diff --git a/internal/handlers/kobo.go b/internal/handlers/kobo.go
index d36efd4..73ab1ee 100644
--- a/internal/handlers/kobo.go
+++ b/internal/handlers/kobo.go
@@ -623,7 +623,7 @@ func (h *KoboHandler) Markup(c *echo.Context) error {
 	}
 
 	if h.annotationSvc != nil && len(processedBooks) > 0 {
-		cutoff := pgtype.Timestamptz{Time: time.Now().Add(-wsync.TombstoneTTL), Valid: true}
+		cutoff := pgtype.Timestamptz{Time: time.Now().Add(-h.annotationSvc.ActiveTombstoneTTL()), Valid: true}
 		for mediaItemID, contentId := range processedBooks {
 			tombstones, _ := h.db.GetTombstonedAnnotationsForBook(c.Request().Context(), database.GetTombstonedAnnotationsForBookParams{
 				MediaItemID: mediaItemID,
diff --git a/internal/handlers/koreader.go b/internal/handlers/koreader.go
index a28b1d0..a19775e 100644
--- a/internal/handlers/koreader.go
+++ b/internal/handlers/koreader.go
@@ -854,7 +854,7 @@ func (h *KOReaderHandler) GetMetadata(c *echo.Context) error {
 		annotationsResponse.Bookmarks = append(annotationsResponse.Bookmarks, koreaderBookmark)
 	}
 
-	cutoff := pgtype.Timestamptz{Time: time.Now().Add(-wsync.TombstoneTTL), Valid: true}
+	cutoff := pgtype.Timestamptz{Time: time.Now().Add(-h.annotationSvc.ActiveTombstoneTTL()), Valid: true}
 	tombstones, _ := h.db.GetTombstonedAnnotationsForBook(c.Request().Context(), database.GetTombstonedAnnotationsForBookParams{
 		MediaItemID: pgBookUUID,
 		UserID:      pgUserID,
diff --git a/internal/sync/annotations.go b/internal/sync/annotations.go
index d047479..4689436 100644
--- a/internal/sync/annotations.go
+++ b/internal/sync/annotations.go
@@ -18,8 +18,38 @@ import (
 	"github.com/jackc/pgx/v5/pgtype"
 )
 
+// TombstoneTTL is the fallback retention for soft-deleted annotations when no
+// settings registry is wired (e.g. in tests). It matches the historical value.
 const TombstoneTTL = 30 * 24 * time.Hour
 
+type AnnotationService struct {
+	db      *database.Queries
+	connMgr *ConnectionManager
+	settings *database.SettingsRegistry
+}
+
+func NewAnnotationService(db *database.Queries, connMgr *ConnectionManager) *AnnotationService {
+	return &AnnotationService{db: db, connMgr: connMgr}
+}
+
+// SetSettings wires the tunable settings registry. When wired, the tombstone
+// TTL is read live from the DB; otherwise the package const TombstoneTTL is
+// used.
+func (s *AnnotationService) SetSettings(reg *database.SettingsRegistry) { s.settings = reg }
+
+// tombstoneTTL returns the active tombstone retention window.
+func (s *AnnotationService) tombstoneTTL() time.Duration {
+	if s.settings != nil {
+		return s.settings.TombstoneTTL()
+	}
+	return TombstoneTTL
+}
+
+// ActiveTombstoneTTL exposes the configured tombstone retention window for
+// callers outside the sync package (e.g. kobo/koreader handlers) that need to
+// compute cutoffs consistently with the service.
+func (s *AnnotationService) ActiveTombstoneTTL() time.Duration { return s.tombstoneTTL() }
+
 type SaveOutcome string
 
 const (
@@ -29,15 +59,6 @@ const (
 	SaveOutcomeDeleted SaveOutcome = "deleted"
 )
 
-type AnnotationService struct {
-	db      *database.Queries
-	connMgr *ConnectionManager
-}
-
-func NewAnnotationService(db *database.Queries, connMgr *ConnectionManager) *AnnotationService {
-	return &AnnotationService{db: db, connMgr: connMgr}
-}
-
 type SaveHighlightRequest struct {
 	MediaItemID      pgtype.UUID
 	UserID           pgtype.UUID
@@ -79,7 +100,7 @@ func (s *AnnotationService) SaveHighlight(ctx context.Context, req SaveHighlight
 	}
 
 	if existing.Deleted.Bool {
-		if existing.DeletedAt.Valid && time.Since(existing.DeletedAt.Time) < TombstoneTTL {
+		if existing.DeletedAt.Valid && time.Since(existing.DeletedAt.Time) < s.tombstoneTTL() {
 			return &SaveHighlightResult{Highlight: existing, Outcome: SaveOutcomeDeleted}, nil
 		}
 		return s.createHighlight(ctx, req, dedupKey)
@@ -238,7 +259,7 @@ func (s *AnnotationService) TombstoneHighlightByID(
 }
 
 func (s *AnnotationService) PurgeExpiredTombstones(ctx context.Context) error {
-	cutoff := pgtype.Timestamptz{Time: time.Now().Add(-TombstoneTTL), Valid: true}
+	cutoff := pgtype.Timestamptz{Time: time.Now().Add(-s.tombstoneTTL()), Valid: true}
 	if err := s.db.PurgeExpiredHighlightTombstones(ctx, cutoff); err != nil {
 		return fmt.Errorf("purge highlight tombstones: %w", err)
 	}
@@ -457,7 +478,7 @@ func (s *AnnotationService) SaveBookmark(ctx context.Context, req SaveBookmarkRe
 	}
 
 	if existing.Deleted.Bool {
-		if existing.DeletedAt.Valid && time.Since(existing.DeletedAt.Time) < TombstoneTTL {
+		if existing.DeletedAt.Valid && time.Since(existing.DeletedAt.Time) < s.tombstoneTTL() {
 			return &SaveBookmarkResult{Bookmark: existing, Outcome: SaveOutcomeDeleted}, nil
 		}
 		return s.createBookmark(ctx, req, dedupKey)