Make SQLite durable under concurrent readers and stop re-delivering stranded webhooks (closes #256)

An operator running `sqlite3 <db> .dump` against their own per-webhook
database wedged it: inbound webhooks rejected with HTTP 500, delivered
webhooks stranded at `pending`, and every one of them POSTed a second
time on the next restart while the event log recorded a single attempt.

Durability. Every SQLite file — main, per-webhook, and archive — now
opens through one path, `internal/database/sqlite_open.go`, in WAL
journal mode with a 10-second busy timeout, `BEGIN IMMEDIATE`
transactions, and a bounded connection pool. WAL is what stops a reader
blocking writers at all. `_txlock=immediate` is what stops a `COMMIT`
failing while its transaction stays open on a pooled connection, which
is how four `database is locked` errors became 593 `cannot start a
transaction within a transaction`. `cache=shared` is gone, because
under it an in-process conflict is SQLITE_LOCKED, which the busy
handler does not retry. The busy timeout is applied before
journal_mode: the driver runs DSN pragmas in order on every new
connection, and `PRAGMA journal_mode` takes a lock, so the reverse
order leaves the one pragma that can block uncovered by the handler
meant to cover it.

Eligibility. `internal/delivery/inflight.go` holds the set of
deliveries the engine owns — taken when a task is queued, when a
target schedules a retry, and by every recovery path before it
re-dispatches; dropped when the worker that ran the task returns.
Recovery and both sweep arms re-dispatch only what the set does not
hold. Nothing decides that from a row's age: a delivery waiting in a
10000-deep channel is arbitrarily old and perfectly healthy, and
reasoning from age re-sends it. `takeForRedispatch` is the single gate
every re-dispatch goes through — ownership first, then a conditional
update confirming the row is still in the status the batch read.

Bookkeeping. `recordResult` and `updateDeliveryStatus` return their
errors instead of logging and dropping them, and a caller whose
bookkeeping write failed writes nothing at all: the delivery keeps
whichever non-terminal status it already held, and the sweeps recover
it. Every recovery path — pending and retrying alike — first settles
any delivery that already holds a successful `DeliveryResult` rather
than sending it again. Recovery continues each delivery's own attempt
numbering instead of restarting at 1. The sweep gains a
`pending`-with-age-bound arm, so a stranded delivery no longer waits
for a restart.

Docs. WAL produces `-wal`/`-shm` sidecars, so the backup and restore
procedures in README.md are corrected against measurement: both
documented procedures were re-run against a live instance, a `-wal`
left by a crash carries data the `.db` alone does not, and an archive
file normally holds its rows in a `-wal` rather than in the `.db`.

README.md

@@ -74,27 +74,41 @@ you can place variables in a `.env` file in the project root (loaded
 automatically via `godotenv/autoload`).
 
 The environment is selected by setting `WEBHOOKER_ENVIRONMENT` to `dev`
-or `prod` (default: `dev`). The setting controls several behaviors:
+or `prod` (default: `dev`). The setting controls exactly one behavior:
 
-| Behavior              | `dev`                            | `prod`                          |
+| Behavior | `dev`                   | `prod`           |
-| --------------------- | -------------------------------- | ------------------------------- |
+| -------- | ----------------------- | ---------------- |
-| CORS                  | Allows any origin (`*`)          | Disabled (no-op)                |
+| CORS     | Allows any origin (`*`) | Disabled (no-op) |
-| Session cookie Secure | `false` (works over plain HTTP)  | `true` (requires HTTPS)         |
 
-The CSRF cookie's `Secure` flag and Origin/Referer validation mode are
+The environment setting does **not** control cookie security. Both the
-determined per-request based on the actual transport protocol, not the
+session cookie and the CSRF cookie get their `Secure` flag, and the
-environment setting. The middleware checks `r.TLS` (direct TLS) and the
+CSRF middleware its Origin/Referer validation mode, from the transport
-`X-Forwarded-Proto` header (TLS-terminating reverse proxy) to decide:
+of each individual request, decided by one predicate —
+`internal/reqtls.IsTLS`. It reports TLS for a direct TLS connection
+(`r.TLS`) or for a TLS-terminating reverse proxy that reports one in
+`X-Forwarded-Proto`:
 
 - **Direct TLS or `X-Forwarded-Proto: https`**: Secure cookies, strict
   Origin/Referer validation.
 - **Plaintext HTTP**: Non-Secure cookies, relaxed Origin/Referer
   checks (token validation still enforced).
 
-This means CSRF protection works correctly in all deployment scenarios:
+The `X-Forwarded-Proto` value is matched case-insensitively on its
-behind a TLS-terminating reverse proxy, with direct TLS, or over plain
+first comma-separated element, trimmed, so `HTTPS` and the appended
-HTTP during development. When running behind a reverse proxy, ensure it
+chains a proxy behind another proxy emits (`https, http`) are all read
-sets the `X-Forwarded-Proto: https` header.
+as TLS.
+
+This means both cookie security and CSRF protection work correctly in
+all deployment scenarios: behind a TLS-terminating reverse proxy, with
+direct TLS, or over plain HTTP during development — a plain-HTTP local
+run gets non-`Secure` cookies and remains usable, and a proxied
+deployment gets `Secure` ones without the operator setting anything.
+When running behind a reverse proxy, ensure it sets the
+`X-Forwarded-Proto: https` header. Unlike `X-Forwarded-For`, this
+header is read from any peer and is **not** gated by
+`TRUSTED_PROXIES`; a correctly configured proxy overwrites whatever a
+client sent. On a listener exposed directly to clients, any client can
+assert it, so do not run one without a proxy in front.
 
 All other differences (log format, security headers, etc.) are
 independent of the environment setting — log format is determined by
@@ -566,9 +580,25 @@ 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
+blocks nothing.
-transient `{name}.db-journal` may exist beside a database while a write
+
-is in flight and is not part of the backup set either.
+**`-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
@@ -576,17 +606,19 @@ 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,
+Every database webhooker opens runs in WAL journal mode. The main and
-so all of them run on SQLite's default rollback journal. There is no
+event databases are also held open for the entire process lifetime —
-WAL. The main and event databases are also held open for the entire
+`WebhookDBManager` caches event database handles and closes them only on
-process lifetime — `WebhookDBManager` caches event database handles and
+webhook deletion or shutdown — so "it looked idle" is not a guarantee
-closes them only on webhook deletion or shutdown — so "it looked idle"
+that nothing was mid-transaction.
-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
+running instance can capture a database and its `-wal` at two different
-that is corrupt or missing state the journal would have rolled back. Use
+instants and yield a file that is corrupt or missing state. Copying a
-one of the two procedures below instead.
+`.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:
@@ -605,8 +637,9 @@ for db in /path/to/data/*.db; do
 done
 ```
 
-`.backup` takes the proper locks and writes a consistent file. Two
+`.backup` reads through the WAL and writes a single consistent file with
-caveats. First, the runtime image is `alpine:3.21` with only
+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
@@ -614,15 +647,37 @@ 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
+archive writer closes and reopens its handle around writes (debounced
-one reopen per second), so an operator can move `archive-{uuid}.db`
+to at most one reopen per second), so an operator can move
-away for offline retention while the service runs, and it is recreated
+`archive-{uuid}.db` away for offline retention while the service runs,
-on the next write (see
+and it is recreated on the next write. See
-[Database Architecture](#database-architecture)). That is a
+[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.
@@ -636,14 +691,22 @@ 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
+3. Carry any `*.db-wal` and `*.db-shm` files that are in the backup.
-   either procedure above are self-consistent and do not need one.
+   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
+   creates the `-wal` and `-shm` sidecars beside the database, so a
-   inside a directory it cannot write is not enough:
+   writable file inside a directory it cannot write is not enough:
 
     ```bash
     chown -R 1000:1000 /path/to/data
@@ -1391,10 +1454,12 @@ 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
+  contend. Every database — main, per-webhook, and archive — is opened
-  `file:{path}?cache=shared&mode=rwc` and no `journal_mode` pragma is
+  through one code path (`internal/database/sqlite_open.go`) in WAL
-  ever issued, so every database runs on SQLite's default rollback
+  journal mode, with a 10-second busy timeout, `BEGIN IMMEDIATE`
-  journal.
+  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
@@ -1853,13 +1918,16 @@ the rest. Nothing dropped is needed for the likeliest use, debugging a
 CSRF rejection. Its three inputs are the TLS decision, `Origin` and
 `Referer`; the latter two are kept, and the first is the scheme of the
 retained URL, because the SDK derives that scheme from
-`r.TLS != nil || r.Header.Get("X-Forwarded-Proto") == "https"` — byte
+`r.TLS != nil || r.Header.Get("X-Forwarded-Proto") == "https"`. That
-for byte the predicate `internal/middleware/csrf.go` uses to choose
+predicate is the SDK's own and is stricter than `internal/reqtls.IsTLS`,
-between the `csrf.Secure(true)` and `csrf.Secure(false)` handlers.
+which this service now uses everywhere it decides transport: the SDK
-That is what the rewrite above preserves it for, and it is why
+reports `http` for the `HTTPS` and `https, http` spellings `reqtls`
-dropping `X-Forwarded-Proto` costs nothing. The dropped provider
+accepts. Only a reported scheme is affected, no decision is, so it is
-headers (`X-GitHub-Event`, `X-Gitlab-Event` and the like) are real
+left to the SDK rather than reimplemented. That is what the rewrite
-signal but are recorded locally on the event, and
+above preserves it for, and it is why dropping `X-Forwarded-Proto`
+costs nothing. The dropped provider headers (`X-GitHub-Event`,
+`X-Gitlab-Event` and the like) are real signal but are recorded
+locally on the event, and
 `Sentry-Trace`/`Baggage` are already reflected in the event's trace
 context.
 
@@ -2515,8 +2583,9 @@ check, see [The login endpoint](#the-login-endpoint).
 
 - **Web UI:** Cookie-based sessions using gorilla/sessions with
   encrypted cookies. Sessions are configured with HttpOnly, SameSite
-  Lax, and Secure (in production). Absolute session lifetime is 7 days,
+  Lax, and Secure whenever the request is on TLS — the flag follows the
-  with a sliding idle timeout on top of it (see
+  request's transport, not the environment. Absolute session lifetime
+  is 7 days, with a sliding idle timeout on top of it (see
   [Sessions](#sessions)).
 - **API (planned):** API key authentication via `Authorization: Bearer`
   header. API keys are stored per-user with usage tracking
@@ -2529,7 +2598,10 @@ check, see [The login endpoint](#the-login-endpoint).
 ### Security
 
 - Passwords hashed with Argon2id (64 MB memory cost)
-- Session cookies are HttpOnly, SameSite Lax, Secure (prod only)
+- Session cookies are HttpOnly, SameSite Lax, and Secure on any request
+  that arrived over TLS (directly or through a reverse proxy reporting
+  it), decided per-request by `internal/reqtls.IsTLS` rather than by the
+  configured environment
 - Session regeneration on login to prevent session fixation attacks
 - Session key is a 32-byte value auto-generated on first startup and
   stored in the database
@@ -2542,9 +2614,10 @@ check, see [The login endpoint](#the-login-endpoint).
   on all state-changing forms (cookie-based double-submit tokens with
   HMAC authentication). Applied to `/pages`, `/sources`, `/source`, and
   `/user` routes. Excluded from `/webhook` (inbound webhook POSTs) and
-  `/api` (stateless API). The middleware auto-detects TLS status
+  `/api` (stateless API). The middleware detects TLS per-request through
-  per-request (via `r.TLS` and `X-Forwarded-Proto`) to set appropriate
+  `internal/reqtls.IsTLS` — the same predicate the session cookie uses —
-  cookie security flags and Origin/Referer validation mode
+  to set appropriate cookie security flags and Origin/Referer validation
+  mode
 - **Optional inbound signature verification** per entrypoint (GitHub
   `X-Hub-Signature-256`, GitLab `X-Gitlab-Token`). Off by default and
   off after an upgrade, so behaviour is unchanged until an operator

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
+	// Opened through OpenSQLite so this handle carries the same WAL
-	sqlDB, err := sql.Open("sqlite", dbURL)
+	// 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_open.go

@@ -0,0 +1,157 @@
+package database
+
+import (
+	"database/sql"
+	"fmt"
+	"net/url"
+	"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
+)
+
+// 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 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) {
+	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.go

@@ -41,6 +41,31 @@ const (
 	// sweep runs.
 	retrySweepInterval = 60 * time.Second
 
+	// pendingSweepMinAge is how long a delivery must have sat
+	// untouched at pending before the sweep will look at it.
+	//
+	// It is not what keeps the sweep off live work — inflightSet is,
+	// and it is exact. This bound sets the re-dispatch cadence for a
+	// delivery that really is stranded: without it, a delivery the
+	// database will not let the engine settle would be re-sent on
+	// every 60-second tick.
+	//
+	// It is nonetheless set clear of the longest legitimate attempt,
+	// so that the two guards do not both have to be right. That
+	// length is MaxTargetTimeoutSeconds (300s), the per-target
+	// timeout the target form accepts — not httpClientTimeout, which
+	// is merely the default. Fifteen minutes leaves a margin of
+	// three times the ceiling rather than the zero margin the two
+	// equal values would have given.
+	pendingSweepMinAge = 15 * time.Minute
+
+	// pendingSweepBatch bounds how many stranded pending deliveries
+	// one sweep of one webhook re-dispatches. The sweep runs every
+	// retrySweepInterval, so a larger backlog drains across
+	// successive sweeps instead of arriving as one burst against a
+	// database that was already struggling to accept writes.
+	pendingSweepBatch = 500
+
 	// MaxInlineBodySize is the maximum event body size that
 	// will be carried inline in a Task through the channel.
 	// Bodies at or above this size are left nil and fetched
@@ -157,6 +182,12 @@ type Engine struct {
 	// dbTarget is retained so the engine can reach the archive
 	// writer registry for webhook eviction and the idle sweep.
 	dbTarget *databaseTarget
+
+	// inflight is the set of deliveries this engine currently owns.
+	// Recovery and the sweeps re-dispatch only what it does not
+	// hold. Held by value: its zero value works, so no constructor
+	// can leave it out. See inflight.go.
+	inflight inflightSet
 }
 
 // New creates and registers the delivery engine with the
@@ -189,12 +220,27 @@ func New(
 // are ready.
 func (e *Engine) Notify(tasks []Task) {
 	for i := range tasks {
+		// Owned before it is queued, and until the worker that runs
+		// it returns. A task can sit in a 10000-deep channel for a
+		// long time on a healthy system, and nothing may re-send it
+		// while it waits. See inflight.go.
+		if !e.inflight.retainIdle(tasks[i].DeliveryID) {
+			e.log.Warn(
+				"delivery already in flight, not queued again",
+				"delivery_id", tasks[i].DeliveryID,
+				"event_id", tasks[i].EventID,
+			)
+
+			continue
+		}
+
 		select {
 		case e.deliveryCh <- tasks[i]:
 		default:
+			e.inflight.release(tasks[i].DeliveryID)
 			e.log.Warn(
 				"delivery channel full, "+
-					"task will be recovered on restart",
+					"task will be recovered by the sweep",
 				"delivery_id", tasks[i].DeliveryID,
 				"event_id", tasks[i].EventID,
 			)
@@ -229,10 +275,20 @@ func (e *Engine) ScheduleRetry(
 		"next_attempt", task.AttemptNum,
 	)
 
+	// The reference is taken here rather than when the timer fires,
+	// so the delivery stays owned across the whole backoff window.
+	// Its caller is a target inside Deliver, so the engine already
+	// owns it; this second reference is what keeps that ownership
+	// alive after the worker returns and the row sits at retrying
+	// with nothing running. Without it the sweep finds the row
+	// orphaned and sends it again.
+	e.inflight.retain(task.DeliveryID)
+
 	time.AfterFunc(delay, func() {
 		select {
 		case e.retryCh <- task:
 		default:
+			e.inflight.release(task.DeliveryID)
 			e.log.Warn(
 				"retry channel full, delivery "+
 					"will be recovered by periodic sweep",
@@ -332,13 +388,35 @@ func (e *Engine) worker(ctx context.Context) {
 		case <-ctx.Done():
 			return
 		case task := <-e.deliveryCh:
-			e.processNewTask(ctx, &task)
+			e.runTask(ctx, &task, e.processNewTask)
 		case task := <-e.retryCh:
-			e.processRetryTask(ctx, &task)
+			e.runTask(ctx, &task, e.processRetryTask)
 		}
 	}
 }
 
+// runTask runs one task and then drops the reference the queueing
+// side took on its delivery.
+//
+// The release is deferred rather than written after the call because
+// every early return inside the processing paths must drop it too: a
+// delivery whose database could not be opened is one the engine has
+// stopped working on, and leaving it owned would hide it from the
+// sweep forever.
+//
+// Ownership does not necessarily end here. A target that scheduled a
+// retry took its own reference before this one is dropped, so the
+// delivery stays owned through the backoff window.
+func (e *Engine) runTask(
+	ctx context.Context,
+	task *Task,
+	run func(context.Context, *Task),
+) {
+	defer e.inflight.release(task.DeliveryID)
+
+	run(ctx, task)
+}
+
 func (e *Engine) recoverPending(ctx context.Context) {
 	defer e.wg.Done()
 
@@ -526,7 +604,16 @@ func (e *Engine) recoverRetryingDeliveries(
 		return
 	}
 
+	settled := e.reconcileDelivered(
+		webhookDB, webhookID, retrying,
+		e.loadTargetMap(retrying),
+	)
+
 	for i := range retrying {
+		if _, ok := settled[retrying[i].ID]; ok {
+			continue
+		}
+
 		e.recoverSingleRetry(
 			webhookDB, webhookID, &retrying[i],
 		)
@@ -588,6 +675,10 @@ func (e *Engine) recoverSingleRetry(
 		d, webhookID, &event, &target, attemptNum+1,
 	)
 
+	if !e.rescheduleRecovered(webhookDB, task, remaining) {
+		return
+	}
+
 	e.log.Info(
 		"recovering retrying delivery",
 		"webhook_id", webhookID,
@@ -595,8 +686,6 @@ func (e *Engine) recoverSingleRetry(
 		"attempt", attemptNum,
 		"remaining_backoff", remaining,
 	)
-
-	e.ScheduleRetry(task, remaining)
 }
 
 func (e *Engine) recoverPendingDeliveries(
@@ -606,12 +695,14 @@ func (e *Engine) recoverPendingDeliveries(
 ) {
 	var deliveries []database.Delivery
 
+	// No Preload: event bodies are read one at a time in
+	// sendRecoveredDeliveries, and only for the deliveries actually
+	// being sent.
 	result := webhookDB.
 		Where(
 			"status = ?",
 			database.DeliveryStatusPending,
 		).
-		Preload("Event").
 		Find(&deliveries)
 
 	if result.Error != nil {
@@ -634,11 +725,137 @@ func (e *Engine) recoverPendingDeliveries(
 		"count", len(deliveries),
 	)
 
+	e.recoverPendingBatch(
+		ctx, webhookDB, webhookID, deliveries,
+	)
+}
+
+// recoverPendingBatch settles every delivery in the batch that was
+// already delivered, and re-dispatches only the rest. Both the
+// restart-time recovery and the periodic sweep go through it, so a
+// pending delivery is treated the same however it was found.
+func (e *Engine) recoverPendingBatch(
+	ctx context.Context,
+	webhookDB *gorm.DB,
+	webhookID string,
+	deliveries []database.Delivery,
+) {
 	targetMap := e.loadTargetMap(deliveries)
 
-	e.sendRecoveredDeliveries(
+	settled := e.reconcileDelivered(
-		ctx, deliveries, webhookID, targetMap,
+		webhookDB, webhookID, deliveries, targetMap,
 	)
+
+	e.sendRecoveredDeliveries(
+		ctx, webhookDB, deliveries, webhookID,
+		targetMap, settled,
+	)
+}
+
+// reconcileDelivered finds the deliveries in a recovered batch that
+// already have a successful DeliveryResult, marks them delivered, and
+// returns their ids so the caller does not send them a second time.
+//
+// This is the state the engine previously had no way to represent. A
+// delivery is left in a non-terminal state by a failed bookkeeping
+// write, and that covers two different histories: nothing was ever
+// sent, or the send reached the receiver and only the status write
+// failed. Re-sending was the sole option, so every stranded row
+// produced a duplicate at the receiver and an event log that recorded
+// one attempt for two POSTs. A successful result row distinguishes
+// them: it is written before the status, so its presence means the
+// wire I/O happened and was recorded, and all that is missing is the
+// status.
+//
+// Every recovery path runs this, not only the pending one. A delivery
+// abandoned at retrying can hold a successful result just as a pending
+// one can — a second attempt that reached the receiver and whose status
+// write then failed sits at retrying with success recorded — and
+// re-sending it is the same duplicate.
+//
+// Deliveries whose result row itself never landed are not in the
+// returned set and are re-sent, recorded as the further attempt they
+// are. That is honest at-least-once delivery rather than a silent
+// duplicate.
+func (e *Engine) reconcileDelivered(
+	webhookDB *gorm.DB,
+	webhookID string,
+	deliveries []database.Delivery,
+	targetMap map[string]database.Target,
+) map[string]struct{} {
+	settled := make(map[string]struct{})
+
+	if len(deliveries) == 0 {
+		return settled
+	}
+
+	ids := make([]string, 0, len(deliveries))
+	for i := range deliveries {
+		ids = append(ids, deliveries[i].ID)
+	}
+
+	var deliveredIDs []string
+
+	err := webhookDB.
+		Model(&database.DeliveryResult{}).
+		Where(
+			"delivery_id IN ? AND success = ?", ids, true,
+		).
+		Distinct().
+		Pluck("delivery_id", &deliveredIDs).Error
+	if err != nil {
+		// Every delivery stays out of the settled set, so the batch
+		// is re-sent exactly as it was before this check existed.
+		// That is the safe direction: a duplicate delivery beats
+		// declaring a delivery successful on a query that failed.
+		e.log.Error(
+			"failed to query successful delivery results; "+
+				"pending deliveries will be re-sent",
+			"webhook_id", webhookID,
+			"error", err,
+		)
+
+		return settled
+	}
+
+	for _, id := range deliveredIDs {
+		settled[id] = struct{}{}
+	}
+
+	if len(settled) == 0 {
+		return settled
+	}
+
+	e.log.Info(
+		"settling recovered deliveries that already succeeded",
+		"webhook_id", webhookID,
+		"count", len(settled),
+	)
+
+	for i := range deliveries {
+		if _, ok := settled[deliveries[i].ID]; !ok {
+			continue
+		}
+
+		// A delivery the engine is working on right now settles
+		// itself; writing over it from here would race that worker.
+		if !e.inflight.retainIdle(deliveries[i].ID) {
+			delete(settled, deliveries[i].ID)
+
+			continue
+		}
+
+		e.settleStatus(
+			webhookDB,
+			&deliveries[i],
+			targetMap[deliveries[i].TargetID].Type,
+			database.DeliveryStatusDelivered,
+		)
+
+		e.inflight.release(deliveries[i].ID)
+	}
+
+	return settled
 }
 
 func (e *Engine) retrySweep(ctx context.Context) {
@@ -722,6 +939,11 @@ func (e *Engine) sweepWebhookRetries(
 		return
 	}
 
+	settled := e.reconcileDelivered(
+		webhookDB, webhookID, retrying,
+		e.loadTargetMap(retrying),
+	)
+
 	for i := range retrying {
 		select {
 		case <-ctx.Done():
@@ -729,10 +951,70 @@ func (e *Engine) sweepWebhookRetries(
 		default:
 		}
 
+		if _, ok := settled[retrying[i].ID]; ok {
+			continue
+		}
+
 		e.sweepSingleRetry(
 			webhookDB, webhookID, &retrying[i],
 		)
 	}
+
+	e.sweepWebhookPending(ctx, webhookDB, webhookID)
+}
+
+// sweepWebhookPending recovers deliveries stranded at pending.
+//
+// A delivery is created pending and leaves that state only when its
+// outcome is written, so a pending row the engine does not own is one
+// whose bookkeeping write failed — the state that used to sit there
+// until a restart, and then produce a duplicate at the receiver. The
+// sweep gives it the same reconcile-then-dispatch treatment restart
+// recovery gets, so it costs a minute rather than an operator
+// noticing.
+//
+// What keeps the sweep off live work is ownership, checked per
+// delivery in takeForRedispatch, not the age bound in this query.
+// A delivery waiting in deliveryCh is pending and arbitrarily old —
+// the channel holds 10000 tasks and 10 workers drain it — so
+// reasoning from the row's age alone re-sends it. See inflight.go.
+func (e *Engine) sweepWebhookPending(
+	ctx context.Context,
+	webhookDB *gorm.DB,
+	webhookID string,
+) {
+	var pending []database.Delivery
+
+	err := webhookDB.
+		Where(
+			"status = ? AND updated_at < ?",
+			database.DeliveryStatusPending,
+			time.Now().Add(-pendingSweepMinAge),
+		).
+		Limit(pendingSweepBatch).
+		Find(&pending).Error
+	if err != nil {
+		e.log.Error(
+			"retry sweep: "+
+				"failed to query pending deliveries",
+			"webhook_id", webhookID,
+			"error", err,
+		)
+
+		return
+	}
+
+	if len(pending) == 0 {
+		return
+	}
+
+	e.log.Info(
+		"retry sweep: recovering stranded pending deliveries",
+		"webhook_id", webhookID,
+		"count", len(pending),
+	)
+
+	e.recoverPendingBatch(ctx, webhookDB, webhookID, pending)
 }
 
 // sweepSingleRetry re-enqueues an orphaned retrying delivery
@@ -789,17 +1071,20 @@ func (e *Engine) sweepSingleRetry(
 		d, webhookID, &event, &target, attemptNum+1,
 	)
 
-	select {
+	if !e.redispatch(
-	case e.retryCh <- task:
+		e.retryCh, webhookDB, task,
-		e.log.Info(
+		database.DeliveryStatusRetrying,
-			"retry sweep: "+
+	) {
-				"recovered orphaned retrying delivery",
+		return
-			"delivery_id", d.ID,
-			"webhook_id", webhookID,
-			"attempt", attemptNum+1,
-		)
-	default:
 	}
+
+	e.log.Info(
+		"retry sweep: "+
+			"recovered orphaned retrying delivery",
+		"delivery_id", d.ID,
+		"webhook_id", webhookID,
+		"attempt", attemptNum+1,
+	)
 }
 
 // failUnretryableRetry terminally fails an orphaned retrying
@@ -822,6 +1107,16 @@ func (e *Engine) failUnretryableRetry(
 	d *database.Delivery,
 	target *database.Target,
 ) {
+	// Terminal, and reached from the recovery paths, so it takes
+	// ownership like every other write they make: a delivery the
+	// engine is still attempting must not be failed underneath the
+	// worker running it.
+	if !e.inflight.retainIdle(d.ID) {
+		return
+	}
+
+	defer e.inflight.release(d.ID)
+
 	e.log.Warn(
 		"failing orphaned retrying delivery: target "+
 			"type no longer supports retries",
@@ -839,7 +1134,7 @@ func (e *Engine) failUnretryableRetry(
 		target.Type,
 	)
 
-	e.recordResult(
+	err := e.recordResult(
 		webhookDB,
 		d,
 		e.countAttempts(webhookDB, d.ID)+1,
@@ -849,6 +1144,11 @@ func (e *Engine) failUnretryableRetry(
 		reason,
 		0,
 	)
+	if err != nil {
+		e.bookkeepingFailed(d, err)
+
+		return
+	}
 
 	// The type is passed rather than assigned onto d: the delivery
 	// is loaded here without its target relation, and populating
@@ -856,7 +1156,7 @@ func (e *Engine) failUnretryableRetry(
 	// whole target row — plaintext config, which for a slack target
 	// is the credential — into the per-webhook event database. See
 	// https://git.eeqj.de/sneak/webhooker/issues/206.
-	e.updateDeliveryStatus(
+	e.settleStatus(
 		webhookDB, d, target.Type,
 		database.DeliveryStatusFailed,
 	)
@@ -878,7 +1178,7 @@ func (e *Engine) processDelivery(
 			"type", d.Target.Type,
 		)
 
-		e.updateDeliveryStatus(
+		e.settleStatus(
 			webhookDB, d, d.Target.Type,
 			database.DeliveryStatusFailed,
 		)
@@ -910,6 +1210,14 @@ func (e *Engine) observeAttempt(
 // recordResult persists a DeliveryResult row describing a
 // single attempt. It is a cross-target helper the targets
 // call.
+//
+// It returns its error rather than swallowing it. A DeliveryResult
+// row is the only record that an attempt happened at all, so a
+// caller that ignored a failed write would go on to mark the
+// delivery delivered — leaving the event log claiming one attempt
+// for a receiver that got two. Every caller must instead stop
+// advancing the delivery's status and let it stay in the
+// non-terminal state it already holds; see bookkeepingFailed.
 func (e *Engine) recordResult(
 	webhookDB *gorm.DB,
 	d *database.Delivery,
@@ -918,7 +1226,7 @@ func (e *Engine) recordResult(
 	statusCode int,
 	respBody, errMsg string,
 	durationMs int64,
-) {
+) error {
 	result := &database.DeliveryResult{
 		DeliveryID:   d.ID,
 		AttemptNum:   attemptNum,
@@ -931,12 +1239,44 @@ func (e *Engine) recordResult(
 
 	err := webhookDB.Create(result).Error
 	if err != nil {
-		e.log.Error(
+		return fmt.Errorf(
-			"failed to record delivery result",
+			"recording delivery result for %s: %w", d.ID, err,
-			"delivery_id", d.ID,
-			"error", err,
 		)
 	}
+
+	return nil
+}
+
+// bookkeepingFailed reports that a delivery's own record of what
+// happened could not be written, and deliberately writes nothing in
+// response.
+//
+// Leaving the row alone is the whole point. A delivery is created
+// pending and only ever leaves that state through
+// updateDeliveryStatus, so a delivery whose bookkeeping write failed
+// is still pending or retrying — the two non-terminal states, per
+// DeliveryStatus.Terminal — and both are swept and recovered. Writing
+// anything here would need the very database that just refused a
+// write, and would be one more thing to fail; not writing cannot.
+//
+// The cost is honest at-least-once behaviour: a send that reached the
+// receiver but whose result row did not land is attempted again, and
+// recorded as the further attempt it is. What no longer happens is the
+// silent duplicate — a second POST the event log denies ever
+// occurred. Where the result row *did* land and only the status write
+// failed, reconcileDelivered settles the row without re-sending.
+func (e *Engine) bookkeepingFailed(
+	d *database.Delivery, err error,
+) {
+	e.log.Error(
+		"delivery bookkeeping write failed; leaving delivery "+
+			"in a recoverable state",
+		"delivery_id", d.ID,
+		"event_id", d.EventID,
+		"target_id", d.TargetID,
+		"status", d.Status,
+		"error", err,
+	)
 }
 
 // updateDeliveryStatus persists a new status for a delivery.
@@ -952,26 +1292,51 @@ func (e *Engine) recordResult(
 //
 // The counter moves only after the row is written, so a transition
 // the database rejected is not claimed as an outcome that happened.
+// For the same reason the error is returned rather than logged and
+// dropped: a delivery whose status write failed has not reached that
+// status, and its caller must not act as though it had.
 func (e *Engine) updateDeliveryStatus(
 	webhookDB *gorm.DB,
 	d *database.Delivery,
 	targetType database.TargetType,
 	status database.DeliveryStatus,
-) {
+) error {
 	err := webhookDB.Model(d).
 		Update("status", status).Error
 	if err != nil {
-		e.log.Error(
+		return fmt.Errorf(
-			"failed to update delivery status",
+			"updating delivery %s to status %s: %w",
-			"delivery_id", d.ID,
+			d.ID, status, err,
-			"status", status,
-			"error", err,
 		)
-
-		return
 	}
 
-	e.mtr.DeliveryStatusChanged(targetType, status)
+	// An empty type means the target row is gone — a delivery being
+	// settled long after its target was deleted. The row still has to
+	// be settled, but the counter is left alone rather than given a
+	// series labelled with the empty string.
+	if targetType != "" {
+		e.mtr.DeliveryStatusChanged(targetType, status)
+	}
+
+	return nil
+}
+
+// settleStatus moves a delivery to its outcome status and reports a
+// failed write through bookkeepingFailed, which leaves the row
+// recoverable. It exists so the target call sites read as one
+// statement rather than four lines of identical error handling.
+func (e *Engine) settleStatus(
+	webhookDB *gorm.DB,
+	d *database.Delivery,
+	targetType database.TargetType,
+	status database.DeliveryStatus,
+) {
+	err := e.updateDeliveryStatus(
+		webhookDB, d, targetType, status,
+	)
+	if err != nil {
+		e.bookkeepingFailed(d, err)
+	}
 }
 
 func truncate(s string, maxLen int) string {
@@ -1065,6 +1430,184 @@ func (e *Engine) countAttempts(
 	return int(resultCount)
 }
 
+// takeForRedispatch decides whether a recovered delivery may be sent
+// again, and takes it if so. It is the single gate every re-dispatch
+// path goes through, and it asks two separate questions in order.
+//
+// First, does the engine already own this delivery? Ownership is
+// exact and mutually exclusive, so a delivery queued, being attempted,
+// or waiting out a retry backoff is refused here, and two dispatchers
+// racing for the same delivery cannot both win. See inflight.go.
+//
+// Second, is the row still in the status that made it eligible? The
+// batch was read some time ago and a worker may have settled a row
+// since. The check is a conditional update rather than a read so the
+// answer cannot go stale between asking and acting.
+//
+// Stamping updated_at is the same statement, and it is a cadence
+// control rather than a claim: the pending sweep selects on that
+// column, so a delivery handed out now is not selected again on the
+// next tick a minute later but after pendingSweepMinAge. A delivery
+// the database refuses to settle is therefore retried on that
+// interval instead of every tick.
+//
+// A failed write is a refusal. It means the database is not accepting
+// writes, which is the condition that stranded the delivery in the
+// first place; an attempt that cannot be recorded is exactly the
+// unlogged duplicate this is all here to prevent.
+//
+// The caller must release ownership if it then fails to queue the
+// task.
+func (e *Engine) takeForRedispatch(
+	webhookDB *gorm.DB,
+	deliveryID string,
+	eligible database.DeliveryStatus,
+) bool {
+	if !e.inflight.retainIdle(deliveryID) {
+		return false
+	}
+
+	res := webhookDB.
+		Model(&database.Delivery{}).
+		Where(
+			"id = ? AND status = ?", deliveryID, eligible,
+		).
+		UpdateColumn("updated_at", time.Now())
+
+	if res.Error != nil {
+		e.log.Error(
+			"failed to mark delivery for re-dispatch; "+
+				"leaving it for a later sweep",
+			"delivery_id", deliveryID,
+			"error", res.Error,
+		)
+		e.inflight.release(deliveryID)
+
+		return false
+	}
+
+	if res.RowsAffected != 1 {
+		// Settled underneath us between the query and here.
+		e.inflight.release(deliveryID)
+
+		return false
+	}
+
+	return true
+}
+
+// queueRecovered puts an owned delivery's task on a worker channel,
+// dropping the ownership the gate took if it does not fit.
+func (e *Engine) queueRecovered(
+	ch chan<- Task, task Task,
+) bool {
+	select {
+	case ch <- task:
+		return true
+	default:
+		e.inflight.release(task.DeliveryID)
+		e.log.Warn(
+			"worker channel full during recovery; "+
+				"delivery will be recovered by a later sweep",
+			"delivery_id", task.DeliveryID,
+			"webhook_id", task.WebhookID,
+		)
+
+		return false
+	}
+}
+
+// redispatch hands a recovered delivery to a worker channel through
+// takeForRedispatch, and reports whether the task was queued.
+func (e *Engine) redispatch(
+	ch chan<- Task,
+	webhookDB *gorm.DB,
+	task Task,
+	eligible database.DeliveryStatus,
+) bool {
+	if !e.takeForRedispatch(
+		webhookDB, task.DeliveryID, eligible,
+	) {
+		return false
+	}
+
+	return e.queueRecovered(ch, task)
+}
+
+// rescheduleRecovered hands an orphaned retrying delivery back to the
+// retry timer, through the same gate. It reports whether the delivery
+// was rescheduled.
+//
+// The reference taken by the gate is dropped as soon as ScheduleRetry
+// has taken its own, which it does before returning: what keeps the
+// delivery owned through the backoff window is ScheduleRetry's
+// reference, not this one.
+func (e *Engine) rescheduleRecovered(
+	webhookDB *gorm.DB, task Task, delay time.Duration,
+) bool {
+	if !e.takeForRedispatch(
+		webhookDB, task.DeliveryID,
+		database.DeliveryStatusRetrying,
+	) {
+		return false
+	}
+
+	defer e.inflight.release(task.DeliveryID)
+
+	e.ScheduleRetry(task, delay)
+
+	return true
+}
+
+// countAttemptsBatch counts the recorded attempts of every delivery
+// in a batch with one grouped query, keyed by delivery id. Deliveries
+// with no attempts are simply absent from the result, which reads back
+// as the zero this caller wants.
+//
+// One query rather than one per delivery: this runs on the recovery
+// path, which is a burst of writes against a database that has just
+// been under enough contention to strand these rows in the first
+// place. See https://git.eeqj.de/sneak/webhooker/issues/256.
+func (e *Engine) countAttemptsBatch(
+	webhookDB *gorm.DB, deliveries []database.Delivery,
+) map[string]int {
+	counts := make(map[string]int, len(deliveries))
+
+	if len(deliveries) == 0 {
+		return counts
+	}
+
+	ids := make([]string, 0, len(deliveries))
+	for i := range deliveries {
+		ids = append(ids, deliveries[i].ID)
+	}
+
+	// One delivery id per recorded attempt, tallied here rather than
+	// grouped in SQL: internal/gormlog forbids (*gorm.DB).Scan, which
+	// a GROUP BY into a struct would need, and an attempt row per
+	// delivery is bounded by the target's MaxRetries.
+	var attemptIDs []string
+
+	err := webhookDB.
+		Model(&database.DeliveryResult{}).
+		Where("delivery_id IN ?", ids).
+		Pluck("delivery_id", &attemptIDs).Error
+	if err != nil {
+		e.log.Error(
+			"failed to count delivery attempts for recovery",
+			"error", err,
+		)
+
+		return counts
+	}
+
+	for _, id := range attemptIDs {
+		counts[id]++
+	}
+
+	return counts
+}
+
 func (e *Engine) loadEvent(
 	webhookDB *gorm.DB, eventID string,
 ) (database.Event, error) {
@@ -1132,6 +1675,10 @@ func buildRecoveryTask(
 func (e *Engine) loadTargetMap(
 	deliveries []database.Delivery,
 ) map[string]database.Target {
+	if len(deliveries) == 0 {
+		return nil
+	}
+
 	seen := make(map[string]bool)
 
 	targetIDs := make([]string, 0, len(deliveries))
@@ -1168,12 +1715,33 @@ func (e *Engine) loadTargetMap(
 	return targetMap
 }
 
+// sendRecoveredDeliveries re-dispatches pending deliveries, skipping
+// the ids in settled — those already reached their receiver and have
+// been marked delivered by reconcileDelivered.
+//
+// The skip and takeForRedispatch's status check answer different
+// questions and neither replaces the other. This one is "did this
+// delivery already succeed", which is what settles the row to
+// delivered instead of sending it, and which is the only thing that
+// keeps the retrying paths from terminally failing a delivery that
+// reconcile just settled. The status check is "is the row still what
+// the batch query said it was", which catches a worker settling it to
+// anything at all in between.
 func (e *Engine) sendRecoveredDeliveries(
 	ctx context.Context,
+	webhookDB *gorm.DB,
 	deliveries []database.Delivery,
 	webhookID string,
 	targetMap map[string]database.Target,
+	settled map[string]struct{},
 ) {
+	// The attempt number continues each delivery's own history
+	// rather than restarting at 1. A recovered delivery may already
+	// have recorded attempts, and numbering the next one 1 again
+	// both collides in the event log and hands the retry path a
+	// backoff computed from the wrong attempt.
+	attempts := e.countAttemptsBatch(webhookDB, deliveries)
+
 	for i := range deliveries {
 		select {
 		case <-ctx.Done():
@@ -1181,6 +1749,10 @@ func (e *Engine) sendRecoveredDeliveries(
 		default:
 		}
 
+		if _, ok := settled[deliveries[i].ID]; ok {
+			continue
+		}
+
 		target, ok := targetMap[deliveries[i].TargetID]
 		if !ok {
 			e.log.Error(
@@ -1192,22 +1764,40 @@ func (e *Engine) sendRecoveredDeliveries(
 			continue
 		}
 
+		if !e.takeForRedispatch(
+			webhookDB, deliveries[i].ID,
+			database.DeliveryStatusPending,
+		) {
+			continue
+		}
+
+		// The body is read here, one delivery at a time and only for
+		// deliveries that are actually being sent, rather than
+		// preloaded across the whole batch. A batch is up to
+		// pendingSweepBatch rows at up to the 1 MB ingest cap, and
+		// most of a sweep's batch is refused by the gate above — so
+		// preloading would hold hundreds of megabytes per webhook per
+		// tick to build tasks it then discards.
+		event, err := e.loadEvent(
+			webhookDB, deliveries[i].EventID,
+		)
+		if err != nil {
+			e.log.Error(
+				"failed to load event for recovered delivery",
+				"delivery_id", deliveries[i].ID,
+				"event_id", deliveries[i].EventID,
+				"error", err,
+			)
+			e.inflight.release(deliveries[i].ID)
+
+			continue
+		}
+
 		task := buildRecoveryTask(
-			&deliveries[i], webhookID,
+			&deliveries[i], webhookID, &event, &target,
-			&deliveries[i].Event, &target, 1,
+			attempts[deliveries[i].ID]+1,
 		)
 
-		select {
+		e.queueRecovered(e.deliveryCh, task)
-		case e.deliveryCh <- task:
-		default:
-			e.log.Warn(
-				"delivery channel full during "+
-					"recovery, remaining deliveries "+
-					"will be recovered on next restart",
-				"delivery_id", deliveries[i].ID,
-			)
-
-			return
-		}
 	}
 }

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(
+	// Opened the way the service opens the main database, so these
-		"file:%s?cache=shared&mode=rwc", dbPath,
+	// 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/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(
+	// Opened the way the service opens a per-webhook database, so
-		"file:%s?cache=shared&mode=rwc", dbPath,
+	// 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/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.
@@ -286,6 +291,26 @@ 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/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(
+	sqlDB, err := database.OpenSQLite(
-		"file:%s?cache=shared&mode=rwc",
 		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/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)
+	// Opened through database.OpenSQLite so an archive file carries
-
+	// the same WAL journaling, busy timeout, immediate-transaction
-	sqlDB, err := sql.Open("sqlite", dbURL)
+	// 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,
 	)

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

internal/handlers/event_resubmit.go

@@ -143,10 +143,10 @@ 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
+	// to the 1 MB ingest cap, and every transaction on these files
-	// transaction would extend how long the per-webhook database is
+	// takes the write lock at BEGIN (_txlock=immediate, see
-	// locked against the receiver, which runs these files in
+	// internal/database/sqlite_open.go), so reading inside it would
-	// SQLite's default journal mode rather than WAL.
+	// hold that lock against the receiver for the length of the read.
 	src, found, err := loadResubmitSource(
 		webhookDB, webhook.ID, eventID.String(),
 	)

internal/handlers/source_delete_test.go

@@ -2,6 +2,7 @@ package handlers_test
 
 import (
 	"context"
+	"errors"
 	"net/http"
 	"net/http/httptest"
 	"os"
@@ -11,6 +12,7 @@ import (
 	"github.com/go-chi/chi"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
+	"gorm.io/gorm"
 	"gorm.io/gorm/clause"
 	"sneak.berlin/go/webhooker/internal/database"
 	"sneak.berlin/go/webhooker/internal/handlers"
@@ -73,6 +75,77 @@ func seedTarget(
 	return tgt
 }
 
+// errInjectedDelete is the failure failDeleteOnTable reports
+// from a delete statement.
+var errInjectedDelete = errors.New("injected delete failure")
+
+// seedEntrypoint inserts an entrypoint for a webhook.
+func seedEntrypoint(
+	t *testing.T,
+	db *database.Database,
+	webhookID string,
+) {
+	t.Helper()
+
+	ep := &database.Entrypoint{
+		WebhookID: webhookID,
+		Path:      "ep-" + webhookID,
+		Active:    true,
+	}
+
+	require.NoError(
+		t,
+		db.DB().Omit(clause.Associations).Create(ep).Error,
+	)
+}
+
+// countRows counts the live (not soft-deleted) rows of a model
+// matching column = value.
+func countRows(
+	t *testing.T,
+	db *database.Database,
+	model any,
+	column, value string,
+) int64 {
+	t.Helper()
+
+	var n int64
+
+	require.NoError(
+		t,
+		db.DB().Model(model).
+			Where(column+" = ?", value).
+			Count(&n).Error,
+	)
+
+	return n
+}
+
+// failDeleteOnTable makes every delete against the named table
+// fail the way a database-level error does: the statement
+// reports an error but leaves the surrounding transaction
+// usable, so a caller that does not check it can go on to
+// commit the statements that did succeed.
+func failDeleteOnTable(
+	t *testing.T,
+	db *database.Database,
+	table string,
+) {
+	t.Helper()
+
+	require.NoError(t, db.DB().Callback().Delete().
+		Before("gorm:delete").
+		Register(
+			"test:fail_delete_"+table,
+			func(tx *gorm.DB) {
+				if tx.Statement.Table == table {
+					_ = tx.AddError(errInjectedDelete)
+				}
+			},
+		),
+	)
+}
+
 // archivePathFor returns the archive database path the
 // delivery engine would use for a webhook: beside the webhook's
 // event database in the data directory.
@@ -209,6 +282,159 @@ func TestHandleSourceDelete_KeepsArchiveFile(t *testing.T) {
 	)
 }
 
+// TestHandleSourceDelete_FailedDeleteKeepsEverything proves
+// that a failing delete statement loses nothing: the
+// configuration is rolled back whole, the event database
+// survives, and the operator is told the deletion failed
+// instead of being redirected as though it worked.
+func TestHandleSourceDelete_FailedDeleteKeepsEverything(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	var (
+		h    *handlers.Handlers
+		sess *session.Session
+		db   *database.Database
+		mgr  *database.WebhookDBManager
+	)
+
+	app := newTestApp(t, &h, &sess, &db, &mgr)
+	app.RequireStart()
+
+	t.Cleanup(app.RequireStop)
+
+	wh := seedWebhook(t, db)
+	seedEntrypoint(t, db, wh.ID)
+	seedTarget(t, db, wh.ID, database.TargetTypeDatabase)
+
+	require.NoError(t, mgr.CreateDB(wh.ID))
+
+	eventDBPath := mgr.DBPath(wh.ID)
+	require.FileExists(t, eventDBPath)
+
+	// The entrypoint delete runs first and succeeds; the target
+	// delete then fails, which is what the whole transaction has
+	// to be rolled back over.
+	failDeleteOnTable(t, db, "targets")
+
+	cookies := authenticatedCookies(
+		t, sess, deleteTestUserID, deleteTestUsername,
+	)
+
+	req := postRequest(
+		"/source/"+wh.ID+"/delete",
+		cookies,
+		map[string]string{paramSourceID: wh.ID},
+	)
+	w := httptest.NewRecorder()
+
+	h.HandleSourceDelete().ServeHTTP(w, req)
+
+	assert.Equal(
+		t, http.StatusInternalServerError, w.Code,
+		"a failed deletion must be reported, not redirected",
+	)
+	assert.Empty(
+		t, w.Header().Get("Location"),
+		"a failed deletion must not redirect to /sources",
+	)
+
+	assert.Equal(
+		t, int64(1),
+		countRows(t, db, &database.Webhook{}, "id", wh.ID),
+		"the webhook must survive a failed deletion",
+	)
+	assert.Equal(
+		t, int64(1),
+		countRows(
+			t, db, &database.Entrypoint{}, "webhook_id", wh.ID,
+		),
+		"the entrypoint delete must be rolled back",
+	)
+	assert.Equal(
+		t, int64(1),
+		countRows(
+			t, db, &database.Target{}, "webhook_id", wh.ID,
+		),
+		"the target must survive a failed deletion",
+	)
+
+	assert.FileExists(
+		t, eventDBPath,
+		"event history must not be destroyed when the "+
+			"configuration delete did not commit",
+	)
+}
+
+// TestHandleSourceDelete_RemovesConfigAndEventDatabase is the
+// positive control for the rollback above: an ordinary deletion
+// still removes the webhook, its children and its event
+// database.
+func TestHandleSourceDelete_RemovesConfigAndEventDatabase(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	var (
+		h    *handlers.Handlers
+		sess *session.Session
+		db   *database.Database
+		mgr  *database.WebhookDBManager
+	)
+
+	app := newTestApp(t, &h, &sess, &db, &mgr)
+	app.RequireStart()
+
+	t.Cleanup(app.RequireStop)
+
+	wh := seedWebhook(t, db)
+	seedEntrypoint(t, db, wh.ID)
+	seedTarget(t, db, wh.ID, database.TargetTypeDatabase)
+
+	require.NoError(t, mgr.CreateDB(wh.ID))
+
+	eventDBPath := mgr.DBPath(wh.ID)
+	require.FileExists(t, eventDBPath)
+
+	cookies := authenticatedCookies(
+		t, sess, deleteTestUserID, deleteTestUsername,
+	)
+
+	req := postRequest(
+		"/source/"+wh.ID+"/delete",
+		cookies,
+		map[string]string{paramSourceID: wh.ID},
+	)
+	w := httptest.NewRecorder()
+
+	h.HandleSourceDelete().ServeHTTP(w, req)
+
+	require.Equal(t, http.StatusSeeOther, w.Code)
+	assert.Equal(t, "/sources", w.Header().Get("Location"))
+
+	assert.Equal(
+		t, int64(0),
+		countRows(t, db, &database.Webhook{}, "id", wh.ID),
+	)
+	assert.Equal(
+		t, int64(0),
+		countRows(
+			t, db, &database.Entrypoint{}, "webhook_id", wh.ID,
+		),
+	)
+	assert.Equal(
+		t, int64(0),
+		countRows(
+			t, db, &database.Target{}, "webhook_id", wh.ID,
+		),
+	)
+	assert.NoFileExists(
+		t, eventDBPath,
+		"a successful deletion removes the event database",
+	)
+}
+
 // TestHandleTargetDelete_EvictsWhenLastDatabaseTargetGone
 // proves that removing the last database target releases the
 // archive writer.

internal/handlers/source_management.go

@@ -625,43 +625,27 @@ func (h *Handlers) deleteWebhookResources(
 	webhook database.Webhook,
 	userID string,
 ) {
-	tx := h.db.DB().Begin()
+	// The configuration delete commits before the event database
-	if tx.Error != nil {
+	// is touched. No transaction spans the main database and the
-		h.log.Error(
+	// filesystem, so one side has to go first: committing the
-			"failed to begin transaction",
+	// configuration first means a later failure leaves an unused
-			"error", tx.Error,
+	// event database file on disk, while removing the event
-		)
+	// database first would mean a failed commit destroys the
-		http.Error(
+	// history of a webhook that still exists. A leftover file can
-			w, "Internal server error",
+	// be removed by hand; deleted history cannot be recovered.
-			http.StatusInternalServerError,
+	err := h.commitWebhookDeletion(&webhook)
-		)
-
-		return
-	}
-
-	tx.Where(
-		"webhook_id = ?", webhook.ID,
-	).Delete(&database.Entrypoint{})
-
-	tx.Where(
-		"webhook_id = ?", webhook.ID,
-	).Delete(&database.Target{})
-
-	tx.Delete(&webhook)
-
-	err := tx.Commit().Error
 	if err != nil {
-		h.log.Error(
+		h.serverError(w, "failed to delete webhook", err)
-			"failed to commit deletion", "error", err,
-		)
-		http.Error(
-			w, "Internal server error",
-			http.StatusInternalServerError,
-		)
 
 		return
 	}
 
+	h.log.Info(
+		"webhook deleted",
+		"webhook_id", webhook.ID,
+		"user_id", userID,
+	)
+
 	// Release the delivery engine's per-webhook archiving state
 	// so a deleted webhook's archive writer (and any handle open
 	// within its debounce window) does not linger for the
@@ -671,22 +655,63 @@ func (h *Handlers) deleteWebhookResources(
 
 	err = h.dbMgr.DeleteDB(webhook.ID)
 	if err != nil {
-		h.log.Error(
+		// The configuration is committed, so the webhook is gone,
-			"failed to delete webhook event database",
+		// but its event database file is still on disk with
-			"webhook_id", webhook.ID,
+		// nothing referencing it. Report the failure rather than
-			"error", err,
+		// redirecting as though everything succeeded: the file
+		// needs removing by hand, and the logged error names it.
+		h.serverError(
+			w, "failed to delete webhook event database", err,
 		)
+
+		return
 	}
 
-	h.log.Info(
-		"webhook deleted",
-		"webhook_id", webhook.ID,
-		"user_id", userID,
-	)
-
 	http.Redirect(w, r, "/sources", http.StatusSeeOther)
 }
 
+// commitWebhookDeletion soft-deletes a webhook's entrypoints,
+// targets and the webhook row in one transaction. Every
+// statement is checked and any failure rolls the whole
+// transaction back, so a caller that gets an error knows the
+// configuration is untouched and the event database must be
+// left alone.
+func (h *Handlers) commitWebhookDeletion(
+	webhook *database.Webhook,
+) error {
+	tx := h.db.DB().Begin()
+	if tx.Error != nil {
+		return tx.Error
+	}
+
+	err := tx.Where(
+		"webhook_id = ?", webhook.ID,
+	).Delete(&database.Entrypoint{}).Error
+	if err != nil {
+		tx.Rollback()
+
+		return err
+	}
+
+	err = tx.Where(
+		"webhook_id = ?", webhook.ID,
+	).Delete(&database.Target{}).Error
+	if err != nil {
+		tx.Rollback()
+
+		return err
+	}
+
+	err = tx.Delete(webhook).Error
+	if err != nil {
+		tx.Rollback()
+
+		return err
+	}
+
+	return tx.Commit().Error
+}
+
 // evictArchiveWriter asks the delivery engine to drop its
 // cached archive writer for a webhook, closing the archive file
 // handle.

internal/middleware/csrf.go

@@ -5,6 +5,7 @@ import (
 
 	"github.com/gorilla/csrf"
 	"sneak.berlin/go/webhooker/internal/logfield"
+	"sneak.berlin/go/webhooker/internal/reqtls"
 )
 
 // CSRFToken retrieves the CSRF token from the request context.
@@ -13,13 +14,6 @@ func CSRFToken(r *http.Request) string {
 	return csrf.Token(r)
 }
 
-// isClientTLS reports whether the client-facing connection uses TLS.
-// It checks for a direct TLS connection (r.TLS) or a TLS-terminating
-// reverse proxy that sets the standard X-Forwarded-Proto header.
-func isClientTLS(r *http.Request) bool {
-	return r.TLS != nil || r.Header.Get("X-Forwarded-Proto") == "https"
-}
-
 // CSRF returns middleware that provides CSRF protection using the
 // gorilla/csrf library. The middleware uses the session authentication
 // key to sign a CSRF cookie and validates a masked token submitted via
@@ -27,9 +21,10 @@ func isClientTLS(r *http.Request) bool {
 // POST/PUT/PATCH/DELETE requests. Requests with an invalid or missing
 // token receive a 403 Forbidden response.
 //
-// The middleware detects the client-facing transport protocol per-request
+// The middleware detects the client-facing transport protocol
-// using r.TLS and the X-Forwarded-Proto header. This allows correct
+// per-request via reqtls.IsTLS, the single TLS predicate the session
-// behavior in all deployment scenarios:
+// cookie also uses. This allows correct behavior in all deployment
+// scenarios:
 //
 //   - Direct HTTPS: strict Referer/Origin checks, Secure cookies.
 //   - Behind a TLS-terminating reverse proxy: strict checks (the
@@ -83,7 +78,7 @@ func (m *Middleware) CSRF() func(http.Handler) http.Handler {
 		httpCSRF := httpProtect(next)
 
 		return http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
-			if isClientTLS(r) {
+			if reqtls.IsTLS(r) {
 				// Client is on TLS (directly or via reverse proxy).
 				// Use Secure cookies and strict Origin/Referer checks.
 				tlsCSRF.ServeHTTP(w, r)

internal/middleware/csrf_test.go

@@ -297,55 +297,176 @@ func TestCSRFToken_NoMiddleware(t *testing.T) {
 }
 
 // --- TLS Detection Tests ---
+//
+// The predicate itself is tested in internal/reqtls. What is tested
+// here is the consequence that actually matters: which of the two
+// gorilla/csrf instances a request is routed to.
+//
+// The two are told apart behaviourally rather than by inspection. On
+// the STRICT (TLS) instance, a state-changing request carrying no
+// Origin header must supply a Referer -- gorilla/csrf rejects it with
+// ErrNoReferer before it ever looks at the token, to defend a
+// TLS site against an HTTP machine-in-the-middle injecting a form. On
+// the RELAXED (plaintext) instance that check is skipped and a valid
+// token is enough. So: valid token, no Origin, no Referer, and the
+// outcome names the instance.
+//
+// Landing on the relaxed instance for a genuinely-HTTPS deployment is
+// the defect: an exact == "https" comparison did exactly that for the
+// uppercase and comma-appended spellings below.
 
-func TestIsClientTLS_DirectTLS(t *testing.T) {
+// csrfTookStrictPath reports whether the CSRF middleware routed a
+// request with the given transport to the strict instance. It also
+// asserts the CSRF cookie's Secure attribute agrees, since the two are
+// set by the same choice and must never disagree.
+func csrfTookStrictPath(
+	t *testing.T,
+	env string,
+	directTLS bool,
+	fwdProto string,
+) bool {
+	t.Helper()
+
+	m, _ := testMiddleware(t, env)
+	csrfMW := m.CSRF()
+
+	newReq := func(method string) *http.Request {
+		r := httptest.NewRequestWithContext(
+			context.Background(), method,
+			"http://example.com/form", nil,
+		)
+
+		if directTLS {
+			r.TLS = &tls.ConnectionState{}
+		}
+
+		if fwdProto != "" {
+			r.Header.Set("X-Forwarded-Proto", fwdProto)
+		}
+
+		return r
+	}
+
+	token, cookies := csrfGetToken(t, csrfMW, newReq(http.MethodGet))
+
+	// Deliberately no Origin and no Referer: that is what makes the
+	// two instances distinguishable.
+	called, code := csrfPostWithToken(
+		t, csrfMW, newReq(http.MethodPost), token, cookies,
+	)
+
+	strict := !called
+
+	if strict {
+		assert.Equal(
+			t, http.StatusForbidden, code,
+			"the strict instance rejects a Referer-less POST",
+		)
+	}
+
+	for _, c := range cookies {
+		if c.Name == csrfCookieName {
+			assert.Equal(
+				t, strict, c.Secure,
+				"the CSRF cookie's Secure attribute and the "+
+					"chosen instance come from one decision "+
+					"and must agree",
+			)
+		}
+	}
+
+	return strict
+}
+
+// TestCSRF_ForwardedProtoSpellingsTakeStrictPath runs the header
+// spellings a real proxy emits through the middleware. The environment
+// is dev -- the DEFAULT when WEBHOOKER_ENVIRONMENT is unset -- to pin
+// that the routing is a per-request transport decision and owes
+// nothing to configuration.
+func TestCSRF_ForwardedProtoSpellingsTakeStrictPath(t *testing.T) {
 	t.Parallel()
 
-	r := httptest.NewRequestWithContext(
+	cases := []struct {
-		context.Background(), http.MethodGet, "/", nil)
+		name   string
-	r.TLS = &tls.ConnectionState{}
+		header string
+		strict bool
+		why    string
+	}{
+		{
+			name:   "lowercase",
+			header: "https",
+			strict: true,
+			why:    "the ordinary spelling",
+		},
+		{
+			name:   "uppercase",
+			header: "HTTPS",
+			strict: true,
+			why:    "the header value is a case-insensitive token",
+		},
+		{
+			name:   "chain with plaintext inner hop",
+			header: "https, http",
+			strict: true,
+			why: "a chained proxy appends its hop; the leftmost " +
+				"element is the browser's connection",
+		},
+		{
+			name:   "chain of two TLS hops",
+			header: "https,https",
+			strict: true,
+			why:    "appended chain with no space after the comma",
+		},
+		{
+			name:   "trailing space",
+			header: "https ",
+			strict: true,
+			why:    "whitespace is not part of the token",
+		},
+		{
+			name:   "plaintext",
+			header: "http",
+			strict: false,
+			why: "the negative control: the proxy reports a " +
+				"plaintext client connection",
+		},
+	}
+
+	for _, tc := range cases {
+		t.Run(tc.name, func(t *testing.T) {
+			t.Parallel()
+
+			assert.Equal(
+				t, tc.strict,
+				csrfTookStrictPath(
+					t, config.EnvironmentDev, false, tc.header,
+				),
+				"X-Forwarded-Proto %q: %s", tc.header, tc.why,
+			)
+		})
+	}
+}
+
+// TestCSRF_DirectTLSTakesStrictPath covers the no-proxy TLS
+// deployment, and TestCSRF_PlaintextTakesRelaxedPath the no-proxy
+// plaintext one -- the local development case that must keep working.
+func TestCSRF_DirectTLSTakesStrictPath(t *testing.T) {
+	t.Parallel()
 
 	assert.True(
-		t, middleware.IsClientTLS(r),
+		t,
-		"should detect direct TLS connection",
+		csrfTookStrictPath(t, config.EnvironmentDev, true, ""),
+		"a request that arrived over TLS takes the strict path",
 	)
 }
 
-func TestIsClientTLS_XForwardedProto(t *testing.T) {
+func TestCSRF_PlaintextTakesRelaxedPath(t *testing.T) {
 	t.Parallel()
 
-	r := httptest.NewRequestWithContext(
-		context.Background(), http.MethodGet, "/", nil)
-	r.Header.Set("X-Forwarded-Proto", "https")
-
-	assert.True(
-		t, middleware.IsClientTLS(r),
-		"should detect TLS via X-Forwarded-Proto",
-	)
-}
-
-func TestIsClientTLS_PlaintextHTTP(t *testing.T) {
-	t.Parallel()
-
-	r := httptest.NewRequestWithContext(
-		context.Background(), http.MethodGet, "/", nil)
-
 	assert.False(
-		t, middleware.IsClientTLS(r),
+		t,
-		"should detect plaintext HTTP",
+		csrfTookStrictPath(t, config.EnvironmentProd, false, ""),
-	)
+		"no TLS and no proxy header is plaintext, in any environment",
-}
-
-func TestIsClientTLS_XForwardedProtoHTTP(t *testing.T) {
-	t.Parallel()
-
-	r := httptest.NewRequestWithContext(
-		context.Background(), http.MethodGet, "/", nil)
-	r.Header.Set("X-Forwarded-Proto", "http")
-
-	assert.False(
-		t, middleware.IsClientTLS(r),
-		"should detect plaintext when X-Forwarded-Proto is http",
 	)
 }
 

internal/middleware/export_test.go

@@ -56,11 +56,6 @@ func ClientKeyForTest(m *Middleware, r *http.Request) string {
 	return m.clientKey(r)
 }
 
-// IsClientTLS exposes isClientTLS for testing.
-func IsClientTLS(r *http.Request) bool {
-	return isClientTLS(r)
-}
-
 // LoginRateLimitConst exposes the loginRateLimit constant: the
 // number of FAILED login attempts one client may make against one
 // submitted username per interval.

internal/reqtls/reqtls.go

@@ -0,0 +1,59 @@
+// Package reqtls answers one question, in one place, for the whole
+// application: did this request reach the service over TLS?
+//
+// It exists because that question used to be answered independently in
+// several packages, by hand, and the answers disagreed. The session
+// cookie's Secure attribute was decided at startup from the configured
+// environment while the CSRF cookie's was decided per-request, so a
+// deployment behind a TLS proxy in the default environment emitted one
+// Secure cookie and one non-Secure cookie on the same response.
+// Everything kept working, which is exactly why nobody noticed.
+//
+// Any code that needs a scheme or a Secure flag must call IsTLS rather
+// than reading the request itself.
+package reqtls
+
+import (
+	"net/http"
+	"strings"
+)
+
+// forwardedProtoHeader is the de-facto standard header by which a
+// TLS-terminating reverse proxy reports the protocol the CLIENT used.
+const forwardedProtoHeader = "X-Forwarded-Proto"
+
+// IsTLS reports whether the client-facing connection uses TLS: either
+// the request arrived over TLS directly, or a reverse proxy terminated
+// TLS and said so in X-Forwarded-Proto.
+//
+// The header is only as trustworthy as whatever sits in front of the
+// listener. A proxy that overwrites it -- which is what the deployment
+// documentation requires -- makes it authoritative; a listener exposed
+// directly to clients lets any client assert it. That is the same
+// exposure every X-Forwarded-* consumer carries.
+func IsTLS(r *http.Request) bool {
+	return r.TLS != nil || forwardedProto(r) == "https"
+}
+
+// forwardedProto reduces X-Forwarded-Proto to a bare, comparable
+// protocol token, or "" when the header is absent or blank.
+//
+// Two shapes that real infrastructure emits do not survive an exact
+// comparison against "https", and both name a TLS client connection:
+//
+//   - "HTTPS", because the header value is a case-insensitive token and
+//     nothing obliges a proxy to emit it lowercased.
+//   - "https, http", because a proxy chained behind another proxy
+//     APPENDS its own hop instead of replacing the value. As with
+//     X-Forwarded-For, the leftmost element is the one nearest the
+//     client, so it is the element that describes the browser's
+//     connection -- the only hop a cookie's Secure attribute is about.
+//
+// Landing on the plaintext path for either of those spellings is not a
+// cosmetic error: it stops gorilla/csrf enforcing the strict Referer
+// check on a site that genuinely is HTTPS.
+func forwardedProto(r *http.Request) string {
+	first, _, _ := strings.Cut(r.Header.Get(forwardedProtoHeader), ",")
+
+	return strings.ToLower(strings.TrimSpace(first))
+}

internal/reqtls/reqtls_test.go

@@ -0,0 +1,209 @@
+package reqtls_test
+
+import (
+	"context"
+	"crypto/tls"
+	"net/http"
+	"net/http/httptest"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"sneak.berlin/go/webhooker/internal/reqtls"
+)
+
+// newReq builds a plaintext request with no forwarding headers.
+func newReq(t *testing.T) *http.Request {
+	t.Helper()
+
+	return httptest.NewRequestWithContext(
+		context.Background(), http.MethodGet, "/", nil,
+	)
+}
+
+func TestIsTLS_DirectTLS(t *testing.T) {
+	t.Parallel()
+
+	r := newReq(t)
+	r.TLS = &tls.ConnectionState{}
+
+	assert.True(
+		t, reqtls.IsTLS(r),
+		"a request that arrived over TLS is TLS",
+	)
+}
+
+func TestIsTLS_PlaintextNoHeader(t *testing.T) {
+	t.Parallel()
+
+	assert.False(
+		t, reqtls.IsTLS(newReq(t)),
+		"no TLS connection and no header means plaintext",
+	)
+}
+
+// protoCase is one X-Forwarded-Proto spelling and the answer IsTLS
+// owes it.
+type protoCase struct {
+	name   string
+	header string
+	want   bool
+	why    string
+}
+
+// protoCases enumerates the header values real infrastructure emits.
+func protoCases() []protoCase {
+	return append(protoTLSCases(), protoPlaintextCases()...)
+}
+
+// protoTLSCases are the spellings that name a TLS client connection.
+// Every one but the first is a spelling an exact == "https"
+// comparison used to miss, silently downgrading a genuinely-HTTPS
+// deployment to the plaintext path.
+func protoTLSCases() []protoCase {
+	return []protoCase{
+		{
+			name:   "lowercase",
+			header: "https",
+			want:   true,
+			why:    "the ordinary spelling",
+		},
+		{
+			name:   "uppercase",
+			header: "HTTPS",
+			want:   true,
+			why: "the value is a case-insensitive token; " +
+				"nothing obliges a proxy to lowercase it",
+		},
+		{
+			name:   "mixed case",
+			header: "HttpS",
+			want:   true,
+			why:    "case folding must be total, not just the two extremes",
+		},
+		{
+			name:   "chain with plaintext inner hop",
+			header: "https, http",
+			want:   true,
+			why: "a chained proxy appends its hop; the leftmost " +
+				"element is the client-facing one",
+		},
+		{
+			name:   "chain of two TLS hops",
+			header: "https,https",
+			want:   true,
+			why:    "appended chain with no space after the comma",
+		},
+		{
+			name:   "trailing space",
+			header: "https ",
+			want:   true,
+			why:    "surrounding whitespace is not part of the token",
+		},
+		{
+			name:   "leading space",
+			header: " https",
+			want:   true,
+			why:    "surrounding whitespace is not part of the token",
+		},
+		{
+			name:   "uppercase chain",
+			header: "HTTPS, HTTP",
+			want:   true,
+			why:    "case folding and chain splitting must compose",
+		},
+	}
+}
+
+// protoPlaintextCases are the values that must NOT be read as TLS.
+func protoPlaintextCases() []protoCase {
+	return []protoCase{
+		{
+			name:   "plaintext",
+			header: "http",
+			want:   false,
+			why:    "the negative control: the proxy reports plaintext",
+		},
+		{
+			name:   "plaintext chain with TLS inner hop",
+			header: "http, https",
+			want:   false,
+			why: "the client-facing hop is plaintext even though " +
+				"an inner hop used TLS",
+		},
+		{
+			name:   "empty",
+			header: "",
+			want:   false,
+			why:    "an empty header asserts nothing",
+		},
+		{
+			name:   "whitespace only",
+			header: "   ",
+			want:   false,
+			why:    "a blank header asserts nothing",
+		},
+		{
+			name:   "unrelated token",
+			header: "ftp",
+			want:   false,
+			why:    "only https means TLS",
+		},
+		{
+			name:   "https as a substring",
+			header: "nothttps",
+			want:   false,
+			why:    "matching must be on the whole token, not a substring",
+		},
+	}
+}
+
+func TestIsTLS_ForwardedProtoSpellings(t *testing.T) {
+	t.Parallel()
+
+	for _, tc := range protoCases() {
+		t.Run(tc.name, func(t *testing.T) {
+			t.Parallel()
+
+			r := newReq(t)
+			r.Header.Set("X-Forwarded-Proto", tc.header)
+
+			assert.Equal(
+				t, tc.want, reqtls.IsTLS(r),
+				"X-Forwarded-Proto %q: %s", tc.header, tc.why,
+			)
+		})
+	}
+}
+
+// TestIsTLS_DirectTLSBeatsPlaintextHeader pins the precedence: a
+// connection this process itself terminated with TLS is a fact, and a
+// header claiming otherwise does not override it.
+func TestIsTLS_DirectTLSBeatsPlaintextHeader(t *testing.T) {
+	t.Parallel()
+
+	r := newReq(t)
+	r.TLS = &tls.ConnectionState{}
+	r.Header.Set("X-Forwarded-Proto", "http")
+
+	assert.True(
+		t, reqtls.IsTLS(r),
+		"an actual TLS connection outranks a header claiming plaintext",
+	)
+}
+
+// TestIsTLS_FirstHeaderValueWins covers a proxy that adds a second
+// header line rather than appending to the existing one. net/http
+// keeps them as separate values; the first is the client-facing hop,
+// matching how the comma-separated form is read.
+func TestIsTLS_FirstHeaderValueWins(t *testing.T) {
+	t.Parallel()
+
+	r := newReq(t)
+	r.Header.Add("X-Forwarded-Proto", "https")
+	r.Header.Add("X-Forwarded-Proto", "http")
+
+	assert.True(
+		t, reqtls.IsTLS(r),
+		"the first header line is the client-facing hop",
+	)
+}

internal/server/sentry.go

@@ -147,10 +147,13 @@ func sentryRoutePattern(hint *sentry.EventHint) string {
 //
 // The scheme is load-bearing and is kept: the SDK derives it from
 // r.TLS != nil || r.Header.Get("X-Forwarded-Proto") == "https"
-// (interfaces.go:180), byte for byte the predicate
+// (interfaces.go:180), which is the reason dropping X-Forwarded-Proto
-// internal/middleware/csrf.go uses, so it is the CSRF TLS decision and
+// from the header allowlist costs nothing. That predicate is the SDK's
-// the reason dropping X-Forwarded-Proto from the header allowlist
+// own and is stricter than reqtls.IsTLS, which this service now uses
-// costs nothing. The host is parsed.Host of the SDK's
+// everywhere it decides transport: the SDK reports "http" for the
+// "HTTPS" and "https, http" spellings reqtls accepts. Only a reported
+// scheme is affected, no decision is, so it is left to the SDK rather
+// than reimplemented. The host is parsed.Host of the SDK's
 // scheme://r.Host/path, so it is whatever the client's Host header
 // carried: this service validates no hostname. It is kept because that
 // same header is on the allowlist, so scrubbing it here would withhold

internal/session/export_test.go

@@ -5,6 +5,6 @@ import "github.com/gorilla/sessions"
 // NewStore exposes the production cookie-store constructor so tests
 // exercise the store the application actually runs with, rather than a
 // lookalike assembled in the test.
-func NewStore(key []byte, secure bool) *sessions.CookieStore {
+func NewStore(key []byte) *sessions.CookieStore {
-	return newStore(key, secure)
+	return newStore(key)
 }

internal/session/session.go

@@ -17,6 +17,7 @@ import (
 	"sneak.berlin/go/webhooker/internal/config"
 	"sneak.berlin/go/webhooker/internal/database"
 	"sneak.berlin/go/webhooker/internal/logger"
+	"sneak.berlin/go/webhooker/internal/reqtls"
 )
 
 const (
@@ -84,10 +85,9 @@ type Params struct {
 
 // Session manages encrypted session storage.
 type Session struct {
-	store  *sessions.CookieStore
+	store *sessions.CookieStore
-	key    []byte // raw 32-byte auth key, also used for CSRF cookie signing
+	key   []byte // raw 32-byte auth key, also used for CSRF cookie signing
-	log    *slog.Logger
+	log   *slog.Logger
-	config *config.Config
 
 	// idleTimeout is the sliding inactivity window. A session that
 	// sees no authenticated request within this window expires,
@@ -104,6 +104,10 @@ type Session struct {
 // cookie. MaxAge is deliberately left at its zero value: for a store
 // it is set through CookieStore.MaxAge (see newStore), and for a
 // single session it is copied from the store's options.
+//
+// Secure is a parameter rather than a constant because it is the one
+// attribute here that is not a policy -- it is a fact about the
+// connection carrying this particular response. See applyTransport.
 func cookieOptions(secure bool) *sessions.Options {
 	return &sessions.Options{
 		Path:     "/",
@@ -121,14 +125,52 @@ func cookieOptions(secure bool) *sessions.Options {
 // Options never touches Codecs -- so a store configured that way still
 // decodes a 30-day-old cookie, leaving the cookie attribute and the
 // codec disagreeing about the same policy. store.MaxAge sets both.
-func newStore(key []byte, secure bool) *sessions.CookieStore {
+//
+// The store's Secure is fixed at true, and is only a template: every
+// write path overwrites it for the request in hand (applyTransport).
+// It is true rather than false so that a write path added later which
+// forgets to call applyTransport fails loudly -- the browser drops the
+// cookie over plaintext HTTP and the developer sees it immediately --
+// instead of silently shipping the authentication credential without
+// Secure, which is the exact failure this store already had once.
+func newStore(key []byte) *sessions.CookieStore {
 	store := sessions.NewCookieStore(key)
-	store.Options = cookieOptions(secure)
+	store.Options = cookieOptions(true)
 	store.MaxAge(secondsPerDay * sessionMaxAgeDays)
 
 	return store
 }
 
+// applyTransport sets the session cookie's Secure attribute from the
+// transport of the request being answered.
+//
+// This is decided per-request, not once at startup. Deciding it at
+// startup from the configured environment is what this replaces, and
+// it got the DEFAULT posture wrong: "dev" is the environment when
+// WEBHOOKER_ENVIRONMENT is unset, so a deployment terminating TLS at a
+// proxy without also setting the environment emitted the
+// authentication cookie with no Secure attribute -- silently, and on
+// the same response as a CSRF cookie that did have one.
+//
+// gorilla/sessions makes this cheap and local: CookieStore.New gives
+// every session its own copy of the store's Options, and
+// CookieStore.Save renders the cookie from that copy rather than from
+// the store. So the flag is set on the one session being saved,
+// without a second store and without reaching across concurrent
+// requests.
+//
+// The flag tracks the transport in BOTH directions rather than being
+// latched on once seen. Secure on a plaintext response is worse than
+// useless: the browser discards such a cookie without any error, so a
+// latched flag would make a plain-HTTP local run impossible to log
+// into. It is also why every write path must call this, including the
+// deletion cookies in Destroy and Regenerate -- a Secure deletion
+// cookie sent over plaintext is dropped too, leaving the session the
+// caller believed it had just revoked.
+func applyTransport(r *http.Request, sess *sessions.Session) {
+	sess.Options.Secure = reqtls.IsTLS(r)
+}
+
 // New creates a new session manager. The cookie store is
 // initialized during the fx OnStart phase after the database is
 // connected, using a session key that is auto-generated and stored
@@ -139,7 +181,6 @@ func New(
 ) (*Session, error) {
 	s := &Session{
 		log:         params.Logger.Get(),
-		config:      params.Config,
 		idleTimeout: params.Config.SessionIdleTimeout,
 		now:         time.Now,
 	}
@@ -172,7 +213,7 @@ func New(
 			}
 
 			s.key = keyBytes
-			s.store = newStore(keyBytes, !params.Config.IsDev())
+			s.store = newStore(keyBytes)
 			s.log.Info("session manager initialized")
 
 			return nil
@@ -196,12 +237,16 @@ func (s *Session) GetKey() []byte {
 	return s.key
 }
 
-// Save saves the session.
+// Save saves the session. Every session-cookie write in the
+// application goes through here or through Regenerate, which is what
+// makes applyTransport a complete answer rather than a best effort.
 func (s *Session) Save(
 	r *http.Request,
 	w http.ResponseWriter,
 	sess *sessions.Session,
 ) error {
+	applyTransport(r, sess)
+
 	return sess.Save(r, w)
 }
 
@@ -340,6 +385,7 @@ func (s *Session) Regenerate(
 	// Destroy the old session
 	oldSess.Options.MaxAge = -1
 	s.ClearUser(oldSess)
+	applyTransport(r, oldSess)
 
 	err := oldSess.Save(r, w)
 	if err != nil {
@@ -368,7 +414,7 @@ func (s *Session) Regenerate(
 	// Apply the standard session options (the destroyed old
 	// session had MaxAge = -1, which store.New might inherit
 	// from the cookie).
-	newSess.Options = cookieOptions(!s.config.IsDev())
+	newSess.Options = cookieOptions(reqtls.IsTLS(r))
 	newSess.Options.MaxAge = secondsPerDay * sessionMaxAgeDays
 
 	return newSess, nil

internal/session/session_test.go

@@ -2,6 +2,7 @@ package session_test
 
 import (
 	"context"
+	"crypto/tls"
 	"log/slog"
 	"net/http"
 	"net/http/httptest"
@@ -73,7 +74,7 @@ func testSessionWithClock(
 	t.Helper()
 
 	key := testKey()
-	store := session.NewStore(key, false)
+	store := session.NewStore(key)
 
 	cfg := &config.Config{
 		Environment:        config.EnvironmentDev,
@@ -880,3 +881,264 @@ func TestDestroy_ThenSave_DeletesCookie(t *testing.T) {
 		"destroyed session cookie should have negative MaxAge",
 	)
 }
+
+// --- Secure Attribute / Transport Tests ---
+
+// transportCase describes one client-facing transport and the Secure
+// attribute the session cookie must carry for it.
+type transportCase struct {
+	name   string
+	tls    bool
+	header string
+	want   bool
+	why    string
+}
+
+// transportCases enumerates the transports the session cookie has to
+// get right. Every https spelling here is one a real proxy emits.
+func transportCases() []transportCase {
+	return []transportCase{
+		{
+			name: "direct TLS",
+			tls:  true,
+			want: true,
+			why:  "this process terminated TLS itself",
+		},
+		{
+			name:   "proxy reports https",
+			header: "https",
+			want:   true,
+			why:    "the ordinary reverse-proxy deployment",
+		},
+		{
+			name:   "proxy reports HTTPS",
+			header: "HTTPS",
+			want:   true,
+			why:    "the header value is a case-insensitive token",
+		},
+		{
+			name:   "appended chain https, http",
+			header: "https, http",
+			want:   true,
+			why:    "the leftmost hop is the browser's connection",
+		},
+		{
+			name:   "appended chain https,https",
+			header: "https,https",
+			want:   true,
+			why:    "two TLS hops, no space after the comma",
+		},
+		{
+			name:   "trailing space",
+			header: "https ",
+			want:   true,
+			why:    "whitespace is not part of the token",
+		},
+		{
+			name:   "proxy reports http",
+			header: "http",
+			want:   false,
+			why: "the negative control: Secure over plaintext is " +
+				"dropped by the browser without a word",
+		},
+		{
+			name: "plaintext, no proxy",
+			want: false,
+			why:  "a plain local run must stay loggable-in",
+		},
+	}
+}
+
+// transportRequest builds a request carrying the case's transport.
+func (tc transportCase) request(t *testing.T) *http.Request {
+	t.Helper()
+
+	r := httptest.NewRequestWithContext(
+		context.Background(), http.MethodGet,
+		"http://example.com/", nil,
+	)
+
+	if tc.tls {
+		r.TLS = &tls.ConnectionState{}
+	}
+
+	if tc.header != "" {
+		r.Header.Set("X-Forwarded-Proto", tc.header)
+	}
+
+	return r
+}
+
+// sessionCookieFrom returns the session cookie from a response, or
+// fails the test if there is none.
+func sessionCookieFrom(
+	t *testing.T,
+	w *httptest.ResponseRecorder,
+) *http.Cookie {
+	t.Helper()
+
+	for _, c := range w.Result().Cookies() {
+		if c.Name == session.SessionName {
+			return c
+		}
+	}
+
+	require.FailNow(t, "no session cookie in response")
+
+	return nil
+}
+
+// TestSave_SecureFollowsRequestTransport is the regression test for
+// the defect this replaces: Secure was fixed at startup from the
+// configured environment, and "dev" is the environment when
+// WEBHOOKER_ENVIRONMENT is unset. A deployment behind a TLS proxy in
+// that DEFAULT posture shipped the authentication cookie with no
+// Secure attribute and said nothing about it.
+//
+// testSession builds its config with EnvironmentDev precisely so that
+// the https cases below fail against the old startup-fixed behaviour.
+func TestSave_SecureFollowsRequestTransport(t *testing.T) {
+	t.Parallel()
+
+	for _, tc := range transportCases() {
+		t.Run(tc.name, func(t *testing.T) {
+			t.Parallel()
+
+			s := testSession(t)
+			r := tc.request(t)
+			w := httptest.NewRecorder()
+
+			sess, err := s.Get(r)
+			require.NoError(t, err)
+
+			s.SetUser(sess, "user-1", "alice")
+			require.NoError(t, s.Save(r, w, sess))
+
+			assert.Equal(
+				t, tc.want, sessionCookieFrom(t, w).Secure,
+				"session cookie Secure for %q: %s",
+				tc.name, tc.why,
+			)
+		})
+	}
+}
+
+// TestSave_SecureTracksTransportBothWays pins that the flag is not
+// latched. One store serves every request, so a Secure cookie set for
+// a proxied request must not leak into a later plaintext response --
+// the browser would silently discard that one, and a local run would
+// become impossible to log into.
+func TestSave_SecureTracksTransportBothWays(t *testing.T) {
+	t.Parallel()
+
+	s := testSession(t)
+
+	secureReq := httptest.NewRequestWithContext(
+		context.Background(), http.MethodGet,
+		"http://example.com/", nil,
+	)
+	secureReq.Header.Set("X-Forwarded-Proto", "https")
+
+	secureW := httptest.NewRecorder()
+
+	secureSess, err := s.Get(secureReq)
+	require.NoError(t, err)
+	require.NoError(t, s.Save(secureReq, secureW, secureSess))
+	require.True(
+		t, sessionCookieFrom(t, secureW).Secure,
+		"proxied request should produce a Secure cookie",
+	)
+
+	plainReq := httptest.NewRequestWithContext(
+		context.Background(), http.MethodGet,
+		"http://example.com/", nil,
+	)
+	plainW := httptest.NewRecorder()
+
+	plainSess, err := s.Get(plainReq)
+	require.NoError(t, err)
+	require.NoError(t, s.Save(plainReq, plainW, plainSess))
+
+	assert.False(
+		t, sessionCookieFrom(t, plainW).Secure,
+		"a later plaintext request must not inherit Secure from "+
+			"the earlier proxied one",
+	)
+}
+
+// TestDestroy_DeletionCookieFollowsTransport covers the trap in the
+// deletion path. The store's template Secure is true, so a logout over
+// plaintext that failed to track the transport would emit a Secure
+// deletion cookie -- which the browser drops, leaving the session the
+// user just tried to end still sitting in the jar.
+func TestDestroy_DeletionCookieFollowsTransport(t *testing.T) {
+	t.Parallel()
+
+	s := testSession(t)
+
+	r := httptest.NewRequestWithContext(
+		context.Background(), http.MethodGet,
+		"http://example.com/", nil,
+	)
+	w := httptest.NewRecorder()
+
+	sess, err := s.Get(r)
+	require.NoError(t, err)
+
+	s.Destroy(sess)
+	require.NoError(t, s.Save(r, w, sess))
+
+	cookie := sessionCookieFrom(t, w)
+
+	require.Negative(
+		t, cookie.MaxAge,
+		"Destroy then Save should emit a deletion cookie",
+	)
+	assert.False(
+		t, cookie.Secure,
+		"a deletion cookie sent over plaintext must not be Secure, "+
+			"or the browser discards it and the session survives",
+	)
+}
+
+// TestRegenerate_BothCookiesFollowTransport covers the login path.
+// Regenerate writes two cookies -- a deletion for the pre-login
+// session and the new authenticated one -- and both have to match the
+// transport or one of them is silently dropped.
+func TestRegenerate_BothCookiesFollowTransport(t *testing.T) {
+	t.Parallel()
+
+	for _, tc := range transportCases() {
+		t.Run(tc.name, func(t *testing.T) {
+			t.Parallel()
+
+			s := testSession(t)
+			r := tc.request(t)
+			w := httptest.NewRecorder()
+
+			oldSess, err := s.Get(r)
+			require.NoError(t, err)
+
+			newSess, err := s.Regenerate(r, w, oldSess)
+			require.NoError(t, err)
+
+			s.SetUser(newSess, "user-1", "alice")
+			require.NoError(t, s.Save(r, w, newSess))
+
+			cookies := w.Result().Cookies()
+			require.Len(
+				t, cookies, 2,
+				"Regenerate then Save writes a deletion cookie "+
+					"and a replacement",
+			)
+
+			for _, c := range cookies {
+				assert.Equal(
+					t, tc.want, c.Secure,
+					"cookie %d Secure for %q: %s",
+					c.MaxAge, tc.name, tc.why,
+				)
+			}
+		})
+	}
+}

internal/session/testing.go

@@ -32,7 +32,6 @@ func NewForTest(
 	return &Session{
 		store:       store,
 		key:         key,
-		config:      cfg,
 		log:         log,
 		idleTimeout: cfg.SessionIdleTimeout,
 		now:         now,