Leave a delivery cut off by a stop for the next start (closes #527)

Stopping the engine cancels the context every http and slack request is
sent with. An attempt cut off that way was recorded as failed, which for
a target with no retries, or on a last retry, ended the delivery failed
and nothing sent it again.

The shared retry core now records nothing for a failed attempt when the
engine's context is cancelled: no result, no circuit breaker outcome, no
status change, no count in the attempt metrics. The delivery stays
pending or retrying and startup recovery sends it again. A target's own
timeout is still a failed attempt. The README says what happens to an
attempt in flight at a stop and no longer claims every attempt is
recorded.

Model: opus-5-5

Dockerfile

@@ -214,16 +214,22 @@ RUN version="$(make version VERSION="$VERSION")"; \
 # (Alpine.js, extracted from its tarball in 3p/) first.
 RUN make build VERSION="$VERSION"
 
-# Rebuild with static linking for Alpine runtime.
+# Rebuild with static linking for the Alpine runtime. The cgo binary the
-# make build already verified compilation.
+# step above builds is dynamically linked against glibc, which Alpine
-# The CGO binary from `make build` is dynamically linked against glibc,
+# (musl) does not have.
-# which doesn't exist on Alpine (musl). Rebuild with static linking so
-# the binary runs on Alpine without glibc.
 #
-# The static flags go in through GO_LDFLAGS rather than a -ldflags of
+# A statically linked glibc still loads shared libraries at run time for
-# their own: the build target composes them with the -X that stamps the
+# getaddrinfo and dlopen, and Alpine has none to load, so the build tags
-# version, so this relink cannot silently drop the stamp.
+# keep both out of the binary: netgo and osusergo select Go's own DNS
-RUN CGO_ENABLED=1 make build VERSION="$VERSION" GO_LDFLAGS='-extldflags "-static"'
+# resolver and user lookup instead of glibc's, and
+# sqlite_omit_load_extension leaves out SQLite extension loading, which
+# webhooker never uses.
+#
+# The static flags and tags go in through GO_LDFLAGS and GO_TAGS rather
+# than a -ldflags of their own: the build target composes them with the
+# -X that stamps the version, so this relink cannot silently drop the
+# stamp.
+RUN CGO_ENABLED=1 make build VERSION="$VERSION" GO_TAGS=netgo,osusergo,sqlite_omit_load_extension GO_LDFLAGS='-extldflags "-static"'
 
 # Runtime stage
 # alpine:3.21, 2026-03-17

Makefile

@@ -16,14 +16,16 @@ VERSION ?= $(shell script/version)
 # exists to correct.
 override VERSION := $(or $(strip $(VERSION)),$(shell script/version))
 
-# Extra linker flags for the build target. The static relink in the
+# Extra linker flags and build tags for the build target. The static
-# Dockerfile adds -extldflags here rather than passing its own -ldflags,
+# relink in the Dockerfile passes -extldflags and its build tags through
-# so composing flags cannot drop the version stamp.
+# these rather than a -ldflags of its own, so composing flags cannot drop
+# the version stamp.
 #
 # The build target itself always passes -trimpath and -s -w, as the Go
 # Dockerfile in REPO_POLICIES.md does: no build paths, symbol table or
 # debug information in the binary.
 GO_LDFLAGS ?=
+GO_TAGS ?=
 
 bootstrap:
 	@script/bootstrap
@@ -53,7 +55,7 @@ check:
 	@script/check
 
 build: assets
-	go build -trimpath -ldflags '$(strip -s -w -X main.version=$(VERSION) $(GO_LDFLAGS))' -o bin/webhooker ./cmd/webhooker
+	go build -trimpath -tags '$(GO_TAGS)' -ldflags '$(strip -s -w -X main.version=$(VERSION) $(GO_LDFLAGS))' -o bin/webhooker ./cmd/webhooker
 
 run: build
 	./bin/webhooker

README.md

@@ -1317,20 +1317,22 @@ webhooker solves this by acting as a durable intermediary:
    nothing is lost if downstream targets are unavailable.
 
 2. **Guaranteed delivery** — Events are queued for delivery to each configured
-   target. Failed deliveries are retried with configurable backoff. Every
+   target. Failed deliveries are retried with configurable backoff. Delivery
-   delivery attempt is logged with status codes, response bodies, and timing.
+   attempts are logged with status codes, response bodies, and timing.
 
     **That guarantee is at-least-once, not exactly-once.** When a send reaches
     its target but the write recording that outcome fails, the delivery is
     deliberately left in a recoverable state rather than marked done — losing a
     delivery is the worse failure — so the pending sweep picks it up about
     fifteen minutes later, or the next restart does, and the target receives a
-    payload it already got. webhooker adds no delivery identifier of its own to
+    payload it already got. A send still in flight when the service stops is
-    an outbound request, so **make your receiver idempotent** against whatever
+    left the same way: its attempt is not recorded, and the next start sends it
-    the payload itself carries.
+    again (see Shutdown). webhooker adds no delivery identifier of its own to an
+    outbound request, so **make your receiver idempotent** against whatever the
+    payload itself carries.
 
 3. **Observability** — Full request/response logging for every webhook received
-   and every delivery attempted. Prometheus metrics expose volume, latency, and
+   and for delivery attempts. Prometheus metrics expose volume, latency, and
    error rates. The web UI provides real-time visibility into event flow.
 
 4. **Fan-out** — A single incoming webhook can be delivered to multiple targets
@@ -1768,7 +1770,7 @@ is what bounds it.
 #### DeliveryResult
 
 The result of a single delivery attempt. Every attempt (including retries) is
-individually logged for full observability.
+individually logged, except one cut off by a stop (see Shutdown).
 
 | Field           | Type    | Description                               |
 | --------------- | ------- | ----------------------------------------- |
@@ -2206,12 +2208,16 @@ This means:
   buffer rather than spawning more goroutines.
 - **Independent results** — each worker records its own delivery result in the
   per-webhook database without coordination.
-- **Graceful shutdown** — cancel the context, workers finish their current task
+- **Graceful shutdown** — the stop hook cancels the workers' context. A worker
-  and exit. The stop hook waits for the pool via `lifecycle.WaitForShutdown`,
+  may still take tasks already queued before it exits. An `http` or `slack`
-  which bounds that wait by fx's stop timeout rather than blocking forever on a
+  request in flight is cut off, and one started after the cancel fails at once.
-  wedged worker. On timeout it logs at `ERROR` and returns an error, and the
+  Neither is recorded or counted in the metrics, and the next start sends the
-  goroutines that did not finish are still running — an unclean shutdown is
+  delivery again (see Shutdown). A `database` or `log` task runs as normal. The
-  reported rather than hidden.
+  stop hook waits for the pool via `lifecycle.WaitForShutdown`, which bounds
+  that wait by fx's stop timeout rather than blocking forever on a wedged
+  worker. On timeout it logs at `ERROR` and returns an error, and the goroutines
+  that did not finish are still running — an unclean shutdown is reported rather
+  than hidden.
 
 **Recovery paths:**
 
@@ -2317,7 +2323,7 @@ getting anywhere.
 | Metric                                 | Type      | Meaning                                                                                                                                                                                                                                                                                                   |
 | -------------------------------------- | --------- | --------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- |
 | `webhooker_events_received_total`      | counter   | Events received and durably stored. Compare against the delivery counters on one dashboard                                                                                                                                                                                                                |
-| `webhooker_delivery_attempts_total`    | counter   | Delivery attempts actually dispatched to a target. A delivery a circuit breaker refused is not one: it is counted as a retry instead, but only when the refusal moves it into `retrying`                                                                                                                  |
+| `webhooker_delivery_attempts_total`    | counter   | Delivery attempts actually dispatched to a target. A delivery a circuit breaker refused is not one: it is counted as a retry instead, but only when the refusal moves it into `retrying`. An attempt cut off by a stop is not counted (see Shutdown)                                                      |
 | `webhooker_deliveries_succeeded_total` | counter   | Deliveries that reached `delivered`                                                                                                                                                                                                                                                                       |
 | `webhooker_deliveries_failed_total`    | counter   | Deliveries that failed terminally and will not be retried                                                                                                                                                                                                                                                 |
 | `webhooker_delivery_retries_total`     | counter   | Deliveries put back into `retrying`                                                                                                                                                                                                                                                                       |
@@ -3284,7 +3290,8 @@ stop-hook log:
 3. `server` — the HTTP drain, bounded by `server.ShutdownTimeout` (**3
    seconds**) and by what the hooks before it left, then a Sentry flush if
    `SENTRY_DSN` is set
-4. `delivery.Engine` — waits for its workers, then closes the archive databases
+4. `delivery.Engine` — cuts off any `http` or `slack` request in flight, waits
+   for its workers, then closes the archive databases
 5. `healthcheck`
 6. `WebhookDBManager`
 7. the database close
@@ -3295,6 +3302,12 @@ by the stop context, so a wedge there consumes the 5 seconds before the HTTP
 server hook is ever entered. The hooks after the server are microsecond-scale in
 normal operation.
 
+The delivery engine cancels a delivery request in flight. That attempt is not
+recorded or counted in the metrics, and the delivery keeps its `pending` or
+`retrying` status, so startup recovery sends it again on the next start (see
+Recovery paths under Bounded Worker Pool). If the receiver already had it, it
+receives it twice: the at-least-once duplicate described under Rationale.
+
 The HTTP drain budget is deliberately **shorter** than the sequence budget. Were
 the two equal, a drain that used its whole budget would exhaust the sequence
 budget at the instant it finished, and every later hook — the delivery engine,
@@ -3419,12 +3432,14 @@ fixed independently of the compiler's:
    phases and the `css-check` and `markdown-check` stages passing (it copies a
    file from each), runs `make build` (which extracts Alpine.js from `3p/`
    first), and then rebuilds the binary with `CGO_ENABLED=1` and static linking
-   so it runs on musl. Both builds go through `make build`, the relink adding
+   so it runs on musl, with the build tags `netgo`, `osusergo` and
-   its `-extldflags` via `GO_LDFLAGS`, so neither can drop the `-X` that stamps
+   `sqlite_omit_load_extension` so it needs none of glibc's shared libraries at
-   the version. The version is the `VERSION` build arg if one is given,
+   run time. Both builds go through `make build`, the relink adding its
-   otherwise derived from the `.git` in the context, and the stage fails if a
+   `-extldflags` via `GO_LDFLAGS` and its tags via `GO_TAGS`, so neither can
-   context with `.git` would stamp an empty version, `dev` or `unknown` (see
+   drop the `-X` that stamps the version. The version is the `VERSION` build arg
-   [Version stamping](#version-stamping)).
+   if one is given, otherwise derived from the `.git` in the context, and the
+   stage fails if a context with `.git` would stamp an empty version, `dev` or
+   `unknown` (see [Version stamping](#version-stamping)).
 7. **Runtime stage** (`alpine:3.21`) — copies the static binary and
    `deploy/docker-entrypoint.sh`, creates the `/var/lib/webhooker` directory for
    all SQLite databases, exposes port 8080, and includes a health check against

internal/database/sqlite_open.go

@@ -241,7 +241,19 @@ func SQLiteDSN(path, mode string) string {
 	)
 	q.Add("_pragma", "journal_mode(WAL)")
 
-	return "file:" + path + "?" + q.Encode()
+	// SQLite reads a file: URI's path only up to the first ? or #, and
+	// decodes %XX escapes in it, so url.URL escapes the path. OmitHost
+	// keeps a relative path as "file:data/x.db"; written
+	// "file://data/x.db", SQLite would reject "data" as the URI's
+	// authority.
+	dsn := url.URL{
+		Scheme:   "file",
+		Path:     path,
+		OmitHost: true,
+		RawQuery: q.Encode(),
+	}
+
+	return dsn.String()
 }
 
 // OpenSQLite opens the SQLite file at path with the service's

internal/database/sqlite_open_test.go

@@ -2,6 +2,8 @@ package database_test
 
 import (
 	"context"
+	"database/sql"
+	"os"
 	"path/filepath"
 	"strings"
 	"testing"
@@ -112,6 +114,79 @@ func TestMainDBAppliesPragmasOnALiveHandle(t *testing.T) {
 	assert.Equal(t, "10000", busy)
 }
 
+// TestOpenSQLiteOpensThePathAskedFor uses a data directory whose name
+// holds ?, # and %. SQLite reads a file: URI's path only up to a ? or
+// #, and decodes %41 to A, so an unescaped path sent every database in
+// that directory to one file outside it.
+func TestOpenSQLiteOpensThePathAskedFor(t *testing.T) {
+	t.Parallel()
+
+	dir := filepath.Join(t.TempDir(), "hooks#1?x%41")
+	require.NoError(t, os.Mkdir(dir, 0o700))
+
+	for _, name := range []string{
+		database.MainDBFileName,
+		"events-" + uuid.New().String() + ".db",
+	} {
+		path := filepath.Join(dir, name)
+
+		sqlDB, err := database.OpenSQLite(
+			path, database.SQLiteModeCreate,
+		)
+		require.NoError(t, err)
+
+		t.Cleanup(func() { assert.NoError(t, sqlDB.Close()) })
+
+		assertOpenedFile(t, sqlDB, path)
+	}
+}
+
+// TestOpenSQLiteOpensARelativePath opens a database at a path relative
+// to the working directory, which is what a relative DATA_DIR such as
+// the README's DATA_DIR=../webhooker-data gives OpenSQLite.
+//
+//nolint:paralleltest // t.Chdir moves the whole process.
+func TestOpenSQLiteOpensARelativePath(t *testing.T) {
+	t.Chdir(t.TempDir())
+	require.NoError(t, os.Mkdir("data", 0o700))
+
+	path := filepath.Join("data", database.MainDBFileName)
+
+	sqlDB, err := database.OpenSQLite(path, database.SQLiteModeCreate)
+	require.NoError(t, err)
+
+	defer func() { require.NoError(t, sqlDB.Close()) }()
+
+	assertOpenedFile(t, sqlDB, path)
+}
+
+// assertOpenedFile checks that sqlDB is the SQLite file at path.
+// database_list names the file SQLite actually opened, as an absolute
+// path with symlinks resolved, so the files are compared, not the names.
+func assertOpenedFile(t *testing.T, sqlDB *sql.DB, path string) {
+	t.Helper()
+
+	var (
+		seq          int
+		schema, file string
+	)
+
+	require.NoError(t, sqlDB.
+		QueryRowContext(t.Context(), "pragma database_list").
+		Scan(&seq, &schema, &file))
+
+	asked, err := os.Stat(path)
+	require.NoError(t, err)
+
+	opened, err := os.Stat(file)
+	require.NoError(t, err)
+
+	assert.True(
+		t, os.SameFile(asked, opened),
+		"asked for %s, SQLite opened %s", path, file,
+	)
+}
+
 // TestConcurrentReaderDoesNotBlockWrites is the unit-scale form of the
 // reproduction in
 // https://git.eeqj.de/sneak/webhooker/issues/256: an operator's

internal/delivery/delivery_totals_test.go

@@ -32,8 +32,9 @@ func targetTotals(
 
 // TestUpdateDeliveryStatus_FinishTimeAndTargetTotals pins what a status
 // write records for the webhook page's statistics: the time a delivery
-// finished, set only when it becomes delivered or failed, and one more
+// finished, set only when it becomes delivered or failed and stored in
-// on its target's delivered or failed total.
+// the same form as created_at, and one more on its target's delivered
+// or failed total.
 func TestUpdateDeliveryStatus_FinishTimeAndTargetTotals(t *testing.T) {
 	t.Parallel()
 
@@ -75,6 +76,16 @@ func TestUpdateDeliveryStatus_FinishTimeAndTargetTotals(t *testing.T) {
 			if tt.finished {
 				require.NotNil(t, stored.FinishedAt)
 				assert.False(t, stored.FinishedAt.Before(before))
+
+				var createdAt, finishedAt string
+
+				require.NoError(t, db.Raw(
+					`SELECT CAST(created_at AS TEXT),
+						CAST(finished_at AS TEXT)
+					FROM deliveries WHERE id = ?`, d.ID,
+				).Row().Scan(&createdAt, &finishedAt))
+				assertStoredTime(t, createdAt)
+				assertStoredTime(t, finishedAt)
 			} else {
 				assert.Nil(t, stored.FinishedAt)
 			}

internal/delivery/engine.go

@@ -1702,7 +1702,10 @@ func writeDeliveryStatus(
 		}).
 		Updates(map[string]any{
 			"status": status,
-			"finished_at": time.Now(),
+			// GORM's clock, the one that stamps created_at. A bare
+			// time.Now() carries a monotonic clock reading, which the
+			// driver would store as an " m=+…" suffix.
+			"finished_at": tx.NowFunc(),
 		})
 	if res.Error != nil || res.RowsAffected == 0 {
 		return res.Error
@@ -1906,12 +1909,13 @@ func (e *Engine) takeForRedispatch(
 		return false
 	}
 
+	// GORM's clock, as writeDeliveryStatus explains.
 	res := webhookDB.
 		Model(&database.Delivery{}).
 		Where(
 			"id = ? AND status = ?", deliveryID, eligible,
 		).
-		UpdateColumn("updated_at", time.Now())
+		UpdateColumn("updated_at", webhookDB.NowFunc())
 
 	if res.Error != nil {
 		e.log.Error(

internal/delivery/engine_lifecycle_test.go

@@ -2,11 +2,16 @@ package delivery_test
 
 import (
 	"context"
+	"io"
+	"net/http"
+	"net/http/httptest"
 	"path/filepath"
+	"sync"
 	"testing"
 	"time"
 
 	"github.com/google/uuid"
+	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 	"go.uber.org/fx"
 	"gorm.io/gorm/clause"
@@ -272,6 +277,154 @@ func TestEngine_StopHookHonoursStopTimeout(t *testing.T) {
 	requireStopHookExpires(t, lc.hooks[0], "delivery engine")
 }
 
+// seedHeldDelivery gives the setup's webhook an http target with
+// maxRetries, pointed at a receiver that keeps every request open until
+// the client gives up on it, and seeds one delivery to that target at
+// status. It returns the task that sends attempt attemptNum of the
+// delivery, and a channel that is closed when a request reaches the
+// receiver.
+func seedHeldDelivery(
+	t *testing.T,
+	s iSetup,
+	maxRetries int,
+	status database.DeliveryStatus,
+	attemptNum int,
+) (delivery.Task, <-chan struct{}) {
+	t.Helper()
+
+	arrived := make(chan struct{})
+
+	var once sync.Once
+
+	ts := httptest.NewServer(http.HandlerFunc(
+		func(_ http.ResponseWriter, r *http.Request) {
+			// The server notices the client hanging up only once the
+			// body has been read; until then r.Context() never ends.
+			_, _ = io.Copy(io.Discard, r.Body)
+
+			once.Do(func() { close(arrived) })
+
+			<-r.Context().Done()
+		},
+	))
+	t.Cleanup(ts.Close)
+
+	cfg := iHTTPConfig(ts.URL)
+	targetID := uuid.New().String()
+
+	iCreateWebhook(t, s.MainDB, s.WebhookID, "hook")
+	iCreateTarget(
+		t, s.MainDB, targetID, s.WebhookID, "held",
+		database.TargetTypeHTTP, cfg, maxRetries,
+	)
+
+	event := iSeedEvent(t, s.WebhookDB, s.WebhookID, `{"held":true}`)
+	d := iSeedDelivery(t, s.WebhookDB, event.ID, targetID, status)
+
+	bodyStr := event.Body
+
+	return iTask(
+		d, event, s.WebhookID, targetID, "held", cfg,
+		maxRetries, attemptNum, &bodyStr,
+	), arrived
+}
+
+// stopDuringAttempt waits until the receiver holds an attempt open, then
+// stops the engine through its real stop hook.
+func stopDuringAttempt(
+	t *testing.T, lc *recordingLifecycle, arrived <-chan struct{},
+) {
+	t.Helper()
+
+	select {
+	case <-arrived:
+	case <-time.After(5 * time.Second):
+		t.Fatal("the delivery attempt never reached the receiver")
+	}
+
+	require.NoError(t, lc.hooks[0].OnStop(context.Background()))
+}
+
+// requireRequeued runs restart recovery on the stopped engine and
+// requires it to queue task's attempt again on ch.
+func requireRequeued(
+	t *testing.T, s iSetup, ch <-chan delivery.Task, task delivery.Task,
+) {
+	t.Helper()
+
+	s.Engine.ExportRecoverWebhookDeliveries(
+		context.Background(), s.WebhookID,
+	)
+
+	select {
+	case got := <-ch:
+		assert.Equal(t, task.DeliveryID, got.DeliveryID)
+		assert.Equal(t, task.AttemptNum, got.AttemptNum)
+	case <-time.After(5 * time.Second):
+		t.Fatal("restart recovery did not queue the delivery again")
+	}
+}
+
+// TestEngine_StopLeavesFireAndForgetAttemptPending is the regression
+// test for a stop that turned an attempt in flight into a terminal
+// failure. Stopping the engine cancels the request; for a target with
+// no retries that was the delivery's only attempt, recorded as failed
+// with "context canceled", and nothing ever sent it again. The
+// delivery must instead stay pending, with no result and no count in
+// the attempt metrics, for restart recovery to send.
+func TestEngine_StopLeavesFireAndForgetAttemptPending(t *testing.T) {
+	t.Parallel()
+
+	s := newISetup(t)
+	reg := mIsolate(t, s)
+	lc := startEngineViaHook(t, s.Engine)
+
+	task, arrived := seedHeldDelivery(
+		t, s, 0, database.DeliveryStatusPending, 1,
+	)
+
+	s.Engine.Notify([]delivery.Task{task})
+	stopDuringAttempt(t, lc, arrived)
+
+	iAssertStatus(
+		t, s.WebhookDB, task.DeliveryID, database.DeliveryStatusPending,
+	)
+	assert.Empty(t, iResults(t, s.WebhookDB, task.DeliveryID))
+	assert.Zero(t, mCounter(t, reg, mAttempts, mTypeHTTP))
+	assert.Zero(t, mHTTPDurations(t, reg))
+
+	requireRequeued(t, s, s.Engine.ExportDeliveryCh(), task)
+}
+
+// TestEngine_StopLeavesLastRetryAttemptRetrying is the same regression
+// for a target with retries, on its last attempt: the cancelled attempt
+// used to exhaust the retries and end the delivery failed. It must stay
+// retrying with only its earlier attempt recorded, and restart recovery
+// must send that last attempt again.
+func TestEngine_StopLeavesLastRetryAttemptRetrying(t *testing.T) {
+	t.Parallel()
+
+	const maxRetries = 2
+
+	s := newISetup(t)
+	lc := startEngineViaHook(t, s.Engine)
+
+	task, arrived := seedHeldDelivery(
+		t, s, maxRetries, database.DeliveryStatusRetrying, maxRetries,
+	)
+	iSeedFailedResult(t, s.WebhookDB, task.DeliveryID)
+
+	s.Engine.ExportScheduleRetry(task, 0)
+	stopDuringAttempt(t, lc, arrived)
+
+	iAssertStatus(
+		t, s.WebhookDB, task.DeliveryID, database.DeliveryStatusRetrying,
+	)
+	assert.Len(t, iResults(t, s.WebhookDB, task.DeliveryID), 1)
+
+	requireRequeued(t, s, s.Engine.ExportRetryCh(), task)
+}
+
 // deliverToArchive gives the setup's webhook a database target,
 // runs one delivery to it through the running engine, and returns
 // the target's ID and archive file path. The archive writer holds

internal/delivery/engine_test.go

@@ -117,6 +117,18 @@ func seedDelivery(
 	return d
 }
 
+// assertStoredTime asserts that text, a timestamp as SQLite holds it,
+// is in the form GORM stores created_at in: the layout of
+// time.Time.String, with no " m=+…" monotonic clock reading after it.
+func assertStoredTime(t *testing.T, text string) {
+	t.Helper()
+
+	_, err := time.Parse(
+		"2006-01-02 15:04:05.999999999 -0700 MST", text,
+	)
+	assert.NoError(t, err, "stored as %q", text)
+}
+
 // httpDeliveryFixture holds the task and delivery needed
 // for HTTP delivery tests.
 type httpDeliveryFixture struct {

internal/delivery/inflight_test.go

@@ -462,7 +462,8 @@ func TestScheduledRetryIsNotSweptDuringBackoff(t *testing.T) {
 
 // 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.
+// next tick a minute later. The stamp is stored in the same form as
+// created_at.
 func TestRedispatchStampsTheRow(t *testing.T) {
 	t.Parallel()
 
@@ -493,4 +494,13 @@ func TestRedispatchStampsTheRow(t *testing.T) {
 		"a re-dispatched delivery must be stamped so the "+
 			"next tick does not select it again",
 	)
+
+	var createdAt, updatedAt string
+
+	require.NoError(t, s.WebhookDB.Raw(
+		`SELECT CAST(created_at AS TEXT), CAST(updated_at AS TEXT)
+		FROM deliveries WHERE id = ?`, d.ID,
+	).Row().Scan(&createdAt, &updatedAt))
+	assertStoredTime(t, createdAt)
+	assertStoredTime(t, updatedAt)
 }

internal/delivery/target.go

@@ -32,7 +32,8 @@ type Scheduler interface {
 // Engine.observeAttempt, alongside the DeliveryResult it records for
 // it. Deliver is also entered for attempts that never happen — an
 // open circuit breaker refuses one — so the count cannot be taken
-// from around this call.
+// from around this call. An attempt cut off by a stop is neither
+// counted nor recorded.
 type Target interface {
 	Deliver(
 		ctx context.Context,

internal/delivery/target_database_archive.go

@@ -277,7 +277,11 @@ func (w *archiveWriter) write(
 		}
 	}
 
-	row.ArchivedAt = time.Now()
+	// GORM's clock, the one that stamps created_at in the other
+	// databases, so this is stored in the same form. A bare time.Now()
+	// carries a monotonic clock reading, which the driver would store
+	// as an " m=+…" suffix.
+	row.ArchivedAt = w.db.NowFunc()
 
 	err := w.db.Create(&row).Error
 	if err != nil {

internal/delivery/target_database_test.go

@@ -150,6 +150,13 @@ func TestArchiveWriter_WritesRow(t *testing.T) {
 	assert.Equal(t, row.ContentType, got[0].ContentType)
 	assert.JSONEq(t, `{"hello":"world"}`, got[0].Body)
 	assert.False(t, got[0].ArchivedAt.IsZero())
+
+	var archivedAt string
+
+	require.NoError(t, w.DB().Raw(
+		"SELECT CAST(archived_at AS TEXT) FROM archived_events",
+	).Row().Scan(&archivedAt))
+	assertStoredTime(t, archivedAt)
 }
 
 func TestArchiveWriter_RecreatesAfterRemoval(

internal/delivery/target_http.go

@@ -57,7 +57,11 @@ type httpCore struct {
 // recorded and no circuit breaker is consulted. A positive
 // maxRetries gates the attempt on the circuit breaker and
 // schedules a backed-off retry on failure.
+//
+// ctx is the context attempt sends its request with. Stopping the
+// engine cancels it; see interruptedByStop.
 func (c *httpCore) deliver(
+	ctx context.Context,
 	webhookDB *gorm.DB,
 	d *database.Delivery,
 	task *Task,
@@ -66,21 +70,55 @@ func (c *httpCore) deliver(
 	attempt func() attemptResult,
 ) {
 	if maxRetries == 0 {
-		c.fireAndForget(webhookDB, d, attempt())
+		c.fireAndForget(ctx, webhookDB, d, attempt())
 
 		return
 	}
 
 	c.withRetry(
-		webhookDB, d, task, sched, maxRetries, attempt,
+		ctx, webhookDB, d, task, sched, maxRetries, attempt,
 	)
 }
 
+// interruptedByStop reports whether an attempt failed because the
+// engine is stopping, which cancels the context its request is made
+// with. Such an attempt is not recorded: no DeliveryResult, no circuit
+// breaker outcome, no status change, no count in the attempt metrics.
+// The delivery stays pending or retrying, and startup recovery sends
+// it again on the next start.
+//
+// A target's own timeout leaves that context alone, so its attempt is
+// still recorded as the failure it is.
+func (c *httpCore) interruptedByStop(
+	ctx context.Context,
+	d *database.Delivery,
+	res attemptResult,
+) bool {
+	if res.success || ctx.Err() == nil {
+		return false
+	}
+
+	c.eng.log.Warn(
+		"delivery attempt interrupted by shutdown; not recorded, "+
+			"it is sent again on the next start",
+		"delivery_id", d.ID,
+		"event_id", d.EventID,
+		"target_id", d.TargetID,
+	)
+
+	return true
+}
+
 func (c *httpCore) fireAndForget(
+	ctx context.Context,
 	webhookDB *gorm.DB,
 	d *database.Delivery,
 	res attemptResult,
 ) {
+	if c.interruptedByStop(ctx, d, res) {
+		return
+	}
+
 	c.eng.observeAttempt(d.Target.Type, res.elapsed())
 
 	err := c.eng.recordResult(
@@ -110,6 +148,7 @@ func (c *httpCore) fireAndForget(
 }
 
 func (c *httpCore) withRetry(
+	ctx context.Context,
 	webhookDB *gorm.DB,
 	d *database.Delivery,
 	task *Task,
@@ -131,6 +170,10 @@ func (c *httpCore) withRetry(
 
 	res := attempt()
 
+	if c.interruptedByStop(ctx, d, res) {
+		return
+	}
+
 	c.eng.observeAttempt(d.Target.Type, res.elapsed())
 
 	err := c.eng.recordResult(
@@ -395,7 +438,7 @@ func (t *httpTarget) Deliver(
 	}
 
 	t.deliver(
-		webhookDB, d, task, sched,
+		ctx, webhookDB, d, task, sched,
 		d.Target.MaxRetries, attempt,
 	)
 }

internal/delivery/target_slack.go

@@ -82,7 +82,7 @@ func (t *slackTarget) Deliver(
 	}
 
 	t.deliver(
-		webhookDB, d, task, sched,
+		ctx, webhookDB, d, task, sched,
 		d.Target.MaxRetries, attempt,
 	)
 }

internal/handlers/delivery_attempts_test.go

@@ -42,9 +42,6 @@ func TestDeliveryAttempts_ReadInTheTargetTypesOwnTerms(t *testing.T) {
 		{database.TargetTypeLog, true, 0, "", "written to the log", ""},
 	}
 
-	// Named for type and outcome, so that no two cases share a name:
-	// Go adds "#01" to a repeated one, and a "#" in the temporary
-	// directory's path cuts the path SQLiteDSN gives SQLite short.
 	for _, tc := range cases {
 		t.Run(string(tc.targetType)+" "+tc.outcome, func(t *testing.T) {
 			t.Parallel()

internal/versionscript/version_script_test.go

@@ -156,7 +156,8 @@ func TestVersion_IsStableAcrossInvocations(t *testing.T) {
 // The build target is the only place composing linker flags. If a
 // future edit drops either half, the binary silently reports "dev"
 // again (the defect this package exists for) or fails to link on
-// Alpine.
+// Alpine. If it stops passing GO_TAGS, the image's static binary links
+// glibc's getaddrinfo and dlopen again.
 func TestMakefile_BuildComposesVersionAndExtraFlags(t *testing.T) {
 	t.Parallel()
 
@@ -164,6 +165,7 @@ func TestMakefile_BuildComposesVersionAndExtraFlags(t *testing.T) {
 
 	require.Contains(t, makefile, "-X main.version=$(VERSION)")
 	require.Contains(t, makefile, "$(GO_LDFLAGS)")
+	require.Contains(t, makefile, "-tags '$(GO_TAGS)'")
 	require.Contains(t, makefile, "VERSION ?= $(shell script/version)")
 }
 
@@ -233,7 +235,9 @@ func TestDockerfile_BuildsThroughTheMakeTarget(t *testing.T) {
 		"a raw go build bypasses the Makefile's -X flag")
 	require.Contains(t, dockerfile, "ARG VERSION")
 	require.Contains(t, dockerfile,
-		`make build VERSION="$VERSION" GO_LDFLAGS='-extldflags "-static"'`)
+		`make build VERSION="$VERSION"`+
+			` GO_TAGS=netgo,osusergo,sqlite_omit_load_extension`+
+			` GO_LDFLAGS='-extldflags "-static"'`)
 }
 
 func read(t *testing.T, path string) string {