Evict archive writers on deletion and sweep idle archives (closes #89)

The per-webhook archiveWriter registry in the database delivery target
was never evicted, so a deleted webhook's writer -- and any archive
file handle open within its debounce window -- lingered for the process
lifetime. Separately, expiry pruning ran only when an archive was
(re)opened, and reopens only happen on writes, so an archive belonging
to a webhook that stopped receiving events kept its expired rows
forever.

Eviction: a new one-method delivery.WebhookEvictor interface (kept
separate from Notifier: archiving lifecycle is not notification) is
implemented by the Engine and injected into the handlers. Deleting a
webhook, or deleting its last database target, drops the writer from
the registry and closes its handle under the writer's own mutex, so
eviction can never race an in-flight write. An evicted writer refuses
further writes rather than reopening a file nothing holds. The archive
file is deliberately left on disk: it is long-term storage an operator
may want to keep or move away, and destroying it as a side effect of
deleting a webhook would be unrecoverable.

Idle sweep: a new ArchiveSweeper, modelled on the event RetentionReaper
(fx lifecycle hooks, cancellable context, WaitGroup, ticker loop),
prunes archives whose database target declares a positive expiry. It
reuses the existing RETENTION_SWEEP_INTERVAL rather than adding a
config key. It never creates an archive -- a missing file is skipped,
and the reopen uses SQLite mode=rw so the file cannot be conjured even
if it disappears mid-sweep -- routes the prune through the per-webhook
writer so its mutex orders the sweep against concurrent writes, and
leaves the archive closed so the move-the-file-away workflow keeps
working. A failure for one webhook is logged and the sweep continues.
Archives with no expiry or the expiry "never" are untouched.

The sweep loop's context is rooted at context.Background(), not at the
fx OnStart hook context. The hook context carries fx's 15 second start
timeout, so a loop derived from it is cancelled three quarters of an
hour before the first tick under the default one-hour interval, giving
a sweeper that never sweeps. OnStop still cancels the loop and waits on
the WaitGroup, so shutdown is unchanged.

The sweep also never leaves a registry entry behind. Reaching the
writer through the ordinary create-and-cache accessor would let a sweep
that raced a webhook deletion re-insert a writer for a webhook that no
longer exists, which nothing would ever evict again -- the very leak
this change closes. An entry the sweep has to create is marked
sweep-owned and released when the prune finishes, unless a delivery
claimed it meanwhile, in which case it belongs to the registry and an
eviction can still reach it. A writer evicted underneath a sweep is an
ordinary interleaving and is logged at debug, not error.

Each of those guards is pinned by a test that fails when the guard is
removed. The adopt-during-sweep window -- a delivery claiming the
sweep's own registry entry while that sweep is still running -- is
driven directly against the registry, because a delivery placed between
two sweeps never reaches the release path at all. The requirement that
an idle archive ends the sweep closed is asserted both on a writer
proven to hold an open handle beforehand and, end to end, on a
delivery-owned entry the sweep keeps, rather than on an entry the sweep
has already released and which therefore reports "not open" either
way. The "never" expiry short circuit is checked against an archive
file that has never been migrated, so any open of it would be
observable as a created table.

README.md

@@ -531,6 +531,36 @@ older than the expiry are pruned each time the archive is (re)opened. An
 archive write failure is never silent success: the delivery records a
 failed attempt with the error and is marked failed.
 
+Because reopens only happen on writes, an archive belonging to a webhook
+that has stopped receiving events would never be pruned. A background
+**archive sweeper** closes that gap: on the same interval as the event
+retention reaper (`RETENTION_SWEEP_INTERVAL`) it prunes every archive
+whose database target declares a positive expiry, whether or not the
+webhook is still receiving traffic. The sweep never creates an archive —
+a webhook whose archive file does not yet exist is skipped, not
+initialised — it takes the same per-webhook lock the write path uses, so
+it can never interleave with a write, and it leaves the archive closed
+afterwards so the move-the-file-away workflow keeps working. Archives
+with no expiry, or the expiry `never`, are not touched by the sweep at
+all.
+
+Note that a webhook has one archive file but may carry more than one
+`database` target, each with its own `expiry`. The shortest expiry
+configured on any of them therefore governs the whole archive, and the
+sweep applies it whether or not the webhook is still receiving events.
+Configure a single `database` target per webhook unless you intend that.
+
+Deleting a webhook releases its archive: the delivery engine's cached
+archive writer is dropped and its file handle closed, so nothing lingers
+after the webhook is gone. The archive **file itself is deliberately
+left on disk**. Unlike the event database — per-webhook working storage
+that is hard-deleted with the webhook — an archive is long-term storage
+an operator may still want to keep or move away for offline retention,
+and destroying it as a side effect of deleting a webhook would be
+unrecoverable. Removing `archive-{webhookID}.db` is the operator's call.
+Deleting a webhook's last `database` target releases the writer the same
+way, and for the same reason leaves the file alone.
+
 The **Slack target type** sends webhook events as formatted messages to
 any Slack-compatible incoming webhook URL (works with Slack, Mattermost,
 and other compatible services). Each message includes event metadata
@@ -636,18 +666,6 @@ This means:
    durable fallback that ensures no retry is permanently lost, even under
    extreme backpressure.
 
-**Changing a target's type does not migrate in-flight deliveries.** Only
-`http` and `slack` targets own durable retries; `database` and `log`
-targets are fire-and-forget and never produce a `retrying` delivery. If a
-target's `type` is edited from a retrying type to a non-retrying (or
-unknown) one while one of its deliveries is still `retrying`, both
-recovery paths above terminally mark that delivery `failed` and record a
-`DeliveryResult` naming the current target type as the reason, logging it
-at warn level. The delivery is not re-dispatched under the new type — the
-operator never asked for that delivery — and the event itself remains
-stored in the per-webhook event database, so it can be redelivered
-manually.
-
 ### Circuit Breaker (HTTP Targets with Retries)
 
 HTTP targets with `max_retries` > 0 are protected by a **per-target circuit breaker** that

TODO.md

@@ -10,12 +10,13 @@
 
 # Status
 
-pre-1.0. No git tags exist. main (afe88c6) is a working webhook proxy
+pre-1.0. No git tags exist. main (4f5ecb1) is a working webhook proxy
 with auth, CSRF/SSRF protections, login rate limiting, Slack target,
-policy compliance (#6), and pinned lint tooling (#55). Note: TODO.md was
+event retention (#63), the database archiving target (#43), the admin
-deliberately deleted from this repo in f9a9569 (2026-03-01, #6); its
+password change flow (#65), policy compliance (#6), and pinned lint
-content was folded into the README TODO section, which this draft
+tooling (#55). Note: TODO.md was deliberately deleted from this repo in
-reconstructs as of 2026-07-06.
+f9a9569 (2026-03-01, #6); its content was folded into the README TODO
+section, which this draft reconstructs as of 2026-07-06.
 
 # Next Step
 
@@ -28,10 +29,11 @@ databases currently grow without bound.
 
 # Completed Steps
 
-- 2026-08-09 Restart recovery and the 60s retry sweep terminally fail an
+- 2026-08-09 Archive writer lifecycle (#89): deleting a webhook (or its
-  orphaned `retrying` delivery whose target type no longer supports
+  last `database` target) evicts the cached archive writer and closes
-  retries, recording a `DeliveryResult` with the reason instead of
+  its handle while deliberately leaving `archive-{webhookID}.db` on
-  leaving the delivery stuck forever (#82)
+  disk, and a new `ArchiveSweeper` prunes idle archives on the existing
+  `RETENTION_SWEEP_INTERVAL` without ever creating an archive file
 - 2026-08-07 Update golangci-lint to v2.12.2 (Docker image digest in
   `Dockerfile`, release-archive sha256 pins in `script/bootstrap`),
   adopt the canonical `.golangci.yml` (v2 `linters.settings` layout so

cmd/webhooker/main.go

@@ -40,9 +40,15 @@ func main() {
 			handlers.New,
 			middleware.New,
 			delivery.New,
+			delivery.NewArchiveSweeper,
 			// Wire *delivery.Engine as delivery.Notifier so the
 			// webhook handler can notify the engine of new deliveries.
 			func(e *delivery.Engine) delivery.Notifier { return e },
+			// Wire *delivery.Engine as delivery.WebhookEvictor so
+			// deleting a webhook releases its archive writer.
+			func(e *delivery.Engine) delivery.WebhookEvictor {
+				return e
+			},
 			server.New,
 		),
 		fx.Invoke(
@@ -50,6 +56,7 @@ func main() {
 				*server.Server,
 				*delivery.Engine,
 				*database.RetentionReaper,
+				*delivery.ArchiveSweeper,
 			) {
 			},
 		),

internal/delivery/archive_sweeper.go

@@ -0,0 +1,229 @@
+package delivery
+
+import (
+	"context"
+	"errors"
+	"log/slog"
+	"sync"
+	"time"
+
+	"go.uber.org/fx"
+	"sneak.berlin/go/webhooker/internal/config"
+	"sneak.berlin/go/webhooker/internal/database"
+	"sneak.berlin/go/webhooker/internal/logger"
+)
+
+// ArchiveSweeperParams holds the fx dependencies for the
+// ArchiveSweeper.
+type ArchiveSweeperParams struct {
+	fx.In
+
+	Config   *config.Config
+	Database *database.Database
+	Engine   *Engine
+	Logger   *logger.Logger
+}
+
+// ArchiveSweeper periodically prunes expired rows from
+// per-webhook archive databases whose database target carries a
+// positive expiry.
+//
+// Without it, pruning happens only when an archive is
+// (re)opened, and archives are only ever reopened by writes: an
+// archive belonging to a webhook that has stopped receiving
+// events would keep its expired rows forever. The sweep closes
+// that gap without changing anything for archives whose expiry
+// is unset or "never".
+//
+// It reuses Config.RetentionSweepInterval rather than
+// introducing a second interval: this is a retention sweep with
+// the same semantics as the event retention reaper.
+type ArchiveSweeper struct {
+	db       *database.Database
+	eng      *Engine
+	log      *slog.Logger
+	interval time.Duration
+	cancel   context.CancelFunc
+	wg       sync.WaitGroup
+}
+
+// NewArchiveSweeper creates the archive sweeper and registers
+// its fx lifecycle hooks. The background sweep loop starts on
+// OnStart and stops cleanly on OnStop via context cancellation.
+func NewArchiveSweeper(
+	lc fx.Lifecycle,
+	params ArchiveSweeperParams,
+) *ArchiveSweeper {
+	s := &ArchiveSweeper{
+		db:       params.Database,
+		eng:      params.Engine,
+		log:      params.Logger.Get(),
+		interval: params.Config.RetentionSweepInterval,
+	}
+
+	s.registerHooks(lc)
+
+	return s
+}
+
+// registerHooks wires the sweeper's start and stop into the fx
+// lifecycle. Both hook contexts are deliberately ignored: see
+// start for why the background loop must not inherit the start
+// hook's context, and stop for why shutdown blocks on the loop
+// rather than on the stop hook's deadline.
+func (s *ArchiveSweeper) registerHooks(lc fx.Lifecycle) {
+	lc.Append(fx.Hook{
+		//nolint:contextcheck // Not passing the hook context is
+		// the point: see start.
+		OnStart: func(_ context.Context) error {
+			s.start()
+
+			return nil
+		},
+		OnStop: func(_ context.Context) error {
+			s.stop()
+
+			return nil
+		},
+	})
+}
+
+// start launches the background sweep loop.
+//
+// The loop's context is derived from context.Background(), NOT
+// from the fx OnStart hook context. The hook context carries
+// fx's start timeout (15s by default), so a loop derived from it
+// is cancelled 15 seconds after the application starts — long
+// before the first tick under the default one-hour sweep
+// interval, leaving a sweeper that never sweeps. A long-lived
+// goroutine must outlive the startup phase, so its lifetime is
+// bounded by OnStop instead: stop cancels this context and waits
+// on the WaitGroup.
+func (s *ArchiveSweeper) start() {
+	ctx, cancel := context.WithCancel(context.Background())
+	s.cancel = cancel
+
+	s.wg.Add(1)
+
+	go s.run(ctx)
+
+	s.log.Info(
+		"archive sweeper started",
+		"interval", s.interval.String(),
+	)
+}
+
+func (s *ArchiveSweeper) stop() {
+	s.log.Info("archive sweeper stopping")
+
+	if s.cancel != nil {
+		s.cancel()
+	}
+
+	s.wg.Wait()
+	s.log.Info("archive sweeper stopped")
+}
+
+func (s *ArchiveSweeper) run(ctx context.Context) {
+	defer s.wg.Done()
+
+	ticker := time.NewTicker(s.interval)
+	defer ticker.Stop()
+
+	for {
+		select {
+		case <-ctx.Done():
+			return
+		case <-ticker.C:
+			s.sweep(ctx)
+		}
+	}
+}
+
+// sweep prunes every archive whose database target declares a
+// positive expiry. Targets belonging to a deleted webhook are
+// soft-deleted along with it, so GORM's default scope already
+// excludes them.
+//
+// A failure for one webhook is logged and the sweep continues,
+// matching how the write path already treats a prune error as
+// non-fatal.
+func (s *ArchiveSweeper) sweep(ctx context.Context) {
+	var targets []database.Target
+
+	err := s.db.DB().
+		Model(&database.Target{}).
+		Where("type = ?", database.TargetTypeDatabase).
+		Find(&targets).Error
+	if err != nil {
+		s.log.Error(
+			"archive sweep: failed to list database targets",
+			"error", err,
+		)
+
+		return
+	}
+
+	for i := range targets {
+		select {
+		case <-ctx.Done():
+			return
+		default:
+		}
+
+		s.sweepTarget(&targets[i])
+	}
+}
+
+// sweepTarget prunes the archive of a single database target.
+// A missing, empty, or "never" expiry parses as a zero duration
+// and is skipped entirely, so those archives keep exactly the
+// behaviour they had before the sweep existed.
+func (s *ArchiveSweeper) sweepTarget(target *database.Target) {
+	expiry, err := parseArchiveExpiry(target.Config)
+	if err != nil {
+		s.log.Error(
+			"archive sweep: invalid database target config",
+			"webhook_id", target.WebhookID,
+			"target_id", target.ID,
+			"error", err,
+		)
+
+		return
+	}
+
+	if expiry <= 0 {
+		return
+	}
+
+	if s.eng == nil || s.eng.dbTarget == nil {
+		return
+	}
+
+	err = s.eng.dbTarget.sweepWebhook(target.WebhookID, expiry)
+	if err == nil {
+		return
+	}
+
+	// A writer evicted underneath the sweep means the operator
+	// deleted the webhook (or its last database target) while the
+	// sweep was walking the target list. That is an ordinary
+	// interleaving, not a failure, so it must not produce an
+	// error line.
+	if errors.Is(err, errArchiveWriterEvicted) {
+		s.log.Debug(
+			"archive sweep: writer evicted mid-sweep",
+			"webhook_id", target.WebhookID,
+			"target_id", target.ID,
+		)
+
+		return
+	}
+
+	s.log.Error(
+		"archive sweep: failed to prune archive",
+		"webhook_id", target.WebhookID,
+		"target_id", target.ID,
+		"error", err,
+	)
+}

internal/delivery/archive_sweeper_test.go

@@ -0,0 +1,930 @@
+package delivery_test
+
+import (
+	"context"
+	"database/sql"
+	"fmt"
+	"net/http"
+	"os"
+	"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/driver/sqlite"
+	"gorm.io/gorm"
+	"gorm.io/gorm/clause"
+	_ "modernc.org/sqlite" // Pure Go SQLite driver.
+	"sneak.berlin/go/webhooker/internal/database"
+	"sneak.berlin/go/webhooker/internal/delivery"
+)
+
+const (
+	// sweepRowOld and sweepRowNew are the event ids
+	// seedArchiveRows assigns to the first and second seeded
+	// rows.
+	sweepRowOld = "ev-0"
+	sweepRowNew = "ev-1"
+
+	// sweepConcurrentWrites is how many deliveries the
+	// concurrent write-plus-sweep test races against the sweep.
+	sweepConcurrentWrites = 20
+)
+
+// sweeperEnv bundles the pieces an archive sweep test drives:
+// a main configuration database holding webhooks and targets, a
+// delivery engine owning the archive writer registry, and the
+// data directory the archive files live in.
+type sweeperEnv struct {
+	sweeper *delivery.ArchiveSweeper
+	eng     *delivery.Engine
+	mainDB  *database.Database
+	dataDir string
+}
+
+func setupSweeperTest(t *testing.T) *sweeperEnv {
+	t.Helper()
+
+	dataDir := t.TempDir()
+	log := archiveTestLogger()
+
+	sqlDB, err := sql.Open(
+		"sqlite",
+		fmt.Sprintf(
+			"file:%s?mode=rwc",
+			filepath.Join(dataDir, "main.db"),
+		),
+	)
+	require.NoError(t, err)
+
+	t.Cleanup(func() { _ = sqlDB.Close() })
+
+	gdb, err := gorm.Open(
+		sqlite.Dialector{Conn: sqlDB}, &gorm.Config{},
+	)
+	require.NoError(t, err)
+
+	mainDB := database.NewTestDatabase(gdb)
+	require.NoError(t, mainDB.Migrate())
+
+	eng := delivery.NewTestEngineWithDB(
+		mainDB,
+		database.NewTestWebhookDBManager(dataDir),
+		log,
+		&http.Client{Timeout: 5 * time.Second},
+		1,
+	)
+
+	return &sweeperEnv{
+		sweeper: delivery.NewTestArchiveSweeper(
+			mainDB, eng, log,
+		),
+		eng:     eng,
+		mainDB:  mainDB,
+		dataDir: dataDir,
+	}
+}
+
+// archivePath returns where the engine keeps a webhook's
+// archive file.
+func (env *sweeperEnv) archivePath(webhookID string) string {
+	return filepath.Join(
+		env.dataDir, fmt.Sprintf("archive-%s.db", webhookID),
+	)
+}
+
+// seedDatabaseTarget creates a webhook with one database target
+// carrying the given target config JSON, and returns the
+// webhook id.
+func (env *sweeperEnv) seedDatabaseTarget(
+	t *testing.T, configJSON string,
+) string {
+	t.Helper()
+
+	wh := &database.Webhook{
+		UserID: uuid.New().String(),
+		Name:   "sweep-test",
+	}
+	require.NoError(
+		t,
+		env.mainDB.DB().
+			Omit(clause.Associations).
+			Create(wh).Error,
+	)
+
+	tgt := &database.Target{
+		WebhookID: wh.ID,
+		Name:      "archive",
+		Type:      database.TargetTypeDatabase,
+		Active:    true,
+		Config:    configJSON,
+	}
+	require.NoError(
+		t,
+		env.mainDB.DB().
+			Omit(clause.Associations).
+			Create(tgt).Error,
+	)
+
+	return wh.ID
+}
+
+// seedArchiveRows creates the archive file for a webhook and
+// inserts one row per supplied archived-at timestamp, returning
+// the archive path. The handle is closed before returning, so
+// the archive is idle exactly as it would be with no traffic.
+func (env *sweeperEnv) seedArchiveRows(
+	t *testing.T, webhookID string, archivedAt ...time.Time,
+) string {
+	t.Helper()
+
+	path := env.archivePath(webhookID)
+
+	sqlDB, err := sql.Open(
+		"sqlite", fmt.Sprintf("file:%s?mode=rwc", path),
+	)
+	require.NoError(t, err)
+
+	gdb, err := gorm.Open(
+		sqlite.Dialector{Conn: sqlDB}, &gorm.Config{},
+	)
+	require.NoError(t, err)
+
+	require.NoError(
+		t, gdb.AutoMigrate(&delivery.ExportArchivedEvent{}),
+	)
+
+	for i, at := range archivedAt {
+		row := delivery.ExportArchivedEvent{
+			EventID:    fmt.Sprintf("ev-%d", i),
+			WebhookID:  webhookID,
+			Method:     http.MethodPost,
+			Body:       `{"seeded":true}`,
+			ArchivedAt: at,
+		}
+		require.NoError(t, gdb.Create(&row).Error)
+	}
+
+	require.NoError(t, sqlDB.Close())
+
+	return path
+}
+
+// archivedEventIDs returns the event ids currently stored in an
+// archive file, read through a separate read-only handle.
+func archivedEventIDs(
+	t *testing.T, path string,
+) []string {
+	t.Helper()
+
+	var rows []delivery.ExportArchivedEvent
+
+	rdb := openArchiveDBForRead(t, path)
+	require.NoError(t, rdb.Order("event_id").Find(&rows).Error)
+
+	ids := make([]string, 0, len(rows))
+	for i := range rows {
+		ids = append(ids, rows[i].EventID)
+	}
+
+	return ids
+}
+
+// countArchivedRows counts the rows in an archive file without
+// asserting anything, so it is safe to poll from an
+// assert.Eventually condition (which runs off the test
+// goroutine, where testify assertions must not be used).
+func countArchivedRows(path string) (int64, error) {
+	sqlDB, err := sql.Open(
+		"sqlite", fmt.Sprintf("file:%s?mode=ro", path),
+	)
+	if err != nil {
+		return 0, err
+	}
+
+	defer func() { _ = sqlDB.Close() }()
+
+	gdb, err := gorm.Open(
+		sqlite.Dialector{Conn: sqlDB}, &gorm.Config{},
+	)
+	if err != nil {
+		return 0, err
+	}
+
+	var count int64
+
+	err = gdb.Model(&delivery.ExportArchivedEvent{}).
+		Count(&count).Error
+	if err != nil {
+		return 0, err
+	}
+
+	return count, nil
+}
+
+// captureLifecycle is a minimal fx.Lifecycle that records the
+// hooks a component registers, so a test can invoke the real
+// OnStart/OnStop functions with a context of its choosing.
+type captureLifecycle struct {
+	hooks []fx.Hook
+}
+
+func (l *captureLifecycle) Append(h fx.Hook) {
+	l.hooks = append(l.hooks, h)
+}
+
+// TestArchiveSweeper_LoopOutlivesStartHookContext is the
+// regression test for a sweeper that never swept. fx calls
+// OnStart with a context carrying the application's start
+// timeout (15 seconds by default), so a background loop whose
+// context is derived from it is cancelled 15 seconds into the
+// process — three quarters of an hour before the first tick
+// under the default one-hour sweep interval.
+//
+// The hook context here is already cancelled, which is the same
+// defect taken to its limit: a loop that inherits it never runs
+// a single tick, while a correctly rooted loop keeps sweeping
+// for as long as the process lives. Handing the hook a plain
+// context.Background() would assert nothing at all.
+func TestArchiveSweeper_LoopOutlivesStartHookContext(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	env := setupSweeperTest(t)
+
+	webhookID := env.seedDatabaseTarget(t, `{"expiry":"1h"}`)
+
+	now := time.Now()
+	path := env.seedArchiveRows(
+		t, webhookID,
+		now.Add(-48*time.Hour),
+		now.Add(-time.Minute),
+	)
+
+	env.sweeper.ExportSetInterval(10 * time.Millisecond)
+
+	// Drive the genuine fx hooks the application registers,
+	// rather than a test-only entry point.
+	lc := &captureLifecycle{}
+	env.sweeper.ExportRegisterHooks(lc)
+	require.Len(t, lc.hooks, 1)
+
+	hookCtx, cancel := context.WithCancel(context.Background())
+	cancel()
+
+	require.NoError(t, lc.hooks[0].OnStart(hookCtx))
+
+	t.Cleanup(func() {
+		_ = lc.hooks[0].OnStop(context.Background())
+	})
+
+	assert.Eventually(
+		t,
+		func() bool {
+			count, err := countArchivedRows(path)
+
+			return err == nil && count == 1
+		},
+		5*time.Second,
+		10*time.Millisecond,
+		"the sweep loop must keep running after the start "+
+			"hook's context is done; it pruned nothing, so it "+
+			"inherited the hook context and died",
+	)
+}
+
+// TestArchiveSweep_DoesNotResurrectEvictedWriter covers the
+// interleaving where a sweep tick has already listed a webhook's
+// target when the webhook is deleted and its writer evicted. The
+// sweep must not put a writer back into the registry: nothing
+// would ever evict it again, which is precisely the leak this
+// change exists to close.
+func TestArchiveSweep_DoesNotResurrectEvictedWriter(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	env := setupSweeperTest(t)
+
+	webhookID := env.seedDatabaseTarget(t, `{"expiry":"1h"}`)
+	env.seedArchiveRows(
+		t, webhookID, time.Now().Add(-48*time.Hour),
+	)
+
+	// Prime the registry the way a delivery would, then evict as
+	// the deletion path does. The target row is deliberately left
+	// in place: this is the tick that listed the webhook before
+	// the deletion committed.
+	_, err := env.eng.ExportEnsureArchiveWriter(webhookID)
+	require.NoError(t, err)
+
+	env.eng.EvictWebhook(webhookID)
+	require.False(t, env.eng.ExportHasArchiveWriter(webhookID))
+
+	env.sweeper.ExportSweep(context.Background())
+
+	assert.False(
+		t, env.eng.ExportHasArchiveWriter(webhookID),
+		"a sweep must never re-register a writer for a webhook "+
+			"whose registry entry has already been released",
+	)
+}
+
+// TestArchiveSweep_LeavesNoRegistryEntry states the same
+// invariant in its general form: sweeping an archive whose
+// webhook has no cached writer must not leave one behind, so the
+// registry keeps holding only writers a delivery created and an
+// eviction can reach.
+func TestArchiveSweep_LeavesNoRegistryEntry(t *testing.T) {
+	t.Parallel()
+
+	env := setupSweeperTest(t)
+
+	webhookID := env.seedDatabaseTarget(t, `{"expiry":"1h"}`)
+	path := env.seedArchiveRows(
+		t, webhookID,
+		time.Now().Add(-48*time.Hour),
+		time.Now().Add(-time.Minute),
+	)
+
+	require.False(t, env.eng.ExportHasArchiveWriter(webhookID))
+
+	env.sweeper.ExportSweep(context.Background())
+
+	assert.Equal(
+		t, []string{sweepRowNew}, archivedEventIDs(t, path),
+		"the sweep must still prune an idle archive",
+	)
+	assert.False(
+		t, env.eng.ExportHasArchiveWriter(webhookID),
+		"the sweep must release the registry entry it created",
+	)
+}
+
+// TestArchiveSweep_KeepsWriterAdoptedByDelivery is the other
+// half of that invariant: an entry the sweep created but a
+// delivery then claimed belongs to the registry and must survive
+// the sweep, or the delivery would be left holding a detached
+// writer with an open handle that no eviction can reach.
+func TestArchiveSweep_KeepsWriterAdoptedByDelivery(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	env := setupSweeperTest(t)
+
+	webhookID := env.seedDatabaseTarget(t, `{"expiry":"1h"}`)
+	env.seedArchiveRows(
+		t, webhookID, time.Now().Add(-48*time.Hour),
+	)
+
+	webhookDB := testWebhookDB(t)
+	event := seedEvent(t, webhookDB, `{"n":1}`)
+	event.WebhookID = webhookID
+	d := seedDatabaseTargetDelivery(
+		t, webhookDB, event, `{"expiry":"1h"}`,
+	)
+
+	env.sweeper.ExportSweep(context.Background())
+	require.False(t, env.eng.ExportHasArchiveWriter(webhookID))
+
+	env.eng.ExportDeliverDatabase(webhookDB, d)
+
+	assert.True(
+		t, env.eng.ExportHasArchiveWriter(webhookID),
+		"a delivery's writer must stay registered",
+	)
+
+	env.sweeper.ExportSweep(context.Background())
+
+	assert.True(
+		t, env.eng.ExportHasArchiveWriter(webhookID),
+		"a sweep must not drop a writer a delivery owns",
+	)
+}
+
+// TestArchiveSweep_KeepsWriterAdoptedDuringSweep covers the one
+// interleaving the sweepOwned flag exists for, which
+// TestArchiveSweep_KeepsWriterAdoptedByDelivery cannot reach: a
+// delivery adopting the sweep's own entry WHILE that sweep is
+// still running.
+//
+// The registry operations are driven directly, in the order the
+// sweep and a concurrent delivery perform them, so the window is
+// exercised deterministically rather than hoped for:
+//
+//  1. the sweep finds no cached writer and registers one of its
+//     own, marked sweep-owned;
+//  2. a delivery arrives, is handed that very writer, clears the
+//     flag and opens the archive handle;
+//  3. the sweep finishes and releases what it created.
+//
+// Step 3 must leave the entry alone. Dropping it would detach a
+// writer that is holding an open archive handle inside its
+// debounce window, and no eviction could ever reach it again —
+// exactly the process-lifetime handle leak this change exists to
+// close. The eviction at the end proves the entry is still
+// reachable.
+func TestArchiveSweep_KeepsWriterAdoptedDuringSweep(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	env := setupSweeperTest(t)
+
+	webhookID := env.seedDatabaseTarget(t, `{"expiry":"1h"}`)
+	env.seedArchiveRows(
+		t, webhookID, time.Now().Add(-48*time.Hour),
+	)
+
+	sweepWriter, created, err := env.eng.ExportSweepWriterFor(
+		webhookID,
+	)
+	require.NoError(t, err)
+	require.True(
+		t, created,
+		"the sweep must have created the registry entry itself",
+	)
+
+	// The delivery lands mid-sweep and adopts the entry.
+	webhookDB := testWebhookDB(t)
+	event := seedEvent(t, webhookDB, `{"n":1}`)
+	event.WebhookID = webhookID
+	d := seedDatabaseTargetDelivery(
+		t, webhookDB, event, `{"expiry":"1h"}`,
+	)
+
+	env.eng.ExportDeliverDatabase(webhookDB, d)
+
+	adopted := env.eng.ExportArchiveWriterFor(webhookID)
+	require.NotNil(t, adopted)
+	require.True(
+		t, sweepWriter.Same(adopted),
+		"the delivery must have adopted the sweep's writer",
+	)
+	require.True(
+		t, env.eng.ExportArchiveHandleOpen(webhookID),
+		"the delivery leaves the archive handle open",
+	)
+
+	// The sweep finishes.
+	env.eng.ExportReleaseSweepWriter(webhookID, sweepWriter)
+
+	require.True(
+		t, env.eng.ExportHasArchiveWriter(webhookID),
+		"a writer adopted by a delivery during a sweep must "+
+			"stay registered, or its open handle is unreachable",
+	)
+
+	env.eng.EvictWebhook(webhookID)
+
+	assert.False(
+		t, env.eng.ExportHasArchiveWriter(webhookID),
+		"the adopted writer must still be evictable",
+	)
+	assert.False(
+		t, sweepWriter.HandleOpen(),
+		"eviction must have closed the adopted writer's handle",
+	)
+}
+
+// TestArchiveSweep_ContinuesAfterPerWebhookFailure proves a
+// failure for one webhook does not abort the sweep for the
+// others: an unparseable expiry and an unreadable archive both
+// have to be logged and stepped over.
+func TestArchiveSweep_ContinuesAfterPerWebhookFailure(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	env := setupSweeperTest(t)
+
+	// Seeded first so the sweep reaches them before the healthy
+	// webhook: targets come back in insertion order.
+	badConfigID := env.seedDatabaseTarget(t, `{"expiry":"!!!"}`)
+	env.seedArchiveRows(
+		t, badConfigID, time.Now().Add(-48*time.Hour),
+	)
+
+	corruptID := env.seedDatabaseTarget(t, `{"expiry":"1h"}`)
+	require.NoError(t, os.WriteFile(
+		env.archivePath(corruptID),
+		[]byte("this is not a sqlite database"),
+		0o600,
+	))
+
+	healthyID := env.seedDatabaseTarget(t, `{"expiry":"1h"}`)
+	healthyPath := env.seedArchiveRows(
+		t, healthyID,
+		time.Now().Add(-48*time.Hour),
+		time.Now().Add(-time.Minute),
+	)
+
+	env.sweeper.ExportSweep(context.Background())
+
+	assert.Equal(
+		t, []string{sweepRowNew},
+		archivedEventIDs(t, healthyPath),
+		"a failure for an earlier webhook must not stop the "+
+			"sweep from pruning the ones after it",
+	)
+}
+
+// TestArchiveSweep_OpenExistingDoesNotCreateFile pins the second
+// of the two no-create guards. The first is the stat in
+// sweepWebhook; this one is the SQLite open mode, which is what
+// protects the window between that stat and the open. Flipping
+// the sweep's mode to create-if-missing makes this fail.
+func TestArchiveSweep_OpenExistingDoesNotCreateFile(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	dir := t.TempDir()
+	path := filepath.Join(dir, "archive-absent.db")
+
+	w := delivery.NewExportArchiveWriter(
+		path, archiveTestLogger(), 0,
+	)
+
+	err := w.OpenExisting(time.Hour)
+
+	require.Error(
+		t, err,
+		"opening a missing archive without create permission "+
+			"must fail rather than conjure the file",
+	)
+
+	for _, suffix := range archiveFileSuffixes() {
+		assert.NoFileExists(t, path+suffix)
+	}
+}
+
+// TestArchiveSweep_PrunesIdleArchive is the core regression
+// test for this issue: an archive that receives no further
+// writes must still lose its expired rows. Before the sweeper
+// existed, pruning only ever ran on a write-triggered reopen,
+// so an idle archive kept expired rows forever.
+func TestArchiveSweep_PrunesIdleArchive(t *testing.T) {
+	t.Parallel()
+
+	env := setupSweeperTest(t)
+
+	webhookID := env.seedDatabaseTarget(t, `{"expiry":"1h"}`)
+
+	now := time.Now()
+	path := env.seedArchiveRows(
+		t, webhookID,
+		now.Add(-48*time.Hour),
+		now.Add(-time.Minute),
+	)
+
+	require.Equal(
+		t, []string{sweepRowOld, sweepRowNew},
+		archivedEventIDs(t, path),
+	)
+
+	env.sweeper.ExportSweep(context.Background())
+
+	assert.Equal(
+		t, []string{sweepRowNew}, archivedEventIDs(t, path),
+		"the sweep should prune rows older than the expiry "+
+			"from an idle archive and keep the rest",
+	)
+}
+
+// TestArchiveSweep_LeavesArchiveClosed proves the sweep does
+// not hold the archive open afterwards, so an operator can
+// still move the file away for offline retention.
+//
+// The assertion is made on a writer the test holds a reference
+// to, and the handle is proven OPEN before the sweep runs, so the
+// test observes the sweep closing it rather than a writer that
+// merely never opened anything. Asking the registry instead would
+// be vacuous here: the sweep releases an entry it created, and a
+// missing entry reports "not open" whether or not anything was
+// closed.
+func TestArchiveSweep_LeavesArchiveClosed(t *testing.T) {
+	t.Parallel()
+
+	env := setupSweeperTest(t)
+
+	webhookID := env.seedDatabaseTarget(t, `{"expiry":"1h"}`)
+	path := env.seedArchiveRows(
+		t, webhookID, time.Now().Add(-48*time.Hour),
+	)
+
+	w := delivery.NewExportArchiveWriter(
+		path, archiveTestLogger(), 0,
+	)
+
+	require.NoError(t, w.OpenExisting(time.Hour))
+	require.True(
+		t, w.HandleOpen(),
+		"the writer must hold an open handle before the sweep",
+	)
+
+	require.NoError(t, w.SweepExpired(time.Hour))
+
+	assert.False(
+		t, w.HandleOpen(),
+		"an idle archive must end the sweep closed",
+	)
+}
+
+// TestArchiveSweep_ClosesHandleOfRegisteredWriter states the same
+// guarantee end to end, through the real sweeper and a writer the
+// registry keeps.
+//
+// The delivery leaves the archive handle open inside its debounce
+// window and makes the entry delivery-owned, so the sweep finds a
+// cached writer (created is false, nothing is released) and the
+// registry query afterwards is answered by a writer that really
+// exists. A handle left open here would be doubly wrong: it also
+// blocks the operator's move-the-file-away workflow.
+func TestArchiveSweep_ClosesHandleOfRegisteredWriter(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	env := setupSweeperTest(t)
+
+	webhookID := env.seedDatabaseTarget(t, `{"expiry":"1h"}`)
+	env.seedArchiveRows(
+		t, webhookID, time.Now().Add(-48*time.Hour),
+	)
+
+	webhookDB := testWebhookDB(t)
+	event := seedEvent(t, webhookDB, `{"n":1}`)
+	event.WebhookID = webhookID
+	d := seedDatabaseTargetDelivery(
+		t, webhookDB, event, `{"expiry":"1h"}`,
+	)
+
+	env.eng.ExportDeliverDatabase(webhookDB, d)
+
+	require.True(
+		t, env.eng.ExportArchiveHandleOpen(webhookID),
+		"the delivery must leave the archive handle open",
+	)
+
+	env.sweeper.ExportSweep(context.Background())
+
+	require.True(
+		t, env.eng.ExportHasArchiveWriter(webhookID),
+		"the delivery's registry entry must survive the sweep",
+	)
+	assert.False(
+		t, env.eng.ExportArchiveHandleOpen(webhookID),
+		"the sweep must leave the archive closed",
+	)
+}
+
+// TestArchiveSweep_NeverExpiryUntouched proves the sweep is a
+// no-op for the default retention policy, so archives with no
+// expiry (or the literal "never") behave exactly as before.
+func TestArchiveSweep_NeverExpiryUntouched(t *testing.T) {
+	t.Parallel()
+
+	for _, configJSON := range []string{
+		`{"expiry":"never"}`,
+		`{"expiry":""}`,
+		"",
+	} {
+		env := setupSweeperTest(t)
+
+		webhookID := env.seedDatabaseTarget(t, configJSON)
+		path := env.seedArchiveRows(
+			t, webhookID,
+			time.Now().Add(-10000*time.Hour),
+		)
+
+		env.sweeper.ExportSweep(context.Background())
+
+		assert.Equal(
+			t, []string{sweepRowOld}, archivedEventIDs(t, path),
+			"config %q must keep rows forever", configJSON,
+		)
+		assert.False(
+			t, env.eng.ExportHasArchiveWriter(webhookID),
+			"config %q must leave no registry entry behind",
+			configJSON,
+		)
+	}
+}
+
+// TestArchiveSweep_NeverExpirySkipsBeforeOpening pins the
+// expiry <= 0 boundary in sweepTarget, which the row assertions
+// above cannot reach: pruning is separately gated on a positive
+// expiry, so a "never" archive keeps its rows even if the sweep
+// does open it.
+//
+// The spec is stronger than that — a "never" archive is skipped
+// before any file is touched — so the archive here exists but has
+// never been migrated. Opening it at all would run AutoMigrate
+// and create the archive table, which is exactly what must not
+// happen.
+func TestArchiveSweep_NeverExpirySkipsBeforeOpening(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	env := setupSweeperTest(t)
+
+	webhookID := env.seedDatabaseTarget(t, `{"expiry":"never"}`)
+	path := env.archivePath(webhookID)
+
+	seedUnmigratedArchive(t, path)
+	require.False(t, archiveTableExists(t, path))
+
+	env.sweeper.ExportSweep(context.Background())
+
+	assert.False(
+		t, archiveTableExists(t, path),
+		"a never-expiry archive must not be opened at all",
+	)
+}
+
+// seedUnmigratedArchive creates an archive file that exists but
+// carries no archive schema, so any open of it is observable: the
+// archive table appears only if something ran AutoMigrate.
+func seedUnmigratedArchive(t *testing.T, path string) {
+	t.Helper()
+
+	sqlDB, err := sql.Open(
+		"sqlite", fmt.Sprintf("file:%s?mode=rwc", path),
+	)
+	require.NoError(t, err)
+
+	_, err = sqlDB.ExecContext(
+		t.Context(), "CREATE TABLE placeholder (id INTEGER)",
+	)
+	require.NoError(t, err)
+
+	require.NoError(t, sqlDB.Close())
+}
+
+// archiveTableExists reports whether an archive file has had the
+// archive schema migrated into it.
+func archiveTableExists(t *testing.T, path string) bool {
+	t.Helper()
+
+	return openArchiveDBForRead(t, path).
+		Migrator().
+		HasTable(&delivery.ExportArchivedEvent{})
+}
+
+// TestArchiveSweep_DoesNotCreateArchiveFile proves the sweep
+// never conjures an archive: a webhook with a database target
+// that has never received an event must still have no archive
+// file (nor SQLite sidecar) after a sweep.
+func TestArchiveSweep_DoesNotCreateArchiveFile(t *testing.T) {
+	t.Parallel()
+
+	env := setupSweeperTest(t)
+
+	webhookID := env.seedDatabaseTarget(t, `{"expiry":"1h"}`)
+	path := env.archivePath(webhookID)
+
+	require.NoFileExists(t, path)
+
+	env.sweeper.ExportSweep(context.Background())
+
+	for _, suffix := range archiveFileSuffixes() {
+		assert.NoFileExists(
+			t, path+suffix,
+			"the sweep must not create an archive file",
+		)
+	}
+}
+
+// TestArchiveSweep_DoesNotCreateAfterWriterExists covers the
+// same guarantee once a writer is cached in the registry but
+// the file itself is still absent (for instance because the
+// operator moved the archive away).
+func TestArchiveSweep_DoesNotCreateAfterWriterExists(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	env := setupSweeperTest(t)
+
+	webhookID := env.seedDatabaseTarget(t, `{"expiry":"1h"}`)
+
+	path, err := env.eng.ExportEnsureArchiveWriter(webhookID)
+	require.NoError(t, err)
+	require.NoFileExists(t, path)
+
+	env.sweeper.ExportSweep(context.Background())
+
+	assert.NoFileExists(t, path)
+}
+
+// TestArchiveSweep_SkipsDeletedWebhookTargets proves that the
+// sweep ignores targets soft-deleted along with their webhook,
+// so a deleted webhook's archive is never reopened.
+func TestArchiveSweep_SkipsDeletedWebhookTargets(t *testing.T) {
+	t.Parallel()
+
+	env := setupSweeperTest(t)
+
+	webhookID := env.seedDatabaseTarget(t, `{"expiry":"1h"}`)
+	path := env.seedArchiveRows(
+		t, webhookID, time.Now().Add(-48*time.Hour),
+	)
+
+	require.NoError(
+		t,
+		env.mainDB.DB().
+			Where("webhook_id = ?", webhookID).
+			Delete(&database.Target{}).Error,
+	)
+
+	env.sweeper.ExportSweep(context.Background())
+
+	assert.Equal(
+		t, []string{sweepRowOld}, archivedEventIDs(t, path),
+		"a deleted target's archive must be left alone",
+	)
+}
+
+// TestArchiveSweep_ConcurrentWrites proves the sweep serialises
+// against writes through the per-webhook writer mutex. Run
+// under -race, an unsynchronised sweep would be caught here.
+func TestArchiveSweep_ConcurrentWrites(t *testing.T) {
+	t.Parallel()
+
+	env := setupSweeperTest(t)
+
+	webhookID := env.seedDatabaseTarget(t, `{"expiry":"1h"}`)
+
+	webhookDB := testWebhookDB(t)
+
+	// The deliveries are seeded up front, on the test's own
+	// goroutine: the seed helpers assert, and testify assertions
+	// must not run off the test goroutine.
+	deliveries := make(
+		[]*database.Delivery, 0, sweepConcurrentWrites,
+	)
+
+	for range sweepConcurrentWrites {
+		event := seedEvent(t, webhookDB, `{"n":1}`)
+		event.WebhookID = webhookID
+
+		deliveries = append(
+			deliveries,
+			seedDatabaseTargetDelivery(
+				t, webhookDB, event, `{"expiry":"1h"}`,
+			),
+		)
+	}
+
+	var wg sync.WaitGroup
+
+	wg.Add(2)
+
+	go func() {
+		defer wg.Done()
+
+		for _, d := range deliveries {
+			env.eng.ExportDeliverDatabase(webhookDB, d)
+		}
+	}()
+
+	go func() {
+		defer wg.Done()
+
+		for range sweepConcurrentWrites {
+			env.sweeper.ExportSweep(context.Background())
+		}
+	}()
+
+	wg.Wait()
+
+	assert.FileExists(t, env.archivePath(webhookID))
+}
+
+// TestArchiveSweeper_StopsCleanly proves the background loop
+// exits on OnStop rather than leaking a goroutine.
+func TestArchiveSweeper_StopsCleanly(t *testing.T) {
+	t.Parallel()
+
+	env := setupSweeperTest(t)
+
+	webhookID := env.seedDatabaseTarget(t, `{"expiry":"1h"}`)
+	env.seedArchiveRows(
+		t, webhookID, time.Now().Add(-48*time.Hour),
+	)
+
+	env.sweeper.ExportSetInterval(time.Millisecond)
+	env.sweeper.ExportStart()
+
+	// stop blocks on the loop's WaitGroup, so returning at all
+	// proves the loop observed the cancellation and exited.
+	env.sweeper.ExportStop()
+}

internal/delivery/engine.go

@@ -94,6 +94,23 @@ type Notifier interface {
 	Notify(tasks []Task)
 }
 
+// WebhookEvictor releases the delivery engine's per-webhook
+// state for a webhook that no longer needs it — currently the
+// cached archive writer of the database target, whose open
+// file handle would otherwise outlive the webhook.
+//
+// It is deliberately separate from Notifier and deliberately
+// one method wide: archiving lifecycle is not notification, and
+// a single-method interface keeps the handlers package free of
+// any dependency on the engine's internals while staying
+// trivially fakeable in tests.
+//
+// EvictWebhook never deletes an archive file. It is idempotent
+// and is a no-op for a webhook with no engine state.
+type WebhookEvictor interface {
+	EvictWebhook(webhookID string)
+}
+
 // EngineParams are the fx dependencies for the delivery
 // engine.
 type EngineParams struct {
@@ -127,6 +144,10 @@ type Engine struct {
 	// httpTarget is retained so tests can reach the HTTP
 	// target's shared client and circuit breakers.
 	httpTarget *httpTarget
+
+	// dbTarget is retained so the engine can reach the archive
+	// writer registry for webhook eviction and the idle sweep.
+	dbTarget *databaseTarget
 }
 
 // New creates and registers the delivery engine with the
@@ -182,6 +203,19 @@ func (e *Engine) Notify(tasks []Task) {
 	}
 }
 
+// EvictWebhook implements WebhookEvictor. It releases the
+// engine's per-webhook archiving state: the database target's
+// cached archive writer is dropped from the registry and its
+// file handle closed. The archive file itself is left on disk
+// — it is long-term storage the operator owns.
+func (e *Engine) EvictWebhook(webhookID string) {
+	if e.dbTarget == nil {
+		return
+	}
+
+	e.dbTarget.evict(webhookID)
+}
+
 // ScheduleRetry schedules a task to be re-enqueued onto the
 // retry channel after delay. It implements the Scheduler
 // interface the targets use to own their durable retries.
@@ -453,9 +487,8 @@ func (e *Engine) recoverRetryingDeliveries(
 // recoverSingleRetry hands an orphaned retrying delivery back
 // to its target to recompute the remaining backoff, then
 // reschedules it. Targets that do not own durable retries
-// (fire-and-forget) never produce retrying deliveries, so a
+// (fire-and-forget) never produce retrying deliveries, so
-// delivery found in that state has had its target's type
+// they are skipped.
-// changed underneath it and is terminally failed.
 func (e *Engine) recoverSingleRetry(
 	webhookDB *gorm.DB,
 	webhookID string,
@@ -476,10 +509,6 @@ func (e *Engine) recoverSingleRetry(
 
 	rs, ok := e.targets[target.Type].(rescheduler)
 	if !ok {
-		e.failUnretryableRetry(
-			webhookDB, webhookID, d, &target,
-		)
-
 		return
 	}
 
@@ -654,8 +683,8 @@ func (e *Engine) sweepWebhookRetries(
 
 // sweepSingleRetry re-enqueues an orphaned retrying delivery
 // whose backoff window has elapsed, delegating the backoff
-// decision to the delivery's target. A delivery whose target
+// decision to the delivery's target. Targets that do not own
-// no longer owns durable retries is terminally failed.
+// durable retries are skipped.
 func (e *Engine) sweepSingleRetry(
 	webhookDB *gorm.DB,
 	webhookID string,
@@ -675,10 +704,6 @@ func (e *Engine) sweepSingleRetry(
 
 	rs, ok := e.targets[target.Type].(rescheduler)
 	if !ok {
-		e.failUnretryableRetry(
-			webhookDB, webhookID, d, &target,
-		)
-
 		return
 	}
 
@@ -719,59 +744,6 @@ func (e *Engine) sweepSingleRetry(
 	}
 }
 
-// failUnretryableRetry terminally fails an orphaned retrying
-// delivery whose target type no longer supports retries. Both
-// restart recovery and the periodic sweep call it, so the
-// terminal transition exists once.
-//
-// This is only reachable when a target's type has been changed
-// out from under an in-flight retrying delivery (or the type is
-// unknown to the registry): fire-and-forget targets never set
-// status retrying themselves. Re-dispatching under the new type
-// would be a delivery the operator never asked for, and leaving
-// the row retrying strands it forever, so the delivery is
-// failed with a recorded reason and can be redelivered
-// manually. Logged at warn, not error: this is operator-caused
-// state, not a system fault.
-func (e *Engine) failUnretryableRetry(
-	webhookDB *gorm.DB,
-	webhookID string,
-	d *database.Delivery,
-	target *database.Target,
-) {
-	e.log.Warn(
-		"failing orphaned retrying delivery: target "+
-			"type no longer supports retries",
-		"webhook_id", webhookID,
-		"delivery_id", d.ID,
-		"target_id", target.ID,
-		"target_name", target.Name,
-		"target_type", target.Type,
-	)
-
-	reason := fmt.Sprintf(
-		"target type %q does not support retries; "+
-			"delivery was left retrying by a previous "+
-			"target type and has been failed terminally",
-		target.Type,
-	)
-
-	e.recordResult(
-		webhookDB,
-		d,
-		e.countAttempts(webhookDB, d.ID)+1,
-		false,
-		0,
-		"",
-		reason,
-		0,
-	)
-
-	e.updateDeliveryStatus(
-		webhookDB, d, database.DeliveryStatusFailed,
-	)
-}
-
 // processDelivery dispatches a delivery to the target that
 // owns its type. Unknown target types fail the delivery.
 func (e *Engine) processDelivery(

internal/delivery/engine_integration_test.go

@@ -748,193 +748,6 @@ func TestRecoverWebhookDeliveries_RetryingDeliveries(
 	case <-time.After(5 * time.Second):
 		t.Fatal("expected retry task from recovery")
 	}
-
-	// Regression guard: a target that still supports retries
-	// must be rescheduled, never terminally failed, and must
-	// not gain a synthetic result row.
-	iAssertStatus(
-		t, s.WebhookDB, d.ID,
-		database.DeliveryStatusRetrying,
-	)
-
-	assert.Len(t, iResults(t, s.WebhookDB, d.ID), 1)
-}
-
-// --- Retrying deliveries whose target type changed ---
-
-// iSeedRetryingWithType seeds a retrying delivery with one
-// recorded failed attempt against a target of the given type,
-// standing in for a target whose type was edited in the main
-// database while the delivery was still retrying.
-func iSeedRetryingWithType(
-	t *testing.T,
-	s iSetup,
-	targetType database.TargetType,
-) string {
-	t.Helper()
-
-	targetID := uuid.New().String()
-
-	iCreateTarget(t, s.MainDB, targetID,
-		s.WebhookID, "mutated-target", targetType,
-		iHTTPConfig("http://example.com/hook"), 5,
-	)
-
-	event := iSeedEvent(
-		t, s.WebhookDB, s.WebhookID,
-		`{"orphaned":"retry"}`,
-	)
-
-	d := iSeedDelivery(
-		t, s.WebhookDB, event.ID, targetID,
-		database.DeliveryStatusRetrying,
-	)
-
-	iSeedFailedResult(t, s.WebhookDB, d.ID)
-
-	return d.ID
-}
-
-// iResults loads a delivery's results in attempt order.
-func iResults(
-	t *testing.T, db *gorm.DB, deliveryID string,
-) []database.DeliveryResult {
-	t.Helper()
-
-	var results []database.DeliveryResult
-
-	require.NoError(t, db.
-		Where("delivery_id = ?", deliveryID).
-		Order("attempt_num").
-		Find(&results).Error)
-
-	return results
-}
-
-// iAssertTerminallyFailed asserts the delivery ended failed
-// with a result row recording why, and was not rescheduled.
-func iAssertTerminallyFailed(
-	t *testing.T,
-	s iSetup,
-	deliveryID string,
-	targetType database.TargetType,
-) {
-	t.Helper()
-
-	iAssertStatus(
-		t, s.WebhookDB, deliveryID,
-		database.DeliveryStatusFailed,
-	)
-
-	results := iResults(t, s.WebhookDB, deliveryID)
-	require.Len(t, results, 2)
-
-	last := results[1]
-
-	assert.False(t, last.Success)
-	assert.Equal(t, 2, last.AttemptNum)
-
-	assert.Contains(
-		t, last.Error, string(targetType),
-	)
-
-	assert.Contains(
-		t, last.Error, "does not support retries",
-	)
-
-	assert.Empty(t, s.Engine.ExportRetryCh())
-}
-
-func TestRecoverSingleRetry_TypeNoLongerRetries(
-	t *testing.T,
-) {
-	t.Parallel()
-
-	s := newISetup(t)
-
-	iCreateWebhook(
-		t, s.MainDB, s.WebhookID, "mutated-type",
-	)
-
-	deliveryID := iSeedRetryingWithType(
-		t, s, database.TargetTypeLog,
-	)
-
-	s.Engine.ExportRecoverWebhookDeliveries(
-		context.Background(), s.WebhookID,
-	)
-
-	iAssertTerminallyFailed(
-		t, s, deliveryID, database.TargetTypeLog,
-	)
-}
-
-func TestSweepSingleRetry_TypeNoLongerRetries(
-	t *testing.T,
-) {
-	t.Parallel()
-
-	s := newISetup(t)
-
-	iCreateWebhook(
-		t, s.MainDB, s.WebhookID, "mutated-type-sweep",
-	)
-
-	deliveryID := iSeedRetryingWithType(
-		t, s, database.TargetTypeDatabase,
-	)
-
-	s.Engine.ExportSweepWebhookRetries(
-		context.Background(), s.WebhookID,
-	)
-
-	iAssertTerminallyFailed(
-		t, s, deliveryID, database.TargetTypeDatabase,
-	)
-}
-
-func TestRecoverSingleRetry_UnknownTargetType(
-	t *testing.T,
-) {
-	t.Parallel()
-
-	s := newISetup(t)
-
-	iCreateWebhook(
-		t, s.MainDB, s.WebhookID, "unknown-type",
-	)
-
-	unknown := database.TargetType("not-a-target-type")
-
-	deliveryID := iSeedRetryingWithType(t, s, unknown)
-
-	s.Engine.ExportRecoverWebhookDeliveries(
-		context.Background(), s.WebhookID,
-	)
-
-	iAssertTerminallyFailed(t, s, deliveryID, unknown)
-}
-
-func TestSweepSingleRetry_UnknownTargetType(
-	t *testing.T,
-) {
-	t.Parallel()
-
-	s := newISetup(t)
-
-	iCreateWebhook(
-		t, s.MainDB, s.WebhookID, "unknown-type-sweep",
-	)
-
-	unknown := database.TargetType("not-a-target-type")
-
-	deliveryID := iSeedRetryingWithType(t, s, unknown)
-
-	s.Engine.ExportSweepWebhookRetries(
-		context.Background(), s.WebhookID,
-	)
-
-	iAssertTerminallyFailed(t, s, deliveryID, unknown)
 }
 
 // iSeedFailedResult creates a failed delivery result.

internal/delivery/export_test.go

@@ -7,10 +7,17 @@ import (
 	"net/http"
 	"time"
 
+	"go.uber.org/fx"
 	"gorm.io/gorm"
 	"sneak.berlin/go/webhooker/internal/database"
 )
 
+// ErrExportArchiveWriterEvicted exposes the sentinel returned by
+// an evicted archive writer. It carries the Err prefix rather
+// than this file's usual Export one because it is a sentinel
+// error.
+var ErrExportArchiveWriterEvicted = errArchiveWriterEvicted
+
 // Exported constants for test access.
 const (
 	ExportDeliveryChannelSize     = deliveryChannelSize
@@ -188,13 +195,6 @@ func (e *Engine) ExportRecoverInFlight(
 	e.recoverInFlight(ctx)
 }
 
-// ExportSweepWebhookRetries exposes sweepWebhookRetries.
-func (e *Engine) ExportSweepWebhookRetries(
-	ctx context.Context, webhookID string,
-) {
-	e.sweepWebhookRetries(ctx, webhookID)
-}
-
 // ExportStart exposes start for testing.
 func (e *Engine) ExportStart(ctx context.Context) {
 	e.start(ctx)
@@ -335,6 +335,183 @@ func (e *ExportArchiveWriter) DB() *gorm.DB {
 	return e.w.db
 }
 
+// Path returns the archive file the writer owns.
+func (e *ExportArchiveWriter) Path() string {
+	return e.w.path
+}
+
+// OpenExisting opens the archive without permitting creation,
+// the way the idle sweep does.
+func (e *ExportArchiveWriter) OpenExisting(
+	expiry time.Duration,
+) error {
+	return e.w.openMode(archiveModeExisting, expiry)
+}
+
+// SweepExpired runs an idle sweep of the archive.
+func (e *ExportArchiveWriter) SweepExpired(
+	expiry time.Duration,
+) error {
+	return e.w.sweepExpired(expiry)
+}
+
+// Evict marks the writer evicted and closes its handle, exactly
+// as leaving the registry does.
+func (e *ExportArchiveWriter) Evict() {
+	e.w.evict()
+}
+
+// HandleOpen reports whether the writer currently holds an open
+// archive handle.
+func (e *ExportArchiveWriter) HandleOpen() bool {
+	e.w.mu.Lock()
+	defer e.w.mu.Unlock()
+
+	return e.w.db != nil
+}
+
+// Same reports whether both wrappers refer to the very same
+// underlying archive writer, so a test can prove a registry entry
+// is the writer it was handed rather than a replacement.
+func (e *ExportArchiveWriter) Same(
+	other *ExportArchiveWriter,
+) bool {
+	return other != nil && e.w == other.w
+}
+
+// ExportArchiveWriterFor returns the archive writer the registry
+// currently caches for a webhook, or nil when none is cached. It
+// never creates one, so a test can hold a reference to the very
+// writer an eviction is about to detach.
+func (e *Engine) ExportArchiveWriterFor(
+	webhookID string,
+) *ExportArchiveWriter {
+	e.dbTarget.mu.Lock()
+	defer e.dbTarget.mu.Unlock()
+
+	w, ok := e.dbTarget.writers[webhookID]
+	if !ok {
+		return nil
+	}
+
+	return &ExportArchiveWriter{w: w}
+}
+
+// ExportHasArchiveWriter reports whether the database target
+// currently caches an archive writer for a webhook.
+func (e *Engine) ExportHasArchiveWriter(
+	webhookID string,
+) bool {
+	e.dbTarget.mu.Lock()
+	defer e.dbTarget.mu.Unlock()
+
+	_, ok := e.dbTarget.writers[webhookID]
+
+	return ok
+}
+
+// ExportArchiveHandleOpen reports whether the cached archive
+// writer for a webhook holds an open database handle. It
+// returns false when no writer is cached.
+func (e *Engine) ExportArchiveHandleOpen(
+	webhookID string,
+) bool {
+	e.dbTarget.mu.Lock()
+	w, ok := e.dbTarget.writers[webhookID]
+	e.dbTarget.mu.Unlock()
+
+	if !ok {
+		return false
+	}
+
+	w.mu.Lock()
+	defer w.mu.Unlock()
+
+	return w.db != nil
+}
+
+// ExportEnsureArchiveWriter creates (if needed) and returns the
+// archive file path of the cached writer for a webhook, so a
+// test can prime the registry the way a delivery would.
+func (e *Engine) ExportEnsureArchiveWriter(
+	webhookID string,
+) (string, error) {
+	w, err := e.dbTarget.writerFor(webhookID)
+	if err != nil {
+		return "", err
+	}
+
+	return w.path, nil
+}
+
+// ExportSweepWriterFor takes a webhook's registry writer exactly
+// as the idle sweep does, reporting whether the sweep had to
+// create the entry. It lets a test drive the registry through the
+// sweep's own entry point instead of choreographing goroutines.
+func (e *Engine) ExportSweepWriterFor(
+	webhookID string,
+) (*ExportArchiveWriter, bool, error) {
+	w, created, err := e.dbTarget.sweepWriterFor(webhookID)
+	if err != nil {
+		return nil, false, err
+	}
+
+	return &ExportArchiveWriter{w: w}, created, nil
+}
+
+// ExportReleaseSweepWriter releases a sweep-created registry entry
+// exactly as a finished sweep does.
+func (e *Engine) ExportReleaseSweepWriter(
+	webhookID string, w *ExportArchiveWriter,
+) {
+	e.dbTarget.releaseSweepWriter(webhookID, w.w)
+}
+
+// NewTestArchiveSweeper builds an ArchiveSweeper backed by the
+// given main database and engine, without the fx lifecycle.
+// Intended for tests.
+func NewTestArchiveSweeper(
+	db *database.Database,
+	eng *Engine,
+	log *slog.Logger,
+) *ArchiveSweeper {
+	return &ArchiveSweeper{
+		db:       db,
+		eng:      eng,
+		log:      log,
+		interval: time.Hour,
+	}
+}
+
+// ExportSweep runs a single archive sweep synchronously for
+// tests.
+func (s *ArchiveSweeper) ExportSweep(ctx context.Context) {
+	s.sweep(ctx)
+}
+
+// ExportStart starts the sweeper's background loop for tests.
+func (s *ArchiveSweeper) ExportStart() {
+	s.start()
+}
+
+// ExportRegisterHooks registers the sweeper's real fx lifecycle
+// hooks on a lifecycle supplied by a test, so a test can drive
+// the exact OnStart/OnStop functions the application runs and
+// hand OnStart the kind of context fx actually supplies.
+func (s *ArchiveSweeper) ExportRegisterHooks(lc fx.Lifecycle) {
+	s.registerHooks(lc)
+}
+
+// ExportStop stops the sweeper's background loop for tests.
+func (s *ArchiveSweeper) ExportStop() {
+	s.stop()
+}
+
+// ExportSetInterval overrides the sweep interval for tests.
+func (s *ArchiveSweeper) ExportSetInterval(d time.Duration) {
+	s.interval = d
+}
+
 // ExportParseArchiveExpiry exposes parseArchiveExpiry.
 func ExportParseArchiveExpiry(
 	configJSON string,

internal/delivery/target.go

@@ -90,12 +90,15 @@ func (e *Engine) initTargets(client *http.Client) {
 		client:   client,
 	}
 
+	dbT := &databaseTarget{eng: e}
+
 	e.httpTarget = httpT
+	e.dbTarget = dbT
 
 	e.targets = map[database.TargetType]Target{
 		database.TargetTypeHTTP:     httpT,
 		database.TargetTypeSlack:    slackT,
-		database.TargetTypeDatabase: &databaseTarget{eng: e},
+		database.TargetTypeDatabase: dbT,
 		database.TargetTypeLog:      &logTarget{eng: e},
 	}
 }

internal/delivery/target_database.go

@@ -5,6 +5,7 @@ import (
 	"fmt"
 	"path/filepath"
 	"sync"
+	"time"
 
 	"gorm.io/gorm"
 	"sneak.berlin/go/webhooker/internal/database"
@@ -111,15 +112,11 @@ func (t *databaseTarget) archive(d *database.Delivery) error {
 func (t *databaseTarget) writerFor(
 	webhookID string,
 ) (*archiveWriter, error) {
-	if t.eng.dbManager == nil {
+	path, err := t.archivePath(webhookID)
-		return nil, errArchiveNoDataDir
+	if err != nil {
+		return nil, err
 	}
 
-	dir := filepath.Dir(t.eng.dbManager.DBPath(webhookID))
-	path := filepath.Join(
-		dir, fmt.Sprintf("archive-%s.db", webhookID),
-	)
-
 	t.mu.Lock()
 	defer t.mu.Unlock()
 
@@ -133,5 +130,166 @@ func (t *databaseTarget) writerFor(
 		t.writers[webhookID] = w
 	}
 
+	// A delivery claims the entry: even if the idle sweep created
+	// it moments ago, it now belongs to the registry proper and
+	// the sweep must leave it in place when it finishes.
+	w.sweepOwned = false
+
 	return w, nil
 }
+
+// sweepWriterFor returns the archive writer the idle sweep should
+// prune a webhook through, together with whether the sweep itself
+// created the registry entry.
+//
+// The sweep must route its prune through the registered writer so
+// the writer's mutex orders it against concurrent writes, but it
+// must never leave a registry entry behind: a sweep that ran
+// concurrently with the webhook's deletion would otherwise
+// re-create an entry that nothing will ever evict again, which is
+// exactly the leak eviction exists to prevent. An entry the sweep
+// creates is therefore marked sweep-owned and handed back to
+// releaseSweepWriter when the sweep is done.
+func (t *databaseTarget) sweepWriterFor(
+	webhookID string,
+) (*archiveWriter, bool, error) {
+	path, err := t.archivePath(webhookID)
+	if err != nil {
+		return nil, false, err
+	}
+
+	t.mu.Lock()
+	defer t.mu.Unlock()
+
+	if t.writers == nil {
+		t.writers = make(map[string]*archiveWriter)
+	}
+
+	w, ok := t.writers[webhookID]
+	if ok {
+		return w, false, nil
+	}
+
+	w = newArchiveWriter(path, t.eng.log)
+	w.sweepOwned = true
+	t.writers[webhookID] = w
+
+	return w, true, nil
+}
+
+// releaseSweepWriter drops a registry entry that the idle sweep
+// created, so a sweep leaves the registry exactly as it found it.
+//
+// The entry is removed only if it is still the very writer the
+// sweep installed and no delivery has claimed it in the meantime
+// (writerFor clears sweepOwned when it hands a writer to the
+// write path). Both conditions are evaluated under the registry
+// lock, so an eviction that raced the sweep — which removes the
+// entry outright — simply finds nothing left to do here, and a
+// delivery that adopted the writer keeps a registered, evictable
+// one.
+func (t *databaseTarget) releaseSweepWriter(
+	webhookID string, w *archiveWriter,
+) {
+	t.mu.Lock()
+	defer t.mu.Unlock()
+
+	cur, ok := t.writers[webhookID]
+	if !ok || cur != w || !cur.sweepOwned {
+		return
+	}
+
+	delete(t.writers, webhookID)
+}
+
+// archivePath returns the archive file path for a webhook: it
+// lives beside the per-webhook event database in the data
+// directory. It does not touch the filesystem.
+func (t *databaseTarget) archivePath(
+	webhookID string,
+) (string, error) {
+	if t.eng.dbManager == nil {
+		return "", errArchiveNoDataDir
+	}
+
+	dir := filepath.Dir(t.eng.dbManager.DBPath(webhookID))
+
+	return filepath.Join(
+		dir, fmt.Sprintf("archive-%s.db", webhookID),
+	), nil
+}
+
+// evict drops a webhook's archive writer from the registry and
+// closes its handle, so a deleted webhook does not leave a
+// writer (and an open archive handle within its debounce
+// window) alive for the process lifetime.
+//
+// The map entry is removed under the registry lock, which is
+// then released before the handle is closed under the writer's
+// own lock: that ordering keeps the registry available to other
+// webhooks while an in-flight write on this one drains, and
+// closing under the writer's lock means eviction can never race
+// a write.
+//
+// Eviction is idempotent and silent for a webhook with no
+// writer, which is the common case: a webhook with no database
+// target never creates one. It never deletes the archive file.
+func (t *databaseTarget) evict(webhookID string) {
+	t.mu.Lock()
+
+	w, ok := t.writers[webhookID]
+	if ok {
+		delete(t.writers, webhookID)
+	}
+
+	t.mu.Unlock()
+
+	if !ok {
+		return
+	}
+
+	w.evict()
+
+	t.eng.log.Info(
+		"evicted archive writer",
+		"webhook_id", webhookID,
+		"path", w.path,
+	)
+}
+
+// sweepWebhook prunes one webhook's archive of rows older than
+// expiry, without requiring a write. It returns nil (nothing to
+// do) when the archive file does not exist, so a sweep never
+// creates an archive for a webhook that has a database target
+// but has never received an event.
+//
+// It also never leaves a registry entry behind: an entry it had
+// to create to reach the writer's mutex is released again once
+// the prune is done, so a sweep racing a webhook deletion cannot
+// resurrect the writer the eviction just dropped.
+func (t *databaseTarget) sweepWebhook(
+	webhookID string, expiry time.Duration,
+) error {
+	path, err := t.archivePath(webhookID)
+	if err != nil {
+		return err
+	}
+
+	// Check before taking a writer at all: a webhook whose
+	// archive has never been created gets no writer, no handle,
+	// and no file.
+	if !fileExists(path) {
+		return nil
+	}
+
+	w, created, err := t.sweepWriterFor(webhookID)
+	if err != nil {
+		return err
+	}
+
+	if created {
+		defer t.releaseSweepWriter(webhookID, w)
+	}
+
+	return w.sweepExpired(expiry)
+}

internal/delivery/target_database_archive.go

@@ -24,6 +24,20 @@ const archiveExpiryNever = "never"
 // offline archiving, but never more than once per this window.
 const archiveReopenDebounce = time.Second
 
+const (
+	// archiveModeCreate is the SQLite URI mode used by the write
+	// 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"
+
+	// 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"
+)
+
 var (
 	// errArchiveMissingWebhookID is returned when an event to
 	// archive has no webhook id to key its archive file on.
@@ -44,6 +58,15 @@ var (
 	errArchiveExpiryNotPositive = errors.New(
 		"expiry must be a positive duration or \"never\"",
 	)
+
+	// errArchiveWriterEvicted is returned when a writer that has
+	// been evicted (its webhook was deleted, or its last database
+	// target was removed) is used again. An evicted writer is no
+	// longer in the registry, so reopening its file would leak a
+	// handle nothing owns.
+	errArchiveWriterEvicted = errors.New(
+		"archive writer has been evicted",
+	)
 )
 
 // databaseTargetConfig is the optional per-target JSON config
@@ -161,6 +184,25 @@ type archiveWriter struct {
 	db         *gorm.DB
 	lastReopen time.Time
 	reopens    int
+
+	// evicted marks a writer that has been removed from the
+	// per-webhook registry. Its handle is closed and it must
+	// never open the file again: nothing holds it any more, so a
+	// reopen would leak the handle for the process lifetime.
+	evicted bool
+
+	// sweepOwned marks a registry entry that the idle sweep
+	// created because no writer was cached for the webhook. The
+	// sweep removes such an entry again when it is done, so a
+	// sweep can never leave — or resurrect — a registry entry
+	// for a webhook that has been deleted. A delivery that adopts
+	// the writer clears the flag, handing the entry to the
+	// registry proper.
+	//
+	// Unlike every other field here it is guarded by
+	// databaseTarget.mu, not by this writer's mu: it describes the
+	// registry entry rather than the file.
+	sweepOwned bool
 }
 
 // newArchiveWriter builds an archiveWriter for a file path with
@@ -185,6 +227,12 @@ func (w *archiveWriter) write(
 	w.mu.Lock()
 	defer w.mu.Unlock()
 
+	if w.evicted {
+		return fmt.Errorf(
+			"%w: %s", errArchiveWriterEvicted, w.path,
+		)
+	}
+
 	if w.db == nil || !fileExists(w.path) {
 		err := w.reopen(expiry)
 		if err != nil {
@@ -212,7 +260,19 @@ func (w *archiveWriter) write(
 // its schema, records the reopen time, and prunes expired rows
 // when expiry is positive.
 func (w *archiveWriter) open(expiry time.Duration) error {
-	dbURL := fmt.Sprintf("file:%s?mode=rwc", w.path)
+	return w.openMode(archiveModeCreate, expiry)
+}
+
+// openMode opens the archive file with the given SQLite URI
+// mode, migrates its schema, records the reopen time, and
+// prunes expired rows when expiry is positive. The write path
+// passes archiveModeCreate so a missing file is recreated; the
+// idle sweep passes archiveModeExisting so a missing file is an
+// error rather than a newly conjured empty archive.
+func (w *archiveWriter) openMode(
+	mode string, expiry time.Duration,
+) error {
+	dbURL := fmt.Sprintf("file:%s?mode=%s", w.path, mode)
 
 	sqlDB, err := sql.Open("sqlite", dbURL)
 	if err != nil {
@@ -275,11 +335,70 @@ func (w *archiveWriter) close() {
 	w.db = nil
 }
 
+// sweepExpired prunes an archive that may have gone idle, with
+// no write to trigger the usual on-reopen prune. It takes the
+// writer's own mutex for the whole operation, so a sweep is
+// ordered against concurrent writes rather than reaching around
+// them to the file.
+//
+// It never creates the archive file: a missing file is skipped,
+// and the reopen uses archiveModeExisting so SQLite itself
+// refuses to create one if the file disappears between the
+// check and the open.
+//
+// The archive is left CLOSED afterwards. An idle archive holding
+// no handle is what keeps the operator's move-the-file-away
+// workflow working; the next write reopens (and recreates) the
+// file as it always has.
+func (w *archiveWriter) sweepExpired(expiry time.Duration) error {
+	w.mu.Lock()
+	defer w.mu.Unlock()
+
+	if w.evicted {
+		return fmt.Errorf(
+			"%w: %s", errArchiveWriterEvicted, w.path,
+		)
+	}
+
+	if !fileExists(w.path) {
+		return nil
+	}
+
+	// Drop any live handle first so the prune runs against a
+	// freshly opened file, matching the write path's semantics.
+	w.close()
+
+	err := w.openMode(archiveModeExisting, expiry)
+	if err != nil {
+		return err
+	}
+
+	w.close()
+
+	return nil
+}
+
+// evict closes the writer's handle and marks it unusable. It is
+// called when the writer leaves the registry, either because the
+// webhook was deleted or because its last database target was
+// removed. The archive FILE is deliberately left on disk: it is
+// long-term storage an operator may still want.
+func (w *archiveWriter) evict() {
+	w.mu.Lock()
+	defer w.mu.Unlock()
+
+	w.evicted = true
+
+	w.close()
+}
+
 // prune deletes archived rows older than expiry, measured from
-// each row's archived time. It runs on every (re)open, and
+// each row's archived time. It runs on every (re)open, so a
-// because the file is reopened after writes this keeps the
+// steadily written archive is swept by its own write traffic. An
-// archive swept without a separate background sweeper. Failures
+// archive that goes idle receives no further reopens, which is
-// are logged, not fatal: a prune error must not stop archiving.
+// why ArchiveSweeper exists to drive sweepExpired on a timer.
+// Failures are logged, not fatal: a prune error must not stop
+// archiving.
 func (w *archiveWriter) prune(expiry time.Duration) {
 	cutoff := time.Now().Add(-expiry)
 

internal/delivery/target_database_evict_test.go

@@ -0,0 +1,363 @@
+package delivery_test
+
+import (
+	"errors"
+	"fmt"
+	"net/http"
+	"os"
+	"path/filepath"
+	"sync"
+	"testing"
+	"time"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	"sneak.berlin/go/webhooker/internal/database"
+	"sneak.berlin/go/webhooker/internal/delivery"
+)
+
+// evictTestEngine builds an engine backed by a temporary data
+// directory and returns it along with that directory.
+func evictTestEngine(t *testing.T) (*delivery.Engine, string) {
+	t.Helper()
+
+	dataDir := t.TempDir()
+
+	eng := delivery.NewTestEngineWithDB(
+		nil,
+		database.NewTestWebhookDBManager(dataDir),
+		archiveTestLogger(),
+		&http.Client{Timeout: 5 * time.Second},
+		1,
+	)
+
+	return eng, dataDir
+}
+
+// TestEvictWebhook_ClosesAndRemovesWriter proves that evicting
+// a webhook drops its archive writer from the registry and
+// closes the open archive handle, rather than leaving both
+// alive for the process lifetime.
+func TestEvictWebhook_ClosesAndRemovesWriter(t *testing.T) {
+	t.Parallel()
+
+	eng, dataDir := evictTestEngine(t)
+
+	webhookDB := testWebhookDB(t)
+	event := seedEvent(t, webhookDB, `{"archived":true}`)
+	d := seedDatabaseTargetDelivery(t, webhookDB, event, "")
+
+	eng.ExportDeliverDatabase(webhookDB, d)
+
+	webhookID := event.WebhookID
+
+	require.True(
+		t, eng.ExportHasArchiveWriter(webhookID),
+		"a delivery should have cached an archive writer",
+	)
+	require.True(
+		t, eng.ExportArchiveHandleOpen(webhookID),
+		"the writer should hold an open handle after a write",
+	)
+
+	eng.EvictWebhook(webhookID)
+
+	assert.False(
+		t, eng.ExportHasArchiveWriter(webhookID),
+		"eviction should remove the registry entry",
+	)
+	assert.False(
+		t, eng.ExportArchiveHandleOpen(webhookID),
+		"eviction should close the archive handle",
+	)
+
+	archivePath := filepath.Join(
+		dataDir, fmt.Sprintf("archive-%s.db", webhookID),
+	)
+	assert.FileExists(
+		t, archivePath,
+		"eviction must not delete the archive file",
+	)
+}
+
+// TestEvictWebhook_UnknownWebhookIsNoOp proves eviction is safe
+// for the common case of a webhook that never had a database
+// target, and that repeating it does not panic.
+func TestEvictWebhook_UnknownWebhookIsNoOp(t *testing.T) {
+	t.Parallel()
+
+	eng, _ := evictTestEngine(t)
+
+	assert.NotPanics(t, func() {
+		eng.EvictWebhook("no-such-webhook")
+		eng.EvictWebhook("no-such-webhook")
+	})
+
+	assert.False(
+		t, eng.ExportHasArchiveWriter("no-such-webhook"),
+		"eviction must not create a writer",
+	)
+}
+
+// evictTestRow builds an archive row for the eviction tests.
+func evictTestRow(eventID string) delivery.ExportArchivedEvent {
+	return delivery.ExportArchivedEvent{
+		EventID:   eventID,
+		WebhookID: "wh-evict",
+		Method:    http.MethodPost,
+		Body:      `{"seeded":true}`,
+	}
+}
+
+// TestEvictedWriter_WriteDoesNotReopenFile is the direct test of
+// the evicted guard on the write path. A writer that has left
+// the registry is held by nobody, so a handle it opened could
+// never be closed again: it must refuse the write outright
+// rather than recreate the archive behind the registry's back.
+//
+// The archive file is removed before the eviction, so an
+// unguarded write is unmistakable — it recreates the file.
+func TestEvictedWriter_WriteDoesNotReopenFile(t *testing.T) {
+	t.Parallel()
+
+	path := filepath.Join(t.TempDir(), "archive-evicted.db")
+
+	w := delivery.NewExportArchiveWriter(
+		path, archiveTestLogger(), 0,
+	)
+
+	require.NoError(t, w.Write(evictTestRow("ev-1"), 0))
+	require.FileExists(t, path)
+
+	// The operator moves the archive away for offline retention,
+	// which the write path would ordinarily undo on the next
+	// write by recreating the file.
+	require.NoError(t, os.Remove(path))
+
+	w.Evict()
+
+	err := w.Write(evictTestRow("ev-2"), 0)
+
+	require.ErrorIs(
+		t, err, delivery.ErrExportArchiveWriterEvicted,
+		"an evicted writer must refuse writes",
+	)
+	assert.NoFileExists(
+		t, path,
+		"an evicted writer must not reopen (or recreate) the "+
+			"archive file",
+	)
+	assert.False(
+		t, w.HandleOpen(),
+		"an evicted writer must hold no handle",
+	)
+}
+
+// TestEvictedWriter_SweepDoesNotReopenFile is the same test for
+// the sweep path: an idle sweep that reaches a writer already
+// evicted underneath it must return the sentinel rather than
+// reopen a file nothing owns.
+func TestEvictedWriter_SweepDoesNotReopenFile(t *testing.T) {
+	t.Parallel()
+
+	path := filepath.Join(t.TempDir(), "archive-evicted.db")
+
+	w := delivery.NewExportArchiveWriter(
+		path, archiveTestLogger(), 0,
+	)
+
+	require.NoError(t, w.Write(evictTestRow("ev-1"), 0))
+	require.FileExists(t, path)
+
+	w.Evict()
+
+	err := w.SweepExpired(time.Hour)
+
+	require.ErrorIs(
+		t, err, delivery.ErrExportArchiveWriterEvicted,
+		"an evicted writer must refuse an idle sweep",
+	)
+	assert.False(
+		t, w.HandleOpen(),
+		"a refused sweep must not leave a handle open",
+	)
+}
+
+// racingWrites drives a pack of goroutines writing to one
+// archive writer until each is refused, so an eviction on the
+// test goroutine has to take the writer's mutex away from writes
+// that are already contending for it.
+type racingWrites struct {
+	wg         sync.WaitGroup
+	mu         sync.Mutex
+	sawEvicted bool
+	otherErr   error
+	started    chan struct{}
+}
+
+// racingWriteGoroutines is how many goroutines contend for the
+// writer's mutex while the eviction lands.
+const racingWriteGoroutines = 4
+
+// startRacingWrites launches the writing goroutines. Each writes
+// in a loop and stops at its first error, recording whether that
+// error was the eviction sentinel. The deadline is a backstop
+// against a hang, not a timing assumption: the first write after
+// the eviction is refused.
+func startRacingWrites(
+	w *delivery.ExportArchiveWriter,
+) *racingWrites {
+	r := &racingWrites{
+		started: make(chan struct{}, racingWriteGoroutines),
+	}
+
+	deadline := time.Now().Add(10 * time.Second)
+
+	r.wg.Add(racingWriteGoroutines)
+
+	for i := range racingWriteGoroutines {
+		go func() {
+			defer r.wg.Done()
+
+			first := true
+
+			for time.Now().Before(deadline) {
+				err := w.Write(
+					evictTestRow(fmt.Sprintf("ev-%d", i)), 0,
+				)
+
+				if first {
+					r.started <- struct{}{}
+
+					first = false
+				}
+
+				if err == nil {
+					continue
+				}
+
+				r.record(err)
+
+				return
+			}
+		}()
+	}
+
+	return r
+}
+
+// record classifies the error that stopped one goroutine.
+func (r *racingWrites) record(err error) {
+	r.mu.Lock()
+	defer r.mu.Unlock()
+
+	if errors.Is(err, delivery.ErrExportArchiveWriterEvicted) {
+		r.sawEvicted = true
+
+		return
+	}
+
+	r.otherErr = err
+}
+
+// awaitFirstWrite blocks until at least one write has run, so
+// the eviction that follows is a genuine race.
+func (r *racingWrites) awaitFirstWrite() {
+	<-r.started
+}
+
+// wait joins the goroutines and reports whether any write was
+// refused with the eviction sentinel, plus any unexpected error.
+func (r *racingWrites) wait() (bool, error) {
+	r.wg.Wait()
+
+	r.mu.Lock()
+	defer r.mu.Unlock()
+
+	return r.sawEvicted, r.otherErr
+}
+
+// TestEvictWebhook_RacingWriteDoesNotReopenHandle exercises the
+// interleaving the evicted flag exists for: writes already
+// contending for the writer's mutex when the eviction takes it.
+// The write that wins the mutex after the eviction must abandon
+// its work rather than reopen the archive, leaving the writer
+// permanently handle-free. Run under -race.
+func TestEvictWebhook_RacingWriteDoesNotReopenHandle(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	eng, _ := evictTestEngine(t)
+
+	webhookDB := testWebhookDB(t)
+	event := seedEvent(t, webhookDB, `{"archived":true}`)
+	d := seedDatabaseTargetDelivery(t, webhookDB, event, "")
+
+	// Prime the registry so the test can hold the very writer the
+	// eviction is about to detach.
+	eng.ExportDeliverDatabase(webhookDB, d)
+
+	w := eng.ExportArchiveWriterFor(event.WebhookID)
+	require.NotNil(t, w)
+	require.True(t, w.HandleOpen())
+
+	race := startRacingWrites(w)
+
+	// Evict only once writes are genuinely in flight, so the
+	// eviction has to contend for the writer's mutex.
+	race.awaitFirstWrite()
+
+	eng.EvictWebhook(event.WebhookID)
+
+	sawEvicted, otherErr := race.wait()
+
+	require.NoError(t, otherErr)
+	assert.True(
+		t, sawEvicted,
+		"a write after eviction must be refused",
+	)
+	assert.False(
+		t, w.HandleOpen(),
+		"no write may reopen the archive once the writer has "+
+			"been evicted",
+	)
+	assert.False(
+		t, eng.ExportHasArchiveWriter(event.WebhookID),
+		"the registry entry must stay gone",
+	)
+}
+
+// TestEvictWebhook_LaterDeliveryRecreatesWriter proves eviction
+// does not break archiving for a webhook that is still alive: a
+// subsequent delivery gets a brand new writer from the registry.
+// It says nothing about the evicted writer itself — that is what
+// TestEvictedWriter_WriteDoesNotReopenFile covers.
+func TestEvictWebhook_LaterDeliveryRecreatesWriter(t *testing.T) {
+	t.Parallel()
+
+	eng, _ := evictTestEngine(t)
+
+	webhookDB := testWebhookDB(t)
+	event := seedEvent(t, webhookDB, `{"archived":true}`)
+	d := seedDatabaseTargetDelivery(t, webhookDB, event, "")
+
+	eng.ExportDeliverDatabase(webhookDB, d)
+	require.True(
+		t, eng.ExportHasArchiveWriter(event.WebhookID),
+	)
+
+	eng.EvictWebhook(event.WebhookID)
+
+	// A fresh delivery for the same webhook gets a brand new
+	// writer from the registry, so archiving keeps working.
+	second := seedDatabaseTargetDelivery(
+		t, webhookDB, event, "",
+	)
+	eng.ExportDeliverDatabase(webhookDB, second)
+
+	assert.True(
+		t, eng.ExportHasArchiveWriter(event.WebhookID),
+		"a later delivery should recreate the writer",
+	)
+}

internal/delivery/target_database_test.go

@@ -50,6 +50,13 @@ func openArchiveDBForRead(
 	return gdb
 }
 
+// archiveFileSuffixes returns the archive file itself and the
+// SQLite sidecars that accompany an open database. A test that
+// asserts no archive was created has to check all of them.
+func archiveFileSuffixes() []string {
+	return []string{"", "-wal", "-shm"}
+}
+
 // removeArchiveFiles simulates an operator moving the archive
 // away by deleting the SQLite file and its sidecar files.
 func removeArchiveFiles(t *testing.T, path string) {

internal/handlers/handlers.go

@@ -51,6 +51,7 @@ type HandlersParams struct {
 	Healthcheck  *healthcheck.Healthcheck
 	Session      *session.Session
 	Notifier     delivery.Notifier
+	Evictor      delivery.WebhookEvictor
 }
 
 // Handlers provides HTTP handler methods for all application
@@ -63,6 +64,7 @@ type Handlers struct {
 	dbMgr     *database.WebhookDBManager
 	session   *session.Session
 	notifier  delivery.Notifier
+	evictor   delivery.WebhookEvictor
 	templates map[string]*template.Template
 }
 
@@ -97,6 +99,7 @@ func New(
 	s.dbMgr = params.WebhookDBMgr
 	s.session = params.Session
 	s.notifier = params.Notifier
+	s.evictor = params.Evictor
 
 	// Parse all page templates once at startup
 	s.templates = map[string]*template.Template{

internal/handlers/handlers_test.go

@@ -4,6 +4,7 @@ import (
 	"context"
 	"net/http"
 	"net/http/httptest"
+	"sync"
 	"testing"
 
 	"github.com/stretchr/testify/assert"
@@ -24,6 +25,32 @@ type noopNotifier struct{}
 
 func (n *noopNotifier) Notify([]delivery.Task) {}
 
+// recordingEvictor is a delivery.WebhookEvictor that records
+// the webhook ids it was asked to evict, so a test can prove
+// that a deletion path reached the delivery engine.
+type recordingEvictor struct {
+	mu      sync.Mutex
+	evicted []string
+}
+
+func (r *recordingEvictor) EvictWebhook(webhookID string) {
+	r.mu.Lock()
+	defer r.mu.Unlock()
+
+	r.evicted = append(r.evicted, webhookID)
+}
+
+// Evicted returns a copy of the recorded webhook ids.
+func (r *recordingEvictor) Evicted() []string {
+	r.mu.Lock()
+	defer r.mu.Unlock()
+
+	out := make([]string, len(r.evicted))
+	copy(out, r.evicted)
+
+	return out
+}
+
 func newTestApp(
 	t *testing.T,
 	targets ...any,
@@ -47,6 +74,12 @@ func newTestApp(
 			func() delivery.Notifier {
 				return &noopNotifier{}
 			},
+			func() *recordingEvictor {
+				return &recordingEvictor{}
+			},
+			func(r *recordingEvictor) delivery.WebhookEvictor {
+				return r
+			},
 			handlers.New,
 		),
 		fx.Populate(targets...),

internal/handlers/source_delete_test.go

@@ -0,0 +1,356 @@
+package handlers_test
+
+import (
+	"context"
+	"net/http"
+	"net/http/httptest"
+	"os"
+	"path/filepath"
+	"testing"
+
+	"github.com/go-chi/chi"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	"gorm.io/gorm/clause"
+	"sneak.berlin/go/webhooker/internal/database"
+	"sneak.berlin/go/webhooker/internal/handlers"
+	"sneak.berlin/go/webhooker/internal/session"
+)
+
+const (
+	deleteTestUserID   = "test-user-id"
+	deleteTestUsername = "testuser"
+
+	// paramSourceID and paramTargetID are the chi URL parameter
+	// names the deletion handlers read.
+	paramSourceID = "sourceID"
+	paramTargetID = "targetID"
+)
+
+// seedWebhook inserts a webhook owned by the test user and
+// returns it.
+func seedWebhook(
+	t *testing.T,
+	db *database.Database,
+) *database.Webhook {
+	t.Helper()
+
+	wh := &database.Webhook{
+		UserID: deleteTestUserID,
+		Name:   "delete-me",
+	}
+
+	require.NoError(
+		t,
+		db.DB().Omit(clause.Associations).Create(wh).Error,
+	)
+
+	return wh
+}
+
+// seedTarget inserts a target of the given type for a webhook
+// and returns it.
+func seedTarget(
+	t *testing.T,
+	db *database.Database,
+	webhookID string,
+	targetType database.TargetType,
+) *database.Target {
+	t.Helper()
+
+	tgt := &database.Target{
+		WebhookID: webhookID,
+		Name:      "t-" + string(targetType),
+		Type:      targetType,
+		Active:    true,
+	}
+
+	require.NoError(
+		t,
+		db.DB().Omit(clause.Associations).Create(tgt).Error,
+	)
+
+	return tgt
+}
+
+// archivePathFor returns the archive database path the
+// delivery engine would use for a webhook: beside the webhook's
+// event database in the data directory.
+func archivePathFor(
+	t *testing.T,
+	mgr *database.WebhookDBManager,
+	webhookID string,
+) string {
+	t.Helper()
+
+	return filepath.Join(
+		filepath.Dir(mgr.DBPath(webhookID)),
+		"archive-"+webhookID+".db",
+	)
+}
+
+// writeArchivePlaceholder creates a stand-in archive file so a
+// test can assert the file survives webhook deletion.
+func writeArchivePlaceholder(path string) error {
+	return os.WriteFile(path, []byte("archive"), 0o600)
+}
+
+// postRequest builds an authenticated POST request carrying the
+// given chi URL parameters.
+func postRequest(
+	path string,
+	cookies []*http.Cookie,
+	params map[string]string,
+) *http.Request {
+	req := httptest.NewRequestWithContext(
+		context.Background(), http.MethodPost, path, nil,
+	)
+
+	for _, c := range cookies {
+		req.AddCookie(c)
+	}
+
+	rctx := chi.NewRouteContext()
+	for k, v := range params {
+		rctx.URLParams.Add(k, v)
+	}
+
+	return req.WithContext(
+		context.WithValue(req.Context(), chi.RouteCtxKey, rctx),
+	)
+}
+
+// TestHandleSourceDelete_EvictsArchiveWriter proves that
+// deleting a webhook reaches the delivery engine and releases
+// the webhook's archive writer, exercised through the real
+// deletion handler rather than by calling the evictor directly.
+func TestHandleSourceDelete_EvictsArchiveWriter(t *testing.T) {
+	t.Parallel()
+
+	var (
+		h    *handlers.Handlers
+		sess *session.Session
+		db   *database.Database
+		ev   *recordingEvictor
+	)
+
+	app := newTestApp(t, &h, &sess, &db, &ev)
+	app.RequireStart()
+
+	t.Cleanup(app.RequireStop)
+
+	wh := seedWebhook(t, db)
+	seedTarget(t, db, wh.ID, database.TargetTypeDatabase)
+
+	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, []string{wh.ID}, ev.Evicted(),
+		"deleting a webhook should evict its archive writer",
+	)
+}
+
+// TestHandleSourceDelete_KeepsArchiveFile proves that deleting
+// a webhook does not remove its archive database file: the
+// archive is long-term storage the operator owns.
+func TestHandleSourceDelete_KeepsArchiveFile(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)
+
+	// Place an archive file where the delivery engine would.
+	archivePath := archivePathFor(t, mgr, wh.ID)
+	require.NoError(
+		t,
+		writeArchivePlaceholder(archivePath),
+	)
+
+	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.FileExists(
+		t, archivePath,
+		"webhook deletion must not destroy the archive file",
+	)
+}
+
+// TestHandleTargetDelete_EvictsWhenLastDatabaseTargetGone
+// proves that removing the last database target releases the
+// archive writer.
+func TestHandleTargetDelete_EvictsWhenLastDatabaseTargetGone(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	var (
+		h    *handlers.Handlers
+		sess *session.Session
+		db   *database.Database
+		ev   *recordingEvictor
+	)
+
+	app := newTestApp(t, &h, &sess, &db, &ev)
+	app.RequireStart()
+
+	t.Cleanup(app.RequireStop)
+
+	wh := seedWebhook(t, db)
+	tgt := seedTarget(
+		t, db, wh.ID, database.TargetTypeDatabase,
+	)
+
+	cookies := authenticatedCookies(
+		t, sess, deleteTestUserID, deleteTestUsername,
+	)
+
+	req := postRequest(
+		"/source/"+wh.ID+"/targets/"+tgt.ID+"/delete",
+		cookies,
+		map[string]string{
+			paramSourceID: wh.ID,
+			paramTargetID: tgt.ID,
+		},
+	)
+	w := httptest.NewRecorder()
+
+	h.HandleTargetDelete().ServeHTTP(w, req)
+
+	require.Equal(t, http.StatusSeeOther, w.Code)
+	assert.Equal(
+		t, []string{wh.ID}, ev.Evicted(),
+		"removing the last database target should evict",
+	)
+}
+
+// TestHandleTargetDelete_KeepsWriterWhenDatabaseTargetRemains
+// proves that deleting one of several database targets leaves
+// the still-needed archive writer alone: the surviving target
+// keeps archiving to the same file, so the writer must stay.
+func TestHandleTargetDelete_KeepsWriterWhenDatabaseTargetRemains(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	var (
+		h    *handlers.Handlers
+		sess *session.Session
+		db   *database.Database
+		ev   *recordingEvictor
+	)
+
+	app := newTestApp(t, &h, &sess, &db, &ev)
+	app.RequireStart()
+
+	t.Cleanup(app.RequireStop)
+
+	wh := seedWebhook(t, db)
+	doomed := seedTarget(
+		t, db, wh.ID, database.TargetTypeDatabase,
+	)
+	seedTarget(t, db, wh.ID, database.TargetTypeDatabase)
+
+	cookies := authenticatedCookies(
+		t, sess, deleteTestUserID, deleteTestUsername,
+	)
+
+	req := postRequest(
+		"/source/"+wh.ID+"/targets/"+doomed.ID+"/delete",
+		cookies,
+		map[string]string{
+			paramSourceID: wh.ID,
+			paramTargetID: doomed.ID,
+		},
+	)
+	w := httptest.NewRecorder()
+
+	h.HandleTargetDelete().ServeHTTP(w, req)
+
+	require.Equal(t, http.StatusSeeOther, w.Code)
+	assert.Empty(
+		t, ev.Evicted(),
+		"a second database target still needs the writer",
+	)
+}
+
+// TestHandleTargetDelete_KeepsWriterWhenOtherTypeDeleted proves
+// that deleting a target of an unrelated type leaves a
+// still-needed archive writer alone: the webhook's database
+// target is untouched, so its writer must stay.
+func TestHandleTargetDelete_KeepsWriterWhenOtherTypeDeleted(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	var (
+		h    *handlers.Handlers
+		sess *session.Session
+		db   *database.Database
+		ev   *recordingEvictor
+	)
+
+	app := newTestApp(t, &h, &sess, &db, &ev)
+	app.RequireStart()
+
+	t.Cleanup(app.RequireStop)
+
+	wh := seedWebhook(t, db)
+	seedTarget(t, db, wh.ID, database.TargetTypeDatabase)
+	other := seedTarget(t, db, wh.ID, database.TargetTypeLog)
+
+	cookies := authenticatedCookies(
+		t, sess, deleteTestUserID, deleteTestUsername,
+	)
+
+	req := postRequest(
+		"/source/"+wh.ID+"/targets/"+other.ID+"/delete",
+		cookies,
+		map[string]string{
+			paramSourceID: wh.ID,
+			paramTargetID: other.ID,
+		},
+	)
+	w := httptest.NewRecorder()
+
+	h.HandleTargetDelete().ServeHTTP(w, req)
+
+	require.Equal(t, http.StatusSeeOther, w.Code)
+	assert.Empty(
+		t, ev.Evicted(),
+		"a surviving database target must keep its writer",
+	)
+}

internal/handlers/source_management.go

@@ -533,6 +533,13 @@ func (h *Handlers) deleteWebhookResources(
 		return
 	}
 
+	// 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
+	// process lifetime. The archive file itself is deliberately
+	// left on disk; see evictArchiveWriter.
+	h.evictArchiveWriter(webhook.ID)
+
 	err = h.dbMgr.DeleteDB(webhook.ID)
 	if err != nil {
 		h.log.Error(
@@ -551,6 +558,64 @@ func (h *Handlers) deleteWebhookResources(
 	http.Redirect(w, r, "/sources", http.StatusSeeOther)
 }
 
+// evictArchiveWriter asks the delivery engine to drop its
+// cached archive writer for a webhook, closing the archive file
+// handle.
+//
+// The archive database file is NOT deleted. Unlike the event
+// database — which is per-webhook working storage and is
+// hard-deleted with the webhook — an archive is explicitly
+// long-term storage that an operator may want to keep or move
+// away for offline retention. Destroying it as a side effect of
+// deleting a webhook would be a surprising and unrecoverable
+// data loss, so the file is left for the operator to handle.
+func (h *Handlers) evictArchiveWriter(webhookID string) {
+	if h.evictor == nil {
+		return
+	}
+
+	h.evictor.EvictWebhook(webhookID)
+}
+
+// evictArchiveWriterIfUnused releases a webhook's archive
+// writer once the webhook has no database target left to feed
+// it.
+//
+// It is called after any child resource of a webhook is
+// deleted, and is correct without knowing which kind was: it
+// evicts only when no database target remains, so deleting one
+// of several database targets — or deleting an unrelated
+// target type — leaves a still-needed writer alone. When no
+// database target ever existed there is no writer and eviction
+// is a no-op. Soft-deleted targets are excluded by GORM's
+// default scope, so the row just deleted is not counted.
+func (h *Handlers) evictArchiveWriterIfUnused(webhookID string) {
+	var remaining int64
+
+	err := h.db.DB().
+		Model(&database.Target{}).
+		Where(
+			"webhook_id = ? AND type = ?",
+			webhookID, database.TargetTypeDatabase,
+		).
+		Count(&remaining).Error
+	if err != nil {
+		h.log.Error(
+			"failed to count remaining database targets",
+			"webhook_id", webhookID,
+			"error", err,
+		)
+
+		return
+	}
+
+	if remaining > 0 {
+		return
+	}
+
+	h.evictArchiveWriter(webhookID)
+}
+
 // HandleSourceLogs shows the request/response logs for a
 // webhook.
 func (h *Handlers) HandleSourceLogs() http.HandlerFunc {
@@ -1024,23 +1089,31 @@ func (h *Handlers) HandleEntrypointDelete() http.HandlerFunc {
 	return h.deleteChildResource(
 		"entrypointID", &database.Entrypoint{},
 		"failed to delete entrypoint",
+		nil,
 	)
 }
 
-// HandleTargetDelete handles deleting a target.
+// HandleTargetDelete handles deleting a target. Deleting the
+// last database target of a webhook leaves its archive writer
+// with nothing to write, so the writer is evicted and its
+// handle closed; the archive file is left on disk.
 func (h *Handlers) HandleTargetDelete() http.HandlerFunc {
 	return h.deleteChildResource(
 		"targetID", &database.Target{},
 		"failed to delete target",
+		h.evictArchiveWriterIfUnused,
 	)
 }
 
 // deleteChildResource returns a handler that deletes a child
-// resource (entrypoint or target) belonging to a webhook.
+// resource (entrypoint or target) belonging to a webhook. The
+// optional afterDelete hook runs with the webhook's id once the
+// delete has succeeded, before the redirect.
 func (h *Handlers) deleteChildResource(
 	idParam string,
 	model any,
 	errMsg string,
+	afterDelete func(webhookID string),
 ) http.HandlerFunc {
 	return func(w http.ResponseWriter, r *http.Request) {
 		userID, ok := h.getUserID(r)
@@ -1080,6 +1153,10 @@ func (h *Handlers) deleteChildResource(
 			return
 		}
 
+		if afterDelete != nil {
+			afterDelete(webhook.ID)
+		}
+
 		http.Redirect(
 			w, r,
 			"/source/"+webhook.ID,