Do not resend a delivery that restart recovery already sent (closes #299)

Restart recovery could find a just-written delivery pending, send it
and release it before the receiver's Notify queued the same delivery.
Notify's claim then succeeded on the released id, and the worker sent
it again because the new-task path never read the delivery's row.

Before sending a new task the worker now reads the delivery's status
by primary key and skips the task unless the row still says pending,
as the retry path already does for retrying. Nothing else can change
the row while the worker owns the delivery. A row left pending by a
failed bookkeeping write is still sent again.

loadRetryDelivery is renamed loadDelivery now that both paths use it.

Model: opus-5-5

README.md

@@ -7,6 +7,13 @@ services, durably stores them, and delivers them to configured targets
 with retry support, logging, and observability. Category: infrastructure
 / web service. License: MIT.
 
+Each entrypoint is a version 4 UUID served at `/webhook/{uuid}`, and
+that UUID is the entrypoint's only credential. webhooker does not use
+shared secrets, HMAC signatures or token headers on the receiver, and
+will not add them — read
+[The entrypoint URL is the authentication secret](#the-entrypoint-url-is-the-authentication-secret)
+before deploying one.
+
 ## Getting Started
 
 ### Prerequisites
@@ -37,9 +44,9 @@ make bootstrap
 # Run all checks (test, lint, format check)
 make check
 
-# Run in development mode. DATA_DIR defaults to /var/lib/webhooker in
-# every environment, so set it (in .env or the shell) to a writable
-# directory when running from a clone.
+# Run the server from the clone. DATA_DIR defaults to
+# /var/lib/webhooker in every environment, so set it (in .env or the
+# shell) to a writable directory.
 DATA_DIR=./data make dev
 
 # Build Docker image
@@ -85,7 +92,8 @@ them at once. A variable already present in the real environment wins
 over the file's value for the same name.
 
 The environment is selected by setting `WEBHOOKER_ENVIRONMENT` to `dev`
-or `prod` (default: `dev`). The setting controls exactly one behavior:
+or `prod` (default: `prod`; `dev` must be set explicitly). The setting
+controls exactly one behavior:
 
 | Behavior | `dev`                   | `prod`           |
 | -------- | ----------------------- | ---------------- |
@@ -127,7 +135,7 @@ TTY detection, and security headers are always applied.
 
 | Variable                | Description                         | Default  |
 | ----------------------- | ----------------------------------- | -------- |
-| `WEBHOOKER_ENVIRONMENT` | `dev` or `prod`                     | `dev`    |
+| `WEBHOOKER_ENVIRONMENT` | `dev` or `prod`                     | `prod`   |
 | `PORT`                  | HTTP listen port                    | `8080`   |
 | `BIND_ADDRESS`          | IP address the HTTP listener binds. Loopback by default, so the cleartext listener is not published on every interface. The Docker image ships `0.0.0.0` instead. See [Bind address](#bind-address) | `127.0.0.1` (image: `0.0.0.0`) |
 | `DATA_DIR`              | Directory for all SQLite databases  | `/var/lib/webhooker` |
@@ -392,10 +400,9 @@ the bucket is. See [Rate Limiting](#rate-limiting).
 
 The remedy is to set `TRUSTED_PROXIES` to your reverse proxy's
 address, which restores per-client buckets. webhooker logs a warning
-at startup whenever `TRUSTED_PROXIES` is empty, in every environment —
-not only when `WEBHOOKER_ENVIRONMENT=prod`, because that variable
-defaults to `dev` and an operator who never set it is precisely the
-one at risk. The warning is informational when nothing proxies to the
+at startup whenever `TRUSTED_PROXIES` is empty, in every environment,
+because behind a proxy every client shares one bucket in `dev` and
+`prod` alike. The warning is informational when nothing proxies to the
 process: with no proxy in front, the peer address is the client's own
 and the buckets are already per-client. See
 [Rate Limiting](#rate-limiting) for what each limit shares.
@@ -631,7 +638,6 @@ decision:
 docker run -d \
   -p 127.0.0.1:8080:8080 \
   -v /path/to/data:/var/lib/webhooker \
-  -e WEBHOOKER_ENVIRONMENT=prod \
   -e BIND_ADDRESS=0.0.0.0 \
   webhooker:latest
 ```
@@ -724,6 +730,66 @@ listing the directory and learning your webhook UUIDs from the
 `events-{uuid}.db` filenames — not the barrier protecting the
 credentials.
 
+### Running under upaas
+
+[upaas](https://git.eeqj.de/sneak/upaas) builds the image from this
+repository's `Dockerfile` and runs it. The app needs:
+
+- **Network and port:** add no port mapping in upaas. upaas publishes
+  every mapped port on all interfaces of the host
+  ([upaas issue 113](https://git.eeqj.de/sneak/upaas/issues/113)),
+  which would put the plain-HTTP admin UI and receiver there. Instead,
+  set the app's Docker Network in upaas to your reverse proxy's Docker
+  network; the proxy then reaches the app at `upaas-` followed by the
+  app name, port `8080`. Leave `PORT` unset: the image's health check
+  probes `8080`.
+- **Volume:** one host directory mounted at `/var/lib/webhooker`.
+  upaas bind-mounts the host path it is given and does not create it,
+  and the container does not start unless UID 1000 owns it (see
+  [Running with Docker](#running-with-docker)). Create it before the
+  first deploy:
+
+    ```bash
+    mkdir -p /path/to/data
+    chown 1000:1000 /path/to/data
+    chmod 750 /path/to/data
+    ```
+
+- **Environment variables:**
+    - `WEBHOOKER_ENVIRONMENT=prod`
+    - `TRUSTED_PROXIES`: your reverse proxy's address on that Docker
+      network. The `remoteIP` field of the `http request` log line for a
+      request that came through the proxy shows it; the health check's
+      own lines show `::1`. See [Trusted proxies](#trusted-proxies).
+    - Leave `BIND_ADDRESS` and `DATA_DIR` unset: the image sets
+      `BIND_ADDRESS` to `0.0.0.0`, and `DATA_DIR` defaults to
+      `/var/lib/webhooker`.
+    - Everything else is optional; see [Configuration](#configuration).
+- **Health check:** the image's own, which requests
+  `/.well-known/healthcheck`. upaas reads the container's health 60
+  seconds after a deploy and marks the deploy failed unless it is
+  `healthy`.
+- **First run:** the first start prints the `admin` password once, in
+  the banner described under [The admin account](#the-admin-account),
+  to the container's log. upaas names the container `upaas-` followed
+  by the app name, so for an app named `webhooker`:
+
+    ```bash
+    docker logs upaas-webhooker
+    ```
+
+  If the password is lost, stop the container, set a new password with
+  the app's own image and volume, and start it again (see
+  [Recovering a lost admin password](#recovering-a-lost-admin-password)):
+
+    ```bash
+    docker stop upaas-webhooker
+    docker run --rm --volumes-from upaas-webhooker \
+        "$(docker inspect -f '{{.Image}}' upaas-webhooker)" \
+        /app/webhooker resetpw -generate admin
+    docker start upaas-webhooker
+    ```
+
 ## Deployment behind a reverse proxy
 
 webhooker terminates no TLS of its own. It serves plaintext HTTP and
@@ -745,17 +811,18 @@ reports.
    serves the admin login form and the unauthenticated receiver with
    no TLS at all, and the proxy in front of it changes nothing about
    that.
-2. **Set `WEBHOOKER_ENVIRONMENT=prod`, and make sure the proxy sends
-   `X-Forwarded-Proto`.** These are two requirements, not one. The
-   environment setting decides CORS and nothing else: the default
+2. **Make sure the environment is not `dev` (leave
+   `WEBHOOKER_ENVIRONMENT` unset or set it to `prod`), and make sure
+   the proxy sends `X-Forwarded-Proto`.** These are two requirements,
+   not one. The environment setting decides CORS and nothing else:
    `dev` answers every origin with `Access-Control-Allow-Origin: *`
    (without credentials), which a server-rendered production
-   deployment has no use for. Cookie `Secure` and the strict
-   Origin/Referer mode are **not** tied to it — they are decided per
-   request from the transport, which behind a proxy means the
-   `X-Forwarded-Proto` header. The block below sets it; without it
-   every request is read as plaintext and cookies ship without
-   `Secure`. See [Configuration](#configuration).
+   deployment has no use for, and `prod` — the default — disables it.
+   Cookie `Secure` and the strict Origin/Referer mode are **not** tied
+   to it — they are decided per request from the transport, which
+   behind a proxy means the `X-Forwarded-Proto` header. The block below
+   sets it; without it every request is read as plaintext and cookies
+   ship without `Secure`. See [Configuration](#configuration).
 3. **Set `TRUSTED_PROXIES` to the proxy's address.** Unset, every rate
    limiter keys on the connecting peer, which behind a proxy is the
    proxy on every request: all clients collapse into one global bucket
@@ -847,7 +914,6 @@ sent — `$scheme` above does.
 With that block, webhooker's environment is:
 
 ```sh
-WEBHOOKER_ENVIRONMENT=prod
 BIND_ADDRESS=127.0.0.1   # the default; stated here to be explicit
 TRUSTED_PROXIES=127.0.0.1
 ```
@@ -1149,14 +1215,38 @@ backups at rest and restrict who can read them.
 
 ## The entrypoint URL is the authentication secret
 
-The receiver verifies nothing about an inbound request. The UUID in an
-entrypoint's URL is its credential: anyone who holds that URL can
-submit events to it, and the receiver checks nothing else about the
-sender. Treat an entrypoint URL the way you would treat an API token.
+**The entrypoint UUID is the credential, and it is the only one.**
+webhooker mints a version 4 UUID per entrypoint and serves it at
+`/webhook/{uuid}`. Possession of that URL is the authentication:
+anyone who holds it can submit events to the entrypoint, and the
+receiver verifies nothing else about the sender.
 
-There is no way to rotate the UUID in place. To retire one, delete the
-entrypoint (or deactivate it, which answers `410`) and create a new
-one, then point the sender at the new URL.
+There is no shared secret, no HMAC signature, no bearer token and no
+second factor on the receiver, and none will be added. This was
+considered and rejected; the implementation that existed was removed
+in [PR #279](https://git.eeqj.de/sneak/webhooker/pulls/279), closing
+[issue #67](https://git.eeqj.de/sneak/webhooker/issues/67) and
+[issue #241](https://git.eeqj.de/sneak/webhooker/issues/241). A
+proposal to reintroduce any of them — including as "defence in depth"
+alongside the UUID — is answered by this section. Inbound signature
+headers a sender sends anyway (`X-Hub-Signature` and its
+per-provider equivalents) are stored and forwarded as ordinary
+headers; nothing checks them.
+
+What that means for an operator:
+
+- **The URL is a capability, so treat it as a secret.** Keep it out of
+  logs, ticket bodies, chat messages and screenshots. Anyone who reads
+  it anywhere can post events as that sender.
+- **Rotating means minting a new entrypoint, not changing a key.**
+  There is no way to rotate the UUID in place. To retire one, delete
+  the entrypoint (or deactivate it, which answers `410`) and create a
+  new one, then point the sender at the new URL.
+- **A sender that cannot be given a secret URL is a constraint on that
+  integration, not a reason to change this.** If a service only
+  supports signed payloads to a well-known URL, raise it as its own
+  problem — pick a different integration path, or accept that it
+  cannot be used. It is not grounds to reintroduce shared secrets.
 
 ## Entrypoints
 
@@ -1476,7 +1566,7 @@ events should be forwarded.
 | `type`           | TargetType | One of: `http`, `slack`, `database`, `log` |
 | `active`         | boolean    | Whether deliveries are enabled (default: true) |
 | `config`         | JSON text  | Type-specific configuration |
-| `max_retries`    | integer    | Maximum retry attempts for `http` and `slack` targets (0 = fire-and-forget, >0 = retries with backoff and a circuit breaker). Ignored by `database` and `log` targets |
+| `max_retries`    | integer    | Total delivery attempts for `http` and `slack` targets, not retries on top of the first: 0 is a single fire-and-forget attempt with no retries and no circuit breaker, and a value of N makes N attempts in all, with exponential backoff and a per-target circuit breaker. Ignored by `database` and `log` targets |
 | `max_queue_size` | integer    | Stored and shown on the target's detail view, but not enforced anywhere yet: nothing in the delivery engine consults it. Queue depth is set by the two fixed 10,000-entry channels |
 
 **Relations:** Belongs to Webhook. Has many Deliveries.
@@ -1484,12 +1574,12 @@ events should be forwarded.
 **Target types:**
 
 - **`http`** — Forward the event as an HTTP POST to a configured URL.
-  Behavior depends on `max_retries`: when `max_retries` is 0 (the
-  default), the target operates in fire-and-forget mode — a single
-  attempt with no retries and no circuit breaker. When `max_retries` is
-  greater than 0, failed deliveries are retried with exponential backoff
-  up to `max_retries` attempts, protected by a per-target circuit
-  breaker.
+  `max_retries` is the total number of delivery attempts, not retries on
+  top of the first: when `max_retries` is 0 (the default), the target
+  operates in fire-and-forget mode, a single attempt with no retries and
+  no circuit breaker; a value of N makes up to N attempts in all,
+  retrying failed deliveries with exponential backoff and protecting them
+  with a per-target circuit breaker.
 - **`slack`** — Post the event as a formatted message to a
   Slack-compatible incoming webhook URL (`webhookUrl` in `config`). It
   is built on the same HTTP core as `http` and honours `max_retries`
@@ -1669,6 +1759,28 @@ retries) is individually logged for full observability.
 
 **Relations:** Belongs to Delivery.
 
+#### Event-tier indexes
+
+These indexes on the per-webhook event databases are declared in the model
+tags, so `AutoMigrate` creates them on a fresh and on an existing database:
+
+| Table              | Columns                     | Serves |
+| ------------------ | --------------------------- | ------ |
+| `deliveries`       | `status`, `deleted_at`      | Startup recovery, the retry and pending sweeps every 60 seconds and the queue-depth sampler every 30 seconds, which select deliveries by status |
+| `deliveries`       | `event_id`, `deleted_at`    | The event log, which loads each event's deliveries, and retention, which selects and deletes the deliveries of expired events |
+| `delivery_results` | `delivery_id`, `deleted_at` | The event log, which loads the attempts of a page's deliveries, and retention, which deletes the attempts of expired events |
+| `events`           | `deleted_at`, `created_at`  | Retention, which selects expired events by age |
+| `events`           | `created_at`                | Retention's delete of the expired events themselves |
+
+GORM's soft delete adds `deleted_at IS NULL` to these queries; retention's
+deletes leave it out, but their lookups of expired rows keep it. SQLite keeps
+no statistics on these tables, and without them it rates the `deleted_at`
+index, which every live row matches, above an index on a column matched
+against several values or compared with `<`. So every index but the last also
+covers `deleted_at`. It comes second, so that retention's deletes can use the
+index without it, except in `events`, where `created_at` is compared with `<`
+and SQLite narrows by a `<` only on the last column it uses.
+
 #### Common Fields
 
 Every entity except `Setting` includes these fields from `BaseModel`.
@@ -2867,6 +2979,10 @@ check, see [The login endpoint](#the-login-endpoint).
 
 ### Authentication
 
+- **Webhook receiver:** the entrypoint UUID in the URL, and nothing
+  else. No shared secret, no HMAC signature, no token header, and none
+  will be added — see
+  [The entrypoint URL is the authentication secret](#the-entrypoint-url-is-the-authentication-secret).
 - **Web UI:** Cookie-based sessions using gorilla/sessions with
   encrypted cookies. Sessions are configured with HttpOnly, SameSite
   Lax, and Secure whenever the request is on TLS — the flag follows the
@@ -2906,7 +3022,8 @@ check, see [The login endpoint](#the-login-endpoint).
   mode
 - **The entrypoint URL is the receiver's only credential.** Nothing
   about an inbound request is verified; possession of the UUID
-  authorises submission (see
+  authorises submission, and no shared secret or signature check will
+  be added alongside it (see
   [The entrypoint URL is the authentication secret](#the-entrypoint-url-is-the-authentication-secret))
 - **SSRF prevention** for HTTP delivery targets: private/reserved IP
   ranges (RFC 1918, loopback, link-local, cloud metadata) are blocked

internal/config/config.go

@@ -585,12 +585,14 @@ func resolveMetricsAuth() (string, string, error) {
 	)
 }
 
-// resolveEnvironment reads WEBHOOKER_ENVIRONMENT, defaulting to
-// dev, and rejects unrecognised values.
+// resolveEnvironment reads WEBHOOKER_ENVIRONMENT, defaulting to prod
+// when it is unset so a deployment that forgets the variable is not
+// silently permissive; dev must be set explicitly. It rejects
+// unrecognised values.
 func resolveEnvironment() (string, error) {
 	environment := os.Getenv("WEBHOOKER_ENVIRONMENT")
 	if environment == "" {
-		environment = EnvironmentDev
+		environment = EnvironmentProd
 	}
 
 	if environment != EnvironmentDev &&
@@ -772,10 +774,8 @@ func (c *Config) warnEgressAllowlist(log *slog.Logger) {
 // everyone else's wrong passwords, and the receiver's limits become
 // service-wide ceilings.
 //
-// The warning is deliberately not gated on WEBHOOKER_ENVIRONMENT. That
-// variable defaults to dev, so gating on it would silence the warning
-// for exactly the operator who forgot to configure the deployment —
-// the case it exists to catch.
+// The warning is deliberately not gated on WEBHOOKER_ENVIRONMENT:
+// behind a proxy every client shares one bucket in dev and prod alike.
 //
 // The default of trusting nobody is deliberate — trusting forwarded
 // headers from arbitrary peers lets any client choose its own bucket —

internal/config/config_test.go

@@ -44,9 +44,9 @@ func TestEnvironmentConfig(t *testing.T) {
 		isProd      bool
 	}{
 		{
-			name:   "default is dev",
-			isDev:  true,
-			isProd: false,
+			name:   "default is prod",
+			isDev:  false,
+			isProd: true,
 		},
 		{
 			name:     "explicit dev",
@@ -848,10 +848,9 @@ func TestEgressAllowlistWarning(t *testing.T) {
 // tells an operator a deployment behind a reverse proxy shares one
 // rate-limit bucket between every client, which turns the receiver
 // limits into service-wide ceilings and collapses login failure
-// counting. It must fire whenever TRUSTED_PROXIES is empty,
-// in any environment: WEBHOOKER_ENVIRONMENT defaults to dev, so gating
-// on it would silence the warning for exactly the operator who never
-// configured the deployment. It stays quiet once proxies are named.
+// counting. It must fire whenever TRUSTED_PROXIES is empty, in any
+// environment, because behind a proxy every client shares one bucket
+// in dev and prod alike. It stays quiet once proxies are named.
 func TestSharedRateLimitBucketWarning(t *testing.T) {
 	tests := []struct {
 		name           string
@@ -871,10 +870,6 @@ func TestSharedRateLimitBucketWarning(t *testing.T) {
 			expectWarning:  false,
 		},
 		{
-			// The default environment. An internet-exposed
-			// deployment whose operator never set
-			// WEBHOOKER_ENVIRONMENT lands here and has exactly
-			// the exposure the warning announces.
 			name:          "dev without trusted proxies warns",
 			environment:   config.EnvironmentDev,
 			expectWarning: true,

internal/database/database.go

@@ -17,12 +17,12 @@ import (
 	"gorm.io/gorm"
 	"sneak.berlin/go/webhooker/internal/banner"
 	"sneak.berlin/go/webhooker/internal/config"
+	"sneak.berlin/go/webhooker/internal/datadir"
 	"sneak.berlin/go/webhooker/internal/gormlog"
 	"sneak.berlin/go/webhooker/internal/logger"
 )
 
 const (
-	dataDirPerm       = 0750
 	randomPasswordLen = 16
 	sessionKeyLen     = 32
 )
@@ -185,7 +185,9 @@ func (d *Database) connect() error {
 // caller's decision.
 func (d *Database) connectTo(dataDir string) error {
 	// Ensure the data directory exists before opening the database.
-	err := os.MkdirAll(dataDir, dataDirPerm)
+	// datadir.DirPerm is the single source of the directory mode; this
+	// package creates the directory too, since either may run first.
+	err := os.MkdirAll(dataDir, datadir.DirPerm)
 	if err != nil {
 		return fmt.Errorf(
 			"creating data directory %s: %w",

internal/database/event_tier_indexes_test.go

@@ -0,0 +1,166 @@
+package database_test
+
+import (
+	"context"
+	"fmt"
+	"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"
+)
+
+// TestWebhookDBManager_OpenAddsEventTierIndexes verifies that opening a
+// per-webhook database that predates these indexes creates them. It
+// stands in for an older database file by dropping the indexes
+// AutoMigrate just created, then reopening the same file.
+func TestWebhookDBManager_OpenAddsEventTierIndexes(t *testing.T) {
+	t.Parallel()
+
+	indexes := []struct {
+		model any
+		name  string
+	}{
+		{&database.Delivery{}, "idx_deliveries_status"},
+		{&database.Delivery{}, "idx_deliveries_event_id"},
+		{&database.DeliveryResult{}, "idx_delivery_results_delivery_id"},
+		{&database.Event{}, "idx_events_deleted_at_created_at"},
+		{&database.Event{}, "idx_events_created_at"},
+	}
+
+	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 fresh database has them.
+	for _, ix := range indexes {
+		require.True(t, db.Migrator().HasIndex(ix.model, ix.name))
+	}
+
+	// Stand in for a database file created before the indexes existed.
+	for _, ix := range indexes {
+		require.NoError(t, db.Migrator().DropIndex(ix.model, ix.name))
+		require.False(t, db.Migrator().HasIndex(ix.model, ix.name))
+	}
+
+	// Drop the cached connection so the next open reopens the file and
+	// runs AutoMigrate against it, as a restart would.
+	require.NoError(t, mgr.CloseAll())
+
+	db, err = mgr.GetDB(webhookID)
+	require.NoError(t, err)
+
+	for _, ix := range indexes {
+		assert.True(t, db.Migrator().HasIndex(ix.model, ix.name),
+			"opening the existing database should create %s", ix.name)
+	}
+}
+
+// TestEventTierQueriesUseTheirIndexes verifies that the statements the
+// indexes are for use them. GORM builds each statement in a dry run as
+// the code named above it does, soft-delete condition included, and
+// SQLite, which keeps no statistics on these tables, must plan to seek
+// on each index listed by the columns in parentheses.
+func TestEventTierQueriesUseTheirIndexes(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)) }()
+
+	db, err := mgr.GetDB(uuid.New().String())
+	require.NoError(t, err)
+
+	dry := db.Session(&gorm.Session{DryRun: true})
+	ids := []string{
+		uuid.New().String(), uuid.New().String(), uuid.New().String(),
+	}
+	cutoff := time.Now()
+
+	var (
+		deliveries []database.Delivery
+		results    []database.DeliveryResult
+		depths     []struct{ Depth int }
+	)
+
+	byStatus := "idx_deliveries_status (status=? AND deleted_at=?)"
+	byEvent := "idx_deliveries_event_id (event_id=? AND deleted_at=?)"
+	byAge := "idx_events_deleted_at_created_at (deleted_at=? AND created_at<?)"
+
+	// The delivery engine: recovery and the retry sweep, the sweep for
+	// stranded pending deliveries, and the queue depth count.
+	assertPlanUses(t, db, dry.Where(
+		"status = ?", database.DeliveryStatusRetrying,
+	).Find(&deliveries), byStatus)
+	assertPlanUses(t, db, dry.Where(
+		"status = ? AND updated_at < ?",
+		database.DeliveryStatusPending, cutoff,
+	).Limit(500).Find(&deliveries), byStatus)
+	assertPlanUses(t, db, dry.Model(&database.Delivery{}).
+		Select("target_id", "status", "count(*) as depth").
+		Where("status IN ?", []database.DeliveryStatus{
+			database.DeliveryStatusPending,
+			database.DeliveryStatusRetrying,
+		}).Group("target_id, status").Find(&depths), byStatus)
+
+	// The event log: each event's deliveries, then their attempts
+	// (loadEventsWithDeliveries, loadDeliveryResults).
+	assertPlanUses(t, db, dry.Where("event_id = ?", ids[0]).
+		Find(&deliveries), byEvent)
+	assertPlanUses(t, db, dry.Where("delivery_id IN ?", ids).
+		Order("attempt_num ASC").Find(&results),
+		"idx_delivery_results_delivery_id (delivery_id=? AND deleted_at=?)")
+
+	// Retention's three deletes (reapExpired), whose subqueries are built
+	// afresh for each statement as it builds them.
+	expiredEventIDs := func() *gorm.DB {
+		return dry.Model(&database.Event{}).Select("id").
+			Where("created_at < ?", cutoff)
+	}
+
+	assertPlanUses(t, db, dry.Unscoped().Where(
+		"delivery_id IN (?)", dry.Model(&database.Delivery{}).
+			Select("id").Where("event_id IN (?)", expiredEventIDs()),
+	).Delete(&database.DeliveryResult{}),
+		"idx_delivery_results_delivery_id (delivery_id=?)", byEvent, byAge)
+	assertPlanUses(t, db, dry.Unscoped().Where(
+		"event_id IN (?)", expiredEventIDs(),
+	).Delete(&database.Delivery{}),
+		"idx_deliveries_event_id (event_id=?)", byAge)
+	assertPlanUses(t, db, dry.Unscoped().Where(
+		"created_at < ?", cutoff,
+	).Delete(&database.Event{}), "idx_events_created_at (created_at<?)")
+}
+
+// assertPlanUses asserts that SQLite's plan for a statement GORM built
+// in a dry run, run with the same SQL and arguments GORM would send,
+// names each of the given indexes.
+func assertPlanUses(
+	t *testing.T, db, built *gorm.DB, indexes ...string,
+) {
+	t.Helper()
+
+	var plan []struct{ Detail string }
+
+	require.NoError(t, db.Raw(
+		"EXPLAIN QUERY PLAN "+built.Statement.SQL.String(),
+		built.Statement.Vars...,
+	).Scan(&plan).Error)
+
+	for _, index := range indexes {
+		assert.Contains(t, fmt.Sprint(plan), index,
+			built.Statement.SQL.String())
+	}
+}

internal/database/model_delivery.go

@@ -1,5 +1,7 @@
 package database
 
+import "gorm.io/gorm"
+
 // DeliveryStatus represents the status of a delivery
 type DeliveryStatus string
 
@@ -29,12 +31,19 @@ func (s DeliveryStatus) Terminal() bool {
 }
 
 // Delivery represents a delivery attempt for an event to a target
+//
+//nolint:lll // a struct tag cannot wrap
 type Delivery struct {
 	BaseModel
 
-	EventID  string         `gorm:"type:uuid;not null"         json:"eventId"`
+	EventID  string         `gorm:"type:uuid;not null;index:idx_deliveries_event_id,priority:1"       json:"eventId"`
 	TargetID string         `gorm:"type:uuid;not null"                                                json:"targetId"`
-	Status   DeliveryStatus `gorm:"not null;default:'pending'" json:"status"`
+	Status   DeliveryStatus `gorm:"not null;default:'pending';index:idx_deliveries_status,priority:1" json:"status"`
+
+	// DeletedAt repeats the BaseModel field only to be the second column
+	// of the event_id and status indexes, for the reason DeliveryResult
+	// gives.
+	DeletedAt gorm.DeletedAt `gorm:"index:idx_deliveries_event_id,priority:2;index:idx_deliveries_status,priority:2" json:"deletedAt,omitzero"`
 
 	// Relations
 	Event           Event            `json:"event,omitzero"`

internal/database/model_delivery_result.go

@@ -1,10 +1,21 @@
 package database
 
+import "gorm.io/gorm"
+
 // DeliveryResult represents the result of a delivery attempt
+//
+//nolint:lll // a struct tag cannot wrap
 type DeliveryResult struct {
 	BaseModel
 
-	DeliveryID   string `gorm:"type:uuid;not null"   json:"deliveryId"`
+	// DeliveryID and DeletedAt make up one index, in that order.
+	// DeletedAt repeats the BaseModel field only to join it: GORM adds
+	// "deleted_at IS NULL" to almost every query, and where a column is
+	// matched against several values SQLite otherwise reads through the
+	// deleted_at index, which every live row matches.
+	DeliveryID string         `gorm:"type:uuid;not null;index:idx_delivery_results_delivery_id,priority:1" json:"deliveryId"`
+	DeletedAt  gorm.DeletedAt `gorm:"index:idx_delivery_results_delivery_id,priority:2"                    json:"deletedAt,omitzero"`
+
 	AttemptNum   int    `gorm:"not null"             json:"attemptNum"`
 	Success      bool   `json:"success"`
 	StatusCode   int    `json:"statusCode,omitempty"`

internal/database/model_event.go

@@ -1,9 +1,27 @@
 package database
 
+import (
+	"time"
+
+	"gorm.io/gorm"
+)
+
 // Event represents a captured webhook event
+//
+//nolint:lll // a struct tag cannot wrap
 type Event struct {
 	BaseModel
 
+	// CreatedAt and DeletedAt repeat the BaseModel fields only to index
+	// them for retention, which finds events by age. Its lookups carry
+	// GORM's "deleted_at IS NULL" (see DeliveryResult) and compare
+	// created_at with <, so their index has deleted_at first: SQLite
+	// narrows by a < only on the last column it uses. Its final delete
+	// has no deleted_at condition and uses the index on created_at
+	// alone. The other tables keep the unindexed BaseModel created_at.
+	CreatedAt time.Time      `gorm:"index;index:idx_events_deleted_at_created_at,priority:2" json:"createdAt"`
+	DeletedAt gorm.DeletedAt `gorm:"index:idx_events_deleted_at_created_at,priority:1"       json:"deletedAt,omitzero"`
+
 	WebhookID    string `gorm:"type:uuid;not null" json:"webhookId"`
 	EntrypointID string `gorm:"type:uuid;not null" json:"entrypointId"`
 

internal/database/webhook_db_manager.go

@@ -13,6 +13,7 @@ import (
 	"gorm.io/driver/sqlite"
 	"gorm.io/gorm"
 	"sneak.berlin/go/webhooker/internal/config"
+	"sneak.berlin/go/webhooker/internal/datadir"
 	"sneak.berlin/go/webhooker/internal/gormlog"
 	"sneak.berlin/go/webhooker/internal/logger"
 )
@@ -53,8 +54,9 @@ func NewWebhookDBManager(
 		log:     params.Logger.Get(),
 	}
 
-	// Create data directory if it doesn't exist
-	err := os.MkdirAll(m.dataDir, dataDirPerm)
+	// Create data directory if it doesn't exist. datadir.DirPerm is the
+	// single source of the directory mode; either package may run first.
+	err := os.MkdirAll(m.dataDir, datadir.DirPerm)
 	if err != nil {
 		return nil, fmt.Errorf(
 			"creating data directory %s: %w",

internal/datadir/lock.go

@@ -29,9 +29,11 @@ import (
 // process that was killed with SIGKILL blocks nothing.
 const LockFileName = "webhooker.lock"
 
-// dirPerm is the mode Acquire creates DATA_DIR with. It matches what
-// internal/database uses, since whichever runs first creates it.
-const dirPerm = 0o750
+// DirPerm is the mode DATA_DIR is created with. It is the single
+// source of that mode: internal/database consumes it rather than
+// keeping its own copy, so the two packages that both create the
+// directory cannot drift into disagreeing about its permissions.
+const DirPerm = 0o750
 
 // ErrLocked reports that another live process holds the data
 // directory. Callers that need to know whether a deployment is running
@@ -64,7 +66,7 @@ func Acquire(dir string) (*Lock, error) {
 		return nil, ErrNoDir
 	}
 
-	err := os.MkdirAll(dir, dirPerm)
+	err := os.MkdirAll(dir, DirPerm)
 	if err != nil {
 		return nil, fmt.Errorf(
 			"creating data directory %s: %w", dir, err,

internal/delivery/engine.go

@@ -438,6 +438,31 @@ func (e *Engine) processNewTask(
 		return
 	}
 
+	// Restart recovery can send and release this delivery before the
+	// receiver's Notify queues it. Ownership cannot refuse a delivery
+	// nobody holds, so the row decides whether it still needs sending.
+	row, err := e.loadDelivery(webhookDB, task.DeliveryID)
+	if err != nil {
+		e.log.Error(
+			"failed to load delivery",
+			"delivery_id", task.DeliveryID,
+			"error", err,
+		)
+
+		return
+	}
+
+	if row.Status != database.DeliveryStatusPending {
+		e.log.Info(
+			"delivery already handled, not sent again",
+			"delivery_id", task.DeliveryID,
+			"event_id", task.EventID,
+			"status", row.Status,
+		)
+
+		return
+	}
+
 	event := buildEventFromTask(task)
 
 	event, err = e.hydrateEvent(
@@ -482,7 +507,7 @@ func (e *Engine) processRetryTask(
 		return
 	}
 
-	d, err := e.loadRetryDelivery(
+	d, err := e.loadDelivery(
 		webhookDB, task.DeliveryID,
 	)
 	if err != nil {
@@ -1643,7 +1668,7 @@ func (e *Engine) hydrateEvent(
 	return event, nil
 }
 
-func (e *Engine) loadRetryDelivery(
+func (e *Engine) loadDelivery(
 	webhookDB *gorm.DB, deliveryID string,
 ) (*database.Delivery, error) {
 	var d database.Delivery

internal/delivery/inflight_test.go

@@ -273,6 +273,73 @@ func TestOwnershipIsReleasedAfterDelivery(t *testing.T) {
 	)
 }
 
+// TestNotifyAfterRecoveryDoesNotSendAgain is the startup race of
+// https://git.eeqj.de/sneak/webhooker/issues/299. The receiver has
+// written a delivery, restart recovery finds it pending, sends it and
+// releases it, and only then does the receiver's Notify for it arrive.
+// Nothing owns the delivery by then, so Notify takes it.
+func TestNotifyAfterRecoveryDoesNotSendAgain(t *testing.T) {
+	t.Parallel()
+
+	targetID := uuid.New().String()
+	s := fSweepSetup(t, targetID, "recovered")
+
+	event := iSeedEvent(
+		t, s.WebhookDB, s.WebhookID, `{"recovered":true}`,
+	)
+
+	d := iSeedDelivery(
+		t, s.WebhookDB, event.ID, targetID,
+		database.DeliveryStatusPending,
+	)
+
+	s.Engine.ExportStart()
+
+	defer func() {
+		require.NoError(
+			t, s.Engine.ExportStop(context.Background()),
+		)
+	}()
+
+	// Restart recovery sends the delivery and lets it go.
+	iWaitForDelivered(t, s.WebhookDB, d.ID)
+	require.Eventually(
+		t,
+		func() bool {
+			return s.Engine.ExportInflightHeld() == 0
+		},
+		5*time.Second, 20*time.Millisecond,
+	)
+
+	body := event.Body
+
+	s.Engine.Notify([]delivery.Task{{
+		DeliveryID:   d.ID,
+		EventID:      event.ID,
+		WebhookID:    s.WebhookID,
+		TargetID:     targetID,
+		TargetName:   "recovered",
+		TargetType:   database.TargetTypeLog,
+		Body:         &body,
+		EntrypointID: event.EntrypointID,
+	}})
+
+	// Notify took the delivery, and a worker releases it once it has
+	// run the task.
+	require.Eventually(
+		t,
+		func() bool {
+			return s.Engine.ExportInflightHeld() == 0
+		},
+		5*time.Second, 20*time.Millisecond,
+	)
+
+	assert.Len(
+		t, iResults(t, s.WebhookDB, d.ID), 1,
+		"the delivery was sent a second time",
+	)
+}
+
 // 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

internal/delivery/redirect_test.go

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

internal/handlers/ui_copy_test.go

@@ -300,3 +300,80 @@ func TestEntrypointCopyButtonIsProgressiveEnhancement(t *testing.T) {
 		"the page must render to completion, not abort partway",
 	)
 }
+
+// maxRetriesHelp is the wording both target forms must carry. The
+// delivery core makes max_retries attempts in total, not that many
+// retries on top of a first try (a fresh delivery starts at attempt 1
+// and target_http gives up once the attempt number reaches
+// max_retries), and 0 is special-cased to a single fire-and-forget
+// attempt with no circuit breaker.
+const maxRetriesHelp = "This is the total number of delivery attempts, " +
+	"not retries on top of the first: a value of 3 makes three attempts " +
+	"in all. 0 means a single attempt with no retries and no circuit " +
+	"breaker."
+
+// TestTargetFormMaxRetriesCopyMatchesBehaviour pins the max_retries
+// help text on both the create form (the add-target form on the webhook
+// detail page) and the edit form, so the copy cannot drift back to
+// calling the number a retry count.
+func TestTargetFormMaxRetriesCopyMatchesBehaviour(t *testing.T) {
+	t.Parallel()
+
+	var h *handlers.Handlers
+
+	var sess *session.Session
+
+	app := newTestApp(t, &h, &sess)
+	app.RequireStart()
+
+	t.Cleanup(app.RequireStop)
+
+	webhook := &database.Webhook{Name: "wh", RetentionDays: 14}
+	webhook.ID = testWebhookID
+
+	entrypoint := database.Entrypoint{Path: "abc123"}
+	entrypoint.ID = "ep-1"
+
+	createBody := renderPage(
+		t, h, sess, "source_detail.html", map[string]any{
+			dataKeyWebhook: webhook,
+			"Entrypoints": handlers.NewEntrypointViews(
+				[]database.Entrypoint{entrypoint},
+			),
+			"Targets": delivery.NewTargetViews(nil),
+			"Events":  []database.Event{},
+			"BaseURL": "https://hooks.example.com",
+		},
+	)
+
+	assert.Contains(
+		t, createBody, maxRetriesHelp,
+		"the add-target form must explain max_retries as total attempts",
+	)
+
+	// A slack target exercises the same max_retries field while needing
+	// only Config.URL from the edit template, so the test data stays
+	// minimal. The Target key mirrors the field names the template reads
+	// off the handler's view value.
+	editBody := renderPage(
+		t, h, sess, "target_edit.html", map[string]any{
+			dataKeyWebhook: webhook,
+			"Target": map[string]any{
+				"ID":         "tg-1",
+				"Name":       "t",
+				"Type":       "slack",
+				"Active":     true,
+				"MaxRetries": 3,
+				"Config": map[string]any{
+					"URL": "https://hooks.slack.com/services/x",
+				},
+			},
+			dataKeyError: "",
+		},
+	)
+
+	assert.Contains(
+		t, editBody, maxRetriesHelp,
+		"the target edit form must explain max_retries as total attempts",
+	)
+}

internal/middleware/csrf_test.go

@@ -380,9 +380,8 @@ func csrfTookStrictPath(
 
 // 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.
+// is set to dev -- the permissive setting -- to pin that the routing is
+// a per-request transport decision and owes nothing to configuration.
 func TestCSRF_ForwardedProtoSpellingsTakeStrictPath(t *testing.T) {
 	t.Parallel()
 

internal/reqtls/reqtls.go

@@ -5,7 +5,7 @@
 // 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
+// deployment behind a TLS proxy in the dev environment emitted one
 // Secure cookie and one non-Secure cookie on the same response.
 // Everything kept working, which is exactly why nobody noticed.
 //

internal/session/session.go

@@ -146,8 +146,8 @@ func newStore(key []byte) *sessions.CookieStore {
 //
 // 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
+// it got the DEFAULT posture wrong: "dev" was then the environment when
+// WEBHOOKER_ENVIRONMENT was 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.

internal/session/session_test.go

@@ -990,8 +990,8 @@ func sessionCookieFrom(
 
 // 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
+// configured environment, and "dev" was then the environment when
+// WEBHOOKER_ENVIRONMENT was unset. A deployment behind a TLS proxy in
 // that DEFAULT posture shipped the authentication cookie with no
 // Secure attribute and said nothing about it.
 //

templates/source_detail.html

@@ -120,10 +120,13 @@
                         <label class="text-sm text-gray-700">Timeout (seconds, blank = default):</label>
                         <input type="number" name="timeout" min="0" max="300" :disabled="targetType !== 'http'" class="input text-sm w-24">
                     </div>
-                    <div x-show="targetType === 'http'" class="flex gap-2 items-center">
-                        <label class="text-sm text-gray-700">Max retries (0 = fire-and-forget):</label>
+                    <div x-show="targetType === 'http'">
+                        <div class="flex gap-2 items-center">
+                            <label class="text-sm text-gray-700">Max retries:</label>
                             <input type="number" name="max_retries" value="0" min="0" max="20" class="input text-sm w-24">
                         </div>
+                        <p class="text-xs text-gray-500 mt-1">This is the total number of delivery attempts, not retries on top of the first: a value of 3 makes three attempts in all. 0 means a single attempt with no retries and no circuit breaker.</p>
+                    </div>
                     <div x-show="targetType === 'slack'">
                         <input type="url" name="url" placeholder="https://hooks.slack.com/services/..." :disabled="targetType !== 'slack'" class="input text-sm">
                         <p class="text-xs text-gray-500 mt-1">Slack or Mattermost incoming webhook URL. Payloads are pretty-printed in code blocks.</p>

templates/target_edit.html

@@ -69,7 +69,7 @@
             <div class="form-group">
                 <label for="max_retries" class="label">Max retries</label>
                 <input type="number" id="max_retries" name="max_retries" value="{{.Target.MaxRetries}}" min="0" max="20" class="input">
-                <p class="text-xs text-gray-500 mt-1">0 is fire-and-forget: one attempt, no circuit breaker.</p>
+                <p class="text-xs text-gray-500 mt-1">This is the total number of delivery attempts, not retries on top of the first: a value of 3 makes three attempts in all. 0 means a single attempt with no retries and no circuit breaker.</p>
             </div>
             {{end}}