diff --git a/internal/delivery/engine.go b/internal/delivery/engine.go
index e023918..1143cbf 100644
--- a/internal/delivery/engine.go
+++ b/internal/delivery/engine.go
@@ -438,6 +438,31 @@ func (e *Engine) processNewTask(
 		return
 	}
 
+	// Restart recovery can send and release this delivery before the
+	// receiver's Notify queues it. Ownership cannot refuse a delivery
+	// nobody holds, so the row decides whether it still needs sending.
+	row, err := e.loadDelivery(webhookDB, task.DeliveryID)
+	if err != nil {
+		e.log.Error(
+			"failed to load delivery",
+			"delivery_id", task.DeliveryID,
+			"error", err,
+		)
+
+		return
+	}
+
+	if row.Status != database.DeliveryStatusPending {
+		e.log.Info(
+			"delivery already handled, not sent again",
+			"delivery_id", task.DeliveryID,
+			"event_id", task.EventID,
+			"status", row.Status,
+		)
+
+		return
+	}
+
 	event := buildEventFromTask(task)
 
 	event, err = e.hydrateEvent(
@@ -482,7 +507,7 @@ func (e *Engine) processRetryTask(
 		return
 	}
 
-	d, err := e.loadRetryDelivery(
+	d, err := e.loadDelivery(
 		webhookDB, task.DeliveryID,
 	)
 	if err != nil {
@@ -1643,7 +1668,7 @@ func (e *Engine) hydrateEvent(
 	return event, nil
 }
 
-func (e *Engine) loadRetryDelivery(
+func (e *Engine) loadDelivery(
 	webhookDB *gorm.DB, deliveryID string,
 ) (*database.Delivery, error) {
 	var d database.Delivery
diff --git a/internal/delivery/inflight_test.go b/internal/delivery/inflight_test.go
index 1c86003..08a0f69 100644
--- a/internal/delivery/inflight_test.go
+++ b/internal/delivery/inflight_test.go
@@ -273,6 +273,73 @@ func TestOwnershipIsReleasedAfterDelivery(t *testing.T) {
 	)
 }
 
+// TestNotifyAfterRecoveryDoesNotSendAgain is the startup race of
+// https://git.eeqj.de/sneak/webhooker/issues/299. The receiver has
+// written a delivery, restart recovery finds it pending, sends it and
+// releases it, and only then does the receiver's Notify for it arrive.
+// Nothing owns the delivery by then, so Notify takes it.
+func TestNotifyAfterRecoveryDoesNotSendAgain(t *testing.T) {
+	t.Parallel()
+
+	targetID := uuid.New().String()
+	s := fSweepSetup(t, targetID, "recovered")
+
+	event := iSeedEvent(
+		t, s.WebhookDB, s.WebhookID, `{"recovered":true}`,
+	)
+
+	d := iSeedDelivery(
+		t, s.WebhookDB, event.ID, targetID,
+		database.DeliveryStatusPending,
+	)
+
+	s.Engine.ExportStart()
+
+	defer func() {
+		require.NoError(
+			t, s.Engine.ExportStop(context.Background()),
+		)
+	}()
+
+	// Restart recovery sends the delivery and lets it go.
+	iWaitForDelivered(t, s.WebhookDB, d.ID)
+	require.Eventually(
+		t,
+		func() bool {
+			return s.Engine.ExportInflightHeld() == 0
+		},
+		5*time.Second, 20*time.Millisecond,
+	)
+
+	body := event.Body
+
+	s.Engine.Notify([]delivery.Task{{
+		DeliveryID:   d.ID,
+		EventID:      event.ID,
+		WebhookID:    s.WebhookID,
+		TargetID:     targetID,
+		TargetName:   "recovered",
+		TargetType:   database.TargetTypeLog,
+		Body:         &body,
+		EntrypointID: event.EntrypointID,
+	}})
+
+	// Notify took the delivery, and a worker releases it once it has
+	// run the task.
+	require.Eventually(
+		t,
+		func() bool {
+			return s.Engine.ExportInflightHeld() == 0
+		},
+		5*time.Second, 20*time.Millisecond,
+	)
+
+	assert.Len(
+		t, iResults(t, s.WebhookDB, d.ID), 1,
+		"the delivery was sent a second time",
+	)
+}
+
 // TestRetryingRecoverySkipsASuccessfulResult is the retrying-side twin
 // of the pending reconcile. A second attempt that reached the receiver
 // and whose status write then failed sits at retrying holding a