {
 		return run(stderr)
 	}
@@ -87,7 +108,7 @@ func dispatch(
 	switch args[0] {
 	case resetpw.Name:
 		return resetpw.Run(args[1:], stdin, stdout, stderr)
-	case "help", "-h", "-help", "--help":
+	case helpCommand, "-h", "-help", "--help":
 		usage(stdout)
 
 		return 0

cmd/webhooker/main_test.go

@@ -121,7 +121,7 @@ func TestDispatch_Help(t *testing.T) {
 	var stdout, stderr bytes.Buffer
 
 	code := dispatch(
-		[]string{"help"}, strings.NewReader(""), &stdout, &stderr,
+		[]string{helpCommand}, strings.NewReader(""), &stdout, &stderr,
 	)
 
 	require.Equal(t, 0, code)

internal/config/config.go

@@ -4,6 +4,7 @@ package config
 import (
 	"errors"
 	"fmt"
+	"io/fs"
 	"log/slog"
 	"net/netip"
 	"os"
@@ -11,13 +12,11 @@ import (
 	"strings"
 	"time"
 
+	"github.com/getsentry/sentry-go"
+	"github.com/joho/godotenv"
 	"go.uber.org/fx"
 	"sneak.berlin/go/webhooker/internal/globals"
 	"sneak.berlin/go/webhooker/internal/logger"
-
-	// Populates the environment from a ./.env file automatically for
-	// development configuration. Kept in one place only (here).
-	_ "github.com/joho/godotenv/autoload"
 )
 
 const (
@@ -33,6 +32,34 @@ const (
 	// defaultPort is the default HTTP listen port.
 	defaultPort = 8080
 
+	// defaultBindAddress is the interface the plaintext HTTP
+	// listener claims when BIND_ADDRESS is unset.
+	//
+	// Loopback, because the listener speaks cleartext and serves
+	// both the admin UI and the unauthenticated receiver: a
+	// wildcard default publishes them on every interface of every
+	// host that never configured anything, which is the failure
+	// this default exists to prevent. Reaching webhooker from off
+	// the host is then a deliberate act — a reverse proxy in front
+	// of it, or an explicit BIND_ADDRESS.
+	//
+	// This is the binary's default only. The Dockerfile ships
+	// ENV BIND_ADDRESS=0.0.0.0, so a container deployment needs
+	// nothing set and is unaffected by this constant. The two
+	// differ because they answer different questions: a container's
+	// network namespace is already the boundary this default is
+	// reaching for, so binding every address inside it exposes
+	// nothing, and what decides exposure there is the publish flag
+	// (-p 127.0.0.1:8080:8080). A loopback bind inside a container
+	// buys no security and makes the process unreachable through
+	// its own published port.
+	//
+	// The split is expressed as two explicit defaults rather than
+	// container auto-detection, because a heuristic that guesses
+	// wrong opens the cleartext port exactly where nobody is
+	// looking.
+	defaultBindAddress = "127.0.0.1"
+
 	// defaultRetentionSweepInterval is how often the retention
 	// reaper deletes events older than each webhook's RetentionDays.
 	defaultRetentionSweepInterval = time.Hour
@@ -56,6 +83,12 @@ const (
 	// IPv6 prefix spends on the ::ffff:0:0/96 wrapper, so a /104
 	// covers the same addresses as an IPv4 /8.
 	mappedV4Offset = 96
+
+	// DotEnvPath is the optional file of KEY=value lines read into the
+	// environment at startup, relative to the process working
+	// directory. Exported so that documentation and tests name the
+	// same path the loader opens.
+	DotEnvPath = ".env"
 )
 
 // ErrInvalidEnvironment is returned when WEBHOOKER_ENVIRONMENT
@@ -75,6 +108,19 @@ var ErrInvalidPort = errors.New("invalid port")
 // nor a bare IP address.
 var ErrInvalidCIDR = errors.New("invalid CIDR")
 
+// ErrInvalidBindAddress is returned when BIND_ADDRESS is set to
+// something that is not an IP address literal.
+var ErrInvalidBindAddress = errors.New("invalid bind address")
+
+// ErrInvalidSentryDSN is returned when SENTRY_DSN is set to something
+// the Sentry SDK cannot parse as a DSN.
+var ErrInvalidSentryDSN = errors.New("invalid Sentry DSN")
+
+// ErrDotEnvUnreadable is returned when the optional .env file exists
+// but cannot be read or parsed. A file that is not there is not an
+// error; a file that is there and broken is.
+var ErrDotEnvUnreadable = errors.New("unreadable .env file")
+
 // ErrIncompleteMetricsAuth is returned when exactly one of
 // METRICS_USERNAME and METRICS_PASSWORD carries a value. Neither
 // fallback is acceptable: serving /metrics on the username alone
@@ -105,6 +151,13 @@ type Config struct {
 	Port            int
 	SentryDSN       string
 
+	// BindAddress is the IP address the plaintext HTTP listener
+	// binds, as an address literal. It defaults to
+	// defaultBindAddress and is never empty: an empty string would
+	// mean the wildcard to net.Listen, which is the opposite of the
+	// default this ships.
+	BindAddress string
+
 	// RetentionSweepInterval is how often the retention reaper runs.
 	// Always positive: it becomes a time.NewTicker period.
 	RetentionSweepInterval time.Duration
@@ -173,12 +226,62 @@ func (c *Config) MetricsAuthEnabled() bool {
 	return c.MetricsUsername != "" && c.MetricsPassword != ""
 }
 
+// SentryEnabled reports whether error reporting is shipped to Sentry.
+// It is the only answer to that question in the codebase: the SDK
+// initialisation, the sentryhttp middleware registration and the
+// startup log's sentryEnabled field all read this one method, so the
+// log cannot report reporting as on while nothing is sending.
+//
+// A non-empty DSN is enough because loadFromEnv already parsed it with
+// the SDK's own parser and refused to build a Config around one the
+// SDK would reject, and because initialising the SDK with a DSN that
+// parsed and failed anyway aborts the process rather than leaving this
+// true and the client absent.
+func (c *Config) SentryEnabled() bool {
+	return c.SentryDSN != ""
+}
+
 // envString returns the value of the named environment variable,
 // or an empty string if not set.
 func envString(key string) string {
 	return os.Getenv(key)
 }
 
+// LoadDotEnv reads DotEnvPath into the environment when that file is
+// present, and reports a file that is present but broken.
+//
+// It has to run before anything reads the environment, so that every
+// reader agrees on what the environment holds — the DATA_DIR lock
+// taken before the fx graph exists as much as loadFromEnv itself. A
+// variable already set in the real environment wins: godotenv never
+// overwrites one.
+//
+// A missing file is not an error. It is a development convenience and
+// most deployments set the environment directly.
+//
+// Any other failure is. godotenv parses the whole file before setting
+// anything, so a single malformed line applies none of it: every
+// variable in the file silently reverts to its default, which defeats
+// the fail-loud guarantee for all of them at once.
+func LoadDotEnv() error {
+	return loadDotEnvFile(DotEnvPath)
+}
+
+// loadDotEnvFile is LoadDotEnv over a named file, so tests can point
+// at a temporary one instead of the process working directory.
+func loadDotEnvFile(path string) error {
+	err := godotenv.Load(path)
+	if err == nil || errors.Is(err, fs.ErrNotExist) {
+		return nil
+	}
+
+	return fmt.Errorf(
+		"%w: %s: %w; nothing in it was applied, so fix the file or "+
+			"remove it",
+		ErrDotEnvUnreadable, path, err,
+	)
+}
+
 // DataDir resolves DATA_DIR, applying DefaultDataDir when it is unset
 // or empty. It is exported so that entry points which must act on the
 // data directory before the fx graph exists — taking the exclusive
@@ -387,6 +490,77 @@ func envPrefixList(key string) ([]netip.Prefix, error) {
 	return prefixes, nil
 }
 
+// envBindAddress returns the value of the named environment variable
+// parsed as an IP address literal. An unset (or empty, or
+// whitespace-only) value yields defaultValue.
+//
+// Only literals are accepted: no hostname is resolved, so `localhost`
+// is an error rather than a DNS lookup at startup whose answer could
+// be either loopback family, could change under the process, and
+// could return several addresses of which only one would be bound. A
+// value with a port in it (`127.0.0.1:8080`) is likewise an error —
+// the port is PORT's business, and silently accepting it would bind
+// something other than what was asked for.
+//
+// A set value that is not a literal is a hard error naming the key
+// and the bad value, so startup fails loudly rather than falling back
+// to a default the operator plainly did not want. A literal that is
+// not an address of this host parses here and fails at listen time
+// instead, which ends the process non-zero.
+func envBindAddress(key, defaultValue string) (string, error) {
+	v := strings.TrimSpace(os.Getenv(key))
+	if v == "" {
+		return defaultValue, nil
+	}
+
+	addr, err := netip.ParseAddr(v)
+	if err != nil {
+		return "", fmt.Errorf(
+			"%w: %s: %q must be an IP address literal such as "+
+				"127.0.0.1, 0.0.0.0 or ::, not a hostname and not "+
+				"host:port: %w",
+			ErrInvalidBindAddress, key, v, err,
+		)
+	}
+
+	return addr.String(), nil
+}
+
+// envSentryDSN returns the value of the named environment variable
+// checked as a Sentry DSN. An unset (or empty, or whitespace-only)
+// value yields "", which means error reporting stays off — the common
+// case, and a normal start.
+//
+// A set value is parsed with sentry.NewDsn, which is the call
+// sentry.Init makes on the DSN it is handed, so what passes here is
+// exactly what the SDK will accept later and the two cannot disagree.
+// Reproducing the check by hand instead would cost this package its
+// dependency on the SDK — already a module dependency, already linked
+// into the binary — in exchange for a second definition of "valid DSN"
+// free to drift from the one that decides.
+//
+// A set value that does not parse is a hard error naming the key, so
+// startup fails loudly. Losing error reporting is the failure this
+// variable exists to prevent, and a typo in a DSN is silent forever:
+// nothing later in the process can notice that reports are going
+// nowhere. The bad value is quoted because it is a URL to a public
+// endpoint carrying a public key, not a secret.
+func envSentryDSN(key string) (string, error) {
+	v := strings.TrimSpace(os.Getenv(key))
+	if v == "" {
+		return "", nil
+	}
+
+	_, err := sentry.NewDsn(v)
+	if err != nil {
+		return "", fmt.Errorf(
+			"%w: %s: %q: %w", ErrInvalidSentryDSN, key, v, err,
+		)
+	}
+
+	return v, nil
+}
+
 // resolveMetricsAuth reads the /metrics basic-auth credentials and
 // rejects a half-set pair, naming both variables either way. The
 // error carries neither value: the password is a secret.
@@ -431,6 +605,27 @@ func resolveEnvironment() (string, error) {
 	return environment, nil
 }
 
+// resolveListener reads the two variables that describe the HTTP
+// listener: which port it claims and which address it claims it on.
+// They are read together because neither is meaningful alone, and
+// because a validation failure in either has to abort startup before
+// anything binds.
+func resolveListener() (int, string, error) {
+	port, err := envPort("PORT", defaultPort)
+	if err != nil {
+		return 0, "", err
+	}
+
+	bindAddress, err := envBindAddress(
+		"BIND_ADDRESS", defaultBindAddress,
+	)
+	if err != nil {
+		return 0, "", err
+	}
+
+	return port, bindAddress, nil
+}
+
 // loadFromEnv builds a Config from the environment. Every value that
 // needs parsing fails loudly when it is set but unparseable: the
 // documented defaults apply only to variables that are unset (or
@@ -442,7 +637,7 @@ func loadFromEnv() (*Config, error) {
 		return nil, err
 	}
 
-	port, err := envPort("PORT", defaultPort)
+	port, bindAddress, err := resolveListener()
 	if err != nil {
 		return nil, err
 	}
@@ -498,6 +693,11 @@ func loadFromEnv() (*Config, error) {
 		return nil, err
 	}
 
+	sentryDSN, err := envSentryDSN("SENTRY_DSN")
+	if err != nil {
+		return nil, err
+	}
+
 	return &Config{
 		DataDir:                DataDir(),
 		Debug:                  debug,
@@ -506,7 +706,8 @@ func loadFromEnv() (*Config, error) {
 		MetricsUsername:        metricsUsername,
 		MetricsPassword:        metricsPassword,
 		Port:                   port,
-		SentryDSN:              envString("SENTRY_DSN"),
+		BindAddress:            bindAddress,
+		SentryDSN:              sentryDSN,
 		RetentionSweepInterval: retentionSweepInterval,
 		SessionIdleTimeout:     sessionIdleTimeout,
 		ReceiverRateLimit:      receiverRateLimit,
@@ -625,6 +826,11 @@ func New(lc fx.Lifecycle, params ConfigParams) (*Config, error) {
 	log.Info("Configuration loaded",
 		"environment", s.Environment,
 		"port", s.Port,
+		// Logged because which interfaces the cleartext listener
+		// answers on is not otherwise observable from inside a
+		// container, and it decides whether anything but the local
+		// host can reach the admin UI.
+		"bindAddress", s.BindAddress,
 		"debug", s.Debug,
 		"maintenanceMode", s.MaintenanceMode,
 		"dataDir", s.DataDir,
@@ -636,7 +842,7 @@ func New(lc fx.Lifecycle, params ConfigParams) (*Config, error) {
 		"receiverRateLimit", s.ReceiverRateLimit,
 		"trustedProxies", len(s.TrustedProxies),
 		"allowedEgressCIDRs", len(s.AllowedEgressCIDRs),
-		"hasSentryDSN", s.SentryDSN != "",
+		"sentryEnabled", s.SentryEnabled(),
 		"hasMetricsAuth", s.MetricsAuthEnabled(),
 	)
 

internal/config/dotenv_test.go

@@ -0,0 +1,158 @@
+package config_test
+
+import (
+	"os"
+	"path/filepath"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	"sneak.berlin/go/webhooker/internal/config"
+)
+
+// dotEnvKey is a throwaway variable name the .env tests write and
+// read, so they cannot disturb real configuration.
+const dotEnvKey = "WEBHOOKER_TEST_DOTENV_VALUE"
+
+// malformedDotEnv is a file godotenv cannot parse. The first line is
+// the realistic typo — a space where the `=` belongs — and the rest
+// make sure nothing downstream treats the file as salvageable line by
+// line.
+const malformedDotEnv = "PORT 19615\n" +
+	"this is not = valid ! syntax\n" +
+	"\"unclosed\n"
+
+// unsetDotEnvKey makes dotEnvKey genuinely absent for the duration of
+// the test and restores it afterwards. t.Setenv registers the restore;
+// the Unsetenv that follows is what the test actually needs, because a
+// variable set to the empty string is still present in os.Environ and
+// godotenv would refuse to overwrite it.
+func unsetDotEnvKey(t *testing.T) {
+	t.Helper()
+	t.Setenv(dotEnvKey, "placeholder")
+	require.NoError(t, os.Unsetenv(dotEnvKey))
+}
+
+// writeDotEnv writes contents to a .env file in a fresh temporary
+// directory and returns its path.
+func writeDotEnv(t *testing.T, contents string) string {
+	t.Helper()
+
+	path := filepath.Join(t.TempDir(), config.DotEnvPath)
+	require.NoError(t, os.WriteFile(path, []byte(contents), 0o600))
+
+	return path
+}
+
+// TestLoadDotEnv_MissingFileIsFine pins the case most deployments are
+// in. The file is optional: it is a development convenience, and a
+// deployment that configures the environment directly must start
+// normally rather than be refused for a file it was never meant to
+// have.
+//
+//nolint:paralleltest // unsetDotEnvKey uses t.Setenv.
+func TestLoadDotEnv_MissingFileIsFine(t *testing.T) {
+	unsetDotEnvKey(t)
+
+	absent := filepath.Join(t.TempDir(), config.DotEnvPath)
+	require.NoError(t, config.LoadDotEnvFileForTest(absent))
+
+	_, present := os.LookupEnv(dotEnvKey)
+	assert.False(t, present, "nothing may be set from an absent file")
+}
+
+// TestLoadDotEnv_AppliesValues pins that a well-formed file still
+// reaches the environment, which is the whole reason the file is read
+// at all.
+//
+//nolint:paralleltest // unsetDotEnvKey uses t.Setenv.
+func TestLoadDotEnv_AppliesValues(t *testing.T) {
+	unsetDotEnvKey(t)
+
+	path := writeDotEnv(t, "# a comment\n"+dotEnvKey+"=from-dot-env\n")
+
+	require.NoError(t, config.LoadDotEnvFileForTest(path))
+	assert.Equal(t, "from-dot-env", os.Getenv(dotEnvKey))
+}
+
+// TestLoadDotEnv_RealEnvironmentWins pins that the file cannot
+// override a variable the process was actually started with. A
+// deployment that sets DATA_DIR in its unit file must not have it
+// silently replaced by a stale .env left in the working directory.
+func TestLoadDotEnv_RealEnvironmentWins(t *testing.T) {
+	t.Setenv(dotEnvKey, "from-environment")
+
+	path := writeDotEnv(t, dotEnvKey+"=from-dot-env\n")
+
+	require.NoError(t, config.LoadDotEnvFileForTest(path))
+	assert.Equal(t, "from-environment", os.Getenv(dotEnvKey))
+}
+
+// TestLoadDotEnv_MalformedFileAborts is the defect this fixes. One bad
+// line makes godotenv apply none of the file, so every variable in it
+// reverts to its default; the process used to start that way with no
+// log line naming the file at all.
+//
+//nolint:paralleltest // unsetDotEnvKey uses t.Setenv.
+func TestLoadDotEnv_MalformedFileAborts(t *testing.T) {
+	unsetDotEnvKey(t)
+
+	path := writeDotEnv(
+		t, malformedDotEnv+dotEnvKey+"=from-dot-env\n",
+	)
+
+	err := config.LoadDotEnvFileForTest(path)
+
+	require.Error(t, err)
+	require.ErrorIs(t, err, config.ErrDotEnvUnreadable)
+	assert.Contains(
+		t, err.Error(), config.DotEnvPath,
+		"the failure must name the file it could not read",
+	)
+
+	_, present := os.LookupEnv(dotEnvKey)
+	assert.False(
+		t, present,
+		"a rejected file must apply nothing, not part of itself",
+	)
+}
+
+// TestLoadDotEnv_UnreadableFileAborts pins that only absence is
+// tolerated. A .env that exists but cannot be read is a file the
+// operator meant to be applied, so it fails like a malformed one
+// rather than being treated as though it were not there.
+func TestLoadDotEnv_UnreadableFileAborts(t *testing.T) {
+	t.Parallel()
+
+	// A directory in the file's place: open succeeds and the read
+	// fails, which no umask or root-ness can turn back into success
+	// the way a chmod could.
+	path := filepath.Join(t.TempDir(), config.DotEnvPath)
+	require.NoError(t, os.Mkdir(path, 0o750))
+
+	err := config.LoadDotEnvFileForTest(path)
+
+	require.Error(t, err)
+	require.ErrorIs(t, err, config.ErrDotEnvUnreadable)
+}
+
+// TestLoadDotEnv_ReadsTheWorkingDirectory pins the path LoadDotEnv
+// itself opens, which the tests above bypass. It is relative to the
+// process working directory, as it was under godotenv/autoload and as
+// the README documents.
+//
+//nolint:paralleltest // t.Chdir moves the whole process.
+func TestLoadDotEnv_ReadsTheWorkingDirectory(t *testing.T) {
+	unsetDotEnvKey(t)
+
+	dir := t.TempDir()
+	require.NoError(t, os.WriteFile(
+		filepath.Join(dir, config.DotEnvPath),
+		[]byte(dotEnvKey+"=from-working-directory\n"),
+		0o600,
+	))
+	t.Chdir(dir)
+
+	require.NoError(t, config.LoadDotEnv())
+	assert.Equal(t, "from-working-directory", os.Getenv(dotEnvKey))
+}

internal/config/env_test.go

@@ -21,6 +21,22 @@ const (
 	envKeyPort            = "PORT"
 	envKeyDebug           = "DEBUG"
 	envKeyMaintenanceMode = "MAINTENANCE_MODE"
+	envKeyBindAddress     = "BIND_ADDRESS"
+)
+
+// Sample BIND_ADDRESS values used by the tables below.
+const (
+	// bindAddressDefault is the shipped default. It is asserted
+	// against the package's own constant in
+	// TestNewUsesDefaultsWhenUnset, so the two cannot drift.
+	bindAddressDefault = "127.0.0.1"
+
+	// bindAddressWildcard is the value a container deployment sets.
+	bindAddressWildcard = "0.0.0.0"
+
+	// bindAddressSample is an arbitrary specific address, standing
+	// for "one interface of several".
+	bindAddressSample = "10.1.2.3"
 )
 
 // envBoolCase is one row of the envBool table.
@@ -291,6 +307,160 @@ func TestEnvPort(t *testing.T) {
 	}
 }
 
+// TestEnvBindAddress covers BIND_ADDRESS parsing.
+//
+// Only IP address literals are accepted. Every rejection below is a
+// value an operator plausibly writes — a hostname, a host:port, a
+// CIDR block — and each has to abort startup rather than fall back to
+// the default, because falling back would bind an address other than
+// the one asked for and, in the wildcard-default case this setting
+// exists to end, publish cleartext on every interface.
+func TestEnvBindAddress(t *testing.T) {
+	for _, tt := range envBindAddressCases() {
+		t.Run(tt.name, func(t *testing.T) {
+			// Cannot use t.Parallel() here because t.Setenv
+			// is incompatible with parallel subtests.
+			if tt.set {
+				t.Setenv(testEnvKey, tt.value)
+			} else {
+				require.NoError(t, os.Unsetenv(testEnvKey))
+			}
+
+			got, err := config.EnvBindAddressForTest(
+				testEnvKey, bindAddressDefault,
+			)
+
+			if tt.expectError {
+				require.Error(t, err)
+				require.ErrorIs(t, err, config.ErrInvalidBindAddress)
+				assert.Contains(t, err.Error(), testEnvKey)
+				assert.Contains(t, err.Error(), tt.value)
+
+				return
+			}
+
+			require.NoError(t, err)
+			assert.Equal(t, tt.expected, got)
+		})
+	}
+}
+
+// envBindAddressCase is one row of the envBindAddress table.
+type envBindAddressCase struct {
+	name        string
+	set         bool
+	value       string
+	expectError bool
+	expected    string
+}
+
+// envBindAddressCases is the envBindAddress table, kept out of the
+// test body so the test itself stays readable.
+func envBindAddressCases() []envBindAddressCase {
+	return append(
+		envBindAddressAcceptedCases(),
+		envBindAddressRejectedCases()...,
+	)
+}
+
+// envBindAddressAcceptedCases are the values that parse: the three
+// spellings of "unset" that take the default, and the literals.
+func envBindAddressAcceptedCases() []envBindAddressCase {
+	return []envBindAddressCase{
+		{
+			name:     "unset returns the default",
+			expected: bindAddressDefault,
+		},
+		{
+			name:     "empty returns the default",
+			set:      true,
+			value:    "",
+			expected: bindAddressDefault,
+		},
+		{
+			name:     "whitespace returns the default",
+			set:      true,
+			value:    "   ",
+			expected: bindAddressDefault,
+		},
+		{
+			name:     "ipv4 wildcard is parsed",
+			set:      true,
+			value:    bindAddressWildcard,
+			expected: bindAddressWildcard,
+		},
+		{
+			name:     "ipv4 literal is parsed",
+			set:      true,
+			value:    bindAddressSample,
+			expected: bindAddressSample,
+		},
+		{
+			name:     "surrounding whitespace is trimmed",
+			set:      true,
+			value:    "  " + bindAddressSample + "  ",
+			expected: bindAddressSample,
+		},
+		{
+			name:     "ipv6 wildcard is parsed",
+			set:      true,
+			value:    "::",
+			expected: "::",
+		},
+		{
+			name:     "ipv6 literal is parsed",
+			set:      true,
+			value:    "2001:db8::5",
+			expected: "2001:db8::5",
+		},
+	}
+}
+
+// envBindAddressRejectedCases are the values that abort startup.
+// Each is something an operator plausibly writes, and none may fall
+// back to the default: the default is loopback, so a silent fallback
+// would bind somewhere other than what was asked for.
+func envBindAddressRejectedCases() []envBindAddressCase {
+	return []envBindAddressCase{
+		{
+			name:        "garbage is rejected",
+			set:         true,
+			value:       "not-an-address",
+			expectError: true,
+		},
+		{
+			name:        "hostname is rejected",
+			set:         true,
+			value:       "localhost",
+			expectError: true,
+		},
+		{
+			name:        "unresolvable hostname is rejected",
+			set:         true,
+			value:       "no-such-host.invalid",
+			expectError: true,
+		},
+		{
+			name:        "host and port is rejected",
+			set:         true,
+			value:       bindAddressDefault + ":8080",
+			expectError: true,
+		},
+		{
+			name:        "bracketed ipv6 is rejected",
+			set:         true,
+			value:       "[::1]",
+			expectError: true,
+		},
+		{
+			name:        "CIDR block is rejected",
+			set:         true,
+			value:       "10.0.0.0/8",
+			expectError: true,
+		},
+	}
+}
+
 // buildConfig constructs a Config through fx exactly as the
 // application does, returning the config and any construction error.
 func buildConfig(t *testing.T) (*config.Config, error) {
@@ -312,58 +482,7 @@ func buildConfig(t *testing.T) (*config.Config, error) {
 }
 
 func TestNewRejectsBadEnvValues(t *testing.T) {
-	tests := []struct {
-		name        string
-		key         string
-		value       string
-		expectError bool
-		check       func(t *testing.T, cfg *config.Config)
-	}{
-		{
-			name:  "valid PORT is used",
-			key:   envKeyPort,
-			value: "9001",
-			check: func(t *testing.T, cfg *config.Config) {
-				t.Helper()
-				assert.Equal(t, 9001, cfg.Port)
-			},
-		},
-		{
-			name:        "unparseable PORT aborts startup",
-			key:         envKeyPort,
-			value:       "eighty-eighty",
-			expectError: true,
-		},
-		{
-			name:        "out-of-range PORT aborts startup",
-			key:         envKeyPort,
-			value:       "70000",
-			expectError: true,
-		},
-		{
-			name:  "valid DEBUG is used",
-			key:   envKeyDebug,
-			value: "true",
-			check: func(t *testing.T, cfg *config.Config) {
-				t.Helper()
-				assert.True(t, cfg.Debug)
-			},
-		},
-		{
-			name:        "unparseable DEBUG aborts startup",
-			key:         envKeyDebug,
-			value:       "ture",
-			expectError: true,
-		},
-		{
-			name:        "unparseable MAINTENANCE_MODE aborts startup",
-			key:         envKeyMaintenanceMode,
-			value:       "sometimes",
-			expectError: true,
-		},
-	}
-
-	for _, tt := range tests {
+	for _, tt := range badEnvValueCases() {
 		t.Run(tt.name, func(t *testing.T) {
 			// Cannot use t.Parallel() here because t.Setenv
 			// is incompatible with parallel subtests.
@@ -387,6 +506,149 @@ func TestNewRejectsBadEnvValues(t *testing.T) {
 	}
 }
 
+// badEnvValueCase is one row of the config.New table: a variable, the
+// value it is set to, and either the assertion that startup fails
+// naming both, or a check on the Config that resulted.
+type badEnvValueCase struct {
+	name        string
+	key         string
+	value       string
+	expectError bool
+	check       func(t *testing.T, cfg *config.Config)
+}
+
+// badEnvValueCases is the config.New table, kept out of the test body
+// so the test itself stays readable. It is assembled from per-variable
+// groups because one literal covering every variable outgrew the
+// function-length budget.
+func badEnvValueCases() []badEnvValueCase {
+	cases := listenerEnvValueCases()
+	cases = append(cases, flagEnvValueCases()...)
+	cases = append(cases, sentryEnvValueCases()...)
+
+	return cases
+}
+
+// listenerEnvValueCases covers the two variables that describe the
+// HTTP listener.
+func listenerEnvValueCases() []badEnvValueCase {
+	return []badEnvValueCase{
+		{
+			name:  "valid PORT is used",
+			key:   envKeyPort,
+			value: "9001",
+			check: func(t *testing.T, cfg *config.Config) {
+				t.Helper()
+				assert.Equal(t, 9001, cfg.Port)
+			},
+		},
+		{
+			name:        "unparseable PORT aborts startup",
+			key:         envKeyPort,
+			value:       "eighty-eighty",
+			expectError: true,
+		},
+		{
+			name:        "out-of-range PORT aborts startup",
+			key:         envKeyPort,
+			value:       "70000",
+			expectError: true,
+		},
+		{
+			name:  "valid BIND_ADDRESS is used",
+			key:   envKeyBindAddress,
+			value: bindAddressWildcard,
+			check: func(t *testing.T, cfg *config.Config) {
+				t.Helper()
+				assert.Equal(
+					t, bindAddressWildcard, cfg.BindAddress,
+				)
+			},
+		},
+		{
+			name:        "unparseable BIND_ADDRESS aborts startup",
+			key:         envKeyBindAddress,
+			value:       "not-an-address",
+			expectError: true,
+		},
+		{
+			name:        "hostname BIND_ADDRESS aborts startup",
+			key:         envKeyBindAddress,
+			value:       "localhost",
+			expectError: true,
+		},
+		{
+			name:        "BIND_ADDRESS with a port aborts startup",
+			key:         envKeyBindAddress,
+			value:       bindAddressDefault + ":8080",
+			expectError: true,
+		},
+	}
+}
+
+// flagEnvValueCases covers the boolean variables.
+func flagEnvValueCases() []badEnvValueCase {
+	return []badEnvValueCase{
+		{
+			name:  "valid DEBUG is used",
+			key:   envKeyDebug,
+			value: "true",
+			check: func(t *testing.T, cfg *config.Config) {
+				t.Helper()
+				assert.True(t, cfg.Debug)
+			},
+		},
+		{
+			name:        "unparseable DEBUG aborts startup",
+			key:         envKeyDebug,
+			value:       "ture",
+			expectError: true,
+		},
+		{
+			name:        "unparseable MAINTENANCE_MODE aborts startup",
+			key:         envKeyMaintenanceMode,
+			value:       "sometimes",
+			expectError: true,
+		},
+	}
+}
+
+// sentryEnvValueCases covers SENTRY_DSN. The three rejected values are
+// the ones measured on the defect: each initialised the SDK with an
+// error and left the process serving with error reporting off.
+func sentryEnvValueCases() []badEnvValueCase {
+	return []badEnvValueCase{
+		{
+			name:  "valid SENTRY_DSN is used",
+			key:   envKeySentryDSN,
+			value: validSentryDSN,
+			check: func(t *testing.T, cfg *config.Config) {
+				t.Helper()
+				assert.Equal(t, validSentryDSN, cfg.SentryDSN)
+				assert.True(t, cfg.SentryEnabled())
+			},
+		},
+		{
+			name:        "unparseable SENTRY_DSN aborts startup",
+			key:         envKeySentryDSN,
+			value:       "not-a-dsn",
+			expectError: true,
+		},
+		{
+			name:        "SENTRY_DSN that is not a URL aborts startup",
+			key:         envKeySentryDSN,
+			value:       "%%%",
+			expectError: true,
+		},
+		{
+			name:        "keyless SENTRY_DSN aborts startup",
+			key:         envKeySentryDSN,
+			value:       "https://example.invalid/1",
+			expectError: true,
+		},
+	}
+}
+
 // TestNewUsesDefaultsWhenUnset proves the fail-loud behaviour did not
 // break the legitimate unset case: absent variables still get their
 // documented defaults.
@@ -395,6 +657,7 @@ func TestNewUsesDefaultsWhenUnset(t *testing.T) {
 
 	for _, key := range []string{
 		envKeyPort, envKeyDebug, envKeyMaintenanceMode,
+		envKeyBindAddress, envKeySentryDSN,
 	} {
 		require.NoError(t, os.Unsetenv(key))
 	}
@@ -406,4 +669,20 @@ func TestNewUsesDefaultsWhenUnset(t *testing.T) {
 	assert.Equal(t, 8080, cfg.Port)
 	assert.False(t, cfg.Debug)
 	assert.False(t, cfg.MaintenanceMode)
+
+	// Loopback, not the wildcard: the default must not publish the
+	// cleartext admin UI and the unauthenticated receiver on every
+	// interface of a host that configured nothing. The value is read
+	// from the package rather than repeated, so the README's
+	// documented default and the compiled-in one are pinned to the
+	// same constant.
+	assert.Equal(
+		t, config.DefaultBindAddressForTest, cfg.BindAddress,
+	)
+	assert.Equal(t, bindAddressDefault, cfg.BindAddress)
+
+	// An absent SENTRY_DSN is the common case and must stay a normal
+	// start with error reporting off, not a refusal.
+	assert.Empty(t, cfg.SentryDSN)
+	assert.False(t, cfg.SentryEnabled())
 }

internal/config/export_test.go

@@ -50,3 +50,25 @@ func EnvPositiveIntForTest(key string, defaultValue int) (int, error) {
 func EnvPortForTest(key string, defaultValue int) (int, error) {
 	return envPort(key, defaultValue)
 }
+
+// EnvSentryDSNForTest exposes envSentryDSN.
+func EnvSentryDSNForTest(key string) (string, error) {
+	return envSentryDSN(key)
+}
+
+// LoadDotEnvFileForTest exposes the loader LoadDotEnv runs, over a
+// caller-named file rather than the process working directory, so
+// each .env state can be covered without moving the test process.
+func LoadDotEnvFileForTest(path string) error {
+	return loadDotEnvFile(path)
+}
+
+// EnvBindAddressForTest exposes envBindAddress.
+func EnvBindAddressForTest(key, defaultValue string) (string, error) {
+	return envBindAddress(key, defaultValue)
+}
+
+// DefaultBindAddressForTest exposes the compiled-in BIND_ADDRESS
+// default, so a test pins the documented value rather than repeating
+// a literal that could drift from it.
+const DefaultBindAddressForTest = defaultBindAddress

internal/config/sentry_test.go

@@ -0,0 +1,141 @@
+package config_test
+
+import (
+	"os"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	"sneak.berlin/go/webhooker/internal/config"
+)
+
+// envKeySentryDSN is the variable envSentryDSN reads in production.
+const envKeySentryDSN = "SENTRY_DSN"
+
+// validSentryDSN is a syntactically complete DSN. The host is under
+// .invalid (RFC 2606), so nothing a test builds around it can reach a
+// real Sentry installation.
+const validSentryDSN = "https://abc123@sentry.invalid/42"
+
+// envSentryDSNCase is one row of the envSentryDSN table.
+type envSentryDSNCase struct {
+	name        string
+	set         bool
+	value       string
+	expectError bool
+	expected    string
+}
+
+// envSentryDSNCases is the envSentryDSN table. The three invalid
+// values are the ones measured on the defect: each initialised the SDK
+// with an error and left the process serving with reporting off.
+func envSentryDSNCases() []envSentryDSNCase {
+	return []envSentryDSNCase{
+		{
+			name:     "unset means reporting off",
+			expected: "",
+		},
+		{
+			name:     "empty means reporting off",
+			set:      true,
+			value:    "",
+			expected: "",
+		},
+		{
+			name:     "whitespace means reporting off",
+			set:      true,
+			value:    "   ",
+			expected: "",
+		},
+		{
+			name:     "a valid DSN is kept",
+			set:      true,
+			value:    validSentryDSN,
+			expected: validSentryDSN,
+		},
+		{
+			name:     "surrounding whitespace is trimmed",
+			set:      true,
+			value:    "  " + validSentryDSN + "\t",
+			expected: validSentryDSN,
+		},
+		{
+			name:        "a value that is not a URL is rejected",
+			set:         true,
+			value:       "not-a-dsn",
+			expectError: true,
+		},
+		{
+			name:        "an unparseable URL is rejected",
+			set:         true,
+			value:       "%%%",
+			expectError: true,
+		},
+		{
+			name:        "a DSN without a public key is rejected",
+			set:         true,
+			value:       "https://example.invalid/1",
+			expectError: true,
+		},
+		{
+			name:        "a DSN without a project id is rejected",
+			set:         true,
+			value:       "https://abc123@sentry.invalid/",
+			expectError: true,
+		},
+		{
+			name:        "a non-HTTP scheme is rejected",
+			set:         true,
+			value:       "ftp://abc123@sentry.invalid/42",
+			expectError: true,
+		},
+	}
+}
+
+// TestEnvSentryDSN covers the helper directly. What it pins beyond the
+// value is the failure shape: a set-but-unparseable DSN names the
+// variable and the value, exactly as the other fail-loud helpers do,
+// so an operator reads the fix off the message.
+func TestEnvSentryDSN(t *testing.T) {
+	for _, tt := range envSentryDSNCases() {
+		t.Run(tt.name, func(t *testing.T) {
+			// Cannot use t.Parallel() here because t.Setenv
+			// is incompatible with parallel subtests.
+			if tt.set {
+				t.Setenv(envKeySentryDSN, tt.value)
+			} else {
+				require.NoError(t, os.Unsetenv(envKeySentryDSN))
+			}
+
+			got, err := config.EnvSentryDSNForTest(envKeySentryDSN)
+
+			if tt.expectError {
+				require.Error(t, err)
+				require.ErrorIs(t, err, config.ErrInvalidSentryDSN)
+				assert.Contains(t, err.Error(), envKeySentryDSN)
+				assert.Contains(t, err.Error(), tt.value)
+				assert.Empty(t, got)
+
+				return
+			}
+
+			require.NoError(t, err)
+			assert.Equal(t, tt.expected, got)
+		})
+	}
+}
+
+// TestSentryEnabled_TracksTheDSN pins that the one method answering
+// "is anything being reported" agrees with the DSN in every state. The
+// startup log, the SDK initialisation and the sentryhttp middleware
+// all read it, so a log field cannot report reporting as on while
+// nothing is sending.
+func TestSentryEnabled_TracksTheDSN(t *testing.T) {
+	t.Parallel()
+
+	assert.False(t, (&config.Config{}).SentryEnabled())
+	assert.True(
+		t,
+		(&config.Config{SentryDSN: validSentryDSN}).SentryEnabled(),
+	)
+}

internal/database/database.go

@@ -4,7 +4,6 @@ package database
 import (
 	"context"
 	"crypto/rand"
-	"database/sql"
 	"encoding/base64"
 	"errors"
 	"fmt"
@@ -16,7 +15,6 @@ import (
 	"go.uber.org/fx"
 	"gorm.io/driver/sqlite"
 	"gorm.io/gorm"
-	_ "modernc.org/sqlite" // Pure Go SQLite driver
 	"sneak.berlin/go/webhooker/internal/banner"
 	"sneak.berlin/go/webhooker/internal/config"
 	"sneak.berlin/go/webhooker/internal/gormlog"
@@ -198,13 +196,11 @@ func (d *Database) connectTo(dataDir string) error {
 
 	// Construct the main application database path inside DATA_DIR.
 	dbPath := filepath.Join(dataDir, MainDBFileName)
-	dbURL := fmt.Sprintf(
-		"file:%s?cache=shared&mode=rwc",
-		dbPath,
-	)
 
-	// Open the database with the pure Go SQLite driver
-	sqlDB, err := sql.Open("sqlite", dbURL)
+	// Opened through OpenSQLite so this handle carries the same WAL
+	// journaling, busy timeout, immediate-transaction locking, and pool
+	// bounds as every other database file. See sqlite_open.go.
+	sqlDB, err := OpenSQLite(dbPath, SQLiteModeCreate)
 	if err != nil {
 		d.log.Error(
 			"failed to open database",

internal/database/sqlite_mode_test.go

@@ -0,0 +1,240 @@
+package database_test
+
+import (
+	"context"
+	"io/fs"
+	"net/http"
+	"os"
+	"path/filepath"
+	"testing"
+
+	"github.com/google/uuid"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	"go.uber.org/fx/fxtest"
+	"sneak.berlin/go/webhooker/internal/config"
+	"sneak.berlin/go/webhooker/internal/database"
+	"sneak.berlin/go/webhooker/internal/globals"
+	"sneak.berlin/go/webhooker/internal/logger"
+)
+
+// ownerOnly is the mode every SQLite file the service owns must have.
+// Spelled out rather than referencing database.SQLiteFilePerm so the
+// test fails if the constant itself is loosened.
+const ownerOnly fs.FileMode = 0o600
+
+// requireOwnerOnly asserts that path exists and is readable and
+// writable by its owner and by nobody else.
+func requireOwnerOnly(t *testing.T, path string) {
+	t.Helper()
+
+	info, err := os.Stat(path)
+	require.NoError(t, err, "%s must exist", path)
+	assert.Equal(
+		t,
+		ownerOnly,
+		info.Mode().Perm(),
+		"%s holds credentials and must not be readable by "+
+			"anyone but its owner",
+		path,
+	)
+}
+
+// requireDatabaseSetOwnerOnly asserts the mode of a database file and
+// of both WAL sidecars. The sidecars carry the same rows as the
+// database, so tightening only the main file fixes nothing.
+func requireDatabaseSetOwnerOnly(t *testing.T, dbPath string) {
+	t.Helper()
+
+	requireOwnerOnly(t, dbPath)
+	requireOwnerOnly(t, dbPath+"-wal")
+	requireOwnerOnly(t, dbPath+"-shm")
+}
+
+// TestMainDatabaseFilesAreOwnerOnly covers the tier the defect was
+// reported against: webhooker.db holds targets.config in plaintext —
+// bearer tokens, API keys, Slack webhook URLs — and the session
+// encryption key.
+func TestMainDatabaseFilesAreOwnerOnly(t *testing.T) {
+	t.Parallel()
+
+	lc := fxtest.NewLifecycle(t)
+
+	l, err := logger.New(lc, logger.LoggerParams{
+		Globals: &globals.Globals{
+			Appname: testAppname,
+			Version: testVersion,
+		},
+	})
+	require.NoError(t, err)
+
+	// A directory the application creates itself, not one t.TempDir
+	// made at 0700, so the mode below is the application's.
+	dataDir := filepath.Join(t.TempDir(), "data")
+
+	db, err := database.New(lc, database.DatabaseParams{
+		Config: &config.Config{DataDir: dataDir},
+		Logger: l,
+	})
+	require.NoError(t, err)
+
+	ctx := context.Background()
+	require.NoError(t, lc.Start(ctx))
+
+	defer func() { require.NoError(t, lc.Stop(ctx)) }()
+
+	// Write through the real model so the WAL is populated and both
+	// sidecars are on disk while the handle is open.
+	require.NoError(t, db.DB().Create(&database.Webhook{
+		Name: testWebhookName,
+	}).Error)
+
+	requireDatabaseSetOwnerOnly(
+		t, filepath.Join(dataDir, database.MainDBFileName),
+	)
+
+	// The data directory grants nothing to `other`. Asserted as a
+	// property rather than as an exact 0750, because MkdirAll applies
+	// the ambient umask: the exact mode is the developer's umask as
+	// much as the application's request, and pinning it would make
+	// `make check` pass or fail on where it is run. The group bits are
+	// deliberately left unasserted — deployments may rely on them.
+	info, err := os.Stat(dataDir)
+	require.NoError(t, err)
+	assert.Zero(
+		t,
+		info.Mode().Perm()&0o007,
+		"the data directory must not be world-accessible",
+	)
+}
+
+// TestPerWebhookEventDatabaseFilesAreOwnerOnly covers the events-*.db
+// tier. These carry no credential canaries since
+// https://git.eeqj.de/sneak/webhooker/issues/206, but they hold every
+// received request body and header.
+func TestPerWebhookEventDatabaseFilesAreOwnerOnly(t *testing.T) {
+	t.Parallel()
+
+	mgr, lc := setupTestWebhookDBManager(t)
+	ctx := context.Background()
+	require.NoError(t, lc.Start(ctx))
+
+	defer func() { require.NoError(t, lc.Stop(ctx)) }()
+
+	webhookID := uuid.New().String()
+
+	db, err := mgr.GetDB(webhookID)
+	require.NoError(t, err)
+
+	require.NoError(t, db.Create(&database.Event{
+		WebhookID:    webhookID,
+		EntrypointID: uuid.New().String(),
+		Method:       http.MethodPost,
+		Body:         "{}",
+	}).Error)
+
+	requireDatabaseSetOwnerOnly(t, mgr.DBPath(webhookID))
+}
+
+// TestArchiveDatabaseFilesAreOwnerOnly covers the archive-*.db tier.
+// internal/delivery builds that path and opens it through OpenSQLite,
+// the same single open path exercised here, so the mode is settled for
+// all three tiers in one place.
+func TestArchiveDatabaseFilesAreOwnerOnly(t *testing.T) {
+	t.Parallel()
+
+	ctx := context.Background()
+	path := filepath.Join(
+		t.TempDir(), "archive-"+uuid.New().String()+".db",
+	)
+
+	sqlDB, err := database.OpenSQLite(path, database.SQLiteModeCreate)
+	require.NoError(t, err)
+
+	defer func() { require.NoError(t, sqlDB.Close()) }()
+
+	_, err = sqlDB.ExecContext(ctx, "create table t (id integer)")
+	require.NoError(t, err)
+
+	requireDatabaseSetOwnerOnly(t, path)
+}
+
+// TestOpenSQLiteTightensFilesLeftWorldReadable is the upgrade case: a
+// data directory an earlier build left at 0644, including a
+// developer's own scratch directory, is fixed when it is opened rather
+// than staying exposed until it is recreated.
+func TestOpenSQLiteTightensFilesLeftWorldReadable(t *testing.T) {
+	t.Parallel()
+
+	dir := t.TempDir()
+	path := filepath.Join(dir, database.MainDBFileName)
+
+	// A database and both sidecars as the pre-fix build left them.
+	for _, p := range []string{path, path + "-wal", path + "-shm"} {
+		require.NoError(t, os.WriteFile(p, nil, 0o644)) //nolint:gosec // the mode under test
+	}
+
+	sqlDB, err := database.OpenSQLite(path, database.SQLiteModeCreate)
+	require.NoError(t, err)
+
+	require.NoError(t, sqlDB.Close())
+
+	requireDatabaseSetOwnerOnly(t, path)
+}
+
+// TestOpenSQLiteExistingModeDoesNotCreateTheFile guards the mechanism
+// the fix uses: OpenSQLite now creates the database file itself, and
+// must not do so for a caller that asked for an existing database. An
+// empty file materialized here would turn a missing-database error
+// into a silently empty one.
+func TestOpenSQLiteExistingModeDoesNotCreateTheFile(t *testing.T) {
+	t.Parallel()
+
+	ctx := context.Background()
+	path := filepath.Join(t.TempDir(), "absent.db")
+
+	sqlDB, err := database.OpenSQLite(path, database.SQLiteModeExisting)
+	if err == nil {
+		// sql.Open is lazy: force the connection that fails.
+		require.Error(t, sqlDB.PingContext(ctx))
+		require.NoError(t, sqlDB.Close())
+	}
+
+	_, statErr := os.Stat(path)
+	assert.ErrorIs(t, statErr, fs.ErrNotExist)
+}
+
+// TestReopenAfterRestartKeepsFilesOwnerOnly is the restart case: a
+// process that closed its files must be able to open them again at
+// 0600, including through a gorm handle, and the sidecars must come
+// back at 0600 too rather than at SQLite's own default.
+func TestReopenAfterRestartKeepsFilesOwnerOnly(t *testing.T) {
+	t.Parallel()
+
+	ctx := context.Background()
+	dir := t.TempDir()
+	path := filepath.Join(dir, database.MainDBFileName)
+
+	first, err := database.OpenSQLite(path, database.SQLiteModeCreate)
+	require.NoError(t, err)
+
+	_, err = first.ExecContext(ctx, "create table t (id integer)")
+	require.NoError(t, err)
+	require.NoError(t, first.Close())
+
+	second, err := database.OpenSQLite(path, database.SQLiteModeCreate)
+	require.NoError(t, err)
+
+	defer func() { require.NoError(t, second.Close()) }()
+
+	_, err = second.ExecContext(ctx, "insert into t (id) values (1)")
+	require.NoError(t, err)
+
+	requireDatabaseSetOwnerOnly(t, path)
+
+	var got int
+
+	require.NoError(t,
+		second.QueryRowContext(ctx, "select id from t").Scan(&got))
+	assert.Equal(t, 1, got)
+}

internal/database/sqlite_open.go

@@ -0,0 +1,252 @@
+package database
+
+import (
+	"database/sql"
+	"errors"
+	"fmt"
+	"io/fs"
+	"net/url"
+	"os"
+	"time"
+
+	_ "modernc.org/sqlite" // Pure Go SQLite driver
+)
+
+// Every SQLite file this service opens — the main database, the
+// per-webhook event databases, and the archive databases — is opened
+// through OpenSQLite, so the durability settings below are properties
+// of the service rather than of one call site.
+//
+// modernc.org/sqlite installs no busy handler and issues no pragmas of
+// its own: it executes only the pragmas named in explicit `_pragma=`
+// DSN parameters, and gorm.io/driver/sqlite adds none when it is
+// handed an existing *sql.DB. Every setting therefore has to be
+// spelled out here or it is simply not in effect.
+// SQLite URI open modes.
+const (
+	// SQLiteModeCreate creates the database file when it is missing.
+	SQLiteModeCreate = "rwc"
+
+	// SQLiteModeExisting requires the file to exist already.
+	SQLiteModeExisting = "rw"
+)
+
+const (
+	// SQLiteBusyTimeout is how long SQLite retries a lock conflict
+	// before returning SQLITE_BUSY.
+	//
+	// Under WAL a reader never blocks a writer, so the only conflict
+	// left is writer against writer: this process's delivery workers
+	// against each other, or against another process holding the write
+	// lock. Those clear in milliseconds. Ten seconds is far above that
+	// and still well inside the receiver's request budget, so an
+	// inbound webhook waits rather than being rejected with a 500.
+	SQLiteBusyTimeout = 10 * time.Second
+
+	// sqliteMaxOpenConns bounds the connection pool for one database
+	// file.
+	//
+	// The pool needs a bound at all because database/sql cannot detect
+	// a connection left mid-transaction: modernc.org/sqlite implements
+	// neither driver.Validator nor driver.SessionResetter, so a
+	// connection whose COMMIT failed is returned to the pool with its
+	// transaction still open and handed out again indefinitely. That is
+	// what turned four `database is locked` errors into 593
+	// `cannot start a transaction within a transaction` in
+	// https://git.eeqj.de/sneak/webhooker/issues/256.
+	//
+	// Four is above the one writer SQLite allows at a time, so reads
+	// still proceed while a write is in flight, and low enough that
+	// contention is resolved by the busy handler rather than by piling
+	// up connections against a lock only one of them can hold.
+	sqliteMaxOpenConns = 4
+
+	// sqliteMaxIdleConns keeps the pool warm without holding every
+	// connection open through an idle period.
+	sqliteMaxIdleConns = 2
+
+	// sqliteConnMaxLifetime and sqliteConnMaxIdleTime retire pooled
+	// connections on a schedule. With _txlock=immediate a failed
+	// COMMIT should no longer be reachable, but these bound the damage
+	// if one happens anyway: a poisoned connection is closed and
+	// replaced within the lifetime instead of wedging the file until
+	// the process restarts.
+	sqliteConnMaxLifetime = 5 * time.Minute
+	sqliteConnMaxIdleTime = time.Minute
+)
+
+// SQLiteFilePerm is the mode every SQLite file this service owns is
+// created with and held at: owner read/write, nothing for group or
+// other.
+//
+// These files hold credentials in plaintext. The main database stores
+// `targets.config` — bearer tokens, API keys, Slack webhook URLs — and
+// the session encryption key. SQLite left to itself creates them 0644
+// (see reserveSQLiteFile), which made the 0750 data directory the only
+// barrier; a bind-mounted directory supplied at 0755 removes it and
+// every local user on the host can read every stored credential.
+//
+// This is a file-mode fix and not encryption at rest. An unattended
+// process needs a key it can read without a human, so the key lands
+// beside the data and an attacker who can read the database can read
+// it too. See https://git.eeqj.de/sneak/webhooker/issues/212.
+const SQLiteFilePerm fs.FileMode = 0o600
+
+// reserveSQLiteFile puts path at SQLiteFilePerm before the driver ever
+// touches it, and tightens any sidecar already on disk.
+//
+// The mode has to be settled here rather than by a chmod after opening,
+// because SQLite picks it: robust_open substitutes
+// SQLITE_DEFAULT_FILE_PERMISSIONS (0644) whenever it is handed mode 0,
+// and findCreateFileMode yields 0 for a main database opened by URI
+// with no `modeof` parameter. A chmod afterwards would leave a window
+// in which the credentials are on disk world-readable.
+//
+// Creating the file ourselves also settles the sidecars, which is the
+// half that could quietly not work. SQLite does not create those at a
+// mode we choose — it derives both from the main database file:
+// `-wal` through findCreateFileMode, which stats the path with the
+// suffix stripped, and `-shm` in unixOpenSharedMemory from an fstat of
+// the already-open database descriptor. A main file at 0600 therefore
+// produces sidecars at 0600. A zero-length file is a valid empty
+// database, so reserving it changes nothing else.
+//
+// create says whether the caller is opening in a mode that may create
+// the database. When it is false a missing file is left missing, so
+// SQLite still reports the absence rather than this function
+// materializing an empty database the caller asked not to create.
+//
+// Chmod of a file that already exists is what tightens a data
+// directory an earlier build left at 0644 — including a developer's
+// own scratch directory — without any migration machinery.
+func reserveSQLiteFile(path string, create bool) error {
+	if create {
+		// gosec G304: the path is the database file the caller asked
+		// to open, and the driver is about to open the same path
+		// anyway. Creating it here is what fixes its mode.
+		f, err := os.OpenFile( //nolint:gosec // see above
+			path, os.O_RDWR|os.O_CREATE, SQLiteFilePerm,
+		)
+		if err != nil {
+			return fmt.Errorf("creating %s: %w", path, err)
+		}
+
+		err = f.Close()
+		if err != nil {
+			return fmt.Errorf("closing %s: %w", path, err)
+		}
+	}
+
+	// O_CREATE leaves an existing file's mode alone, and umask can only
+	// have narrowed a new one. Chmod settles both cases at exactly
+	// SQLiteFilePerm.
+	for _, p := range append(
+		[]string{path}, sqliteSidecarPaths(path)...,
+	) {
+		err := os.Chmod(p, SQLiteFilePerm)
+		if err != nil && !errors.Is(err, fs.ErrNotExist) {
+			return fmt.Errorf("securing %s: %w", p, err)
+		}
+	}
+
+	return nil
+}
+
+// sqliteSidecarPaths returns the files SQLite maintains beside a
+// database under WAL. They carry the same rows as the database itself,
+// so a fix that tightens only the main file has fixed nothing.
+func sqliteSidecarPaths(path string) []string {
+	return []string{path + "-wal", path + "-shm"}
+}
+
+// SQLiteDSN builds the connection string for one database file.
+//
+// mode is the SQLite URI open mode: "rwc" to create the file when it
+// is missing, "rw" to require that it already exists.
+//
+// Three settings carry the fix for
+// https://git.eeqj.de/sneak/webhooker/issues/256 and none of them is
+// optional:
+//
+//   - journal_mode=WAL, so a reader — an operator running
+//     `sqlite3 <db> .dump` over their own data — takes a snapshot
+//     instead of blocking every writer behind it.
+//
+//   - busy_timeout, so a writer that does meet a lock waits for it.
+//     Without one SQLite gives up immediately; nothing above it
+//     retries.
+//
+//   - _txlock=immediate, so every transaction takes the write lock at
+//     BEGIN. A deferred transaction acquires it lazily on its first
+//     write, and that upgrade returns SQLITE_BUSY *without* consulting
+//     the busy handler, because SQLite cannot block a transaction that
+//     may already hold a read snapshot. Such a COMMIT then fails while
+//     the transaction stays open on the connection. A busy timeout
+//     alone does not prevent this; BEGIN IMMEDIATE does, by putting
+//     the wait somewhere the handler applies.
+//
+// Note what is absent: `cache=shared`. Under a shared cache an
+// in-process conflict is reported as SQLITE_LOCKED rather than
+// SQLITE_BUSY, and the busy handler does not retry SQLITE_LOCKED — so
+// leaving it in would have defeated the busy timeout for exactly the
+// contention this service generates. Dropping it is part of the fix,
+// not housekeeping.
+//
+// synchronous is deliberately left at SQLite's default of FULL: this
+// is a webhook receiver whose one promise is that an event it answered
+// 200 for is durable.
+// The order of the _pragma parameters is load-bearing.
+// modernc.org/sqlite executes them in the order they appear, on every
+// new connection, before the connection is handed to the pool. Setting
+// journal_mode first means that pragma itself runs with no busy
+// handler installed: the pool opens connections lazily, so the moment
+// a new one is created is a moment the database is under load, and
+// PRAGMA journal_mode takes a lock. It would fail immediately with
+// SQLITE_BUSY and fail the query that caused the connection to be
+// opened. busy_timeout is therefore set first, so every pragma after
+// it — and the whole life of the connection — is covered.
+func SQLiteDSN(path, mode string) string {
+	q := url.Values{}
+	q.Set("mode", mode)
+	q.Set("_txlock", "immediate")
+	q.Add(
+		"_pragma",
+		fmt.Sprintf(
+			"busy_timeout(%d)",
+			SQLiteBusyTimeout.Milliseconds(),
+		),
+	)
+	q.Add("_pragma", "journal_mode(WAL)")
+
+	return "file:" + path + "?" + q.Encode()
+}
+
+// OpenSQLite opens the SQLite file at path with the service's
+// durability settings and pool bounds applied. mode is the SQLite URI
+// open mode ("rwc" or "rw").
+//
+// The file and its WAL sidecars are settled at SQLiteFilePerm before
+// the driver sees the path; see reserveSQLiteFile.
+//
+// The handle is returned rather than a *gorm.DB because the callers
+// wrap it in gorm themselves with their own logger.
+func OpenSQLite(path, mode string) (*sql.DB, error) {
+	err := reserveSQLiteFile(path, mode == SQLiteModeCreate)
+	if err != nil {
+		return nil, err
+	}
+
+	sqlDB, err := sql.Open("sqlite", SQLiteDSN(path, mode))
+	if err != nil {
+		return nil, fmt.Errorf(
+			"opening sqlite database %s: %w", path, err,
+		)
+	}
+
+	sqlDB.SetMaxOpenConns(sqliteMaxOpenConns)
+	sqlDB.SetMaxIdleConns(sqliteMaxIdleConns)
+	sqlDB.SetConnMaxLifetime(sqliteConnMaxLifetime)
+	sqlDB.SetConnMaxIdleTime(sqliteConnMaxIdleTime)
+
+	return sqlDB, nil
+}

internal/database/sqlite_open_test.go

@@ -0,0 +1,178 @@
+package database_test
+
+import (
+	"context"
+	"path/filepath"
+	"strings"
+	"testing"
+
+	"github.com/google/uuid"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	"gorm.io/gorm"
+	"sneak.berlin/go/webhooker/internal/database"
+)
+
+// livePragma reads a pragma off a live handle. Reading the DSN back
+// would prove only that the string was built; these tests assert that
+// SQLite actually applied it.
+func livePragma(t *testing.T, db *gorm.DB, name string) string {
+	t.Helper()
+
+	var v string
+
+	row := db.Raw("pragma " + name).Row()
+	require.NoError(t, row.Scan(&v))
+
+	return v
+}
+
+func TestSQLiteDSNCarriesTheDurabilitySettings(t *testing.T) {
+	t.Parallel()
+
+	dsn := database.SQLiteDSN(
+		"/var/lib/webhooker/webhooker.db",
+		database.SQLiteModeCreate,
+	)
+
+	assert.Contains(t, dsn, "journal_mode%28WAL%29")
+	assert.Contains(t, dsn, "busy_timeout%2810000%29")
+	assert.Contains(t, dsn, "_txlock=immediate")
+	assert.Contains(t, dsn, "mode=rwc")
+
+	// busy_timeout must come first. The driver runs these in order on
+	// every new connection, and PRAGMA journal_mode takes a lock — a
+	// connection opened while the database is busy would fail on that
+	// pragma, with no busy handler yet installed to wait it out.
+	assert.Less(
+		t,
+		strings.Index(dsn, "busy_timeout"),
+		strings.Index(dsn, "journal_mode"),
+		"busy_timeout must be applied before journal_mode",
+	)
+
+	// cache=shared turns an in-process conflict into SQLITE_LOCKED,
+	// which the busy handler does not retry. It must never come back.
+	// See https://git.eeqj.de/sneak/webhooker/issues/256.
+	assert.NotContains(t, strings.ToLower(dsn), "cache=shared")
+}
+
+// TestPerWebhookDBAppliesPragmasOnALiveHandle is the check the issue
+// asks for by name: the settings are confirmed by querying the running
+// database, not by inspecting the connection string.
+func TestPerWebhookDBAppliesPragmasOnALiveHandle(t *testing.T) {
+	t.Parallel()
+
+	mgr, lc := setupTestWebhookDBManager(t)
+	ctx := context.Background()
+	require.NoError(t, lc.Start(ctx))
+
+	defer func() { require.NoError(t, lc.Stop(ctx)) }()
+
+	webhookID := uuid.New().String()
+
+	db, err := mgr.GetDB(webhookID)
+	require.NoError(t, err)
+
+	assert.Equal(
+		t, "wal",
+		strings.ToLower(livePragma(t, db, "journal_mode")),
+	)
+	assert.Equal(
+		t, "10000", livePragma(t, db, "busy_timeout"),
+	)
+}
+
+func TestMainDBAppliesPragmasOnALiveHandle(t *testing.T) {
+	t.Parallel()
+
+	ctx := context.Background()
+	dir := t.TempDir()
+
+	sqlDB, err := database.OpenSQLite(
+		filepath.Join(dir, database.MainDBFileName),
+		database.SQLiteModeCreate,
+	)
+	require.NoError(t, err)
+
+	defer func() { require.NoError(t, sqlDB.Close()) }()
+
+	var journal string
+
+	require.NoError(t, sqlDB.
+		QueryRowContext(ctx, "pragma journal_mode").
+		Scan(&journal))
+	assert.Equal(t, "wal", strings.ToLower(journal))
+
+	var busy string
+
+	require.NoError(t, sqlDB.
+		QueryRowContext(ctx, "pragma busy_timeout").
+		Scan(&busy))
+	assert.Equal(t, "10000", busy)
+}
+
+// TestConcurrentReaderDoesNotBlockWrites is the unit-scale form of the
+// reproduction in
+// https://git.eeqj.de/sneak/webhooker/issues/256: an operator's
+// long-held read of their own data used to make every concurrent write
+// fail. Under WAL the reader takes a snapshot and the writes proceed.
+func TestConcurrentReaderDoesNotBlockWrites(t *testing.T) {
+	t.Parallel()
+
+	mgr, lc := setupTestWebhookDBManager(t)
+	ctx := context.Background()
+	require.NoError(t, lc.Start(ctx))
+
+	defer func() { require.NoError(t, lc.Stop(ctx)) }()
+
+	webhookID := uuid.New().String()
+
+	db, err := mgr.GetDB(webhookID)
+	require.NoError(t, err)
+
+	// A second handle on the same file, holding a read transaction
+	// open across every write below — what `sqlite3 <db> .dump` is.
+	readerSQL, err := database.OpenSQLite(
+		mgr.DBPath(webhookID), database.SQLiteModeExisting,
+	)
+	require.NoError(t, err)
+
+	defer func() { require.NoError(t, readerSQL.Close()) }()
+
+	readerConn, err := readerSQL.Conn(ctx)
+	require.NoError(t, err)
+
+	defer func() { require.NoError(t, readerConn.Close()) }()
+
+	_, err = readerConn.ExecContext(ctx, "begin deferred")
+	require.NoError(t, err)
+
+	_, err = readerConn.ExecContext(
+		ctx, "select count(*) from events",
+	)
+	require.NoError(t, err)
+
+	for range 25 {
+		err = db.Transaction(func(tx *gorm.DB) error {
+			return tx.Create(&database.Event{
+				WebhookID:    webhookID,
+				EntrypointID: uuid.New().String(),
+				Method:       "POST",
+				Body:         "{}",
+			}).Error
+		})
+		require.NoError(t, err)
+	}
+
+	_, err = readerConn.ExecContext(ctx, "commit")
+	require.NoError(t, err)
+
+	var count int64
+
+	require.NoError(
+		t,
+		db.Model(&database.Event{}).Count(&count).Error,
+	)
+	assert.Equal(t, int64(25), count)
+}

internal/database/webhook_db_manager.go

@@ -2,7 +2,6 @@ package database
 
 import (
 	"context"
-	"database/sql"
 	"errors"
 	"fmt"
 	"log/slog"
@@ -234,12 +233,11 @@ func (m *WebhookDBManager) openDB(
 	webhookID string,
 ) (*gorm.DB, error) {
 	path := m.dbPath(webhookID)
-	dbURL := fmt.Sprintf(
-		"file:%s?cache=shared&mode=rwc",
-		path,
-	)
 
-	sqlDB, err := sql.Open("sqlite", dbURL)
+	// See sqlite_open.go: WAL, a busy timeout, immediate-transaction
+	// locking, and a bounded pool, all of which this file needs most —
+	// it is the one every delivery worker writes to concurrently.
+	sqlDB, err := OpenSQLite(path, SQLiteModeCreate)
 	if err != nil {
 		return nil, fmt.Errorf(
 			"opening webhook database %s: %w",

internal/delivery/engine_integration_test.go

@@ -2,7 +2,6 @@ package delivery_test
 
 import (
 	"context"
-	"database/sql"
 	"encoding/json"
 	"fmt"
 	"io"
@@ -70,11 +69,12 @@ func iMainDB(t *testing.T) *gorm.DB {
 		t.TempDir(), "main-test.db",
 	)
 
-	dsn := fmt.Sprintf(
-		"file:%s?cache=shared&mode=rwc", dbPath,
+	// Opened the way the service opens the main database, so these
+	// tests cannot pass against journal and locking settings
+	// production does not use.
+	sqlDB, err := database.OpenSQLite(
+		dbPath, database.SQLiteModeCreate,
 	)
-
-	sqlDB, err := sql.Open("sqlite", dsn)
 	require.NoError(t, err)
 
 	t.Cleanup(func() { _ = sqlDB.Close() })
@@ -377,6 +377,17 @@ func TestProcessRetryTask_SuccessfulRetry(t *testing.T) {
 
 	bodyStr := event.Body
 	cfg := iHTTPConfig(ts.URL)
+
+	// The target row exists because the engine confirms a scheduled
+	// retry's target has not been deleted before it runs it. A retry
+	// task whose target id names no row at all is a state the service
+	// does not produce: the handler read that target to build the
+	// task. See https://git.eeqj.de/sneak/webhooker/issues/107.
+	iCreateTarget(
+		t, s.MainDB, targetID, s.WebhookID, "retry-target",
+		database.TargetTypeHTTP, cfg, 5,
+	)
+
 	task := iTask(
 		d, event, s.WebhookID, targetID,
 		"retry-target", cfg, 5, 2, &bodyStr,
@@ -456,6 +467,12 @@ func TestProcessRetryTask_LargeBody_FetchFromDB(
 	)
 
 	cfg := iHTTPConfig(ts.URL)
+
+	iCreateTarget(
+		t, s.MainDB, targetID, s.WebhookID, "retry-large",
+		database.TargetTypeHTTP, cfg, 5,
+	)
+
 	task := iTask(
 		d, event, s.WebhookID, targetID,
 		"retry-large", cfg, 5, 2, nil,
@@ -558,6 +575,12 @@ func TestWorkerLifecycle_ProcessesRetryChannel(
 
 	bodyStr := event.Body
 	cfg := iHTTPConfig(ts.URL)
+
+	iCreateTarget(
+		t, s.MainDB, targetID, s.WebhookID, "retry-chan-test",
+		database.TargetTypeHTTP, cfg, 5,
+	)
+
 	task := iTask(
 		d, event, s.WebhookID, targetID,
 		"retry-chan-test", cfg, 5, 2, &bodyStr,

internal/delivery/engine_test.go

@@ -3,7 +3,6 @@ package delivery_test
 import (
 	"bytes"
 	"context"
-	"database/sql"
 	"encoding/json"
 	"fmt"
 	"log/slog"
@@ -37,11 +36,12 @@ func testWebhookDB(t *testing.T) *gorm.DB {
 		t.TempDir(), "events-test.db",
 	)
 
-	dsn := fmt.Sprintf(
-		"file:%s?cache=shared&mode=rwc", dbPath,
+	// Opened the way the service opens a per-webhook database, so
+	// these tests cannot pass against journal and locking settings
+	// production does not use.
+	sqlDB, err := database.OpenSQLite(
+		dbPath, database.SQLiteModeCreate,
 	)
-
-	sqlDB, err := sql.Open("sqlite", dsn)
 	require.NoError(t, err)
 
 	t.Cleanup(func() { _ = sqlDB.Close() })

internal/delivery/event_db_isolation_test.go

@@ -96,7 +96,15 @@ func TestEventDBHoldsNoTargetRows(t *testing.T) {
 	)
 	assertNoTargetRows(t, dbPath)
 
-	// A retry.
+	// A retry. Its target exists in the main database, because the
+	// engine confirms a scheduled retry's target has not been
+	// deleted before running it; see
+	// https://git.eeqj.de/sneak/webhooker/issues/107.
+	iCreateTarget(
+		t, s.MainDB, targetID, s.WebhookID, "leaky-target",
+		database.TargetTypeHTTP, cfg, 5,
+	)
+
 	rd := iSeedDelivery(
 		t, s.WebhookDB, event.ID, targetID,
 		database.DeliveryStatusRetrying,

internal/delivery/event_timestamp_test.go

@@ -0,0 +1,442 @@
+package delivery_test
+
+import (
+	"context"
+	"encoding/json"
+	"io"
+	"net/http"
+	"net/http/httptest"
+	"testing"
+	"time"
+
+	"github.com/google/uuid"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	"gorm.io/gorm"
+	"sneak.berlin/go/webhooker/internal/database"
+	"sneak.berlin/go/webhooker/internal/delivery"
+)
+
+// tsEventCreatedAt is the receipt time seeded on the events these
+// tests deliver. It is far enough from both the zero time and from
+// now that neither can be mistaken for it.
+func tsEventCreatedAt() time.Time {
+	return time.Date(
+		2026, time.March, 4, 5, 6, 7, 0, time.UTC,
+	)
+}
+
+// tsZeroStamp is what a Slack message renders when the event handed
+// to FormatSlackMessage carries no CreatedAt.
+const tsZeroStamp = "*Timestamp:* `0001-01-01T00:00:00Z`"
+
+// tsEventBody is the body seeded on every event in this file. It is
+// small enough that a Task can inline it.
+const tsEventBody = `{"hello":"world"}`
+
+// tsUndeliverableHook stands in for a Slack incoming webhook on the
+// tests that never send: the config parser requires a URL, but no
+// request is made.
+const tsUndeliverableHook = "https://hooks.slack.com/services/T/B/x"
+
+// tsSink is a stand-in Slack incoming webhook that records the raw
+// body posted to it.
+type tsSink struct {
+	*httptest.Server
+
+	bodies chan []byte
+}
+
+func newTSSink(t *testing.T) *tsSink {
+	t.Helper()
+
+	s := &tsSink{bodies: make(chan []byte, 8)}
+
+	s.Server = httptest.NewServer(http.HandlerFunc(
+		func(w http.ResponseWriter, r *http.Request) {
+			body, _ := io.ReadAll(r.Body)
+
+			select {
+			case s.bodies <- body:
+			default:
+			}
+
+			w.WriteHeader(http.StatusOK)
+		},
+	))
+
+	t.Cleanup(s.Close)
+
+	return s
+}
+
+// text returns the Slack message text from the single payload the
+// sink received.
+func (s *tsSink) text(t *testing.T) string {
+	t.Helper()
+
+	select {
+	case raw := <-s.bodies:
+		t.Logf("raw slack payload: %s", raw)
+
+		var payload struct {
+			Text string `json:"text"`
+		}
+
+		require.NoError(t, json.Unmarshal(raw, &payload))
+
+		return payload.Text
+	case <-time.After(5 * time.Second):
+		t.Fatal("slack sink received no payload")
+
+		return ""
+	}
+}
+
+func tsSlackConfig(t *testing.T, url string) string {
+	t.Helper()
+
+	data, err := json.Marshal(
+		delivery.SlackTargetConfig{WebhookURL: url},
+	)
+	require.NoError(t, err)
+
+	return string(data)
+}
+
+// tsSeedEvent writes an event whose CreatedAt is tsEventCreatedAt
+// rather than the write time, so an assertion on the rendered
+// timestamp cannot pass by accident against "roughly now".
+func tsSeedEvent(
+	t *testing.T, db *gorm.DB, webhookID string,
+) database.Event {
+	t.Helper()
+
+	event := database.Event{
+		WebhookID:    webhookID,
+		EntrypointID: uuid.New().String(),
+		Method:       http.MethodPost,
+		Headers:      `{}`,
+		Body:         tsEventBody,
+		ContentType:  "application/json",
+	}
+	event.ID = uuid.New().String()
+	event.CreatedAt = tsEventCreatedAt()
+	event.UpdatedAt = tsEventCreatedAt()
+
+	require.NoError(t, db.Create(&event).Error)
+
+	var stored database.Event
+
+	require.NoError(t,
+		db.First(&stored, "id = ?", event.ID).Error,
+	)
+	require.Equal(t,
+		tsEventCreatedAt().UTC(), stored.CreatedAt.UTC(),
+		"seeded created_at did not round-trip",
+	)
+
+	return event
+}
+
+// tsSeedTarget writes the slack target row into the main database.
+// The retry path confirms the target still exists before sending.
+func tsSeedTarget(
+	t *testing.T, mainDB *gorm.DB, webhookID, config string,
+) database.Target {
+	t.Helper()
+
+	target := database.Target{
+		WebhookID: webhookID,
+		Name:      "slack-sink",
+		Type:      database.TargetTypeSlack,
+		Config:    config,
+		Active:    true,
+	}
+
+	require.NoError(t, mainDB.Create(&target).Error)
+
+	return target
+}
+
+func tsTask(
+	d database.Delivery,
+	event database.Event,
+	webhookID string,
+	target database.Target,
+	attemptNum int,
+	body *string,
+) delivery.Task {
+	return delivery.Task{
+		DeliveryID:   d.ID,
+		EventID:      event.ID,
+		WebhookID:    webhookID,
+		EntrypointID: event.EntrypointID,
+		TargetID:     target.ID,
+		TargetName:   target.Name,
+		TargetType:   database.TargetTypeSlack,
+		TargetConfig: target.Config,
+		MaxRetries:   0,
+		Method:       event.Method,
+		Headers:      event.Headers,
+		ContentType:  event.ContentType,
+		Body:         body,
+		AttemptNum:   attemptNum,
+	}
+}
+
+func tsAssertRealTimestamp(t *testing.T, text string) {
+	t.Helper()
+
+	assert.NotContains(t, text, tsZeroStamp,
+		"slack message carries the zero timestamp",
+	)
+	assert.Contains(t, text,
+		"*Timestamp:* `"+
+			tsEventCreatedAt().UTC().Format(time.RFC3339)+"`",
+		"slack message does not carry the event's receipt time",
+	)
+}
+
+// tsCase is one end-to-end delivery of a seeded event to a slack
+// sink, over whichever engine path `process` names.
+type tsCase struct {
+	// status is the delivery row's status before the engine runs.
+	// The retry path refuses a delivery that is not retrying.
+	status database.DeliveryStatus
+
+	// inlineBody mirrors a Task built for a body under
+	// MaxInlineBodySize. When false the engine reads the body back
+	// from the stored row.
+	inlineBody bool
+
+	attemptNum int
+
+	process func(
+		ctx context.Context, e *delivery.Engine, task *delivery.Task,
+	)
+}
+
+// run delivers one event through the named path and returns the
+// Slack message text the sink received.
+func (c tsCase) run(t *testing.T) (iSetup, database.Delivery, string) {
+	t.Helper()
+
+	s := newISetup(t)
+	sink := newTSSink(t)
+
+	cfg := tsSlackConfig(t, sink.URL)
+	target := tsSeedTarget(t, s.MainDB, s.WebhookID, cfg)
+	event := tsSeedEvent(t, s.WebhookDB, s.WebhookID)
+
+	d := iSeedDelivery(
+		t, s.WebhookDB, event.ID, target.ID, c.status,
+	)
+
+	var body *string
+
+	if c.inlineBody {
+		bodyStr := event.Body
+		body = &bodyStr
+	}
+
+	task := tsTask(
+		d, event, s.WebhookID, target, c.attemptNum, body,
+	)
+
+	c.process(context.TODO(), s.Engine, &task)
+
+	return s, d, sink.text(t)
+}
+
+// TestSlackFirstAttemptCarriesEventTimestamp covers the path an
+// event takes on its first delivery: the task comes from the
+// receiver and the engine reconstructs the event from it.
+func TestSlackFirstAttemptCarriesEventTimestamp(t *testing.T) {
+	t.Parallel()
+
+	s, d, text := tsCase{
+		status:     database.DeliveryStatusPending,
+		inlineBody: true,
+		attemptNum: 1,
+		process: func(
+			ctx context.Context,
+			e *delivery.Engine,
+			task *delivery.Task,
+		) {
+			e.ExportProcessNewTask(ctx, task)
+		},
+	}.run(t)
+
+	tsAssertRealTimestamp(t, text)
+
+	iAssertStatus(t, s.WebhookDB, d.ID,
+		database.DeliveryStatusDelivered,
+	)
+}
+
+// TestSlackFirstAttemptLargeBodyCarriesEventTimestamp covers the
+// first-attempt path for an event whose body exceeded
+// MaxInlineBodySize, so the task carries no body and the engine
+// reads it back from the stored row.
+func TestSlackFirstAttemptLargeBodyCarriesEventTimestamp(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	_, _, text := tsCase{
+		status:     database.DeliveryStatusPending,
+		inlineBody: false,
+		attemptNum: 1,
+		process: func(
+			ctx context.Context,
+			e *delivery.Engine,
+			task *delivery.Task,
+		) {
+			e.ExportProcessNewTask(ctx, task)
+		},
+	}.run(t)
+
+	tsAssertRealTimestamp(t, text)
+}
+
+// TestSlackRetryCarriesEventTimestamp covers the retry path, which
+// reconstructs the event from the same task the first attempt used.
+func TestSlackRetryCarriesEventTimestamp(t *testing.T) {
+	t.Parallel()
+
+	s, d, text := tsCase{
+		status:     database.DeliveryStatusRetrying,
+		inlineBody: true,
+		attemptNum: 2,
+		process: func(
+			ctx context.Context,
+			e *delivery.Engine,
+			task *delivery.Task,
+		) {
+			e.ExportProcessRetryTask(ctx, task)
+		},
+	}.run(t)
+
+	tsAssertRealTimestamp(t, text)
+
+	iAssertStatus(t, s.WebhookDB, d.ID,
+		database.DeliveryStatusDelivered,
+	)
+}
+
+// TestFormatSlackMessageOverTaskReconstructedEvent asserts on the
+// formatted message directly, over the event the delivery paths
+// reconstruct from a Task. It is the unit-level guard under the
+// end-to-end tests: revert the CreatedAt population in hydrateEvent
+// and this fails on the zero timestamp.
+func TestFormatSlackMessageOverTaskReconstructedEvent(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	s := newISetup(t)
+
+	cfg := tsSlackConfig(t, tsUndeliverableHook)
+	target := tsSeedTarget(t, s.MainDB, s.WebhookID, cfg)
+	event := tsSeedEvent(t, s.WebhookDB, s.WebhookID)
+
+	d := iSeedDelivery(
+		t, s.WebhookDB, event.ID, target.ID,
+		database.DeliveryStatusPending,
+	)
+
+	bodyStr := event.Body
+	task := tsTask(d, event, s.WebhookID, target, 1, &bodyStr)
+
+	rebuilt, err := s.Engine.ExportEventForTask(
+		s.WebhookDB, &task,
+	)
+	require.NoError(t, err)
+	assert.False(t, rebuilt.CreatedAt.IsZero(),
+		"reconstructed event carries the zero time",
+	)
+	assert.Equal(t,
+		tsEventCreatedAt().UTC(), rebuilt.CreatedAt.UTC(),
+	)
+
+	tsAssertRealTimestamp(
+		t, delivery.FormatSlackMessage(&rebuilt),
+	)
+}
+
+// TestFormatSlackMessageZeroTimestamp asserts the rendering choice
+// directly, without going through the engine: a zero CreatedAt (the
+// shape a reaped-row fallback produces) renders as "unknown" rather
+// than the year-1 zero time, while a real CreatedAt still renders as
+// RFC3339.
+func TestFormatSlackMessageZeroTimestamp(t *testing.T) {
+	t.Parallel()
+
+	zeroEvent := database.Event{
+		Method:      http.MethodPost,
+		ContentType: testContentType,
+		Body:        tsEventBody,
+	}
+
+	zeroText := delivery.FormatSlackMessage(&zeroEvent)
+
+	assert.NotContains(t, zeroText, "0001-01-01",
+		"slack message carries the zero-time year",
+	)
+	assert.Contains(t, zeroText, "*Timestamp:* `unknown`",
+		"slack message does not mark an unset receipt time as unknown",
+	)
+
+	nonZeroEvent := zeroEvent
+	nonZeroEvent.CreatedAt = tsEventCreatedAt()
+
+	nonZeroText := delivery.FormatSlackMessage(&nonZeroEvent)
+
+	assert.Contains(t, nonZeroText,
+		"*Timestamp:* `"+
+			tsEventCreatedAt().UTC().Format(time.RFC3339)+"`",
+		"slack message does not render a real receipt time as RFC3339",
+	)
+}
+
+// TestEventReconstructionSurvivesAReapedRow pins the fallback: an
+// event row reaped by retention while its delivery still holds the
+// body inline is still delivered, with the receipt time unset,
+// rather than dropped.
+func TestEventReconstructionSurvivesAReapedRow(t *testing.T) {
+	t.Parallel()
+
+	s := newISetup(t)
+
+	cfg := tsSlackConfig(t, tsUndeliverableHook)
+	target := tsSeedTarget(t, s.MainDB, s.WebhookID, cfg)
+	event := tsSeedEvent(t, s.WebhookDB, s.WebhookID)
+
+	d := iSeedDelivery(
+		t, s.WebhookDB, event.ID, target.ID,
+		database.DeliveryStatusPending,
+	)
+
+	bodyStr := event.Body
+	task := tsTask(d, event, s.WebhookID, target, 1, &bodyStr)
+
+	require.NoError(t, s.WebhookDB.Unscoped().Delete(
+		&database.Event{}, "id = ?", event.ID,
+	).Error)
+
+	rebuilt, err := s.Engine.ExportEventForTask(
+		s.WebhookDB, &task,
+	)
+	require.NoError(t, err)
+	assert.Equal(t, bodyStr, rebuilt.Body)
+	assert.True(t, rebuilt.CreatedAt.IsZero())
+
+	// A task with no inlined body has nothing left to deliver, so
+	// the same reaped row is an error there.
+	noBody := task
+	noBody.Body = nil
+
+	_, err = s.Engine.ExportEventForTask(s.WebhookDB, &noBody)
+	require.Error(t, err)
+}

internal/delivery/export_test.go

@@ -33,6 +33,11 @@ const (
 	// response is written against this number, so a test has to
 	// be able to name it.
 	ExportMaxBodyLog = maxBodyLog
+
+	// ExportPendingSweepMinAge is how long a delivery must sit at
+	// pending before the sweep treats it as stranded. A test has to
+	// name it to age a row past the bound.
+	ExportPendingSweepMinAge = pendingSweepMinAge
 )
 
 // ExportIsBlockedIP exposes isBlockedIP for testing.
@@ -146,6 +151,16 @@ func (e *Engine) ExportProcessRetryTask(
 	e.processRetryTask(ctx, task)
 }
 
+// ExportEventForTask exposes the event reconstruction the delivery
+// paths run: buildEventFromTask followed by hydrateEvent.
+func (e *Engine) ExportEventForTask(
+	webhookDB *gorm.DB, task *Task,
+) (database.Event, error) {
+	return e.hydrateEvent(
+		webhookDB, buildEventFromTask(task), task,
+	)
+}
+
 // ExportProcessDelivery exposes processDelivery.
 func (e *Engine) ExportProcessDelivery(
 	ctx context.Context,
@@ -286,6 +301,26 @@ func (e *Engine) ExportWedgeWorker(release <-chan struct{}) {
 	})
 }
 
+// ExportInflightHeld reports how many deliveries the engine currently
+// owns, so a test can prove ownership is released rather than leaked.
+func (e *Engine) ExportInflightHeld() int {
+	return e.inflight.held()
+}
+
+// ExportRetainDelivery takes the first reference on a delivery, as the
+// queueing side does. It lets a test put a delivery into the state a
+// worker or a full channel would, without running the pool.
+func (e *Engine) ExportRetainDelivery(deliveryID string) bool {
+	return e.inflight.retainIdle(deliveryID)
+}
+
+// ExportRecoverRetryingDeliveries exposes recoverRetryingDeliveries.
+func (e *Engine) ExportRecoverRetryingDeliveries(
+	webhookDB *gorm.DB, webhookID string,
+) {
+	e.recoverRetryingDeliveries(webhookDB, webhookID)
+}
+
 // ExportDeliveryCh returns the delivery channel.
 func (e *Engine) ExportDeliveryCh() chan Task {
 	return e.deliveryCh

internal/delivery/inflight.go

@@ -0,0 +1,110 @@
+package delivery
+
+import "sync"
+
+// inflightSet records which deliveries the engine currently owns.
+//
+// A delivery is owned from the moment a task for it is handed to a
+// channel or to a retry timer until the engine has no further plan for
+// it in memory. Restart recovery and both arms of the periodic sweep
+// re-dispatch only deliveries the set does not hold, which is what
+// makes them exact rather than a guess about how long a row has sat at
+// pending.
+//
+// This replaces reasoning from timestamps. A delivery's row says
+// pending from creation until its outcome is written, which covers
+// four different situations — never dispatched, waiting in a channel,
+// being attempted right now, and genuinely stranded — and no column
+// distinguishes them. Only the engine knows which, and it knows
+// exactly. `deliveryChannelSize` is 10000 against 10 workers, so a
+// perfectly healthy delivery can wait far longer than any age bound
+// worth setting before its attempt even begins; an age bound alone
+// re-sends it. See
+// https://git.eeqj.de/sneak/webhooker/issues/256.
+//
+// In-memory state is sufficient because a data directory admits one
+// process: internal/datadir takes an flock on it at startup and a
+// second instance refuses to run. Deliveries owned by a process that
+// died are not in any successor's set, and restart recovery is what
+// picks those up.
+//
+// References are counted rather than held as a plain set because
+// ownership outlives the worker that took it. A target that schedules
+// a retry from inside Deliver adds a reference while the worker still
+// holds one, so the delivery stays owned across the gap between the
+// worker returning and the timer firing — the window in which a sweep
+// would otherwise find the row at retrying and send it again.
+//
+// The zero value is ready to use, and the Engine holds one by value.
+// That is deliberate: an engine built by a constructor that forgot to
+// initialise this would not refuse to re-dispatch anything, and the
+// symptom would be duplicate deliveries rather than a failure anybody
+// notices.
+type inflightSet struct {
+	mu  sync.Mutex
+	ids map[string]int
+}
+
+// retain adds a reference to a delivery the caller already knows the
+// engine owns, so that ownership survives the current holder letting
+// go. It cannot fail.
+func (s *inflightSet) retain(deliveryID string) {
+	s.mu.Lock()
+	defer s.mu.Unlock()
+
+	if s.ids == nil {
+		s.ids = make(map[string]int)
+	}
+
+	s.ids[deliveryID]++
+}
+
+// retainIdle takes the first reference on a delivery, and reports
+// whether it got it. It fails when the engine already owns the
+// delivery, which is what makes two claimants — restart recovery and
+// the sweep run concurrently, or two sweep arms — mutually exclusive
+// rather than merely atomic.
+func (s *inflightSet) retainIdle(deliveryID string) bool {
+	s.mu.Lock()
+	defer s.mu.Unlock()
+
+	if s.ids[deliveryID] > 0 {
+		return false
+	}
+
+	if s.ids == nil {
+		s.ids = make(map[string]int)
+	}
+
+	s.ids[deliveryID] = 1
+
+	return true
+}
+
+// release drops one reference. The delivery becomes eligible for
+// re-dispatch again once the last one goes.
+func (s *inflightSet) release(deliveryID string) {
+	s.mu.Lock()
+	defer s.mu.Unlock()
+
+	n := s.ids[deliveryID] - 1
+	if n <= 0 {
+		delete(s.ids, deliveryID)
+
+		return
+	}
+
+	s.ids[deliveryID] = n
+}
+
+// held reports how many deliveries the engine currently owns. It
+// exists so a test can assert that ownership is released rather than
+// leaked: a reference that is never dropped hides its delivery from
+// every sweep for the life of the process, which is the one way this
+// mechanism can fail silently.
+func (s *inflightSet) held() int {
+	s.mu.Lock()
+	defer s.mu.Unlock()
+
+	return len(s.ids)
+}

internal/delivery/inflight_test.go

@@ -0,0 +1,428 @@
+package delivery_test
+
+import (
+	"context"
+	"path/filepath"
+	"strings"
+	"sync"
+	"testing"
+	"time"
+
+	"github.com/google/uuid"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	"sneak.berlin/go/webhooker/internal/database"
+	"sneak.berlin/go/webhooker/internal/delivery"
+)
+
+// These tests pin the rule that decides whether a delivery may be
+// handed back to a worker: the engine re-dispatches only what it does
+// not already own. Age alone is not that rule — a healthy delivery
+// waiting in a 10000-deep channel is old and must not be re-sent. See
+// https://git.eeqj.de/sneak/webhooker/issues/256.
+
+// fSweepSetup seeds the main database with the webhook row the sweep
+// enumerates, and returns the setup.
+func fSweepSetup(
+	t *testing.T, targetID, name string,
+) iSetup {
+	t.Helper()
+
+	s := newISetup(t)
+
+	iCreateTarget(t, s.MainDB, targetID,
+		s.WebhookID, name,
+		database.TargetTypeLog, "", 0,
+	)
+
+	require.NoError(t, s.MainDB.Create(&database.Webhook{
+		BaseModel: database.BaseModel{ID: s.WebhookID},
+		UserID:    uuid.New().String(),
+		Name:      name,
+	}).Error)
+
+	return s
+}
+
+// fDrain collects every task the engine has queued.
+//
+// Every caller drives the dispatch paths synchronously and has already
+// waited for them to return, so anything they queued is in the channel
+// by now. The short grace covers nothing but scheduler jitter, and is
+// kept small because one of these tests runs the drain forty times.
+func fDrain(e *delivery.Engine) []delivery.Task {
+	var out []delivery.Task
+
+	for {
+		select {
+		case task := <-e.ExportDeliveryCh():
+			out = append(out, task)
+		case task := <-e.ExportRetryCh():
+			out = append(out, task)
+		case <-time.After(25 * time.Millisecond):
+			return out
+		}
+	}
+}
+
+// TestArchiveHandleIsWAL closes the last gap in the durability
+// evidence: the main and per-webhook tiers each assert their journal
+// mode on a live handle, and the archive tier gets its settings from
+// the same code path but nothing checked the running file.
+func TestArchiveHandleIsWAL(t *testing.T) {
+	t.Parallel()
+
+	w := delivery.NewExportArchiveWriter(
+		filepath.Join(t.TempDir(), "archive-wal.db"),
+		archiveTestLogger(), 0,
+	)
+
+	require.NoError(t, w.Open(0))
+
+	var mode string
+
+	row := w.DB().Raw("pragma journal_mode").Row()
+	require.NoError(t, row.Scan(&mode))
+	assert.Equal(t, "wal", strings.ToLower(mode))
+
+	var busy string
+
+	row = w.DB().Raw("pragma busy_timeout").Row()
+	require.NoError(t, row.Scan(&busy))
+	assert.Equal(t, "10000", busy)
+}
+
+// TestSweepLeavesAQueuedDeliveryAlone is the case the age bound cannot
+// see. The delivery is queued and untouched, so its row is arbitrarily
+// old and still perfectly healthy; only ownership distinguishes it
+// from a stranded one.
+func TestSweepLeavesAQueuedDeliveryAlone(t *testing.T) {
+	t.Parallel()
+
+	targetID := uuid.New().String()
+	s := fSweepSetup(t, targetID, "queued")
+
+	event := iSeedEvent(
+		t, s.WebhookDB, s.WebhookID, `{"queued":true}`,
+	)
+
+	d := iSeedDelivery(
+		t, s.WebhookDB, event.ID, targetID,
+		database.DeliveryStatusPending,
+	)
+	rAgePending(t, s.WebhookDB, d.ID)
+
+	// Queued exactly as the receiver queues it, and never dequeued:
+	// no workers are running in this engine.
+	s.Engine.Notify([]delivery.Task{{
+		DeliveryID: d.ID,
+		EventID:    event.ID,
+		WebhookID:  s.WebhookID,
+		TargetID:   targetID,
+	}})
+
+	require.Equal(t, 1, s.Engine.ExportInflightHeld())
+
+	s.Engine.ExportSweepWebhookRetries(
+		context.Background(), s.WebhookID,
+	)
+
+	tasks := fDrain(s.Engine)
+	assert.Len(
+		t, tasks, 1,
+		"the sweep must not queue a delivery that is "+
+			"already waiting for a worker",
+	)
+}
+
+// TestRecoveryAndSweepDoNotDoubleDispatch drives the two entry points
+// the engine starts concurrently against one aged pending row. Before
+// ownership they both dispatched it.
+func TestRecoveryAndSweepDoNotDoubleDispatch(t *testing.T) {
+	t.Parallel()
+
+	targetID := uuid.New().String()
+	s := fSweepSetup(t, targetID, "racing")
+
+	event := iSeedEvent(
+		t, s.WebhookDB, s.WebhookID, `{"racing":true}`,
+	)
+
+	ctx := context.Background()
+
+	for range 40 {
+		d := iSeedDelivery(
+			t, s.WebhookDB, event.ID, targetID,
+			database.DeliveryStatusPending,
+		)
+		rAgePending(t, s.WebhookDB, d.ID)
+
+		var wg sync.WaitGroup
+
+		wg.Go(func() {
+			s.Engine.ExportRecoverPendingDeliveries(
+				ctx, s.WebhookDB, s.WebhookID,
+			)
+		})
+		wg.Go(func() {
+			s.Engine.ExportSweepWebhookRetries(
+				ctx, s.WebhookID,
+			)
+		})
+		wg.Wait()
+
+		tasks := fDrain(s.Engine)
+		require.Len(
+			t, tasks, 1,
+			"delivery %s dispatched %d times",
+			d.ID, len(tasks),
+		)
+
+		// No worker runs in this engine, so the reference the winner
+		// took is never released and earlier iterations' deliveries
+		// stay owned — which is itself the property under test, since
+		// both paths see them on every subsequent pass.
+	}
+}
+
+// TestConcurrentClaimsOfOneDeliveryYieldOneOwner exercises the
+// exclusion directly, rather than arguing it from a SQL predicate.
+func TestConcurrentClaimsOfOneDeliveryYieldOneOwner(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	eng := newISetup(t).Engine
+	deliveryID := uuid.New().String()
+
+	var (
+		wg  sync.WaitGroup
+		mu  sync.Mutex
+		won int
+	)
+
+	for range 64 {
+		wg.Go(func() {
+			if eng.ExportRetainDelivery(deliveryID) {
+				mu.Lock()
+				won++
+				mu.Unlock()
+			}
+		})
+	}
+
+	wg.Wait()
+
+	assert.Equal(t, 1, won)
+	assert.Equal(t, 1, eng.ExportInflightHeld())
+}
+
+// TestOwnershipIsReleasedAfterDelivery guards the other direction: a
+// leaked reference hides a delivery from every sweep for the life of
+// the process.
+func TestOwnershipIsReleasedAfterDelivery(t *testing.T) {
+	t.Parallel()
+
+	s := newISetup(t)
+	targetID := uuid.New().String()
+
+	iCreateTarget(t, s.MainDB, targetID,
+		s.WebhookID, "released",
+		database.TargetTypeLog, "", 0,
+	)
+
+	event := iSeedEvent(
+		t, s.WebhookDB, s.WebhookID, `{"released":true}`,
+	)
+
+	d := iSeedDelivery(
+		t, s.WebhookDB, event.ID, targetID,
+		database.DeliveryStatusPending,
+	)
+
+	s.Engine.ExportStart()
+
+	defer func() {
+		require.NoError(
+			t, s.Engine.ExportStop(context.Background()),
+		)
+	}()
+
+	body := `{"released":true}`
+
+	s.Engine.Notify([]delivery.Task{{
+		DeliveryID:   d.ID,
+		EventID:      event.ID,
+		WebhookID:    s.WebhookID,
+		TargetID:     targetID,
+		TargetName:   "released",
+		TargetType:   database.TargetTypeLog,
+		Body:         &body,
+		EntrypointID: event.EntrypointID,
+	}})
+
+	iWaitForDelivered(t, s.WebhookDB, d.ID)
+
+	assert.Eventually(
+		t,
+		func() bool {
+			return s.Engine.ExportInflightHeld() == 0
+		},
+		2*time.Second, 20*time.Millisecond,
+		"the delivery stayed owned after it was delivered",
+	)
+}
+
+// TestRetryingRecoverySkipsASuccessfulResult is the retrying-side twin
+// of the pending reconcile. A second attempt that reached the receiver
+// and whose status write then failed sits at retrying holding a
+// successful result, and re-sending it is the same duplicate.
+func TestRetryingRecoverySkipsASuccessfulResult(t *testing.T) {
+	t.Parallel()
+
+	targetID := uuid.New().String()
+	s := fSweepSetup(t, targetID, "retry-settled")
+
+	event := iSeedEvent(
+		t, s.WebhookDB, s.WebhookID, `{"retry":true}`,
+	)
+
+	d := iSeedDelivery(
+		t, s.WebhookDB, event.ID, targetID,
+		database.DeliveryStatusRetrying,
+	)
+	rSeedResult(t, s.WebhookDB, d.ID, 1, false)
+	rSeedResult(t, s.WebhookDB, d.ID, 2, true)
+
+	s.Engine.ExportRecoverRetryingDeliveries(
+		s.WebhookDB, s.WebhookID,
+	)
+
+	assert.Empty(
+		t, fDrain(s.Engine),
+		"a retrying delivery holding a successful result "+
+			"must not be sent again",
+	)
+
+	iAssertStatus(
+		t, s.WebhookDB, d.ID,
+		database.DeliveryStatusDelivered,
+	)
+}
+
+// TestRetryingSweepSkipsASuccessfulResult is the same rule on the
+// periodic sweep's retrying arm.
+func TestRetryingSweepSkipsASuccessfulResult(t *testing.T) {
+	t.Parallel()
+
+	targetID := uuid.New().String()
+	s := fSweepSetup(t, targetID, "retry-swept")
+
+	event := iSeedEvent(
+		t, s.WebhookDB, s.WebhookID, `{"swept":true}`,
+	)
+
+	d := iSeedDelivery(
+		t, s.WebhookDB, event.ID, targetID,
+		database.DeliveryStatusRetrying,
+	)
+	rSeedResult(t, s.WebhookDB, d.ID, 1, false)
+	rSeedResult(t, s.WebhookDB, d.ID, 2, true)
+
+	s.Engine.ExportSweepWebhookRetries(
+		context.Background(), s.WebhookID,
+	)
+
+	assert.Empty(t, fDrain(s.Engine))
+
+	iAssertStatus(
+		t, s.WebhookDB, d.ID,
+		database.DeliveryStatusDelivered,
+	)
+
+	var attempts int64
+
+	require.NoError(t, s.WebhookDB.
+		Model(&database.DeliveryResult{}).
+		Where("delivery_id = ?", d.ID).
+		Count(&attempts).Error)
+	assert.Equal(
+		t, int64(2), attempts,
+		"settling must not invent an attempt",
+	)
+}
+
+// TestScheduledRetryIsNotSweptDuringBackoff closes the window between
+// a target scheduling a retry and the timer firing. The row says
+// retrying and nothing is running, which is exactly what an orphaned
+// retry looks like from the database.
+func TestScheduledRetryIsNotSweptDuringBackoff(t *testing.T) {
+	t.Parallel()
+
+	targetID := uuid.New().String()
+	s := fSweepSetup(t, targetID, "backoff")
+
+	event := iSeedEvent(
+		t, s.WebhookDB, s.WebhookID, `{"backoff":true}`,
+	)
+
+	d := iSeedDelivery(
+		t, s.WebhookDB, event.ID, targetID,
+		database.DeliveryStatusRetrying,
+	)
+
+	s.Engine.ExportScheduleRetry(delivery.Task{
+		DeliveryID: d.ID,
+		EventID:    event.ID,
+		WebhookID:  s.WebhookID,
+		TargetID:   targetID,
+		AttemptNum: 2,
+	}, time.Hour)
+
+	require.Equal(t, 1, s.Engine.ExportInflightHeld())
+
+	s.Engine.ExportSweepWebhookRetries(
+		context.Background(), s.WebhookID,
+	)
+
+	assert.Empty(
+		t, fDrain(s.Engine),
+		"the sweep must not duplicate a retry that is "+
+			"already scheduled",
+	)
+}
+
+// TestRedispatchStampsTheRow pins the cadence control: a stranded
+// delivery that has just been handed out is not selected again by the
+// next tick a minute later.
+func TestRedispatchStampsTheRow(t *testing.T) {
+	t.Parallel()
+
+	targetID := uuid.New().String()
+	s := fSweepSetup(t, targetID, "stamped")
+
+	event := iSeedEvent(
+		t, s.WebhookDB, s.WebhookID, `{"stamped":true}`,
+	)
+
+	d := iSeedDelivery(
+		t, s.WebhookDB, event.ID, targetID,
+		database.DeliveryStatusPending,
+	)
+	rAgePending(t, s.WebhookDB, d.ID)
+
+	ctx := context.Background()
+
+	s.Engine.ExportSweepWebhookRetries(ctx, s.WebhookID)
+	require.Len(t, fDrain(s.Engine), 1)
+
+	var row database.Delivery
+
+	require.NoError(t, s.WebhookDB.
+		First(&row, "id = ?", d.ID).Error)
+	assert.WithinDuration(
+		t, time.Now(), row.UpdatedAt, time.Minute,
+		"a re-dispatched delivery must be stamped so the "+
+			"next tick does not select it again",
+	)
+}

internal/delivery/metrics_test.go

@@ -229,6 +229,13 @@ func mExhaustRetries(t *testing.T, s iSetup) {
 	body := event.Body
 	cfg := iHTTPConfig(ts.URL)
 
+	// The retry below is only run if its target still exists; see
+	// https://git.eeqj.de/sneak/webhooker/issues/107.
+	iCreateTarget(
+		t, s.MainDB, targetID, s.WebhookID, "metrics-fail",
+		database.TargetTypeHTTP, cfg, 2,
+	)
+
 	first := iTask(
 		d, event, s.WebhookID, targetID,
 		"metrics-fail", cfg, 2, 1, &body,
@@ -289,6 +296,13 @@ func TestDeliveryMetrics_CircuitBreakerGauge(t *testing.T) {
 	// rather than the budget is what stops the delivery.
 	maxRetries := delivery.ExportDefaultFailureThreshold + 5
 
+	// The retries below are only run if their target still exists;
+	// see https://git.eeqj.de/sneak/webhooker/issues/107.
+	iCreateTarget(
+		t, s.MainDB, targetID, s.WebhookID, "metrics-trip",
+		database.TargetTypeHTTP, cfg, maxRetries,
+	)
+
 	first := iTask(
 		d, event, s.WebhookID, targetID,
 		"metrics-trip", cfg, maxRetries, 1, &body,
@@ -353,6 +367,11 @@ func TestDeliveryMetrics_BreakerBlockedIsNotAnAttempt(
 	cfg := iHTTPConfig(ts.URL)
 	maxRetries := delivery.ExportDefaultFailureThreshold + 5
 
+	iCreateTarget(
+		t, s.MainDB, targetID, s.WebhookID, "metrics-blocked",
+		database.TargetTypeHTTP, cfg, maxRetries,
+	)
+
 	first := iTask(
 		d, event, s.WebhookID, targetID,
 		"metrics-blocked", cfg, maxRetries, 1, &body,

internal/delivery/queue_depth_gormlog_test.go

@@ -3,8 +3,6 @@ package delivery_test
 import (
 	"bytes"
 	"context"
-	"database/sql"
-	"fmt"
 	"log/slog"
 	"net/http"
 	"path/filepath"
@@ -54,12 +52,10 @@ func (q *qdSyncBuf) String() string {
 func qdMainDB(t *testing.T, log *slog.Logger) *gorm.DB {
 	t.Helper()
 
-	dsn := fmt.Sprintf(
-		"file:%s?cache=shared&mode=rwc",
+	sqlDB, err := database.OpenSQLite(
 		filepath.Join(t.TempDir(), "main-gormlog.db"),
+		database.SQLiteModeCreate,
 	)
-
-	sqlDB, err := sql.Open("sqlite", dsn)
 	require.NoError(t, err)
 
 	t.Cleanup(func() { _ = sqlDB.Close() })

internal/delivery/recovery_durability_test.go

@@ -0,0 +1,378 @@
+package delivery_test
+
+import (
+	"context"
+	"net/http"
+	"net/http/httptest"
+	"sync/atomic"
+	"testing"
+	"time"
+
+	"github.com/google/uuid"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	"gorm.io/gorm"
+	"sneak.berlin/go/webhooker/internal/database"
+	"sneak.berlin/go/webhooker/internal/delivery"
+)
+
+// These tests cover the delivery half of
+// https://git.eeqj.de/sneak/webhooker/issues/256: a delivery that
+// reached its receiver but whose bookkeeping write failed used to be
+// left at pending and re-sent on the next restart, giving the receiver
+// a second copy while the event log recorded one attempt.
+
+// rSeedResult records a DeliveryResult against a delivery, standing in
+// for the attempt row the send path writes before the status.
+func rSeedResult(
+	t *testing.T,
+	db *gorm.DB,
+	deliveryID string,
+	attemptNum int,
+	success bool,
+) {
+	t.Helper()
+
+	require.NoError(t, db.Create(&database.DeliveryResult{
+		DeliveryID: deliveryID,
+		AttemptNum: attemptNum,
+		Success:    success,
+	}).Error)
+}
+
+// rAgePending backdates a delivery past the sweep's age bound, which is
+// what separates a stranded delivery from one a worker still holds.
+func rAgePending(
+	t *testing.T, db *gorm.DB, deliveryID string,
+) {
+	t.Helper()
+
+	old := time.Now().Add(
+		-2 * delivery.ExportPendingSweepMinAge,
+	)
+
+	require.NoError(t, db.Model(&database.Delivery{}).
+		Where("id = ?", deliveryID).
+		UpdateColumn("updated_at", old).Error)
+}
+
+func TestRecoverySkipsPendingWithSuccessfulResult(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	s := newISetup(t)
+	targetID := uuid.New().String()
+
+	iCreateTarget(t, s.MainDB, targetID,
+		s.WebhookID, "already-delivered",
+		database.TargetTypeLog, "", 0,
+	)
+
+	event := iSeedEvent(
+		t, s.WebhookDB, s.WebhookID, `{"delivered":true}`,
+	)
+
+	// The delivery whose send succeeded and whose result row landed:
+	// only the status write failed, so it sits at pending.
+	done := iSeedDelivery(
+		t, s.WebhookDB, event.ID, targetID,
+		database.DeliveryStatusPending,
+	)
+	rSeedResult(t, s.WebhookDB, done.ID, 1, true)
+
+	// A delivery that was genuinely never attempted.
+	fresh := iSeedDelivery(
+		t, s.WebhookDB, event.ID, targetID,
+		database.DeliveryStatusPending,
+	)
+
+	s.Engine.ExportRecoverPendingDeliveries(
+		context.Background(), s.WebhookDB, s.WebhookID,
+	)
+
+	select {
+	case task := <-s.Engine.ExportDeliveryCh():
+		assert.Equal(
+			t, fresh.ID, task.DeliveryID,
+			"only the unattempted delivery may be re-sent",
+		)
+	case <-time.After(2 * time.Second):
+		t.Fatal("expected the unattempted delivery")
+	}
+
+	select {
+	case task := <-s.Engine.ExportDeliveryCh():
+		t.Fatalf(
+			"re-sent an already delivered delivery: %s",
+			task.DeliveryID,
+		)
+	case <-time.After(200 * time.Millisecond):
+	}
+
+	// It is settled rather than merely skipped: leaving it pending
+	// would strand it again on the next sweep.
+	iAssertStatus(
+		t, s.WebhookDB, done.ID,
+		database.DeliveryStatusDelivered,
+	)
+}
+
+// TestRecoveryContinuesTheAttemptNumbering pins the audit trail: a
+// recovered delivery that already recorded two attempts is re-sent as
+// attempt three, not as attempt one again.
+func TestRecoveryContinuesTheAttemptNumbering(t *testing.T) {
+	t.Parallel()
+
+	s := newISetup(t)
+	targetID := uuid.New().String()
+
+	iCreateTarget(t, s.MainDB, targetID,
+		s.WebhookID, "numbering",
+		database.TargetTypeLog, "", 0,
+	)
+
+	event := iSeedEvent(
+		t, s.WebhookDB, s.WebhookID, `{"numbering":true}`,
+	)
+
+	d := iSeedDelivery(
+		t, s.WebhookDB, event.ID, targetID,
+		database.DeliveryStatusPending,
+	)
+
+	rSeedResult(t, s.WebhookDB, d.ID, 1, false)
+	rSeedResult(t, s.WebhookDB, d.ID, 2, false)
+
+	s.Engine.ExportRecoverPendingDeliveries(
+		context.Background(), s.WebhookDB, s.WebhookID,
+	)
+
+	select {
+	case task := <-s.Engine.ExportDeliveryCh():
+		assert.Equal(t, d.ID, task.DeliveryID)
+		assert.Equal(t, 3, task.AttemptNum)
+	case <-time.After(2 * time.Second):
+		t.Fatal("expected the delivery to be recovered")
+	}
+}
+
+// TestSweepRecoversStrandedPending is the half that removes the
+// restart requirement: a delivery left at pending is picked up by the
+// periodic sweep.
+func TestSweepRecoversStrandedPending(t *testing.T) {
+	t.Parallel()
+
+	targetID := uuid.New().String()
+	s := fSweepSetup(t, targetID, "stranded")
+
+	event := iSeedEvent(
+		t, s.WebhookDB, s.WebhookID, `{"stranded":true}`,
+	)
+
+	stranded := iSeedDelivery(
+		t, s.WebhookDB, event.ID, targetID,
+		database.DeliveryStatusPending,
+	)
+	rAgePending(t, s.WebhookDB, stranded.ID)
+
+	// A delivery a worker may still be holding: young, and therefore
+	// none of the sweep's business.
+	inFlight := iSeedDelivery(
+		t, s.WebhookDB, event.ID, targetID,
+		database.DeliveryStatusPending,
+	)
+
+	s.Engine.ExportSweepWebhookRetries(
+		context.Background(), s.WebhookID,
+	)
+
+	select {
+	case task := <-s.Engine.ExportDeliveryCh():
+		assert.Equal(t, stranded.ID, task.DeliveryID)
+	case <-time.After(2 * time.Second):
+		t.Fatal("expected the stranded delivery")
+	}
+
+	select {
+	case task := <-s.Engine.ExportDeliveryCh():
+		t.Fatalf(
+			"swept an in-flight delivery: %s",
+			task.DeliveryID,
+		)
+	case <-time.After(200 * time.Millisecond):
+	}
+
+	iAssertStatus(
+		t, s.WebhookDB, inFlight.ID,
+		database.DeliveryStatusPending,
+	)
+}
+
+// TestSweepClaimsAStrandedDeliveryOnlyOnce guards the repeat the sweep
+// would otherwise be: the row stays pending for as long as the attempt
+// runs, and a sweep a minute later must not send it a second time.
+func TestSweepClaimsAStrandedDeliveryOnlyOnce(t *testing.T) {
+	t.Parallel()
+
+	targetID := uuid.New().String()
+	s := fSweepSetup(t, targetID, "claimed")
+
+	event := iSeedEvent(
+		t, s.WebhookDB, s.WebhookID, `{"claimed":true}`,
+	)
+
+	d := iSeedDelivery(
+		t, s.WebhookDB, event.ID, targetID,
+		database.DeliveryStatusPending,
+	)
+	rAgePending(t, s.WebhookDB, d.ID)
+
+	ctx := context.Background()
+
+	s.Engine.ExportSweepWebhookRetries(ctx, s.WebhookID)
+
+	select {
+	case task := <-s.Engine.ExportDeliveryCh():
+		assert.Equal(t, d.ID, task.DeliveryID)
+	case <-time.After(2 * time.Second):
+		t.Fatal("expected the stranded delivery")
+	}
+
+	// The delivery is still pending — nothing has run it yet — but
+	// the claim must keep the next sweep off it.
+	iAssertStatus(
+		t, s.WebhookDB, d.ID,
+		database.DeliveryStatusPending,
+	)
+
+	s.Engine.ExportSweepWebhookRetries(ctx, s.WebhookID)
+
+	select {
+	case task := <-s.Engine.ExportDeliveryCh():
+		t.Fatalf(
+			"sent a claimed delivery again: %s",
+			task.DeliveryID,
+		)
+	case <-time.After(200 * time.Millisecond):
+	}
+}
+
+// TestSweepSettlesStrandedPendingWithoutResending is the sweep's own
+// version of the reconcile: a stranded delivery holding a successful
+// result is settled where it stands, and the receiver hears nothing.
+func TestSweepSettlesStrandedPendingWithoutResending(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	targetID := uuid.New().String()
+	s := fSweepSetup(t, targetID, "settled")
+
+	event := iSeedEvent(
+		t, s.WebhookDB, s.WebhookID, `{"settled":true}`,
+	)
+
+	d := iSeedDelivery(
+		t, s.WebhookDB, event.ID, targetID,
+		database.DeliveryStatusPending,
+	)
+	rSeedResult(t, s.WebhookDB, d.ID, 1, true)
+	rAgePending(t, s.WebhookDB, d.ID)
+
+	s.Engine.ExportSweepWebhookRetries(
+		context.Background(), s.WebhookID,
+	)
+
+	select {
+	case task := <-s.Engine.ExportDeliveryCh():
+		t.Fatalf(
+			"re-sent a delivery that already succeeded: %s",
+			task.DeliveryID,
+		)
+	case <-time.After(200 * time.Millisecond):
+	}
+
+	iAssertStatus(
+		t, s.WebhookDB, d.ID,
+		database.DeliveryStatusDelivered,
+	)
+
+	var attempts int64
+
+	require.NoError(t, s.WebhookDB.
+		Model(&database.DeliveryResult{}).
+		Where("delivery_id = ?", d.ID).
+		Count(&attempts).Error)
+	assert.Equal(
+		t, int64(1), attempts,
+		"settling must not invent an attempt",
+	)
+}
+
+// TestFailedResultWriteLeavesDeliveryRecoverable is the rule the
+// targets now follow: a bookkeeping write that fails must not advance
+// the status, because pending and retrying are the states the sweeps
+// recover and delivered is a claim the database refused to record.
+func TestFailedResultWriteLeavesDeliveryRecoverable(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	s := newISetup(t)
+	targetID := uuid.New().String()
+
+	var hits atomic.Int64
+
+	ts := httptest.NewServer(http.HandlerFunc(
+		func(w http.ResponseWriter, _ *http.Request) {
+			hits.Add(1)
+			w.WriteHeader(http.StatusOK)
+		},
+	))
+	defer ts.Close()
+
+	event := iSeedEvent(
+		t, s.WebhookDB, s.WebhookID, `{"unwritable":true}`,
+	)
+
+	d := iSeedDelivery(
+		t, s.WebhookDB, event.ID, targetID,
+		database.DeliveryStatusPending,
+	)
+
+	// Drop the table the attempt row goes in, so the send succeeds
+	// and only the bookkeeping write fails.
+	require.NoError(
+		t,
+		s.WebhookDB.Exec("drop table delivery_results").Error,
+	)
+
+	full := &database.Delivery{
+		EventID:  event.ID,
+		TargetID: targetID,
+		Status:   database.DeliveryStatusPending,
+		Event:    event,
+		Target: database.Target{
+			Name:   "unwritable",
+			Type:   database.TargetTypeHTTP,
+			Config: iHTTPConfig(ts.URL),
+		},
+	}
+	full.ID = d.ID
+
+	s.Engine.ExportDeliverHTTP(
+		context.Background(), s.WebhookDB, full,
+		&delivery.Task{DeliveryID: d.ID, AttemptNum: 1},
+	)
+
+	assert.Equal(
+		t, int64(1), hits.Load(),
+		"the send itself must still happen",
+	)
+
+	iAssertStatus(
+		t, s.WebhookDB, d.ID,
+		database.DeliveryStatusPending,
+	)
+}

internal/delivery/redirect_test.go

@@ -170,7 +170,8 @@ func TestDelivery_CrossOriginRedirectDropsOriginScopedHeaders(
 // Stripping must not fire within the configured origin, or every
 // destination that redirects its own path would lose its
 // credential and start answering 401 — and would lose the inbound
-// signature the receiver verifies.
+// signature header the target endpoint verifies. webhooker's own
+// receiver verifies no signature; it only forwards the header.
 func TestDelivery_SameOriginRedirectKeepsOriginScopedHeaders(
 	t *testing.T,
 ) {

internal/delivery/target_database.go

@@ -58,12 +58,17 @@ func (t *databaseTarget) Deliver(
 			"error", err,
 		)
 
-		t.eng.recordResult(
+		recErr := t.eng.recordResult(
 			webhookDB, d, 1, false, 0, "",
 			err.Error(), elapsed.Milliseconds(),
 		)
+		if recErr != nil {
+			t.eng.bookkeepingFailed(d, recErr)
 
-		t.eng.updateDeliveryStatus(
+			return
+		}
+
+		t.eng.settleStatus(
 			webhookDB, d, d.Target.Type,
 			database.DeliveryStatusFailed,
 		)
@@ -71,12 +76,17 @@ func (t *databaseTarget) Deliver(
 		return
 	}
 
-	t.eng.recordResult(
+	recErr := t.eng.recordResult(
 		webhookDB, d, 1, true, 0, "", "",
 		elapsed.Milliseconds(),
 	)
+	if recErr != nil {
+		t.eng.bookkeepingFailed(d, recErr)
 
-	t.eng.updateDeliveryStatus(
+		return
+	}
+
+	t.eng.settleStatus(
 		webhookDB, d, d.Target.Type,
 		database.DeliveryStatusDelivered,
 	)

internal/delivery/target_database_archive.go

@@ -1,7 +1,6 @@
 package delivery
 
 import (
-	"database/sql"
 	"encoding/json"
 	"errors"
 	"fmt"
@@ -12,6 +11,7 @@ import (
 
 	"gorm.io/driver/sqlite"
 	"gorm.io/gorm"
+	"sneak.berlin/go/webhooker/internal/database"
 	"sneak.berlin/go/webhooker/internal/gormlog"
 )
 
@@ -30,13 +30,13 @@ const (
 	// path: open the archive file, creating it if missing, so a
 	// first write (or a write after the operator moved the file
 	// away) recreates it.
-	archiveModeCreate = "rwc"
+	archiveModeCreate = database.SQLiteModeCreate
 
 	// archiveModeExisting is the SQLite URI mode used by the idle
 	// sweep: open read-write but never create. A sweep must never
 	// conjure an empty archive file for a webhook that has a
 	// database target but has never received an event.
-	archiveModeExisting = "rw"
+	archiveModeExisting = database.SQLiteModeExisting
 )
 
 var (
@@ -273,9 +273,11 @@ func (w *archiveWriter) open(expiry time.Duration) error {
 func (w *archiveWriter) openMode(
 	mode string, expiry time.Duration,
 ) error {
-	dbURL := fmt.Sprintf("file:%s?mode=%s", w.path, mode)
-
-	sqlDB, err := sql.Open("sqlite", dbURL)
+	// Opened through database.OpenSQLite so an archive file carries
+	// the same WAL journaling, busy timeout, immediate-transaction
+	// locking, and pool bounds as every other database file. See
+	// internal/database/sqlite_open.go.
+	sqlDB, err := database.OpenSQLite(w.path, mode)
 	if err != nil {
 		return fmt.Errorf(
 			"opening archive database %s: %w", w.path, err,

internal/delivery/target_http.go

@@ -77,14 +77,19 @@ func (c *httpCore) fireAndForget(
 ) {
 	c.eng.observeAttempt(d.Target.Type, res.elapsed())
 
-	c.eng.recordResult(
+	err := c.eng.recordResult(
 		webhookDB, d, 1, res.success,
 		res.statusCode, res.respBody, res.errMsg,
 		res.duration,
 	)
+	if err != nil {
+		c.eng.bookkeepingFailed(d, err)
+
+		return
+	}
 
 	if res.success {
-		c.eng.updateDeliveryStatus(
+		c.eng.settleStatus(
 			webhookDB, d, d.Target.Type,
 			database.DeliveryStatusDelivered,
 		)
@@ -92,7 +97,7 @@ func (c *httpCore) fireAndForget(
 		return
 	}
 
-	c.eng.updateDeliveryStatus(
+	c.eng.settleStatus(
 		webhookDB, d, d.Target.Type,
 		database.DeliveryStatusFailed,
 	)
@@ -122,16 +127,25 @@ func (c *httpCore) withRetry(
 
 	c.eng.observeAttempt(d.Target.Type, res.elapsed())
 
-	c.eng.recordResult(
+	err := c.eng.recordResult(
 		webhookDB, d, attemptNum, res.success,
 		res.statusCode, res.respBody, res.errMsg,
 		res.duration,
 	)
+	if err != nil {
+		// The breaker still learns the outcome: it describes the
+		// target's health, which is unaffected by this database's.
+		c.recordCircuitOutcome(cb, res.success)
+
+		c.eng.bookkeepingFailed(d, err)
+
+		return
+	}
 
 	if res.success {
 		cb.RecordSuccess()
 
-		c.eng.updateDeliveryStatus(
+		c.eng.settleStatus(
 			webhookDB, d, d.Target.Type,
 			database.DeliveryStatusDelivered,
 		)
@@ -146,6 +160,20 @@ func (c *httpCore) withRetry(
 	)
 }
 
+// recordCircuitOutcome feeds one attempt's outcome to the target's
+// circuit breaker.
+func (c *httpCore) recordCircuitOutcome(
+	cb *CircuitBreaker, success bool,
+) {
+	if success {
+		cb.RecordSuccess()
+
+		return
+	}
+
+	cb.RecordFailure()
+}
+
 func (c *httpCore) circuitBreakerBlock(
 	webhookDB *gorm.DB,
 	d *database.Delivery,
@@ -169,7 +197,7 @@ func (c *httpCore) circuitBreakerBlock(
 		"cooldown_remaining", remaining,
 	)
 
-	c.eng.updateDeliveryStatus(
+	c.eng.settleStatus(
 		webhookDB, d, d.Target.Type,
 		database.DeliveryStatusRetrying,
 	)
@@ -189,7 +217,7 @@ func (c *httpCore) handleRetry(
 	attemptNum int,
 ) {
 	if attemptNum >= maxRetries {
-		c.eng.updateDeliveryStatus(
+		c.eng.settleStatus(
 			webhookDB, d, d.Target.Type,
 			database.DeliveryStatusFailed,
 		)
@@ -197,7 +225,7 @@ func (c *httpCore) handleRetry(
 		return
 	}
 
-	c.eng.updateDeliveryStatus(
+	c.eng.settleStatus(
 		webhookDB, d, d.Target.Type,
 		database.DeliveryStatusRetrying,
 	)
@@ -332,12 +360,17 @@ func (t *httpTarget) Deliver(
 			"error", err,
 		)
 
-		t.eng.recordResult(
+		recErr := t.eng.recordResult(
 			webhookDB, d, task.AttemptNum,
 			false, 0, "", err.Error(), 0,
 		)
+		if recErr != nil {
+			t.eng.bookkeepingFailed(d, recErr)
 
-		t.eng.updateDeliveryStatus(
+			return
+		}
+
+		t.eng.settleStatus(
 			webhookDB, d, d.Target.Type,
 			database.DeliveryStatusFailed,
 		)

internal/delivery/target_log.go

@@ -55,12 +55,17 @@ func (t *logTarget) Deliver(
 
 	t.eng.observeAttempt(d.Target.Type, elapsed)
 
-	t.eng.recordResult(
+	err := t.eng.recordResult(
 		webhookDB, d, 1, true, 0, "", "",
 		elapsed.Milliseconds(),
 	)
+	if err != nil {
+		t.eng.bookkeepingFailed(d, err)
 
-	t.eng.updateDeliveryStatus(
+		return
+	}
+
+	t.eng.settleStatus(
 		webhookDB, d, d.Target.Type,
 		database.DeliveryStatusDelivered,
 	)

internal/delivery/target_slack.go

@@ -95,12 +95,17 @@ func (t *slackTarget) failConfig(
 	d *database.Delivery,
 	err error,
 ) {
-	t.eng.recordResult(
+	recErr := t.eng.recordResult(
 		webhookDB, d, 1,
 		false, 0, "", err.Error(), 0,
 	)
+	if recErr != nil {
+		t.eng.bookkeepingFailed(d, recErr)
 
-	t.eng.updateDeliveryStatus(
+		return
+	}
+
+	t.eng.settleStatus(
 		webhookDB, d, d.Target.Type,
 		database.DeliveryStatusFailed,
 	)
@@ -226,10 +231,15 @@ func FormatSlackMessage(
 		event.ContentType,
 	)
 
+	timestamp := "unknown"
+	if !event.CreatedAt.IsZero() {
+		timestamp = event.CreatedAt.UTC().Format(time.RFC3339)
+	}
+
 	fmt.Fprintf(
 		&b,
 		"*Timestamp:* `%s`\n",
-		event.CreatedAt.UTC().Format(time.RFC3339),
+		timestamp,
 	)
 
 	fmt.Fprintf(

internal/delivery/terminal_state_test.go

@@ -0,0 +1,531 @@
+package delivery_test
+
+import (
+	"context"
+	"net/http"
+	"net/http/httptest"
+	"sync/atomic"
+	"testing"
+
+	"github.com/google/uuid"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	"sneak.berlin/go/webhooker/internal/database"
+	"sneak.berlin/go/webhooker/internal/delivery"
+)
+
+// The two terminal-state gaps of
+// https://git.eeqj.de/sneak/webhooker/issues/107: a delivery failed
+// with nothing in its event log to say why, and a retrying delivery
+// whose target was deleted, which used to keep sending and then never
+// terminalise.
+
+// tUnknownType is a target type no build implements. It stands in for
+// a target whose type was written by a build that knew a type this one
+// does not.
+const tUnknownType = database.TargetType("pubsub")
+
+// tSeedDeletedTarget creates a target, a retrying delivery against it
+// with one recorded failed attempt, and then deletes the target the
+// way the source page does.
+//
+// It asserts the delete is soft, because that is the whole reason the
+// engine could not tell a deleted target from a target id that never
+// named a row: the surviving row is invisible to a scoped read.
+func tSeedDeletedTarget(
+	t *testing.T,
+	s iSetup,
+	name, url string,
+) string {
+	t.Helper()
+
+	targetID := uuid.New().String()
+
+	iCreateTarget(
+		t, s.MainDB, targetID, s.WebhookID, name,
+		database.TargetTypeHTTP, iHTTPConfig(url), 5,
+	)
+
+	event := iSeedEvent(
+		t, s.WebhookDB, s.WebhookID, `{"target":"deleted"}`,
+	)
+
+	d := iSeedDelivery(
+		t, s.WebhookDB, event.ID, targetID,
+		database.DeliveryStatusRetrying,
+	)
+
+	iSeedFailedResult(t, s.WebhookDB, d.ID)
+
+	require.NoError(t, s.MainDB.Delete(
+		&database.Target{}, "id = ?", targetID,
+	).Error)
+
+	var scoped, unscoped int64
+
+	require.NoError(t, s.MainDB.
+		Model(&database.Target{}).
+		Where("id = ?", targetID).
+		Count(&scoped).Error)
+
+	require.NoError(t, s.MainDB.Unscoped().
+		Model(&database.Target{}).
+		Where("id = ?", targetID).
+		Count(&unscoped).Error)
+
+	require.Zero(t, scoped,
+		"the deleted target is still visible to a scoped read",
+	)
+	require.Equal(t, int64(1), unscoped,
+		"the delete was hard, so this test proves nothing about "+
+			"the soft-delete case it exists for",
+	)
+
+	return d.ID
+}
+
+// tLastResult returns a delivery's final recorded attempt, asserting
+// the expected number of them.
+func tLastResult(
+	t *testing.T,
+	s iSetup,
+	deliveryID string,
+	want int,
+) database.DeliveryResult {
+	t.Helper()
+
+	results := iResults(t, s.WebhookDB, deliveryID)
+	require.Len(t, results, want)
+
+	return results[want-1]
+}
+
+// --- 1. A failure with nothing recorded ---
+
+func TestProcessDelivery_UnknownTargetType_RecordsWhy(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	s := newISetup(t)
+
+	targetID := uuid.New().String()
+
+	event := iSeedEvent(
+		t, s.WebhookDB, s.WebhookID, `{"unknown":"type"}`,
+	)
+
+	seeded := iSeedDelivery(
+		t, s.WebhookDB, event.ID, targetID,
+		database.DeliveryStatusPending,
+	)
+
+	target := database.Target{
+		Name:   "mystery",
+		Type:   tUnknownType,
+		Config: iHTTPConfig("http://example.com/hook"),
+	}
+	target.ID = targetID
+
+	d := database.Delivery{
+		EventID:  event.ID,
+		TargetID: targetID,
+		Status:   database.DeliveryStatusPending,
+		Event:    event,
+		Target:   target,
+	}
+	d.ID = seeded.ID
+
+	body := event.Body
+	task := iTask(
+		seeded, event, s.WebhookID, targetID, "mystery",
+		target.Config, 0, 1, &body,
+	)
+	task.TargetType = tUnknownType
+
+	s.Engine.ExportProcessDelivery(
+		context.Background(), s.WebhookDB, &d, &task,
+	)
+
+	iAssertStatus(
+		t, s.WebhookDB, d.ID, database.DeliveryStatusFailed,
+	)
+
+	last := tLastResult(t, s, d.ID, 1)
+
+	assert.False(t, last.Success)
+	assert.Equal(t, 1, last.AttemptNum)
+	assert.Contains(t, last.Error, string(tUnknownType),
+		"the recorded reason does not name the offending type",
+	)
+}
+
+// --- 2. A retrying delivery whose target is gone ---
+
+func TestRecoverSingleRetry_TargetDeleted(t *testing.T) {
+	t.Parallel()
+
+	s := newISetup(t)
+
+	iCreateWebhook(
+		t, s.MainDB, s.WebhookID, "deleted-target-recovery",
+	)
+
+	deliveryID := tSeedDeletedTarget(
+		t, s, "gone-on-recovery", "http://example.com/hook",
+	)
+
+	s.Engine.ExportRecoverWebhookDeliveries(
+		context.Background(), s.WebhookID,
+	)
+
+	iAssertStatus(
+		t, s.WebhookDB, deliveryID,
+		database.DeliveryStatusFailed,
+	)
+
+	last := tLastResult(t, s, deliveryID, 2)
+
+	assert.False(t, last.Success)
+	assert.Equal(t, 2, last.AttemptNum)
+	assert.Contains(t, last.Error, "gone-on-recovery")
+	assert.Contains(t, last.Error, "was deleted")
+
+	assert.Empty(t, s.Engine.ExportRetryCh(),
+		"a delivery whose target is gone was rescheduled",
+	)
+	assert.Zero(t, s.Engine.ExportInflightHeld(),
+		"the terminal path leaked its ownership reference",
+	)
+}
+
+func TestSweepSingleRetry_TargetDeleted(t *testing.T) {
+	t.Parallel()
+
+	s := newISetup(t)
+
+	iCreateWebhook(
+		t, s.MainDB, s.WebhookID, "deleted-target-sweep",
+	)
+
+	deliveryID := tSeedDeletedTarget(
+		t, s, "gone-on-sweep", "http://example.com/hook",
+	)
+
+	// Twice, because the bug was an error the sweep repeated every
+	// minute for the life of the database: the second sweep must
+	// find nothing left to do.
+	s.Engine.ExportSweepWebhookRetries(
+		context.Background(), s.WebhookID,
+	)
+	s.Engine.ExportSweepWebhookRetries(
+		context.Background(), s.WebhookID,
+	)
+
+	iAssertStatus(
+		t, s.WebhookDB, deliveryID,
+		database.DeliveryStatusFailed,
+	)
+
+	last := tLastResult(t, s, deliveryID, 2)
+
+	assert.Contains(t, last.Error, "gone-on-sweep")
+	assert.Contains(t, last.Error, "was deleted")
+
+	assert.Empty(t, s.Engine.ExportRetryCh())
+	assert.Zero(t, s.Engine.ExportInflightHeld())
+}
+
+// TestSweepSingleRetry_TargetNeverExisted covers the other half of the
+// soft-delete distinction: an id with no row at all, deleted or
+// otherwise, must not be reported as something the operator deleted.
+func TestSweepSingleRetry_TargetNeverExisted(t *testing.T) {
+	t.Parallel()
+
+	s := newISetup(t)
+
+	iCreateWebhook(
+		t, s.MainDB, s.WebhookID, "target-never-existed",
+	)
+
+	targetID := uuid.New().String()
+
+	event := iSeedEvent(
+		t, s.WebhookDB, s.WebhookID, `{"target":"absent"}`,
+	)
+
+	d := iSeedDelivery(
+		t, s.WebhookDB, event.ID, targetID,
+		database.DeliveryStatusRetrying,
+	)
+
+	iSeedFailedResult(t, s.WebhookDB, d.ID)
+
+	s.Engine.ExportSweepWebhookRetries(
+		context.Background(), s.WebhookID,
+	)
+
+	iAssertStatus(
+		t, s.WebhookDB, d.ID, database.DeliveryStatusFailed,
+	)
+
+	last := tLastResult(t, s, d.ID, 2)
+
+	assert.Contains(t, last.Error, targetID)
+	assert.Contains(t, last.Error, "no longer exists")
+	assert.NotContains(t, last.Error, "was deleted",
+		"an id that never named a row was reported as a deletion",
+	)
+}
+
+// TestFailMissingTargetRetry_WritesNoTargetRow holds the new terminal
+// path to the same rule as the existing one: no target row, and so no
+// plaintext target config, may be written into the per-webhook event
+// database. See https://git.eeqj.de/sneak/webhooker/issues/206.
+func TestFailMissingTargetRetry_WritesNoTargetRow(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	s := newISetup(t)
+
+	iCreateWebhook(
+		t, s.MainDB, s.WebhookID, "no-target-row-deleted",
+	)
+
+	hookURL := "https://hooks.slack.com/services/T00/B00/x"
+
+	deliveryID := tSeedDeletedTarget(
+		t, s, "credential-bearing", hookURL,
+	)
+
+	s.Engine.ExportSweepWebhookRetries(
+		context.Background(), s.WebhookID,
+	)
+
+	iAssertStatus(
+		t, s.WebhookDB, deliveryID,
+		database.DeliveryStatusFailed,
+	)
+
+	var configs []string
+
+	require.NoError(t, s.WebhookDB.
+		Table("targets").
+		Pluck("config", &configs).Error)
+
+	assert.Empty(t, configs,
+		"the deleted-target terminal path wrote a target row "+
+			"into the per-webhook event database",
+	)
+}
+
+// --- 3. The scheduled retry chain ---
+
+// tRetryChainSetup wires a counting sink and a retrying delivery
+// against a live target pointing at it, and returns the task a
+// scheduled retry would carry — config and all, snapshotted as
+// ScheduleRetry snapshots it.
+func tRetryChainSetup(
+	t *testing.T,
+	s iSetup,
+	name string,
+	hits *atomic.Int64,
+) (delivery.Task, string) {
+	t.Helper()
+
+	ts := httptest.NewServer(http.HandlerFunc(
+		func(w http.ResponseWriter, _ *http.Request) {
+			hits.Add(1)
+			w.WriteHeader(http.StatusOK)
+		},
+	))
+	t.Cleanup(ts.Close)
+
+	iCreateWebhook(t, s.MainDB, s.WebhookID, name)
+
+	targetID := uuid.New().String()
+	cfg := iHTTPConfig(ts.URL)
+
+	iCreateTarget(
+		t, s.MainDB, targetID, s.WebhookID, name,
+		database.TargetTypeHTTP, cfg, 5,
+	)
+
+	event := iSeedEvent(
+		t, s.WebhookDB, s.WebhookID, `{"chain":"retry"}`,
+	)
+
+	d := iSeedDelivery(
+		t, s.WebhookDB, event.ID, targetID,
+		database.DeliveryStatusRetrying,
+	)
+
+	iSeedFailedResult(t, s.WebhookDB, d.ID)
+
+	body := event.Body
+
+	return iTask(
+		d, event, s.WebhookID, targetID, name, cfg, 5, 2, &body,
+	), targetID
+}
+
+// TestProcessRetryTask_TargetDeleted_MakesNoAttempt is the half the
+// deployability audit found worse than filed: terminalising on
+// recovery and sweep alone leaves the already-scheduled timer chain
+// running, and it holds the target's configuration from before the
+// deletion, so it goes on sending to a destination that was removed.
+func TestProcessRetryTask_TargetDeleted_MakesNoAttempt(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	s := newISetup(t)
+
+	var hits atomic.Int64
+
+	task, targetID := tRetryChainSetup(
+		t, s, "gone-mid-chain", &hits,
+	)
+
+	require.NoError(t, s.MainDB.Delete(
+		&database.Target{}, "id = ?", targetID,
+	).Error)
+
+	s.Engine.ExportProcessRetryTask(
+		context.Background(), &task,
+	)
+
+	assert.Zero(t, hits.Load(),
+		"a scheduled retry fired at a target the operator "+
+			"had already deleted",
+	)
+
+	iAssertStatus(
+		t, s.WebhookDB, task.DeliveryID,
+		database.DeliveryStatusFailed,
+	)
+
+	last := tLastResult(t, s, task.DeliveryID, 2)
+
+	assert.False(t, last.Success)
+	assert.Contains(t, last.Error, "was deleted")
+
+	assert.Zero(t, s.Engine.ExportInflightHeld())
+}
+
+// TestProcessRetryTask_TargetPresent_StillDelivers is the guard's
+// mutation check: a liveness check that refused every retry would pass
+// the test above and break every retry there is.
+func TestProcessRetryTask_TargetPresent_StillDelivers(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	s := newISetup(t)
+
+	var hits atomic.Int64
+
+	task, _ := tRetryChainSetup(t, s, "still-there", &hits)
+
+	s.Engine.ExportProcessRetryTask(
+		context.Background(), &task,
+	)
+
+	assert.Equal(t, int64(1), hits.Load())
+
+	iAssertStatus(
+		t, s.WebhookDB, task.DeliveryID,
+		database.DeliveryStatusDelivered,
+	)
+}
+
+// TestProcessRetryTask_TargetUnreadable_StillDelivers pins the other
+// half of the guard: only a target that is confirmed gone stops a
+// retry. A main database that cannot be read is a transient fault, and
+// a guard that abandoned deliveries on one would be a worse bug than
+// the one it fixes.
+func TestProcessRetryTask_TargetUnreadable_StillDelivers(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	s := newISetup(t)
+
+	var hits atomic.Int64
+
+	task, _ := tRetryChainSetup(t, s, "unreadable-main", &hits)
+
+	sqlDB, err := s.MainDB.DB()
+	require.NoError(t, err)
+	require.NoError(t, sqlDB.Close())
+
+	s.Engine.ExportProcessRetryTask(
+		context.Background(), &task,
+	)
+
+	assert.Equal(t, int64(1), hits.Load(),
+		"a retry was abandoned because the main database "+
+			"could not be read, not because its target was gone",
+	)
+
+	iAssertStatus(
+		t, s.WebhookDB, task.DeliveryID,
+		database.DeliveryStatusDelivered,
+	)
+}
+
+// TestRecoverSingleRetry_TargetUnreadable_LeavesDeliveryAlone is the
+// same rule on the recovery path. A read failure that is not
+// "record not found" must leave every retrying delivery of every
+// webhook exactly as it was.
+func TestRecoverSingleRetry_TargetUnreadable_LeavesDeliveryAlone(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	s := newISetup(t)
+
+	iCreateWebhook(
+		t, s.MainDB, s.WebhookID, "unreadable-on-recovery",
+	)
+
+	targetID := uuid.New().String()
+
+	iCreateTarget(
+		t, s.MainDB, targetID, s.WebhookID, "healthy",
+		database.TargetTypeHTTP,
+		iHTTPConfig("http://example.com/hook"), 5,
+	)
+
+	event := iSeedEvent(
+		t, s.WebhookDB, s.WebhookID, `{"still":"retrying"}`,
+	)
+
+	d := iSeedDelivery(
+		t, s.WebhookDB, event.ID, targetID,
+		database.DeliveryStatusRetrying,
+	)
+
+	iSeedFailedResult(t, s.WebhookDB, d.ID)
+
+	sqlDB, err := s.MainDB.DB()
+	require.NoError(t, err)
+	require.NoError(t, sqlDB.Close())
+
+	s.Engine.ExportRecoverRetryingDeliveries(
+		s.WebhookDB, s.WebhookID,
+	)
+
+	iAssertStatus(
+		t, s.WebhookDB, d.ID,
+		database.DeliveryStatusRetrying,
+	)
+
+	assert.Len(t, iResults(t, s.WebhookDB, d.ID), 1,
+		"an unreadable main database produced a terminal "+
+			"failure row",
+	)
+
+	assert.Zero(t, s.Engine.ExportInflightHeld())
+}

internal/handlers/event_body.go

@@ -92,11 +92,10 @@ func (h *Handlers) HandleEventBodyDownload() http.HandlerFunc {
 // once per range.
 //
 // One consequence is worth keeping in view: the read finishes
-// before the client is written to, so no read lock is held for
-// the length of a slow download. These per-webhook databases
-// run in SQLite's default journal mode rather than WAL, so a
-// lock held that long would block the receiver from recording
-// new events.
+// before the client is written to, so nothing is held open for
+// the length of a slow download. Under WAL a read no longer
+// blocks the receiver, but it does pin the WAL against
+// checkpointing, and a download can last minutes.
 func (h *Handlers) serveEventBody(
 	w http.ResponseWriter,
 	r *http.Request,

internal/handlers/event_resubmit.go

@@ -139,10 +139,10 @@ func (h *Handlers) resubmitEvent(
 	}
 
 	// Read before the write transaction is opened. The body can be up
-	// to the 1 MB ingest cap, and holding a read of it inside the
-	// transaction would extend how long the per-webhook database is
-	// locked against the receiver, which runs these files in
-	// SQLite's default journal mode rather than WAL.
+	// to the 1 MB ingest cap, and every transaction on these files
+	// takes the write lock at BEGIN (_txlock=immediate, see
+	// internal/database/sqlite_open.go), so reading inside it would
+	// hold that lock against the receiver for the length of the read.
 	src, found, err := loadResubmitSource(
 		webhookDB, webhook.ID, eventID.String(),
 	)

internal/handlers/source_detail_baseurl_test.go

@@ -0,0 +1,283 @@
+package handlers_test
+
+import (
+	"context"
+	"crypto/tls"
+	"net/http"
+	"net/http/httptest"
+	"regexp"
+	"testing"
+
+	"github.com/go-chi/chi"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	"sneak.berlin/go/webhooker/internal/database"
+	"sneak.berlin/go/webhooker/internal/handlers"
+	"sneak.berlin/go/webhooker/internal/session"
+)
+
+// The only two schemes a rendered entrypoint URL may carry,
+// whatever the request claimed.
+const (
+	schemeHTTPS = "https"
+	schemeHTTP  = "http"
+)
+
+// entrypointURLPattern captures the entrypoint URL the source
+// detail page renders, which is the operator-visible product of
+// BaseURL. Asserting on the extracted string rather than on a
+// substring of the page proves the raw header value cannot reach
+// the scheme by any route.
+var entrypointURLPattern = regexp.MustCompile(
+	`<code id="entrypoint-url-[^"]*"[^>]*>([^<]*)</code>`,
+)
+
+// baseURLFixture is one started app plus the webhook whose
+// entrypoint URL the BaseURL cases read.
+type baseURLFixture struct {
+	handlers *handlers.Handlers
+	session  *session.Session
+	webhook  string
+	path     string
+}
+
+// newBaseURLFixture starts the app and seeds a webhook with one
+// entrypoint.
+func newBaseURLFixture(t *testing.T) *baseURLFixture {
+	t.Helper()
+
+	var (
+		h    *handlers.Handlers
+		sess *session.Session
+		db   *database.Database
+	)
+
+	app := newTestApp(t, &h, &sess, &db)
+	app.RequireStart()
+
+	t.Cleanup(app.RequireStop)
+
+	wh := seedWebhook(t, db)
+	seedEntrypoint(t, db, wh.ID)
+
+	return &baseURLFixture{
+		handlers: h,
+		session:  sess,
+		webhook:  wh.ID,
+		path:     "ep-" + wh.ID,
+	}
+}
+
+// entrypointURL renders the source detail page for the fixture's
+// webhook over a request the caller shapes, and returns the
+// entrypoint URL as an operator would copy it.
+func (f *baseURLFixture) entrypointURL(
+	t *testing.T,
+	host string,
+	shape func(*http.Request),
+) string {
+	t.Helper()
+
+	req := httptest.NewRequestWithContext(
+		context.Background(),
+		http.MethodGet,
+		"/source/"+f.webhook,
+		nil,
+	)
+	req.Host = host
+
+	shape(req)
+
+	for _, c := range authenticatedCookies(
+		t, f.session, deleteTestUserID, deleteTestUsername,
+	) {
+		req.AddCookie(c)
+	}
+
+	rctx := chi.NewRouteContext()
+	rctx.URLParams.Add(paramSourceID, f.webhook)
+	req = req.WithContext(
+		context.WithValue(
+			req.Context(), chi.RouteCtxKey, rctx,
+		),
+	)
+
+	w := httptest.NewRecorder()
+	f.handlers.HandleSourceDetail().ServeHTTP(w, req)
+
+	require.Equal(t, http.StatusOK, w.Code)
+
+	match := entrypointURLPattern.FindStringSubmatch(w.Body.String())
+	require.Len(
+		t, match, 2,
+		"the page must render exactly one entrypoint URL",
+	)
+
+	return match[1]
+}
+
+// forwardedProto returns a request shaper setting
+// X-Forwarded-Proto, or leaving the request alone for "".
+func forwardedProto(value string) func(*http.Request) {
+	return func(r *http.Request) {
+		if value == "" {
+			return
+		}
+
+		r.Header.Set("X-Forwarded-Proto", value)
+	}
+}
+
+// baseURLCase is one X-Forwarded-Proto spelling and the scheme
+// the rendered entrypoint URL owes it.
+type baseURLCase struct {
+	name   string
+	header string
+	scheme string
+	why    string
+}
+
+// baseURLCases enumerate the spellings a proxy really emits. The
+// scheme is only ever http or https: the header value itself is
+// never a scheme, however it is spelled.
+func baseURLCases() []baseURLCase {
+	return []baseURLCase{
+		{
+			name:   "lowercase",
+			header: schemeHTTPS,
+			scheme: schemeHTTPS,
+			why:    "the ordinary spelling",
+		},
+		{
+			name:   "uppercase",
+			header: "HTTPS",
+			scheme: schemeHTTPS,
+			why: "the token is case-insensitive; the scheme " +
+				"in a copyable URL is not",
+		},
+		{
+			name:   "chain with plaintext inner hop",
+			header: "https, http",
+			scheme: schemeHTTPS,
+			why: "a chained proxy appends its hop; the " +
+				"leftmost element faces the client",
+		},
+		{
+			name:   "chain of two TLS hops",
+			header: "https,https",
+			scheme: schemeHTTPS,
+			why:    "appended chain with no space after the comma",
+		},
+		{
+			name:   "trailing space",
+			header: "https ",
+			scheme: schemeHTTPS,
+			why:    "whitespace is not part of the token",
+		},
+		{
+			name:   "plaintext",
+			header: schemeHTTP,
+			scheme: schemeHTTP,
+			why:    "the negative control: the proxy reports plaintext",
+		},
+		{
+			name:   "no header",
+			header: "",
+			scheme: schemeHTTP,
+			why:    "a plaintext request asserting nothing is http",
+		},
+		{
+			name:   "garbage token",
+			header: "javascript:alert(1)//",
+			scheme: schemeHTTP,
+			why: "anything that is not https is not TLS, and " +
+				"the token never becomes the scheme",
+		},
+	}
+}
+
+// TestSourceDetailBaseURL_ForwardedProtoSpellings is the
+// regression test for the entrypoint URL an operator pastes into
+// the sending system: a header spelling that used to land in the
+// scheme verbatim produced a URL no sender could deliver to.
+func TestSourceDetailBaseURL_ForwardedProtoSpellings(t *testing.T) {
+	t.Parallel()
+
+	const host = "hooks.example.com"
+
+	fixture := newBaseURLFixture(t)
+
+	for _, tc := range baseURLCases() {
+		t.Run(tc.name, func(t *testing.T) {
+			t.Parallel()
+
+			assert.Equal(
+				t,
+				tc.scheme+"://"+host+"/webhook/"+fixture.path,
+				fixture.entrypointURL(
+					t, host, forwardedProto(tc.header),
+				),
+				"X-Forwarded-Proto %q: %s", tc.header, tc.why,
+			)
+		})
+	}
+}
+
+// TestSourceDetailBaseURL_DirectTLSBeatsPlaintextHeader pins the
+// precedence the old code had backwards: it let any present
+// header overwrite what the connection itself proved, so a
+// direct-TLS request behind a proxy reporting http rendered an
+// http URL.
+func TestSourceDetailBaseURL_DirectTLSBeatsPlaintextHeader(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	const host = "hooks.example.com"
+
+	fixture := newBaseURLFixture(t)
+
+	got := fixture.entrypointURL(t, host, func(r *http.Request) {
+		r.TLS = &tls.ConnectionState{}
+		r.Header.Set("X-Forwarded-Proto", "http")
+	})
+
+	assert.Equal(
+		t,
+		"https://"+host+"/webhook/"+fixture.path,
+		got,
+		"a connection this process terminated with TLS "+
+			"outranks a header claiming plaintext",
+	)
+}
+
+// TestSourceDetailBaseURL_KeepsHostAuthority pins the host half
+// of the URL: it is taken from the request unchanged, so the
+// deployments that do not sit on port 443 still get a URL that
+// works. Constraining the host would break exactly these.
+func TestSourceDetailBaseURL_KeepsHostAuthority(t *testing.T) {
+	t.Parallel()
+
+	fixture := newBaseURLFixture(t)
+
+	hosts := []string{
+		"hooks.example.com:8443",
+		"[2001:db8::1]:8443",
+		"internal-host",
+	}
+
+	for _, host := range hosts {
+		t.Run(host, func(t *testing.T) {
+			t.Parallel()
+
+			assert.Equal(
+				t,
+				"https://"+host+"/webhook/"+fixture.path,
+				fixture.entrypointURL(
+					t, host, forwardedProto("HTTPS"),
+				),
+				"the authority must survive verbatim, port and all",
+			)
+		})
+	}
+}

internal/handlers/source_management.go

@@ -13,6 +13,7 @@ import (
 	"gorm.io/gorm"
 	"sneak.berlin/go/webhooker/internal/database"
 	"sneak.berlin/go/webhooker/internal/delivery"
+	"sneak.berlin/go/webhooker/internal/reqtls"
 )
 
 // WebhookListItem holds data for the webhook list view.
@@ -427,16 +428,16 @@ func (h *Handlers) renderSourceDetail(
 		}
 	}
 
-	host := r.Host
-	scheme := "https"
-
-	if r.TLS == nil {
-		scheme = "http"
+	scheme := "http"
+	if reqtls.IsTLS(r) {
+		scheme = "https"
 	}
 
-	if fwdProto := r.Header.Get("X-Forwarded-Proto"); fwdProto != "" {
-		scheme = fwdProto
-	}
+	// The host is the client's Host header, unvalidated. It is
+	// inert only because source_detail.html renders BaseURL as
+	// text inside a <code> element; putting it in an href or any
+	// other URL context needs it constrained first.
+	baseURL := scheme + "://" + r.Host
 
 	// The template calls Webhook methods, which take pointer
 	// receivers; html/template cannot address a value stored in a map.
@@ -448,7 +449,7 @@ func (h *Handlers) renderSourceDetail(
 		"Entrypoints": NewEntrypointViews(entrypoints),
 		"Targets":     delivery.NewTargetViews(targets),
 		"Events":      events,
-		"BaseURL":     scheme + "://" + host,
+		"BaseURL":     baseURL,
 	}
 
 	h.renderTemplate(w, r, "source_detail.html", data)

internal/server/bind_address_test.go

@@ -0,0 +1,336 @@
+package server_test
+
+import (
+	"context"
+	"net"
+	"net/http"
+	"strconv"
+	"testing"
+	"time"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	"go.uber.org/fx"
+	"sneak.berlin/go/webhooker/internal/config"
+	"sneak.berlin/go/webhooker/internal/globals"
+	"sneak.berlin/go/webhooker/internal/server"
+)
+
+const (
+	// loopbackV4 is the shipped BIND_ADDRESS default.
+	loopbackV4 = "127.0.0.1"
+
+	// wildcardV4 is the value a container deployment must set,
+	// where a loopback-bound process is unreachable from outside
+	// its network namespace even with a published port.
+	wildcardV4 = "0.0.0.0"
+
+	// unavailableAddr is a TEST-NET-1 address (RFC 5737). It is a
+	// well-formed literal that no host is assigned, so binding it
+	// fails with EADDRNOTAVAIL rather than succeeding somewhere
+	// unexpected.
+	unavailableAddr = "192.0.2.1"
+
+	// listenReadyTimeout bounds the wait for the listener to accept
+	// connections. The bind itself is immediate; this only covers
+	// goroutine scheduling.
+	listenReadyTimeout = 3 * time.Second
+
+	// listenPollInterval is how often the readiness wait retries.
+	listenPollInterval = 10 * time.Millisecond
+
+	// dialTimeout bounds a single connection attempt in these
+	// tests. Everything dialled here is on this host, so a dial
+	// that is not answered immediately is a failure, not slowness.
+	dialTimeout = time.Second
+)
+
+// freePort returns a TCP port that is free on every local address at
+// the moment it returns, by taking one on the wildcard and releasing
+// it. The window between release and re-bind is the standard one
+// every "pick a free port" helper carries.
+func freePort(t *testing.T) int {
+	t.Helper()
+
+	var listenCfg net.ListenConfig
+
+	l, err := listenCfg.Listen(t.Context(), "tcp", "0.0.0.0:0")
+	require.NoError(t, err)
+
+	addr, ok := l.Addr().(*net.TCPAddr)
+	require.True(t, ok, "listener is not TCP")
+	require.NoError(t, l.Close())
+
+	return addr.Port
+}
+
+// otherLocalAddr returns a local IPv4 address that is not
+// loopbackV4, or skips the test when the host has none.
+//
+// The bind-address tests need a second address of this host to stand
+// in for "another interface": what a wildcard bind claims and a
+// loopback bind does not. 127.0.0.2 is that address on Linux, where
+// the whole 127.0.0.0/8 is local; elsewhere an interface address is
+// used instead. Each candidate is proven bindable before it is
+// returned, so a host that offers neither skips rather than fails on
+// something that was never about the code under test.
+func otherLocalAddr(t *testing.T) string {
+	t.Helper()
+
+	candidates := []string{"127.0.0.2"}
+
+	ifaceAddrs, err := net.InterfaceAddrs()
+	require.NoError(t, err)
+
+	for _, a := range ifaceAddrs {
+		ipNet, ok := a.(*net.IPNet)
+		if !ok {
+			continue
+		}
+
+		ip4 := ipNet.IP.To4()
+		if ip4 == nil || ip4.String() == loopbackV4 {
+			continue
+		}
+
+		candidates = append(candidates, ip4.String())
+	}
+
+	var listenCfg net.ListenConfig
+
+	for _, candidate := range candidates {
+		l, listenErr := listenCfg.Listen(
+			t.Context(), "tcp", net.JoinHostPort(candidate, "0"),
+		)
+		if listenErr != nil {
+			continue
+		}
+
+		require.NoError(t, l.Close())
+
+		return candidate
+	}
+
+	t.Skip("host has no second local IPv4 address to bind")
+
+	return ""
+}
+
+// startBoundServer starts the wired app with the given bind address
+// on a free port and returns that port. The app is stopped on
+// cleanup.
+func startBoundServer(t *testing.T, bindAddress string) int {
+	t.Helper()
+
+	port := freePort(t)
+
+	env := newTestEnv(t)
+	env.cfg.BindAddress = bindAddress
+	env.cfg.Port = port
+
+	app := fx.New(
+		fx.NopLogger,
+		fx.Supply(env.log, env.cfg, env.mw, env.hnd),
+		fx.Provide(globals.New, server.New),
+		fx.Invoke(func(*server.Server) {}),
+	)
+
+	startCtx, cancelStart := context.WithTimeout(
+		context.Background(), lifecycleTimeout,
+	)
+	defer cancelStart()
+
+	require.NoError(t, app.Start(startCtx))
+
+	t.Cleanup(func() {
+		stopCtx, cancelStop := context.WithTimeout(
+			context.Background(), lifecycleTimeout,
+		)
+		defer cancelStop()
+
+		require.NoError(t, app.Stop(stopCtx))
+	})
+
+	return port
+}
+
+// dialable reports whether a TCP connection to addr succeeds.
+func dialable(ctx context.Context, addr string) bool {
+	dialer := net.Dialer{Timeout: dialTimeout}
+
+	conn, err := dialer.DialContext(ctx, "tcp", addr)
+	if err != nil {
+		return false
+	}
+
+	_ = conn.Close()
+
+	return true
+}
+
+// requireDialable waits for addr to accept connections, failing the
+// test if it never does.
+func requireDialable(t *testing.T, addr string) {
+	t.Helper()
+
+	deadline := time.Now().Add(listenReadyTimeout)
+	for time.Now().Before(deadline) {
+		if dialable(t.Context(), addr) {
+			return
+		}
+
+		time.Sleep(listenPollInterval)
+	}
+
+	t.Fatalf("nothing accepted connections on %s", addr)
+}
+
+// TestListenAddr pins how BindAddress and Port are rendered into the
+// listen address.
+//
+// The defect this covers was a bare fmt.Sprintf(":%d", port), which
+// binds every interface with no way to say otherwise. The IPv6 rows
+// are here because an unbracketed IPv6 host would produce an address
+// net.Listen rejects, turning a valid configuration into a startup
+// failure.
+func TestListenAddr(t *testing.T) {
+	t.Parallel()
+
+	tests := []struct {
+		name        string
+		bindAddress string
+		port        int
+		expected    string
+	}{
+		{
+			name:        "loopback default",
+			bindAddress: loopbackV4,
+			port:        8080,
+			expected:    "127.0.0.1:8080",
+		},
+		{
+			name:        "ipv4 wildcard",
+			bindAddress: wildcardV4,
+			port:        8080,
+			expected:    "0.0.0.0:8080",
+		},
+		{
+			name:        "ipv6 wildcard is bracketed",
+			bindAddress: "::",
+			port:        8080,
+			expected:    "[::]:8080",
+		},
+		{
+			name:        "ipv6 literal is bracketed",
+			bindAddress: "2001:db8::5",
+			port:        9001,
+			expected:    "[2001:db8::5]:9001",
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			t.Parallel()
+
+			assert.Equal(t, tt.expected, server.ListenAddrForTest(
+				&config.Config{
+					BindAddress: tt.bindAddress,
+					Port:        tt.port,
+				},
+			))
+		})
+	}
+}
+
+// TestBindAddress_LoopbackIsNotOnOtherAddresses proves the fix end to
+// end: with BIND_ADDRESS at its loopback default, the cleartext
+// listener answers on loopback and has not claimed any other address
+// of this host.
+//
+// The second address is proven free by binding it on the same port
+// while the server runs. That is the assertion that fails against the
+// old wildcard bind — a wildcard listener owns the port on every
+// address, so this bind would return EADDRINUSE. Dialling from
+// another machine is what the operator cares about, and this is the
+// in-process form of it: the socket the remote host would connect to
+// does not exist.
+func TestBindAddress_LoopbackIsNotOnOtherAddresses(t *testing.T) {
+	t.Parallel()
+
+	other := otherLocalAddr(t)
+	port := startBoundServer(t, loopbackV4)
+
+	// Positive control: the service really is up and serving.
+	requireDialable(t, net.JoinHostPort(loopbackV4, strconv.Itoa(port)))
+
+	var listenCfg net.ListenConfig
+
+	l, err := listenCfg.Listen(
+		t.Context(), "tcp",
+		net.JoinHostPort(other, strconv.Itoa(port)),
+	)
+	require.NoError(
+		t, err,
+		"port %d on %s is taken while bound to %s: the listener "+
+			"claimed more than its configured address",
+		port, other, loopbackV4,
+	)
+
+	require.NoError(t, l.Close())
+}
+
+// TestBindAddress_WildcardReachesOtherAddresses is the counterpart:
+// the value a container deployment sets does reach the addresses the
+// default withholds. Without this, a loopback-only bind would pass
+// the test above by never listening at all.
+func TestBindAddress_WildcardReachesOtherAddresses(t *testing.T) {
+	t.Parallel()
+
+	other := otherLocalAddr(t)
+	port := startBoundServer(t, wildcardV4)
+
+	requireDialable(t, net.JoinHostPort(other, strconv.Itoa(port)))
+}
+
+// TestBindAddress_ServesRequestsOnConfiguredAddress proves the bound
+// listener serves the application rather than merely accepting TCP,
+// so a bind address that is honoured cannot be mistaken for one that
+// is honoured and broken.
+func TestBindAddress_ServesRequestsOnConfiguredAddress(t *testing.T) {
+	t.Parallel()
+
+	port := startBoundServer(t, loopbackV4)
+	addr := net.JoinHostPort(loopbackV4, strconv.Itoa(port))
+	requireDialable(t, addr)
+
+	req, err := http.NewRequestWithContext(
+		t.Context(), http.MethodGet,
+		"http://"+addr+"/.well-known/healthcheck", nil,
+	)
+	require.NoError(t, err)
+
+	client := &http.Client{Timeout: dialTimeout}
+
+	resp, err := client.Do(req)
+	require.NoError(t, err)
+
+	defer func() { _ = resp.Body.Close() }()
+
+	assert.Equal(t, http.StatusOK, resp.StatusCode)
+}
+
+// TestBindAddress_UnavailableAddressShutsDownTheApp covers the half
+// of the fail-loud rule that configuration parsing cannot reach. A
+// syntactically valid address that is not assigned to this host
+// parses fine and fails at bind time, after fx has already reported
+// RUNNING. It must end the process non-zero rather than leave it
+// alive with nothing listening.
+func TestBindAddress_UnavailableAddressShutsDownTheApp(t *testing.T) {
+	t.Parallel()
+
+	env := newTestEnv(t)
+	env.cfg.BindAddress = unavailableAddr
+	env.cfg.Port = freePort(t)
+
+	requireListenFailureExit(t, env)
+}

internal/server/early_shutdown_test.go

@@ -0,0 +1,91 @@
+package server_test
+
+import (
+	"context"
+	"testing"
+
+	"github.com/stretchr/testify/require"
+	"go.uber.org/fx"
+	"sneak.berlin/go/webhooker/internal/globals"
+	"sneak.berlin/go/webhooker/internal/server"
+)
+
+// earlyStopIterations is how many start/stop cycles the race test
+// runs. The window it aims at is the gap between the OnStart hook
+// returning and the serving goroutine reaching its first field
+// access, which is microseconds wide. The race detector reports an
+// unsynchronised pair whenever it observes one, but it has to observe
+// one, so a single cycle can miss purely on scheduling. Repetition
+// makes the observation reliable; the collaborators are built once,
+// so the cycles themselves are cheap.
+const earlyStopIterations = 25
+
+// TestEarlyShutdown_NoPanicAndNoRace stops the application
+// immediately after starting it, before the serving goroutine has
+// necessarily run at all.
+//
+// Two defects live in that window. The OnStart hook returns as soon
+// as it has spawned the serving goroutine, so fx runs the stop
+// sequence against a Server whose serving goroutine may not have
+// executed a single line. cleanShutdown called Shutdown on an
+// httpServer that goroutine was supposed to assign, which was a nil
+// dereference on an early SIGTERM; and it read httpServer and
+// sentryEnabled with nothing ordering those reads against the
+// goroutine's writes, which is a data race that only surfaces once
+// something both starts and stops the server. Nothing did before this
+// test: the listen-failure test never binds, and the router tests
+// bypass the lifecycle entirely.
+//
+// httpServer is now built in New, on the constructing goroutine, so
+// it is written before any hook exists and can never be nil.
+// sentryEnabled is atomic. This test is what catches either one
+// coming back — under -race, which is how the suite runs.
+func TestEarlyShutdown_NoPanicAndNoRace(t *testing.T) {
+	t.Parallel()
+
+	// Built once: the collaborators are not what is under test, and
+	// standing up a database per iteration would make repetition too
+	// expensive to be worth having.
+	env := newTestEnv(t)
+	env.cfg.BindAddress = loopbackV4
+
+	for range earlyStopIterations {
+		requireStartStopIsClean(t, env)
+	}
+}
+
+// requireStartStopIsClean runs one start/stop cycle with no wait in
+// between, failing the test if either half errors.
+//
+// Each cycle gets a fresh fx app, so the Server under test is
+// constructed anew every time — that construction is where the
+// httpServer write now happens, and reusing one Server would test it
+// only once.
+func requireStartStopIsClean(t *testing.T, env *testEnv) {
+	t.Helper()
+
+	env.cfg.Port = freePort(t)
+
+	app := fx.New(
+		fx.NopLogger,
+		fx.Supply(env.log, env.cfg, env.mw, env.hnd),
+		fx.Provide(globals.New, server.New),
+		fx.Invoke(func(*server.Server) {}),
+	)
+
+	startCtx, cancelStart := context.WithTimeout(
+		context.Background(), lifecycleTimeout,
+	)
+	defer cancelStart()
+
+	require.NoError(t, app.Start(startCtx))
+
+	// No sleep and no readiness wait: stopping while the serving
+	// goroutine is still in flight is the whole point.
+	stopCtx, cancelStop := context.WithTimeout(
+		context.Background(), lifecycleTimeout,
+	)
+	defer cancelStop()
+
+	require.NoError(t, app.Stop(stopCtx))
+}

internal/server/export_test.go

@@ -55,6 +55,16 @@ func NewRouterForTest(
 	return s.router
 }
 
+// ListenAddrForTest exposes the address the HTTP listener binds for
+// a given Config, so the rendering of host and port — IPv6
+// bracketing above all — can be pinned without standing up a
+// listener.
+func ListenAddrForTest(cfg *config.Config) string {
+	s := &Server{params: ServerParams{Config: cfg}}
+
+	return s.listenAddr()
+}
+
 // ProbePattern is the route NewRouterWithProbeForTest adds to the
 // production route tree.
 const ProbePattern = "/probe"
@@ -84,8 +94,8 @@ func NewRouterWithProbeForTest(
 		mw:     mw,
 		h:      h,
 		params: ServerParams{Config: cfg},
-		sentryEnabled: sentryEnabled,
 	}
+	s.sentryEnabled.Store(sentryEnabled)
 	s.SetupRoutes()
 	s.router.Handle(ProbePattern, probe)
 

internal/server/http.go

@@ -2,8 +2,9 @@ package server
 
 import (
 	"errors"
-	"fmt"
+	"net"
 	"net/http"
+	"strconv"
 	"time"
 )
 
@@ -24,26 +25,52 @@ const (
 	httpMaxHeaderBytes = 1 << 20
 )
 
-func (s *Server) serveUntilShutdown() {
-	listenAddr := fmt.Sprintf(":%d", s.params.Config.Port)
-	s.httpServer = &http.Server{
-		Addr:           listenAddr,
+// listenAddr renders the address the HTTP listener binds.
+//
+// The host half is always present: an empty host would be the
+// wildcard, and the whole point of BIND_ADDRESS is that binding every
+// interface is a choice the operator makes rather than one the
+// process makes for them. Config guarantees a literal, so
+// JoinHostPort's bracketing is enough to make IPv6 well formed.
+func (s *Server) listenAddr() string {
+	return net.JoinHostPort(
+		s.params.Config.BindAddress,
+		strconv.Itoa(s.params.Config.Port),
+	)
+}
+
+// newHTTPServer builds the HTTP server for this Server's
+// configuration.
+//
+// It is called from New, on the constructing goroutine, rather than
+// from the serving goroutine that used to assign s.httpServer
+// directly. Two goroutines reach that field — the serving goroutine
+// and the fx stop hook, which calls Shutdown on it — with nothing
+// ordering them. Constructing it during New puts the write before
+// every hook fx will later run, which both removes the race and rules
+// out the nil dereference a stop that arrived before the serving
+// goroutine had run would have caused.
+func (s *Server) newHTTPServer() *http.Server {
+	return &http.Server{
+		Addr:           s.listenAddr(),
 		ReadTimeout:    httpReadTimeout,
 		WriteTimeout:   httpWriteTimeout,
 		MaxHeaderBytes: httpMaxHeaderBytes,
 		Handler:        s,
 	}
+}
 
+func (s *Server) serveUntilShutdown() {
 	// add routes
 	// this does any necessary setup in each handler
 	s.SetupRoutes()
 
-	s.log.Info("http begin listen", "listenaddr", listenAddr)
+	s.log.Info("http begin listen", "listenaddr", s.httpServer.Addr)
 
 	err := s.httpServer.ListenAndServe()
 	if err != nil && !errors.Is(err, http.ErrServerClosed) {
 		s.log.Error("listen error", "error", err)
-		s.shutdownOnListenFailure()
+		s.shutdownWithFailure()
 	}
 }
 

internal/server/listen_failure_test.go

@@ -36,9 +36,9 @@ const lifecycleTimeout = 15 * time.Second
 //
 // The port is occupied by a listener this test holds open, on a
 // kernel-chosen port, so the failure is the real EADDRINUSE the
-// operator hits when a second instance starts. Loopback is enough to
-// collide with the server's wildcard bind: a listening socket on a
-// specific address blocks the wildcard from claiming the same port.
+// operator hits when a second instance starts. The server is pointed
+// at the same loopback address, so the collision is a direct one on
+// the exact address it asks the kernel for.
 func TestListenFailure_ShutsDownTheApp(t *testing.T) {
 	t.Parallel()
 
@@ -55,11 +55,27 @@ func TestListenFailure_ShutsDownTheApp(t *testing.T) {
 	require.True(t, ok, "listener is not TCP")
 
 	// The collaborators come from the wired graph rather than stubs,
-	// so the Server under test is the one that ships. Only the port
-	// is test-specific.
+	// so the Server under test is the one that ships. Only the
+	// listen address is test-specific.
 	env := newTestEnv(t)
+	env.cfg.BindAddress = loopbackV4
 	env.cfg.Port = addr.Port
 
+	requireListenFailureExit(t, env)
+}
+
+// requireListenFailureExit starts the wired app over env and asserts
+// that it gives up on its own with the listen-failure status, then
+// completes its stop sequence.
+//
+// Two different listen failures share it — a port already in use and
+// an address that is not on this host — because what has to hold for
+// both is the same: the failure is discovered after fx has already
+// reported RUNNING, so the only thing that can turn it into a visible
+// exit is the shutdown path under test.
+func requireListenFailureExit(t *testing.T, env *testEnv) {
+	t.Helper()
+
 	app := fx.New(
 		fx.NopLogger,
 		fx.Supply(env.log, env.cfg, env.mw, env.hnd),
@@ -77,7 +93,7 @@ func TestListenFailure_ShutsDownTheApp(t *testing.T) {
 	select {
 	case sig := <-app.Wait():
 		require.Equal(
-			t, server.ListenFailureExitCode, sig.ExitCode,
+			t, server.StartupFailureExitCode, sig.ExitCode,
 			"listen failure must exit non-zero",
 		)
 	case <-time.After(listenFailureDeadline):

internal/server/routes.go

@@ -81,7 +81,7 @@ func (s *Server) setupGlobalMiddleware() {
 	// Sentry error reporting (if SENTRY_DSN is set). Repanic is
 	// true so panics still bubble up to the Recoverer middleware
 	// registered immediately above.
-	if s.sentryEnabled {
+	if s.sentryEnabled.Load() {
 		sentryHandler := sentryhttp.New(sentryhttp.Options{
 			Repanic: true,
 		})

internal/server/sentry_failure_test.go

@@ -0,0 +1,99 @@
+package server_test
+
+import (
+	"context"
+	"net"
+	"strconv"
+	"testing"
+	"time"
+
+	"github.com/stretchr/testify/require"
+	"go.uber.org/fx"
+	"sneak.berlin/go/webhooker/internal/config"
+	"sneak.berlin/go/webhooker/internal/globals"
+	"sneak.berlin/go/webhooker/internal/server"
+)
+
+// TestSentryInitFailure_ShutsDownTheApp pins that error reporting
+// which is configured and cannot be started ends the application
+// instead of serving without it.
+//
+// The measured defect logged `sentry init failure` and kept running,
+// so the deployment served traffic with reporting off while every
+// other signal — SENTRY_DSN still set, the startup summary's own
+// field — said it was on. Nothing later in the process can notice
+// that reports are going nowhere, which is why this exits rather than
+// degrades.
+//
+// The DSN is placed on a hand-built Config, which is the only way to
+// reach this branch at all: loadFromEnv now parses SENTRY_DSN with
+// sentry.NewDsn, the same call sentry.Init makes, so a DSN that
+// survives configuration cannot fail initialisation in the SDK
+// version this pins. The branch stays because that is a property of
+// the SDK's current implementation rather than of its contract.
+func TestSentryInitFailure_ShutsDownTheApp(t *testing.T) {
+	t.Parallel()
+
+	port := freePort(t)
+
+	env := newTestEnvWithConfig(t, &config.Config{
+		DataDir:     t.TempDir(),
+		Environment: config.EnvironmentDev,
+		BindAddress: loopbackV4,
+		Port:        port,
+		SentryDSN:   "not-a-dsn",
+	})
+
+	app := fx.New(
+		fx.NopLogger,
+		fx.Supply(env.log, env.cfg, env.mw, env.hnd),
+		fx.Provide(globals.New, server.New),
+		fx.Invoke(func(*server.Server) {}),
+	)
+
+	startCtx, cancelStart := context.WithTimeout(
+		context.Background(), lifecycleTimeout,
+	)
+	defer cancelStart()
+
+	require.NoError(t, app.Start(startCtx))
+
+	select {
+	case sig := <-app.Wait():
+		require.Equal(
+			t, server.StartupFailureExitCode, sig.ExitCode,
+			"a sentry failure must exit non-zero",
+		)
+	case <-time.After(listenFailureDeadline):
+		t.Fatal("a sentry failure left the app running")
+	}
+
+	// The stop sequence still has to complete: the failure must reach
+	// shutdown through fx rather than around it.
+	stopCtx, cancelStop := context.WithTimeout(
+		context.Background(), lifecycleTimeout,
+	)
+	defer cancelStop()
+
+	require.NoError(t, app.Stop(stopCtx))
+
+	// And it must give up before it listens. A process that bound the
+	// port and then exited would have accepted requests it could not
+	// report on, which is the state under test in miniature.
+	requireBindable(t, port)
+}
+
+// requireBindable asserts that the port is free, which it is only if
+// the server under test never claimed it.
+func requireBindable(t *testing.T, port int) {
+	t.Helper()
+
+	var listenCfg net.ListenConfig
+
+	listener, err := listenCfg.Listen(
+		t.Context(), "tcp",
+		net.JoinHostPort(loopbackV4, strconv.Itoa(port)),
+	)
+	require.NoError(t, err, "the server bound a port it then gave up")
+	require.NoError(t, listener.Close())
+}

internal/server/server.go

@@ -9,6 +9,7 @@ import (
 	"net/http"
 	"os"
 	"os/signal"
+	"sync/atomic"
 	"syscall"
 	"time"
 
@@ -50,12 +51,13 @@ const (
 	minSentryFlush = 250 * time.Millisecond
 )
 
-// ListenFailureExitCode is the status the process exits with when the
-// HTTP listener cannot be established, or dies for a reason other
-// than a requested shutdown. It must stay non-zero: systemd
-// `Restart=on-failure` and Docker's restart policies key off it, and a
-// zero exit would read as a deliberate stop.
-const ListenFailureExitCode = 1
+// StartupFailureExitCode is the status the process exits with when
+// the serving goroutine gives up: the HTTP listener cannot be
+// established or dies for a reason other than a requested shutdown, or
+// error reporting is configured and cannot be started. It must stay
+// non-zero: systemd `Restart=on-failure` and Docker's restart policies
+// key off it, and a zero exit would read as a deliberate stop.
+const StartupFailureExitCode = 1
 
 // SentryFlushBudget reports how long the Sentry flush may run when
 // remaining is the time left on the fx stop context after the HTTP
@@ -89,7 +91,14 @@ type ServerParams struct {
 // graceful shutdown.
 type Server struct {
 	startupTime time.Time
-	sentryEnabled bool
+
+	// sentryEnabled is written by the serving goroutine, in
+	// enableSentry, and read by the fx stop hook in cleanShutdown.
+	// Nothing orders those two: the OnStart hook returns as soon as
+	// the goroutine is spawned, so a stop can be running while
+	// enableSentry is still deciding. It is atomic to supply the
+	// edge the goroutines do not.
+	sentryEnabled atomic.Bool
 	log           *slog.Logger
 	cancelFunc    context.CancelFunc
 	httpServer    *http.Server
@@ -107,6 +116,7 @@ func New(lc fx.Lifecycle, params ServerParams) (*Server, error) {
 	s.mw = params.Middleware
 	s.h = params.Handlers
 	s.log = params.Logger.Get()
+	s.httpServer = s.newHTTPServer()
 
 	lc.Append(fx.Hook{
 		OnStart: func(_ context.Context) error {
@@ -126,11 +136,25 @@ func New(lc fx.Lifecycle, params ServerParams) (*Server, error) {
 }
 
 // Run configures Sentry and starts serving HTTP requests.
+//
+// A Sentry failure ends the application instead of listening. It runs
+// before the listener rather than after it so that the process never
+// binds a port it is about to give up.
 func (s *Server) Run() {
 	s.configure()
 
 	// logging before sentry, because sentry logs
-	s.enableSentry()
+	err := s.enableSentry()
+	if err != nil {
+		s.log.Error(
+			"SENTRY_DSN is set but error reporting could not be "+
+				"started; refusing to serve with it off",
+			"error", err,
+		)
+		s.shutdownWithFailure()
+
+		return
+	}
 
 	s.serve()
 }
@@ -141,11 +165,23 @@ func (s *Server) MaintenanceMode() bool {
 	return s.params.Config.MaintenanceMode
 }
 
-func (s *Server) enableSentry() {
-	s.sentryEnabled = false
+// enableSentry initialises the Sentry SDK when error reporting is
+// configured, and reports the failure when it is configured and cannot
+// be initialised. A DSN that is not set is not a failure: reporting
+// stays off and the server starts normally.
+//
+// There is no fallback to running with reporting off. An operator who
+// set SENTRY_DSN asked for failures to be visible, and serving traffic
+// with reporting quietly off is the one state nothing can ever tell
+// them about — the DSN is still set, so every later signal says it is
+// on. Config already refused a DSN the SDK cannot parse, which is what
+// a typo produces, so reaching this branch means the SDK refused
+// something that parsed: not a condition to guess at either.
+func (s *Server) enableSentry() error {
+	s.sentryEnabled.Store(false)
 
-	if s.params.Config.SentryDSN == "" {
-		return
+	if !s.params.Config.SentryEnabled() {
+		return nil
 	}
 
 	err := sentry.Init(sentryClientOptions(
@@ -157,19 +193,19 @@ func (s *Server) enableSentry() {
 		),
 	))
 	if err != nil {
-		s.log.Error("sentry init failure", "error", err)
-		// Don't use fatal since we still want the service to run
-		return
+		return fmt.Errorf("initialising sentry: %w", err)
 	}
 
 	s.log.Info("sentry error reporting activated")
-	s.sentryEnabled = true
+	s.sentryEnabled.Store(true)
+
+	return nil
 }
 
 // serve installs the signal watcher, starts the listener and blocks
 // until the server's context is cancelled. The process exit status is
 // fx's to decide — from a signal, or from the code
-// shutdownOnListenFailure hands the Shutdowner — so this reports
+// shutdownWithFailure hands the Shutdowner — so this reports
 // nothing back to its caller.
 func (s *Server) serve() {
 	ctx, cancelFunc := context.WithCancel(context.Background())
@@ -199,20 +235,24 @@ func (s *Server) serve() {
 	// Do not call cleanShutdown() here to avoid double invocation.
 }
 
-// shutdownOnListenFailure ends the application after the HTTP
-// listener failed. The fx OnStart hook returns as soon as the serving
-// goroutine is spawned, so nothing downstream of it ever learns that
-// the listen failed: fx reports RUNNING and the process sits alive
-// with nothing bound, which is invisible to systemd and Docker
-// restart policies. Asking the Shutdowner to stop the app with a
-// non-zero code is what turns that into a visible failure.
+// shutdownWithFailure ends the application non-zero from the serving
+// goroutine. It is how anything on that goroutine fails fatally: the
+// fx OnStart hook returns as soon as the goroutine is spawned, so
+// nothing downstream of it ever learns that the goroutine gave up. fx
+// reports RUNNING and the process sits alive having done neither what
+// it was asked nor anything visible instead, which systemd and
+// Docker restart policies cannot see. Asking the Shutdowner to stop
+// the app with a non-zero code is what turns that into a visible
+// failure, and it is the whole of "fatal" here — no panic, no
+// os.Exit, and every stop hook still runs.
 //
-// The context cancel that follows only unwinds serve()'s own wait.
-// The shutdown itself runs through fx's normal stop sequence, so the
-// clean-shutdown drain in cleanShutdown is reached unchanged.
-func (s *Server) shutdownOnListenFailure() {
+// The context cancel that follows only unwinds serve()'s own wait,
+// and is skipped before serve has installed one. The shutdown itself
+// runs through fx's normal stop sequence, so the clean-shutdown drain
+// in cleanShutdown is reached unchanged.
+func (s *Server) shutdownWithFailure() {
 	err := s.params.Shutdowner.Shutdown(
-		fx.ExitCode(ListenFailureExitCode),
+		fx.ExitCode(StartupFailureExitCode),
 	)
 	if err != nil {
 		s.log.Error("shutdown request failed", "error", err)
@@ -242,7 +282,7 @@ func (s *Server) cleanShutdown(ctx context.Context) {
 
 	s.cleanupForExit()
 
-	if s.sentryEnabled {
+	if s.sentryEnabled.Load() {
 		s.flushSentry(ctx)
 	}
 }