diff --git a/persistence/playlist_repository.go b/persistence/playlist_repository.go
index e984b8852..397838f07 100644
--- a/persistence/playlist_repository.go
+++ b/persistence/playlist_repository.go
@@ -324,6 +324,13 @@ func (r *playlistRepository) refreshCounters(pls *model.Playlist) error {
 	pls.SongCount = int(res.Count)
 	pls.Duration = res.Duration
 	pls.Size = int64(res.Size)
+	// The generated 2x2 grid depends on the track set, so re-resolve the cover whenever it
+	// changes. No clear: the old cover keeps serving until the worker rebuilds (no flicker).
+	item := model.ArtworkQueueItem{ItemKind: "pl", ItemID: pls.ID, ImageType: model.ImageTypePrimary,
+		Priority: model.ArtworkPriorityScan}
+	if err := NewArtworkQueueRepository(r.ctx, r.db).Enqueue(item); err != nil {
+		log.Warn(r.ctx, "could not enqueue playlist artwork after content change", "id", pls.ID, err)
+	}
 	return nil
 }
 
diff --git a/persistence/playlist_repository_test.go b/persistence/playlist_repository_test.go
index 8dc86d887..ec5259400 100644
--- a/persistence/playlist_repository_test.go
+++ b/persistence/playlist_repository_test.go
@@ -260,6 +260,21 @@ var _ = Describe("PlaylistRepository", func() {
 		Expect(repo.Exists(newPls.ID)).To(BeFalse())
 	})
 
+	It("enqueues the playlist's artwork when its track set changes", func() {
+		ctx := request.WithUser(log.NewContext(GinkgoT().Context()), model.User{ID: "userid", UserName: "userid", IsAdmin: true})
+		newPls := model.Playlist{Name: "Grid PL", OwnerID: "userid"}
+		newPls.AddMediaFilesByID([]string{"1001", "1002"})
+		Expect(repo.Put(&newPls)).To(Succeed())
+		DeferCleanup(func() { _ = repo.Delete(newPls.ID) })
+
+		queued, err := NewArtworkQueueRepository(ctx, GetDBXBuilder()).DequeueBatch(1000)
+		Expect(err).ToNot(HaveOccurred())
+		Expect(queued).To(ContainElement(SatisfyAll(
+			HaveField("ItemKind", "pl"),
+			HaveField("ItemID", newPls.ID),
+		)))
+	})
+
 	Describe("GetAll", func() {
 		It("returns all playlists from DB", func() {
 			all, err := repo.GetAll()