Test a pending delivery whose target is found only on lookup

When the batch's target map lacks a delivery's target, as it does
for every delivery when the batch query fails, sendRecoveredDeliveries
looks the target up on its own. The new test hands it an empty map
and checks the healthy delivery is queued once, with its real target
id and type.

Model: opus-5-5

README.md

@@ -2051,7 +2051,7 @@ rescans the database anyway).
 | ----------- | -------- |
 | **Closed**  | Normal operation. Deliveries flow through. Consecutive failures are counted. |
 | **Open**    | Target appears down. Deliveries are skipped and rescheduled for after the cooldown. |
-| **Half-Open** | Cooldown expired. One probe delivery is allowed to test if the target has recovered. |
+| **Half-Open** | Cooldown expired. One probe delivery is allowed to test if the target has recovered. Other deliveries are rescheduled for one whole cooldown later. |
 
 **Transitions:**
 
@@ -2089,7 +2089,9 @@ operations), and log targets (stdout) do not use circuit breakers.
 When a circuit is open and a new delivery arrives, the engine marks the
 delivery as `retrying` and schedules a retry timer for after the
 remaining cooldown period. This ensures no deliveries are lost — they're
-just delayed until the target is healthy again.
+just delayed until the target is healthy again. A delivery already in
+`retrying` keeps that status without another database write each time
+the breaker turns it away.
 
 ### Metrics
 
@@ -2103,7 +2105,7 @@ arriving and being stored, they are just not getting anywhere.
 | Metric | Type | Meaning |
 | ------ | ---- | ------- |
 | `webhooker_events_received_total` | counter | Events received and durably stored. Compare against the delivery counters on one dashboard |
-| `webhooker_delivery_attempts_total` | counter | Delivery attempts actually dispatched to a target. A delivery an open circuit breaker refused is not one: it is counted as a retry instead |
+| `webhooker_delivery_attempts_total` | counter | Delivery attempts actually dispatched to a target. A delivery a circuit breaker refused is not one: it is counted as a retry instead, but only when the refusal moves it into `retrying` |
 | `webhooker_deliveries_succeeded_total` | counter | Deliveries that reached `delivered` |
 | `webhooker_deliveries_failed_total` | counter | Deliveries that failed terminally and will not be retried |
 | `webhooker_delivery_retries_total` | counter | Deliveries put back into `retrying` |

internal/delivery/circuit_breaker.go

@@ -76,12 +76,20 @@ func (cb *CircuitBreaker) Allow() bool {
 	}
 }
 
-// CooldownRemaining returns how much time is left before
-// an open circuit transitions to half-open.
+// CooldownRemaining returns how long a delivery that Allow refused
+// should wait before it is tried again. Closed, it returns zero.
+// Open, it returns what is left of the cooldown, or zero once that
+// has passed. Half-open, it returns the whole cooldown: the one
+// probe delivery is still in flight, and if it fails the circuit
+// reopens for that long.
 func (cb *CircuitBreaker) CooldownRemaining() time.Duration {
 	cb.mu.Lock()
 	defer cb.mu.Unlock()
 
+	if cb.state == CircuitHalfOpen {
+		return cb.cooldown
+	}
+
 	if cb.state != CircuitOpen {
 		return 0
 	}

internal/delivery/circuit_breaker_test.go

@@ -267,7 +267,7 @@ func TestCircuitBreaker_CooldownRemaining_ClosedReturnsZero(
 	)
 }
 
-func TestCircuitBreaker_CooldownRemaining_HalfOpenReturnsZero(
+func TestCircuitBreaker_CooldownRemaining_HalfOpenReturnsCooldown(
 	t *testing.T,
 ) {
 	t.Parallel()
@@ -282,9 +282,11 @@ func TestCircuitBreaker_CooldownRemaining_HalfOpenReturnsZero(
 
 	require.True(t, cb.Allow())
 
-	assert.Equal(t, time.Duration(0),
+	// The cooldown newShortCooldownCB gives the breaker.
+	assert.Equal(t, 50*time.Millisecond,
 		cb.CooldownRemaining(),
-		"half-open circuit should have zero cooldown remaining",
+		"a delivery refused while half-open should wait "+
+			"a whole cooldown",
 	)
 }
 

internal/delivery/engine.go

@@ -728,9 +728,7 @@ func (e *Engine) recoverSingleRetry(
 		// webhook on one bad read would be a far larger fault than
 		// the strand it is meant to clear.
 		if errors.Is(err, gorm.ErrRecordNotFound) {
-			e.failMissingTargetRetry(
-				webhookDB, webhookID, d,
-			)
+			e.failMissingTarget(webhookDB, webhookID, d)
 
 			return
 		}
@@ -1133,9 +1131,7 @@ func (e *Engine) sweepSingleRetry(
 		// Deleted is terminal, unreadable is not; see
 		// recoverSingleRetry.
 		if errors.Is(err, gorm.ErrRecordNotFound) {
-			e.failMissingTargetRetry(
-				webhookDB, webhookID, d,
-			)
+			e.failMissingTarget(webhookDB, webhookID, d)
 
 			return
 		}
@@ -1249,19 +1245,19 @@ func (e *Engine) failUnretryableRetry(
 	e.failDelivery(webhookDB, d, target.Type, reason)
 }
 
-// failMissingTargetRetry terminally fails an orphaned retrying
-// delivery whose target row is gone. Both restart recovery and the
-// periodic sweep call it, so the transition exists once.
+// failMissingTarget terminally fails a recovered delivery, pending or
+// retrying, whose target row is gone. Restart recovery and the periodic
+// sweep call it for both statuses, so the transition exists once.
 //
-// Until it existed both paths logged the failed lookup and returned,
-// which left the delivery retrying for the life of the database and
+// Until it existed those paths logged the failed lookup and moved on,
+// which left the delivery where it was for the life of the database and
 // the sweep repeating the same error every minute forever. Failing it
 // with a recorded reason is the treatment the other orphaned-retry
 // cases already get, so all of them read alike in the event log.
 //
 // Logged at warn rather than error: a deleted target is an operator
 // action, not a system fault.
-func (e *Engine) failMissingTargetRetry(
+func (e *Engine) failMissingTarget(
 	webhookDB *gorm.DB,
 	webhookID string,
 	d *database.Delivery,
@@ -1274,13 +1270,37 @@ func (e *Engine) failMissingTargetRetry(
 
 	defer e.inflight.release(d.ID)
 
+	// The batch was read before ownership was taken, and a worker may
+	// have settled the delivery and let it go in between. Only a row
+	// still in the status the batch read is failed.
+	row, err := e.loadDelivery(webhookDB, d.ID)
+	if err != nil {
+		e.log.Error(
+			"failed to load delivery",
+			"delivery_id", d.ID,
+			"error", err,
+		)
+
+		return
+	}
+
+	if row.Status != d.Status {
+		e.log.Debug(
+			"delivery already handled, not failed",
+			"delivery_id", d.ID,
+			"status", row.Status,
+		)
+
+		return
+	}
+
 	targetType, reason := e.missingTargetReason(d.TargetID)
 
 	e.log.Warn(
-		"failing orphaned retrying delivery: "+
-			"its target no longer exists",
+		"failing recovered delivery: its target no longer exists",
 		"webhook_id", webhookID,
 		"delivery_id", d.ID,
+		"status", d.Status,
 		"target_id", d.TargetID,
 		"target_type", targetType,
 	)
@@ -1314,15 +1334,14 @@ func (e *Engine) missingTargetReason(
 	if err != nil {
 		return "", fmt.Sprintf(
 			"target %s no longer exists; the delivery "+
-				"cannot be retried and has been failed "+
-				"terminally",
+				"has been failed terminally",
 			targetID,
 		)
 	}
 
 	return target.Type, fmt.Sprintf(
 		"target %q (type %s) was deleted; the delivery "+
-			"cannot be retried and has been failed terminally",
+			"has been failed terminally",
 		target.Name, target.Type,
 	)
 }
@@ -2021,13 +2040,30 @@ func (e *Engine) sendRecoveredDeliveries(
 
 		target, ok := targetMap[deliveries[i].TargetID]
 		if !ok {
-			e.log.Error(
-				"target not found for delivery",
-				"delivery_id", deliveries[i].ID,
-				"target_id", deliveries[i].TargetID,
-			)
+			// A missing entry does not mean the target is gone: the
+			// map is also empty when its query failed. Only a lookup
+			// that finds no row ends the delivery; any other error
+			// leaves it pending for the next sweep. See
+			// recoverSingleRetry.
+			var err error
 
-			continue
+			target, err = e.loadTarget(deliveries[i].TargetID)
+			if errors.Is(err, gorm.ErrRecordNotFound) {
+				e.failMissingTarget(webhookDB, webhookID, &deliveries[i])
+
+				continue
+			}
+
+			if err != nil {
+				e.log.Error(
+					"failed to load target for recovered delivery",
+					"delivery_id", deliveries[i].ID,
+					"target_id", deliveries[i].TargetID,
+					"error", err,
+				)
+
+				continue
+			}
 		}
 
 		if !e.takeForRedispatch(

internal/delivery/engine_test.go

@@ -17,6 +17,7 @@ import (
 	"time"
 
 	"github.com/google/uuid"
+	"github.com/prometheus/client_golang/prometheus"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 	"gorm.io/driver/sqlite"
@@ -24,6 +25,7 @@ import (
 	_ "modernc.org/sqlite"
 	"sneak.berlin/go/webhooker/internal/database"
 	"sneak.berlin/go/webhooker/internal/delivery"
+	"sneak.berlin/go/webhooker/internal/metrics"
 )
 
 // testContentType is the event content type used in tests.
@@ -894,6 +896,100 @@ func TestDeliverHTTP_CircuitBreakerBlocks(t *testing.T) {
 	)
 }
 
+// recordingScheduler keeps the delay of every retry it is asked to
+// schedule, and schedules nothing.
+type recordingScheduler struct {
+	delays []time.Duration
+}
+
+func (s *recordingScheduler) ScheduleRetry(
+	_ delivery.Task, delay time.Duration,
+) {
+	s.delays = append(s.delays, delay)
+}
+
+// TestDeliverHTTP_HalfOpenBreakerDelaysQueuedTasks proves that while a
+// half-open breaker's one probe delivery is in flight, every other task
+// for the target is put back with a whole cooldown as its delay rather
+// than none, and that its status is written the first time the breaker
+// turns it away and not on each pass after that.
+func TestDeliverHTTP_HalfOpenBreakerDelaysQueuedTasks(t *testing.T) {
+	t.Parallel()
+
+	db := testWebhookDB(t)
+	e := testEngine(t, 1)
+
+	// Every write of retrying moves the retry counter, so on a registry
+	// this test owns the counter is the number of those writes.
+	reg := prometheus.NewRegistry()
+	e.ExportSetMetrics(metrics.New(reg))
+
+	targetID := uuid.New().String()
+	cb := newShortCooldownCB(t)
+	e.ExportSetCircuitBreaker(targetID, cb)
+
+	for range delivery.ExportDefaultFailureThreshold {
+		cb.RecordFailure()
+	}
+
+	time.Sleep(60 * time.Millisecond)
+
+	require.True(t, cb.Allow(), "the probe delivery should go through")
+	require.Equal(t, delivery.CircuitHalfOpen, cb.State())
+
+	cfg := newHTTPTargetConfig(
+		"http://will-not-be-called.invalid",
+	)
+	sched := &recordingScheduler{}
+
+	const queued, passes = 3, 4
+
+	for range queued {
+		event := seedEvent(t, db, `{"cb":"half-open"}`)
+		dlv := seedDelivery(
+			t, db, event.ID, targetID,
+			database.DeliveryStatusPending,
+		)
+
+		for range passes {
+			// Each pass starts from the stored row, as a retry does.
+			var row database.Delivery
+
+			require.NoError(t, db.First(
+				&row, "id = ?", dlv.ID,
+			).Error)
+
+			fix := buildHTTPFixture(
+				row, event, targetID,
+				"test-cb-half-open", cfg, 5, 1,
+			)
+
+			e.ExportDeliverHTTPWithScheduler(
+				context.TODO(), db, fix.Delivery, fix.Task, sched,
+			)
+		}
+
+		assertDeliveryStatus(t, db, dlv.ID,
+			database.DeliveryStatusRetrying,
+		)
+	}
+
+	require.Len(t, sched.delays, queued*passes)
+
+	for _, delay := range sched.delays {
+		// The cooldown newShortCooldownCB gives the breaker.
+		assert.Equal(t, 50*time.Millisecond, delay,
+			"a task turned away while half-open should wait "+
+				"a whole cooldown",
+		)
+	}
+
+	assert.InDelta(t, float64(queued),
+		mCounter(t, reg, mRetries, mTypeHTTP), 0,
+		"status should be written once per task, not once per pass",
+	)
+}
+
 func TestGetCircuitBreaker_CreatesOnDemand(t *testing.T) {
 	t.Parallel()
 

internal/delivery/export_test.go

@@ -101,6 +101,19 @@ func (e *Engine) ExportDeliverHTTP(
 	e.httpTarget.Deliver(ctx, webhookDB, d, task, e)
 }
 
+// ExportDeliverHTTPWithScheduler delivers via the http target, handing
+// any retry to sched instead of the engine, so a test can see the
+// delay each retry is given.
+func (e *Engine) ExportDeliverHTTPWithScheduler(
+	ctx context.Context,
+	webhookDB *gorm.DB,
+	d *database.Delivery,
+	task *Task,
+	sched Scheduler,
+) {
+	e.httpTarget.Deliver(ctx, webhookDB, d, task, sched)
+}
+
 // ExportDeliverDatabase delivers via the database target.
 func (e *Engine) ExportDeliverDatabase(
 	webhookDB *gorm.DB, d *database.Delivery,
@@ -179,6 +192,14 @@ func (e *Engine) ExportGetCircuitBreaker(
 	return e.httpTarget.getCircuitBreaker(targetID)
 }
 
+// ExportSetCircuitBreaker makes cb the http target's circuit breaker
+// for targetID, so a test can use one with a short cooldown.
+func (e *Engine) ExportSetCircuitBreaker(
+	targetID string, cb *CircuitBreaker,
+) {
+	e.httpTarget.circuitBreakers.Store(targetID, cb)
+}
+
 // ExportParseHTTPConfig exposes parseHTTPConfig.
 func (e *Engine) ExportParseHTTPConfig(
 	configJSON string,
@@ -321,6 +342,31 @@ func (e *Engine) ExportRecoverRetryingDeliveries(
 	e.recoverRetryingDeliveries(webhookDB, webhookID)
 }
 
+// ExportFailMissingTarget exposes failMissingTarget, so a test can hand
+// it a delivery as a batch read it earlier.
+func (e *Engine) ExportFailMissingTarget(
+	webhookDB *gorm.DB,
+	webhookID string,
+	d *database.Delivery,
+) {
+	e.failMissingTarget(webhookDB, webhookID, d)
+}
+
+// ExportSendRecoveredDeliveries exposes sendRecoveredDeliveries, so a
+// test can hand it a target map that lacks a delivery's target.
+func (e *Engine) ExportSendRecoveredDeliveries(
+	ctx context.Context,
+	webhookDB *gorm.DB,
+	deliveries []database.Delivery,
+	webhookID string,
+	targetMap map[string]database.Target,
+	settled map[string]struct{},
+) {
+	e.sendRecoveredDeliveries(
+		ctx, webhookDB, deliveries, webhookID, targetMap, settled,
+	)
+}
+
 // ExportDeliveryCh returns the delivery channel.
 func (e *Engine) ExportDeliveryCh() chan Task {
 	return e.deliveryCh

internal/delivery/metrics_test.go

@@ -412,9 +412,10 @@ func TestDeliveryMetrics_BreakerBlockedIsNotAnAttempt(
 
 	s.Engine.ExportProcessRetryTask(context.TODO(), &blocked)
 
-	// The breaker refused it: rescheduled, so the retry counter
-	// moved, but nothing was attempted or timed.
-	assert.InDelta(t, retriesBefore+1,
+	// The breaker refused it: rescheduled without rewriting the
+	// retrying status it already had, so the retry counter did not
+	// move, and nothing was attempted or timed.
+	assert.InDelta(t, retriesBefore,
 		mCounter(t, reg, mRetries, mTypeHTTP), 0)
 	assert.InDelta(t, threshold,
 		mCounter(t, reg, mAttempts, mTypeHTTP), 0)

internal/delivery/target_http.go

@@ -197,10 +197,14 @@ func (c *httpCore) circuitBreakerBlock(
 		"cooldown_remaining", remaining,
 	)
 
-	c.eng.settleStatus(
-		webhookDB, d, d.Target.Type,
-		database.DeliveryStatusRetrying,
-	)
+	// A delivery already at retrying is left as it is, so a task
+	// the breaker keeps turning away writes nothing each time.
+	if d.Status != database.DeliveryStatusRetrying {
+		c.eng.settleStatus(
+			webhookDB, d, d.Target.Type,
+			database.DeliveryStatusRetrying,
+		)
+	}
 
 	retryTask := *task
 	sched.ScheduleRetry(retryTask, remaining)

internal/delivery/terminal_state_test.go

@@ -18,16 +18,17 @@ import (
 // https://git.eeqj.de/sneak/webhooker/issues/107: a delivery failed
 // with nothing in its event log to say why, and a retrying delivery
 // whose target was deleted, which used to keep sending and then never
-// terminalise.
+// terminalise. Section 4 is the same deleted-target gap for a pending
+// delivery: https://git.eeqj.de/sneak/webhooker/issues/293.
 
 // tUnknownType is a target type no build implements. It stands in for
 // a target whose type was written by a build that knew a type this one
 // does not.
 const tUnknownType = database.TargetType("pubsub")
 
-// tSeedDeletedTarget creates a target, a retrying delivery against it
-// with one recorded failed attempt, and then deletes the target the
-// way the source page does.
+// tSeedDeletedTarget creates a target, a delivery against it at the
+// given status with one recorded failed attempt, and then deletes the
+// target the way the source page does.
 //
 // It asserts the delete is soft, because that is the whole reason the
 // engine could not tell a deleted target from a target id that never
@@ -36,6 +37,7 @@ func tSeedDeletedTarget(
 	t *testing.T,
 	s iSetup,
 	name, url string,
+	status database.DeliveryStatus,
 ) string {
 	t.Helper()
 
@@ -51,8 +53,7 @@ func tSeedDeletedTarget(
 	)
 
 	d := iSeedDelivery(
-		t, s.WebhookDB, event.ID, targetID,
-		database.DeliveryStatusRetrying,
+		t, s.WebhookDB, event.ID, targetID, status,
 	)
 
 	iSeedFailedResult(t, s.WebhookDB, d.ID)
@@ -173,6 +174,7 @@ func TestRecoverSingleRetry_TargetDeleted(t *testing.T) {
 
 	deliveryID := tSeedDeletedTarget(
 		t, s, "gone-on-recovery", "http://example.com/hook",
+		database.DeliveryStatusRetrying,
 	)
 
 	s.Engine.ExportRecoverWebhookDeliveries(
@@ -210,6 +212,7 @@ func TestSweepSingleRetry_TargetDeleted(t *testing.T) {
 
 	deliveryID := tSeedDeletedTarget(
 		t, s, "gone-on-sweep", "http://example.com/hook",
+		database.DeliveryStatusRetrying,
 	)
 
 	// Twice, because the bug was an error the sweep repeated every
@@ -278,11 +281,11 @@ func TestSweepSingleRetry_TargetNeverExisted(t *testing.T) {
 	)
 }
 
-// TestFailMissingTargetRetry_WritesNoTargetRow holds the new terminal
-// path to the same rule as the existing one: no target row, and so no
+// TestFailMissingTarget_WritesNoTargetRow holds the new terminal path
+// to the same rule as the existing one: no target row, and so no
 // plaintext target config, may be written into the per-webhook event
 // database. See https://git.eeqj.de/sneak/webhooker/issues/206.
-func TestFailMissingTargetRetry_WritesNoTargetRow(
+func TestFailMissingTarget_WritesNoTargetRow(
 	t *testing.T,
 ) {
 	t.Parallel()
@@ -297,6 +300,7 @@ func TestFailMissingTargetRetry_WritesNoTargetRow(
 
 	deliveryID := tSeedDeletedTarget(
 		t, s, "credential-bearing", hookURL,
+		database.DeliveryStatusRetrying,
 	)
 
 	s.Engine.ExportSweepWebhookRetries(
@@ -529,3 +533,260 @@ func TestRecoverSingleRetry_TargetUnreadable_LeavesDeliveryAlone(
 
 	assert.Zero(t, s.Engine.ExportInflightHeld())
 }
+
+// --- 4. A pending delivery whose target is gone ---
+
+func TestRecoverPending_TargetDeleted(t *testing.T) {
+	t.Parallel()
+
+	s := newISetup(t)
+
+	deliveryID := tSeedDeletedTarget(
+		t, s, "gone-while-pending", "http://example.com/hook",
+		database.DeliveryStatusPending,
+	)
+
+	s.Engine.ExportRecoverWebhookDeliveries(
+		context.Background(), s.WebhookID,
+	)
+
+	iAssertStatus(
+		t, s.WebhookDB, deliveryID,
+		database.DeliveryStatusFailed,
+	)
+
+	last := tLastResult(t, s, deliveryID, 2)
+
+	assert.False(t, last.Success)
+	assert.Equal(t, 2, last.AttemptNum)
+	assert.Contains(t, last.Error, "gone-while-pending")
+	assert.Contains(t, last.Error, "was deleted")
+
+	assert.Empty(t, fDrain(s.Engine),
+		"a delivery whose target is gone was sent",
+	)
+	assert.Zero(t, s.Engine.ExportInflightHeld(),
+		"the terminal path leaked its ownership reference",
+	)
+}
+
+// TestRecoverPending_TargetDeleted_LeavesAnOwnedDeliveryAlone: the
+// terminal write takes ownership like every other recovery write, so a
+// delivery the engine still holds is not failed underneath its worker.
+func TestRecoverPending_TargetDeleted_LeavesAnOwnedDeliveryAlone(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	s := newISetup(t)
+
+	deliveryID := tSeedDeletedTarget(
+		t, s, "gone-but-owned", "http://example.com/hook",
+		database.DeliveryStatusPending,
+	)
+
+	require.True(t, s.Engine.ExportRetainDelivery(deliveryID))
+
+	s.Engine.ExportRecoverWebhookDeliveries(
+		context.Background(), s.WebhookID,
+	)
+
+	iAssertStatus(
+		t, s.WebhookDB, deliveryID,
+		database.DeliveryStatusPending,
+	)
+
+	assert.Len(t, iResults(t, s.WebhookDB, deliveryID), 1,
+		"a delivery the engine owns was failed underneath it",
+	)
+}
+
+// TestFailMissingTarget_LeavesASettledDeliveryAlone: the recovery paths
+// read their batch before taking ownership, and a worker may send a
+// delivery and let it go in between. The terminal write goes by the row
+// as it is now, not as the batch read it.
+func TestFailMissingTarget_LeavesASettledDeliveryAlone(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	s := newISetup(t)
+
+	deliveryID := tSeedDeletedTarget(
+		t, s, "gone-after-sending", "http://example.com/hook",
+		database.DeliveryStatusPending,
+	)
+
+	var batch database.Delivery
+
+	require.NoError(t, s.WebhookDB.First(
+		&batch, "id = ?", deliveryID,
+	).Error)
+
+	// A worker settles the delivery after the batch was read.
+	require.NoError(t, s.WebhookDB.Model(&database.Delivery{}).
+		Where("id = ?", deliveryID).
+		Update("status", database.DeliveryStatusDelivered).Error)
+
+	s.Engine.ExportFailMissingTarget(
+		s.WebhookDB, s.WebhookID, &batch,
+	)
+
+	iAssertStatus(
+		t, s.WebhookDB, deliveryID,
+		database.DeliveryStatusDelivered,
+	)
+
+	assert.Len(t, iResults(t, s.WebhookDB, deliveryID), 1,
+		"a delivery settled after the batch read was then failed",
+	)
+	assert.Zero(t, s.Engine.ExportInflightHeld())
+}
+
+// TestSweepPending_TargetDeleted sweeps twice over a batch that also
+// holds a healthy stranded delivery. The one whose target is gone is
+// failed once and then left alone; the healthy one is queued by the
+// first sweep and not again by the second.
+func TestSweepPending_TargetDeleted(t *testing.T) {
+	t.Parallel()
+
+	liveTargetID := uuid.New().String()
+	s := fSweepSetup(t, liveTargetID, "still-there")
+
+	deliveryID := tSeedDeletedTarget(
+		t, s, "gone-on-pending-sweep", "http://example.com/hook",
+		database.DeliveryStatusPending,
+	)
+	rAgePending(t, s.WebhookDB, deliveryID)
+
+	event := iSeedEvent(
+		t, s.WebhookDB, s.WebhookID, `{"target":"live"}`,
+	)
+
+	healthy := iSeedDelivery(
+		t, s.WebhookDB, event.ID, liveTargetID,
+		database.DeliveryStatusPending,
+	)
+	rAgePending(t, s.WebhookDB, healthy.ID)
+
+	ctx := context.Background()
+
+	s.Engine.ExportSweepWebhookRetries(ctx, s.WebhookID)
+
+	tasks := fDrain(s.Engine)
+	require.Len(t, tasks, 1,
+		"the first sweep did not queue the healthy delivery",
+	)
+	assert.Equal(t, healthy.ID, tasks[0].DeliveryID)
+
+	s.Engine.ExportSweepWebhookRetries(ctx, s.WebhookID)
+
+	assert.Empty(t, fDrain(s.Engine),
+		"the second sweep queued a delivery again",
+	)
+
+	iAssertStatus(
+		t, s.WebhookDB, deliveryID,
+		database.DeliveryStatusFailed,
+	)
+
+	last := tLastResult(t, s, deliveryID, 2)
+
+	assert.Contains(t, last.Error, "gone-on-pending-sweep")
+	assert.Contains(t, last.Error, "was deleted")
+}
+
+// TestSendRecoveredDeliveries_TargetMissingFromMap: the batch's target
+// map is empty when its query failed, so every delivery in the batch is
+// looked up on its own. A healthy one is sent to the target that lookup
+// finds.
+func TestSendRecoveredDeliveries_TargetMissingFromMap(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	s := newISetup(t)
+
+	targetID := uuid.New().String()
+
+	iCreateTarget(
+		t, s.MainDB, targetID, s.WebhookID, "found-on-lookup",
+		database.TargetTypeLog, "", 0,
+	)
+
+	event := iSeedEvent(
+		t, s.WebhookDB, s.WebhookID, `{"map":"empty"}`,
+	)
+
+	d := iSeedDelivery(
+		t, s.WebhookDB, event.ID, targetID,
+		database.DeliveryStatusPending,
+	)
+
+	s.Engine.ExportSendRecoveredDeliveries(
+		context.Background(), s.WebhookDB,
+		[]database.Delivery{d}, s.WebhookID,
+		map[string]database.Target{}, nil,
+	)
+
+	tasks := fDrain(s.Engine)
+	require.Len(t, tasks, 1,
+		"the healthy delivery was not queued exactly once",
+	)
+	assert.Equal(t, d.ID, tasks[0].DeliveryID)
+	assert.Equal(t, targetID, tasks[0].TargetID)
+	assert.Equal(t, database.TargetTypeLog, tasks[0].TargetType)
+
+	iAssertStatus(
+		t, s.WebhookDB, d.ID,
+		database.DeliveryStatusPending,
+	)
+}
+
+// TestRecoverPending_TargetUnreadable_LeavesDeliveryAlone: a failed
+// read of the main database is not a deleted target. Restart recovery
+// holds every pending delivery of the webhook in one batch, so failing
+// on this would fail all of them.
+func TestRecoverPending_TargetUnreadable_LeavesDeliveryAlone(
+	t *testing.T,
+) {
+	t.Parallel()
+
+	s := newISetup(t)
+
+	targetID := uuid.New().String()
+
+	iCreateTarget(
+		t, s.MainDB, targetID, s.WebhookID, "healthy",
+		database.TargetTypeLog, "", 0,
+	)
+
+	event := iSeedEvent(
+		t, s.WebhookDB, s.WebhookID, `{"still":"pending"}`,
+	)
+
+	d := iSeedDelivery(
+		t, s.WebhookDB, event.ID, targetID,
+		database.DeliveryStatusPending,
+	)
+
+	sqlDB, err := s.MainDB.DB()
+	require.NoError(t, err)
+	require.NoError(t, sqlDB.Close())
+
+	s.Engine.ExportRecoverPendingDeliveries(
+		context.Background(), s.WebhookDB, s.WebhookID,
+	)
+
+	iAssertStatus(
+		t, s.WebhookDB, d.ID,
+		database.DeliveryStatusPending,
+	)
+
+	assert.Empty(t, iResults(t, s.WebhookDB, d.ID),
+		"an unreadable main database produced a terminal "+
+			"failure row",
+	)
+	assert.Empty(t, fDrain(s.Engine))
+	assert.Zero(t, s.Engine.ExportInflightHeld())
+}