diff --git a/core/artwork/worker.go b/core/artwork/worker.go
index bc3e47af0..4be32fee8 100644
--- a/core/artwork/worker.go
+++ b/core/artwork/worker.go
@@ -155,8 +155,10 @@ func (w *Worker) process(ctx context.Context, item model.ArtworkQueueItem) {
 			log.Warn(ctx, "artwork: could not delete processed queue item", "kind", item.ItemKind, "id", item.ItemID, err)
 		}
 	case outcomeFoundStale, outcomeFailed:
+		// MarkFailedIfUnchanged, not MarkFailed: a scan that re-enqueued this row mid-flight reset
+		// retry_at, so stale backoff must not stomp its fresh, immediate eligibility.
 		retryAt := time.Now().Add(backoff(item.Attempts))
-		if err := queue.MarkFailed(item.ItemKind, item.ItemID, item.ImageType, retryAt); err != nil {
+		if err := queue.MarkFailedIfUnchanged(item.ItemKind, item.ItemID, item.ImageType, item.RetryAt, retryAt); err != nil {
 			log.Warn(ctx, "artwork: could not reschedule failed queue item", "kind", item.ItemKind, "id", item.ItemID, err)
 		}
 	}
diff --git a/core/artwork/worker_test.go b/core/artwork/worker_test.go
index 7865b6cfc..1fe904e21 100644
--- a/core/artwork/worker_test.go
+++ b/core/artwork/worker_test.go
@@ -189,6 +189,30 @@ var _ = Describe("Worker", func() {
 			Expect(ia.Source).To(Equal("folder"))
 		})
 
+		It("keeps a fresh re-enqueue ahead of a stale failure backoff", func() {
+			conf.Server.CoverArtPriority = "external"
+			ds.MockedAlbum.(*tests.MockAlbumRepo).SetData(model.Albums{{ID: "al8", Name: "Album"}})
+			prov.albumImage = func(context.Context, string) (*url.URL, error) {
+				return nil, errors.New("agent timed out")
+			}
+			racing := &reenqueueOnDequeue{MockArtworkQueueRepo: queueRepo}
+			ds.MockedArtworkQueue = racing
+			w = NewWorker(ds, store, prov, ffm)
+			Expect(queueRepo.Enqueue(model.ArtworkQueueItem{ItemKind: "al", ItemID: "al8"})).To(Succeed())
+			dequeued := findQueued(queueRepo, "al", "al8").RetryAt
+
+			n, err := w.drain(ctx, 1)
+			Expect(err).ToNot(HaveOccurred())
+			Expect(n).To(Equal(1))
+
+			// The concurrent re-enqueue reset retry_at; the failure path must not stomp it
+			// with stale backoff nor bump attempts, so the row stays immediately eligible.
+			it := findQueued(queueRepo, "al", "al8")
+			Expect(it).ToNot(BeNil())
+			Expect(it.Attempts).To(BeZero())
+			Expect(it.RetryAt).To(BeTemporally("==", dequeued.Add(time.Minute)))
+		})
+
 		It("returns zero when the queue is empty", func() {
 			n, err := w.drain(ctx, 2)
 			Expect(err).ToNot(HaveOccurred())
diff --git a/model/artwork.go b/model/artwork.go
index 0aec6489a..8db11ce69 100644
--- a/model/artwork.go
+++ b/model/artwork.go
@@ -88,6 +88,9 @@ type ArtworkQueueRepository interface {
 	DequeueBatch(n int) ([]ArtworkQueueItem, error)
 	// MarkFailed increments attempts and pushes retry_at into the future.
 	MarkFailed(kind, id, imageType string, retryAt time.Time) error
+	// MarkFailedIfUnchanged applies the failure backoff only while retry_at still matches
+	// seenRetryAt; a concurrent re-enqueue (which resets retry_at) keeps its fresh eligibility.
+	MarkFailedIfUnchanged(kind, id, imageType string, seenRetryAt, retryAt time.Time) error
 	Delete(kind, id, imageType string) error
 	// DeleteIfUnchanged deletes the row only if its retry_at still matches retryAt, so a
 	// concurrent re-enqueue (which resets retry_at) survives instead of being erased.
diff --git a/persistence/artwork_queue_repository.go b/persistence/artwork_queue_repository.go
index 4a6a68eb1..59e130204 100644
--- a/persistence/artwork_queue_repository.go
+++ b/persistence/artwork_queue_repository.go
@@ -66,6 +66,17 @@ func (r *artworkQueueRepository) MarkFailed(kind, id, imageType string, retryAt
 	return err
 }
 
+// MarkFailedIfUnchanged applies the backoff only while retry_at still equals seenRetryAt;
+// a concurrent Enqueue resets retry_at, so its fresh eligibility survives untouched.
+func (r *artworkQueueRepository) MarkFailedIfUnchanged(kind, id, imageType string, seenRetryAt, retryAt time.Time) error {
+	upd := Update(r.tableName).
+		Set("attempts", Expr("attempts + 1")).
+		Set("retry_at", retryAt).
+		Where(Eq{"item_kind": kind, "item_id": id, "image_type": imageType, "retry_at": seenRetryAt})
+	_, err := r.executeSQL(upd)
+	return err
+}
+
 func (r *artworkQueueRepository) Delete(kind, id, imageType string) error {
 	return r.delete(Eq{"item_kind": kind, "item_id": id, "image_type": imageType})
 }
diff --git a/persistence/artwork_queue_repository_test.go b/persistence/artwork_queue_repository_test.go
index e96802284..0a6ddefdc 100644
--- a/persistence/artwork_queue_repository_test.go
+++ b/persistence/artwork_queue_repository_test.go
@@ -54,6 +54,34 @@ var _ = Describe("ArtworkQueueRepository", func() {
 		Expect(got[0].Attempts).To(Equal(2))
 	})
 
+	It("MarkFailedIfUnchanged applies backoff only while retry_at is unchanged", func() {
+		Expect(repo.Enqueue(item("al", "m1", model.ArtworkPriorityScan))).To(Succeed())
+		// Anchor retry_at in the past (attempts -> 1) so it can never collide with the re-enqueue's now.
+		Expect(repo.MarkFailed("al", "m1", model.ImageTypePrimary, time.Now().Add(-time.Hour))).To(Succeed())
+		got, err := repo.DequeueBatch(10)
+		Expect(err).ToNot(HaveOccurred())
+		Expect(got).To(HaveLen(1))
+		original := got[0].RetryAt
+
+		// A concurrent scan re-enqueues, resetting retry_at to now.
+		Expect(repo.Enqueue(item("al", "m1", model.ArtworkPriorityScan))).To(Succeed())
+
+		// Failing with the stale retry_at is a no-op: the re-enqueued row keeps its fresh state.
+		future := time.Now().Add(48 * time.Hour)
+		Expect(repo.MarkFailedIfUnchanged("al", "m1", model.ImageTypePrimary, original, future)).To(Succeed())
+		got, _ = repo.DequeueBatch(10)
+		Expect(got).To(HaveLen(1), "the fresh re-enqueue stays immediately eligible")
+		Expect(got[0].Attempts).To(Equal(1), "the stale failure must not bump attempts")
+		current := got[0].RetryAt
+
+		// Failing with the current retry_at applies the backoff and bumps attempts.
+		Expect(repo.MarkFailedIfUnchanged("al", "m1", model.ImageTypePrimary, current, future)).To(Succeed())
+		got, _ = repo.DequeueBatch(10)
+		Expect(got).To(BeEmpty(), "backed-off row is hidden until the future retry_at")
+		all, _ := repo.Count()
+		Expect(all).To(Equal(int64(1)))
+	})
+
 	It("deletes on completion and counts", func() {
 		Expect(repo.Enqueue(item("al", "c1", 0))).To(Succeed())
 		n, _ := repo.Count()
diff --git a/tests/mock_artwork_queue_repo.go b/tests/mock_artwork_queue_repo.go
index 8d01ef9c0..421e0dd15 100644
--- a/tests/mock_artwork_queue_repo.go
+++ b/tests/mock_artwork_queue_repo.go
@@ -84,6 +84,19 @@ func (m *MockArtworkQueueRepo) MarkFailed(kind, id, imageType string, retryAt ti
 	return nil
 }
 
+func (m *MockArtworkQueueRepo) MarkFailedIfUnchanged(kind, id, imageType string, seenRetryAt, retryAt time.Time) error {
+	if m.Err != nil {
+		return m.Err
+	}
+	k := iaKey(kind, id, imageType)
+	if it, ok := m.Data[k]; ok && it.RetryAt.Equal(seenRetryAt) {
+		it.Attempts++
+		it.RetryAt = retryAt
+		m.Data[k] = it
+	}
+	return nil
+}
+
 func (m *MockArtworkQueueRepo) Delete(kind, id, imageType string) error {
 	if m.Err != nil {
 		return m.Err