feat(sync): wire annotation sync into all device and web handlers

Complete the annotation sync pipeline across all ingest and serve paths.
Previously, annotations sent inline with KOReader progress pushes were
silently discarded, and no annotations were ever served back to devices.

INGEST (device → server):

KOReader (koreader.go):
  - Add processBookAnnotations helper that processes inline highlights,
    notes, and bookmarks from every progress push (immediate + checkpoint)
  - Highlights get CRE→CFI position conversion before SaveHighlight
  - KOReader 'notes' (text + notes) stored as highlights with NoteText
    to ensure correct round-trip classification
  - Bookmarks routed through SaveBookmark with device sync data
  - Called from both updateProgressForBook and handleCheckpointSync

Kobo (kobo.go):
  - Markup handler: annotations and bookmarks route through
    AnnotationService (SaveHighlight/SaveBookmark)
  - Bookmark handler: same routing with device sync data
  - SyncFromServer handler: same routing
  - All handlers fall back to direct DB calls when annotationSvc == nil

Web reader (media.go):
  - CreateMediaHighlight → SaveHighlight (Source="web", ModifiedAt=now)
  - CreateMediaNote → SaveNote (Source="web")
  - DeleteMediaHighlight → TombstoneHighlightByID
  - DeleteMediaNote → TombstoneNoteByID (was hard delete, now tombstone)
  - All fall back to old behavior when annotationSvc == nil

SERVE (server → device):

KOReader GetMetadata (koreader.go):
  - Query and serve bookmarks from media_bookmarks table (was missing)
  - Serve deleted_highlights and deleted_bookmarks arrays containing
    device_sync_data + dedup_key for client-side deletion
  - Highlights/notes already served with reverse CFI conversion

Kobo Markup handler (kobo.go):
  - Track processed books during sync
  - Query tombstones per book, extract bookmark_id from device_sync_data
  - Return DeletedAnnotations array in KoboSyncStatus response

Conflict resolution (conflicts.go):
  - Enable annotation conflict types in ResolveConflict handler
  - Add applyAnnotationResolution dispatching to:
    applyHighlightResolution / applyBookmarkResolution / applyNoteResolution
  - Each looks up by dedup_key and applies winner's fields
  - Allow manual override of auto_resolved conflicts
    (changed check from != "unresolved" to == "user_resolved")

Infrastructure:
  - AnnotationService field + SetAnnotationService in router Config
  - Inject AnnotationService into KOReader, Kobo, Media handlers
  - Start tombstone purger goroutine in main.go (24h interval)
  - Test helpers: construct AnnotationService in test setup

internal/handlers/conflicts.go

@@ -225,7 +225,7 @@ func (h *ConflictHandler) ResolveConflict(c *echo.Context) error {
 		return echo.NewHTTPError(http.StatusForbidden, "access denied")
 	}
 
-	if conflict.ResolutionStatus.String != "unresolved" {
+	if conflict.ResolutionStatus.String == "user_resolved" {
 		return echo.NewHTTPError(http.StatusBadRequest, "conflict already resolved")
 	}
 
@@ -258,6 +258,12 @@ func (h *ConflictHandler) ResolveConflict(c *echo.Context) error {
 		}
 	}
 
+	if conflict.ConflictType == "annotation_highlight" || conflict.ConflictType == "annotation_bookmark" || conflict.ConflictType == "annotation_note" {
+		if err := h.applyAnnotationResolution(conflict.MediaItemID, conflict.UserID, winnerData, conflict.ConflictType); err == nil {
+			appliedTo["annotations"] = true
+		}
+	}
+
 	resolutionData := map[string]interface{}{
 		"winner":      req.Winner,
 		"applied_to":  appliedTo,
@@ -356,6 +362,143 @@ func (h *ConflictHandler) applyProgressResolution(mediaItemID pgtype.UUID, userI
 	return err
 }
 
+func (h *ConflictHandler) applyAnnotationResolution(mediaItemID pgtype.UUID, userID pgtype.UUID, winnerData map[string]interface{}, conflictType string) error {
+	ctx := context.Background()
+
+	dedupKey, _ := winnerData["dedup_key"].(string)
+	if dedupKey == "" {
+		return errors.New("missing dedup_key in winner data")
+	}
+
+	switch conflictType {
+	case "annotation_highlight":
+		return h.applyHighlightResolution(ctx, mediaItemID, userID, dedupKey, winnerData)
+	case "annotation_bookmark":
+		return h.applyBookmarkResolution(ctx, mediaItemID, userID, dedupKey, winnerData)
+	case "annotation_note":
+		return h.applyNoteResolution(ctx, mediaItemID, userID, dedupKey, winnerData)
+	default:
+		return errors.New("unknown annotation conflict type")
+	}
+}
+
+func (h *ConflictHandler) applyHighlightResolution(ctx context.Context, mediaItemID pgtype.UUID, userID pgtype.UUID, dedupKey string, data map[string]interface{}) error {
+	existing, err := h.db.GetMediaHighlightByDedupKey(ctx, database.GetMediaHighlightByDedupKeyParams{
+		MediaItemID: mediaItemID,
+		DedupKey:    pgtype.Text{String: dedupKey, Valid: true},
+	})
+	if err != nil {
+		return err
+	}
+
+	params := database.UpdateMediaHighlightForSyncParams{
+		ID:                existing.ID,
+		SelectionText:     existing.SelectionText,
+		StartPosition:     existing.StartPosition,
+		EndPosition:       existing.EndPosition,
+		Color:             existing.Color,
+		NoteText:          existing.NoteText,
+		PercentageStart:   existing.PercentageStart,
+		PercentageEnd:     existing.PercentageEnd,
+		EpubcfiStart:      existing.EpubcfiStart,
+		EpubcfiEnd:        existing.EpubcfiEnd,
+		ChapterReference:  existing.ChapterReference,
+		LastModifiedAt:    pgtype.Timestamptz{Time: time.Now(), Valid: true},
+		LastModifiedSource: pgtype.Text{String: "conflict_resolution", Valid: true},
+		DeviceSyncData:     existing.DeviceSyncData,
+	}
+
+	if v, ok := data["selection_text"].(string); ok {
+		params.SelectionText = v
+	}
+	if v, ok := data["color"].(string); ok {
+		params.Color = pgtype.Text{String: v, Valid: true}
+	}
+	if v, ok := data["note_text"].(string); ok {
+		params.NoteText = pgtype.Text{String: v, Valid: true}
+	}
+	if v, ok := data["start_position"].(string); ok {
+		params.StartPosition = pgtype.Text{String: v, Valid: true}
+	}
+	if v, ok := data["end_position"].(string); ok {
+		params.EndPosition = pgtype.Text{String: v, Valid: true}
+	}
+
+	_, err = h.db.UpdateMediaHighlightForSync(ctx, params)
+	return err
+}
+
+func (h *ConflictHandler) applyBookmarkResolution(ctx context.Context, mediaItemID pgtype.UUID, userID pgtype.UUID, dedupKey string, data map[string]interface{}) error {
+	existing, err := h.db.GetMediaBookmarkByDedupKey(ctx, database.GetMediaBookmarkByDedupKeyParams{
+		MediaItemID: mediaItemID,
+		DedupKey:    pgtype.Text{String: dedupKey, Valid: true},
+	})
+	if err != nil {
+		return err
+	}
+
+	params := database.UpdateMediaBookmarkForSyncParams{
+		ID:                existing.ID,
+		PageNumber:        existing.PageNumber,
+		ChapterNumber:     existing.ChapterNumber,
+		CfiPosition:       existing.CfiPosition,
+		Title:             existing.Title,
+		Position:          existing.Position,
+		Notes:             existing.Notes,
+		PercentageLocation: existing.PercentageLocation,
+		EpubcfiLocation:   existing.EpubcfiLocation,
+		ChapterReference:  existing.ChapterReference,
+		LastModifiedAt:    pgtype.Timestamptz{Time: time.Now(), Valid: true},
+		LastModifiedSource: pgtype.Text{String: "conflict_resolution", Valid: true},
+		DeviceSyncData:     existing.DeviceSyncData,
+	}
+
+	if v, ok := data["title"].(string); ok {
+		params.Title = v
+	}
+	if v, ok := data["notes"].(string); ok {
+		params.Notes = pgtype.Text{String: v, Valid: true}
+	}
+
+	_, err = h.db.UpdateMediaBookmarkForSync(ctx, params)
+	return err
+}
+
+func (h *ConflictHandler) applyNoteResolution(ctx context.Context, mediaItemID pgtype.UUID, userID pgtype.UUID, dedupKey string, data map[string]interface{}) error {
+	existing, err := h.db.GetMediaNoteByDedupKey(ctx, database.GetMediaNoteByDedupKeyParams{
+		MediaItemID: mediaItemID,
+		DedupKey:    pgtype.Text{String: dedupKey, Valid: true},
+	})
+	if err != nil {
+		return err
+	}
+
+	params := database.UpdateMediaNoteForSyncParams{
+		ID:                 existing.ID,
+		Content:            existing.Content,
+		Position:           existing.Position,
+		PercentageLocation: existing.PercentageLocation,
+		CharacterStart:     existing.CharacterStart,
+		CharacterEnd:       existing.CharacterEnd,
+		EpubcfiLocation:    existing.EpubcfiLocation,
+		ChapterReference:   existing.ChapterReference,
+		ParagraphReference: existing.ParagraphReference,
+		LastModifiedAt:     pgtype.Timestamptz{Time: time.Now(), Valid: true},
+		LastModifiedSource: pgtype.Text{String: "conflict_resolution", Valid: true},
+		DeviceSyncData:     existing.DeviceSyncData,
+	}
+
+	if v, ok := data["content"].(string); ok {
+		params.Content = v
+	}
+	if v, ok := data["position"].(string); ok {
+		params.Position = pgtype.Text{String: v, Valid: true}
+	}
+
+	_, err = h.db.UpdateMediaNoteForSync(ctx, params)
+	return err
+}
+
 func (h *ConflictHandler) notifyDevicesOfResolution(mediaItemID pgtype.UUID, data map[string]interface{}) []string {
 	devices, err := h.db.ListDevicesByType(context.Background(), "koreader")
 	if err != nil {

internal/handlers/kobo.go

@@ -3,6 +3,7 @@ package handlers
 import (
 	"bookhoard/internal/database"
 	wsync "bookhoard/internal/sync"
+	"encoding/json"
 	"fmt"
 	"log"
 	"net/http"
@@ -19,6 +20,7 @@ type KoboHandler struct {
 	db             *database.Queries
 	connManager    *wsync.ConnectionManager
 	progressSvc    *wsync.ProgressService
+	annotationSvc  *wsync.AnnotationService
 	libraryService LibraryPathResolver
 }
 
@@ -30,6 +32,10 @@ func (h *KoboHandler) SetProgressService(svc *wsync.ProgressService) {
 	h.progressSvc = svc
 }
 
+func (h *KoboHandler) SetAnnotationService(svc *wsync.AnnotationService) {
+	h.annotationSvc = svc
+}
+
 func (h *KoboHandler) SetLibraryService(svc LibraryPathResolver) {
 	h.libraryService = svc
 }
@@ -245,9 +251,16 @@ type KoboInitResponse struct {
 }
 
 type KoboSyncStatus struct {
-	Status          string `json:"Status"`
-	MarkupsSynced   int    `json:"MarkupsSynced"`
-	BookmarksSynced int    `json:"BookmarksSynced"`
+	Status            string                 `json:"Status"`
+	MarkupsSynced     int                    `json:"MarkupsSynced"`
+	BookmarksSynced   int                    `json:"BookmarksSynced"`
+	DeletedAnnotations []KoboDeletedAnnotation `json:"DeletedAnnotations,omitempty"`
+}
+
+type KoboDeletedAnnotation struct {
+	ContentId  string `json:"ContentId"`
+	BookmarkId string `json:"BookmarkId"`
+	Type       string `json:"Type"`
 }
 
 type KoboServerSyncData struct {
@@ -311,7 +324,7 @@ func (h *KoboHandler) Initialization(c *echo.Context) error {
 		}
 
 		bookmarkCount := 0
-		annotations, _ := h.db.GetAnnotationsForBook(c.Request().Context(), database.GetAnnotationsForBookParams{
+		annotations, _ := h.db.GetActiveAnnotationsForBook(c.Request().Context(), database.GetActiveAnnotationsForBookParams{
 			MediaItemID: pgtype.UUID{Bytes: item.ID.Bytes, Valid: true},
 			UserID:      pgUserID,
 		})
@@ -403,6 +416,7 @@ func (h *KoboHandler) Markup(c *echo.Context) error {
 	markupsSynced := 0
 	bookmarksSynced := 0
 	unlinkedBooks := 0
+	processedBooks := make(map[pgtype.UUID]string)
 
 	for _, readingSync := range req.ReadingSync {
 		bookhoardUUID, err, _ := h.mapContentIdToBookhoardUUID(c, readingSync.ContentId, deviceUUID)
@@ -412,6 +426,7 @@ func (h *KoboHandler) Markup(c *echo.Context) error {
 		}
 
 		pgMediaUUID := pgtype.UUID{Bytes: bookhoardUUID, Valid: true}
+		processedBooks[pgMediaUUID] = readingSync.ContentId
 		percentage := readingSync.PercentRead / 100.0
 
 		// Kobo only sends a percentage. For fixed-layout & comic formats the page
@@ -465,29 +480,72 @@ func (h *KoboHandler) Markup(c *echo.Context) error {
 		}
 
 		pgMediaUUID := pgtype.UUID{Bytes: bookhoardUUID, Valid: true}
+		processedBooks[pgMediaUUID] = bookmarkSync.ContentId
 
 		switch bookmarkSync.BookmarkType {
 		case "annotation":
 			if bookmarkSync.BookmarkText != "" {
-				h.db.CreateMediaHighlight(c.Request().Context(), database.CreateMediaHighlightParams{
-					MediaItemID:   pgMediaUUID,
-					UserID:        pgUserID,
-					SelectionText: bookmarkSync.BookmarkText,
-					StartPosition: pgtype.Text{String: bookmarkSync.BookmarkId, Valid: true},
-					EndPosition:   pgtype.Text{String: bookmarkSync.BookmarkId, Valid: true},
-					Color:         pgtype.Text{String: "#ffff00", Valid: true},
-				})
-				bookmarksSynced++
+				if h.annotationSvc != nil {
+					deviceData, _ := json.Marshal(map[string]interface{}{
+						"bookmark_id":  bookmarkSync.BookmarkId,
+						"date_created": bookmarkSync.DateCreated,
+					})
+
+					result, err := h.annotationSvc.SaveHighlight(c.Request().Context(), wsync.SaveHighlightRequest{
+						MediaItemID:    pgMediaUUID,
+						UserID:         pgUserID,
+						SelectionText:  bookmarkSync.BookmarkText,
+						StartPosition:  bookmarkSync.BookmarkId,
+						EndPosition:    bookmarkSync.BookmarkId,
+						Color:          "#ffff00",
+						NoteText:       bookmarkSync.BookmarkTitle,
+						Source:         "kobo",
+						DeviceSyncData: deviceData,
+					})
+					if err == nil && result.Outcome != wsync.SaveOutcomeDeleted {
+						bookmarksSynced++
+					}
+				} else {
+					h.db.CreateMediaHighlight(c.Request().Context(), database.CreateMediaHighlightParams{
+						MediaItemID:   pgMediaUUID,
+						UserID:        pgUserID,
+						SelectionText: bookmarkSync.BookmarkText,
+						StartPosition: pgtype.Text{String: bookmarkSync.BookmarkId, Valid: true},
+						EndPosition:   pgtype.Text{String: bookmarkSync.BookmarkId, Valid: true},
+						Color:         pgtype.Text{String: "#ffff00", Valid: true},
+					})
+					bookmarksSynced++
+				}
 			}
 		case "bookmark":
 			if bookmarkSync.BookmarkText != "" {
-				h.db.CreateMediaNote(c.Request().Context(), database.CreateMediaNoteParams{
-					MediaItemID: pgMediaUUID,
-					UserID:      pgUserID,
-					Content:     bookmarkSync.BookmarkText,
-					Position:    pgtype.Text{String: bookmarkSync.BookmarkId, Valid: true},
-				})
-				bookmarksSynced++
+				if h.annotationSvc != nil {
+					deviceData, _ := json.Marshal(map[string]interface{}{
+						"bookmark_id":  bookmarkSync.BookmarkId,
+						"date_created": bookmarkSync.DateCreated,
+					})
+
+					result, err := h.annotationSvc.SaveBookmark(c.Request().Context(), wsync.SaveBookmarkRequest{
+						MediaItemID:    pgMediaUUID,
+						UserID:         pgUserID,
+						Title:          bookmarkSync.BookmarkText,
+						Position:       bookmarkSync.BookmarkId,
+						ChapterNumber:  int32(bookmarkSync.Chapter),
+						Source:         "kobo",
+						DeviceSyncData: deviceData,
+					})
+					if err == nil && result.Outcome != wsync.SaveOutcomeDeleted {
+						bookmarksSynced++
+					}
+				} else {
+					h.db.CreateMediaNote(c.Request().Context(), database.CreateMediaNoteParams{
+						MediaItemID: pgMediaUUID,
+						UserID:      pgUserID,
+						Content:     bookmarkSync.BookmarkText,
+						Position:    pgtype.Text{String: bookmarkSync.BookmarkId, Valid: true},
+					})
+					bookmarksSynced++
+				}
 			}
 		case "last-read-place":
 			if bookmarkSync.BookmarkId != "" {
@@ -564,6 +622,32 @@ func (h *KoboHandler) Markup(c *echo.Context) error {
 		BookmarksSynced: bookmarksSynced,
 	}
 
+	if h.annotationSvc != nil && len(processedBooks) > 0 {
+		cutoff := pgtype.Timestamptz{Time: time.Now().Add(-wsync.TombstoneTTL), Valid: true}
+		for mediaItemID, contentId := range processedBooks {
+			tombstones, _ := h.db.GetTombstonedAnnotationsForBook(c.Request().Context(), database.GetTombstonedAnnotationsForBookParams{
+				MediaItemID: mediaItemID,
+				UserID:      pgUserID,
+				DeletedAt:   cutoff,
+			})
+			for _, ts := range tombstones {
+				var dd map[string]interface{}
+				if len(ts.DeviceSyncData) > 0 {
+					json.Unmarshal(ts.DeviceSyncData, &dd)
+				}
+				bookmarkID, _ := dd["bookmark_id"].(string)
+				if bookmarkID == "" {
+					continue
+				}
+				response.DeletedAnnotations = append(response.DeletedAnnotations, KoboDeletedAnnotation{
+					ContentId:  contentId,
+					BookmarkId: bookmarkID,
+					Type:       ts.AnnotationType,
+				})
+			}
+		}
+	}
+
 	// Include unlinked books count if any
 	if unlinkedBooks > 0 {
 		// For now, just log it. In production, this should trigger an alert
@@ -606,25 +690,67 @@ func (h *KoboHandler) Bookmark(c *echo.Context) error {
 		switch bookmarkSync.BookmarkType {
 		case "annotation":
 			if bookmarkSync.BookmarkText != "" {
-				h.db.CreateMediaHighlight(c.Request().Context(), database.CreateMediaHighlightParams{
-					MediaItemID:   pgMediaUUID,
-					UserID:        pgUserID,
-					SelectionText: bookmarkSync.BookmarkText,
-					StartPosition: pgtype.Text{String: bookmarkSync.BookmarkId, Valid: true},
-					EndPosition:   pgtype.Text{String: bookmarkSync.BookmarkId, Valid: true},
-					Color:         pgtype.Text{String: "#ffff00", Valid: true},
-				})
-				bookmarksSynced++
+				if h.annotationSvc != nil {
+					deviceData, _ := json.Marshal(map[string]interface{}{
+						"bookmark_id":  bookmarkSync.BookmarkId,
+						"date_created": bookmarkSync.DateCreated,
+					})
+
+					result, err := h.annotationSvc.SaveHighlight(c.Request().Context(), wsync.SaveHighlightRequest{
+						MediaItemID:    pgMediaUUID,
+						UserID:         pgUserID,
+						SelectionText:  bookmarkSync.BookmarkText,
+						StartPosition:  bookmarkSync.BookmarkId,
+						EndPosition:    bookmarkSync.BookmarkId,
+						Color:          "#ffff00",
+						NoteText:       bookmarkSync.BookmarkTitle,
+						Source:         "kobo",
+						DeviceSyncData: deviceData,
+					})
+					if err == nil && result.Outcome != wsync.SaveOutcomeDeleted {
+						bookmarksSynced++
+					}
+				} else {
+					h.db.CreateMediaHighlight(c.Request().Context(), database.CreateMediaHighlightParams{
+						MediaItemID:   pgMediaUUID,
+						UserID:        pgUserID,
+						SelectionText: bookmarkSync.BookmarkText,
+						StartPosition: pgtype.Text{String: bookmarkSync.BookmarkId, Valid: true},
+						EndPosition:   pgtype.Text{String: bookmarkSync.BookmarkId, Valid: true},
+						Color:         pgtype.Text{String: "#ffff00", Valid: true},
+					})
+					bookmarksSynced++
+				}
 			}
 		case "bookmark":
 			if bookmarkSync.BookmarkText != "" {
-				h.db.CreateMediaNote(c.Request().Context(), database.CreateMediaNoteParams{
-					MediaItemID: pgMediaUUID,
-					UserID:      pgUserID,
-					Content:     bookmarkSync.BookmarkText,
-					Position:    pgtype.Text{String: bookmarkSync.BookmarkId, Valid: true},
-				})
-				bookmarksSynced++
+				if h.annotationSvc != nil {
+					deviceData, _ := json.Marshal(map[string]interface{}{
+						"bookmark_id":  bookmarkSync.BookmarkId,
+						"date_created": bookmarkSync.DateCreated,
+					})
+
+					result, err := h.annotationSvc.SaveBookmark(c.Request().Context(), wsync.SaveBookmarkRequest{
+						MediaItemID:    pgMediaUUID,
+						UserID:         pgUserID,
+						Title:          bookmarkSync.BookmarkText,
+						Position:       bookmarkSync.BookmarkId,
+						ChapterNumber:  int32(bookmarkSync.Chapter),
+						Source:         "kobo",
+						DeviceSyncData: deviceData,
+					})
+					if err == nil && result.Outcome != wsync.SaveOutcomeDeleted {
+						bookmarksSynced++
+					}
+				} else {
+					h.db.CreateMediaNote(c.Request().Context(), database.CreateMediaNoteParams{
+						MediaItemID: pgMediaUUID,
+						UserID:      pgUserID,
+						Content:     bookmarkSync.BookmarkText,
+						Position:    pgtype.Text{String: bookmarkSync.BookmarkId, Valid: true},
+					})
+					bookmarksSynced++
+				}
 			}
 		}
 	}
@@ -756,36 +882,79 @@ func (h *KoboHandler) SyncFromServer(c *echo.Context) error {
 
 		for _, bookmark := range syncData.Bookmarks {
 			if bookmark.BookmarkType == "bookmark" {
-				h.db.CreateMediaNote(c.Request().Context(), database.CreateMediaNoteParams{
-					MediaItemID: pgMediaUUID,
-					UserID:      pgUserID,
-					Content:     bookmark.BookmarkText,
-					Position:    pgtype.Text{String: bookmark.BookmarkId, Valid: true},
-				})
-				bookmarksSent++
+				if h.annotationSvc != nil {
+					result, err := h.annotationSvc.SaveBookmark(c.Request().Context(), wsync.SaveBookmarkRequest{
+						MediaItemID: pgMediaUUID,
+						UserID:      pgUserID,
+						Title:       bookmark.BookmarkText,
+						Position:    bookmark.BookmarkId,
+						Source:      "kobo",
+					})
+					if err == nil && result.Outcome != wsync.SaveOutcomeDeleted {
+						bookmarksSent++
+					}
+				} else {
+					h.db.CreateMediaNote(c.Request().Context(), database.CreateMediaNoteParams{
+						MediaItemID: pgMediaUUID,
+						UserID:      pgUserID,
+						Content:     bookmark.BookmarkText,
+						Position:    pgtype.Text{String: bookmark.BookmarkId, Valid: true},
+					})
+					bookmarksSent++
+				}
 			} else if bookmark.BookmarkType == "annotation" {
-				h.db.CreateMediaHighlight(c.Request().Context(), database.CreateMediaHighlightParams{
-					MediaItemID:   pgMediaUUID,
-					UserID:        pgUserID,
-					SelectionText: bookmark.BookmarkText,
-					StartPosition: pgtype.Text{String: bookmark.BookmarkId, Valid: true},
-					EndPosition:   pgtype.Text{String: bookmark.BookmarkId, Valid: true},
-					Color:         pgtype.Text{String: "#ffff00", Valid: true},
-				})
-				highlightsSent++
+				if h.annotationSvc != nil {
+					result, err := h.annotationSvc.SaveHighlight(c.Request().Context(), wsync.SaveHighlightRequest{
+						MediaItemID:   pgMediaUUID,
+						UserID:        pgUserID,
+						SelectionText: bookmark.BookmarkText,
+						StartPosition: bookmark.BookmarkId,
+						EndPosition:   bookmark.BookmarkId,
+						Color:         "#ffff00",
+						Source:        "kobo",
+					})
+					if err == nil && result.Outcome != wsync.SaveOutcomeDeleted {
+						highlightsSent++
+					}
+				} else {
+					h.db.CreateMediaHighlight(c.Request().Context(), database.CreateMediaHighlightParams{
+						MediaItemID:   pgMediaUUID,
+						UserID:        pgUserID,
+						SelectionText: bookmark.BookmarkText,
+						StartPosition: pgtype.Text{String: bookmark.BookmarkId, Valid: true},
+						EndPosition:   pgtype.Text{String: bookmark.BookmarkId, Valid: true},
+						Color:         pgtype.Text{String: "#ffff00", Valid: true},
+					})
+					highlightsSent++
+				}
 			}
 		}
 
 		for _, highlight := range syncData.Highlights {
-			h.db.CreateMediaHighlight(c.Request().Context(), database.CreateMediaHighlightParams{
-				MediaItemID:   pgMediaUUID,
-				UserID:        pgUserID,
-				SelectionText: highlight.BookmarkText,
-				StartPosition: pgtype.Text{String: highlight.BookmarkId, Valid: true},
-				EndPosition:   pgtype.Text{String: highlight.BookmarkId, Valid: true},
-				Color:         pgtype.Text{String: "#ffff00", Valid: true},
-			})
-			highlightsSent++
+			if h.annotationSvc != nil {
+				result, err := h.annotationSvc.SaveHighlight(c.Request().Context(), wsync.SaveHighlightRequest{
+					MediaItemID:   pgMediaUUID,
+					UserID:        pgUserID,
+					SelectionText: highlight.BookmarkText,
+					StartPosition: highlight.BookmarkId,
+					EndPosition:   highlight.BookmarkId,
+					Color:         "#ffff00",
+					Source:        "kobo",
+				})
+				if err == nil && result.Outcome != wsync.SaveOutcomeDeleted {
+					highlightsSent++
+				}
+			} else {
+				h.db.CreateMediaHighlight(c.Request().Context(), database.CreateMediaHighlightParams{
+					MediaItemID:   pgMediaUUID,
+					UserID:        pgUserID,
+					SelectionText: highlight.BookmarkText,
+					StartPosition: pgtype.Text{String: highlight.BookmarkId, Valid: true},
+					EndPosition:   pgtype.Text{String: highlight.BookmarkId, Valid: true},
+					Color:         pgtype.Text{String: "#ffff00", Valid: true},
+				})
+				highlightsSent++
+			}
 		}
 	}
 

internal/handlers/koreader.go

@@ -4,6 +4,7 @@ import (
 	"bookhoard/internal/database"
 	wsync "bookhoard/internal/sync"
 	"context"
+	"encoding/json"
 	"fmt"
 	"log"
 	"net/http"
@@ -19,6 +20,7 @@ type KOReaderHandler struct {
 	connManager    *wsync.ConnectionManager
 	queue          *wsync.SyncQueueProcessor
 	progressSvc    *wsync.ProgressService
+	annotationSvc  *wsync.AnnotationService
 	libraryService LibraryPathResolver
 }
 
@@ -34,6 +36,27 @@ func (h *KOReaderHandler) SetProgressService(svc *wsync.ProgressService) {
 	h.progressSvc = svc
 }
 
+func (h *KOReaderHandler) SetAnnotationService(svc *wsync.AnnotationService) {
+	h.annotationSvc = svc
+}
+
+func (h *KOReaderHandler) convertHighlightPositions(ctx context.Context, mediaItemID pgtype.UUID, pos0, pos1 string) (string, string) {
+	if pos0 == "" || h.libraryService == nil {
+		return "", ""
+	}
+	mediaItem, err := h.db.GetMediaItem(ctx, mediaItemID)
+	if err != nil {
+		return "", ""
+	}
+	epubPath, err := h.libraryService.ResolveMediaPath(ctx, mediaItem.LibraryID, mediaItem.FilePath)
+	if err != nil || epubPath == "" {
+		return "", ""
+	}
+	startLoc := wsync.ConvertToCanonical(wsync.LocatorSourceKOReader, pos0, 0, "", mediaItem.FormatGroup, epubPath, "")
+	endLoc := wsync.ConvertToCanonical(wsync.LocatorSourceKOReader, pos1, 0, "", mediaItem.FormatGroup, epubPath, "")
+	return startLoc.CFI, endLoc.CFI
+}
+
 func (h *KOReaderHandler) SetLibraryService(svc LibraryPathResolver) {
 	h.libraryService = svc
 }
@@ -154,9 +177,11 @@ type KOReaderProgressData struct {
 }
 
 type KOReaderAnnotations struct {
-	Highlights []KOReaderHighlight `json:"highlights,omitempty"`
-	Notes      []KOReaderNote      `json:"notes,omitempty"`
-	Bookmarks  []KOReaderBookmark  `json:"bookmarks,omitempty"`
+	Highlights        []KOReaderHighlight `json:"highlights,omitempty"`
+	Notes             []KOReaderNote      `json:"notes,omitempty"`
+	Bookmarks         []KOReaderBookmark  `json:"bookmarks,omitempty"`
+	DeletedHighlights []map[string]interface{} `json:"deleted_highlights,omitempty"`
+	DeletedBookmarks  []map[string]interface{} `json:"deleted_bookmarks,omitempty"`
 }
 
 type KOReaderLibraryResponse struct {
@@ -396,6 +421,7 @@ func (h *KOReaderHandler) handleCheckpointSync(c *echo.Context, device database.
 		if synced {
 			booksEnqueued++
 		}
+		h.processBookAnnotations(c.Request().Context(), device.ID, userID, mediaItemID, book)
 		bookResults = append(bookResults, KOReaderBookSyncResult{
 			SHA256:   book.SHA256,
 			BookUUID: uuid.UUID(mediaItemID.Bytes).String(),
@@ -441,6 +467,102 @@ func (h *KOReaderHandler) enqueueProgressForBook(c *echo.Context, deviceID pgtyp
 	return h.queue.EnqueueProgress(update)
 }
 
+func (h *KOReaderHandler) processBookAnnotations(ctx context.Context, deviceID, userID, mediaItemID pgtype.UUID, book KOReaderBookProgress) {
+	if h.annotationSvc == nil {
+		return
+	}
+
+	for _, hl := range book.Highlights {
+		startPos := hl.Pos0
+		endPos := hl.Pos1
+		epubcfiStart, epubcfiEnd := h.convertHighlightPositions(ctx, mediaItemID, startPos, endPos)
+
+		pctStart := 0.0
+		if hl.Percentage != nil {
+			pctStart = *hl.Percentage
+		}
+
+		deviceData, _ := json.Marshal(map[string]interface{}{
+			"datetime": hl.Datetime,
+			"pos0":     hl.Pos0,
+			"pos1":     hl.Pos1,
+			"page":     hl.Page,
+		})
+
+		h.annotationSvc.SaveHighlight(ctx, wsync.SaveHighlightRequest{
+			MediaItemID:      mediaItemID,
+			UserID:           userID,
+			SelectionText:    hl.Text,
+			StartPosition:    startPos,
+			EndPosition:      endPos,
+			Color:            hl.Color,
+			NoteText:         hl.Notes,
+			PercentageStart:  pctStart,
+			EpubcfiStart:     epubcfiStart,
+			EpubcfiEnd:       epubcfiEnd,
+			Source:           "koreader",
+			DeviceSyncData:   deviceData,
+		})
+	}
+
+	for _, note := range book.Notes {
+		startPos := note.Pos0
+		endPos := note.Pos1
+		epubcfiStart, epubcfiEnd := h.convertHighlightPositions(ctx, mediaItemID, startPos, endPos)
+
+		pctStart := 0.0
+		if note.Percentage != nil {
+			pctStart = *note.Percentage
+		}
+
+		deviceData, _ := json.Marshal(map[string]interface{}{
+			"datetime": note.Datetime,
+			"pos0":     note.Pos0,
+			"pos1":     note.Pos1,
+			"page":     note.Page,
+		})
+
+		h.annotationSvc.SaveHighlight(ctx, wsync.SaveHighlightRequest{
+			MediaItemID:      mediaItemID,
+			UserID:           userID,
+			SelectionText:    note.Text,
+			StartPosition:    startPos,
+			EndPosition:      endPos,
+			NoteText:         note.Notes,
+			PercentageStart:  pctStart,
+			EpubcfiStart:     epubcfiStart,
+			EpubcfiEnd:       epubcfiEnd,
+			Source:           "koreader",
+			DeviceSyncData:   deviceData,
+		})
+	}
+
+	for _, bookmark := range book.Bookmarks {
+		position := ""
+		if bookmark.Pos0 != "" {
+			position = bookmark.Pos0
+		} else if bookmark.Page > 0 {
+			position = fmt.Sprintf("page:%d", bookmark.Page)
+		}
+
+		deviceData, _ := json.Marshal(map[string]interface{}{
+			"datetime": bookmark.Datetime,
+			"pos0":     bookmark.Pos0,
+			"page":     bookmark.Page,
+		})
+
+		h.annotationSvc.SaveBookmark(ctx, wsync.SaveBookmarkRequest{
+			MediaItemID:    mediaItemID,
+			UserID:         userID,
+			Title:          bookmark.Text,
+			Position:       position,
+			ChapterNumber:  int32(bookmark.Chapter),
+			Source:         "koreader",
+			DeviceSyncData: deviceData,
+		})
+	}
+}
+
 func (h *KOReaderHandler) updateProgressForBook(c *echo.Context, deviceID pgtype.UUID, userID pgtype.UUID, mediaItemID pgtype.UUID, book KOReaderBookProgress) error {
 	ctx := c.Request().Context()
 
@@ -522,7 +644,11 @@ func (h *KOReaderHandler) updateProgressForBook(c *echo.Context, deviceID pgtype
 		}
 
 		_, err := h.progressSvc.SaveProgress(ctx, saveReq)
-		return err
+		if err != nil {
+			return err
+		}
+		h.processBookAnnotations(ctx, deviceID, userID, mediaItemID, book)
+		return nil
 	}
 
 	_, err := h.db.UpdateUniversalProgress(ctx, database.UpdateUniversalProgressParams{
@@ -558,6 +684,8 @@ func (h *KOReaderHandler) updateProgressForBook(c *echo.Context, deviceID pgtype
 		},
 	)
 
+	h.processBookAnnotations(ctx, deviceID, userID, mediaItemID, book)
+
 	return nil
 }
 
@@ -657,7 +785,7 @@ func (h *KOReaderHandler) GetMetadata(c *echo.Context) error {
 		progressData.TotalPages = &progress
 	}
 
-	annotations, err := h.db.GetAnnotationsForBook(c.Request().Context(), database.GetAnnotationsForBookParams{
+	annotations, err := h.db.GetActiveAnnotationsForBook(c.Request().Context(), database.GetActiveAnnotationsForBookParams{
 		MediaItemID: pgBookUUID,
 		UserID:      pgUserID,
 	})
@@ -670,13 +798,29 @@ func (h *KOReaderHandler) GetMetadata(c *echo.Context) error {
 
 	for _, ann := range annotations {
 		if ann.AnnotationType == "highlight" {
-			annotationsResponse.Highlights = append(annotationsResponse.Highlights, KOReaderHighlight{
+			pos0 := ann.StartPosition.String
+			pos1 := ann.EndPosition.String
+			if ann.EpubcfiStart.Valid && ann.EpubcfiStart.String != "" {
+				if converted := h.reverseConvertCFI(c, mediaItem, ann.EpubcfiStart.String); converted != "" {
+					pos0 = converted
+				}
+			}
+			if ann.EpubcfiEnd.Valid && ann.EpubcfiEnd.String != "" {
+				if converted := h.reverseConvertCFI(c, mediaItem, ann.EpubcfiEnd.String); converted != "" {
+					pos1 = converted
+				}
+			}
+			highlight := KOReaderHighlight{
 				Text:     ann.SelectionText,
-				Pos0:     ann.StartPosition.String,
-				Pos1:     ann.EndPosition.String,
+				Pos0:     pos0,
+				Pos1:     pos1,
 				Color:    ann.Color.String,
 				Datetime: ann.CreatedAt.Time.Format(time.RFC3339),
-			})
+			}
+			if ann.NoteText.Valid && ann.NoteText.String != "" {
+				highlight.Notes = ann.NoteText.String
+			}
+			annotationsResponse.Highlights = append(annotationsResponse.Highlights, highlight)
 		} else if ann.AnnotationType == "note" {
 			annotationsResponse.Notes = append(annotationsResponse.Notes, KOReaderNote{
 				Text:     ann.SelectionText,
@@ -686,6 +830,52 @@ func (h *KOReaderHandler) GetMetadata(c *echo.Context) error {
 		}
 	}
 
+	bookmarks, _ := h.db.GetMediaBookmarks(c.Request().Context(), database.GetMediaBookmarksParams{
+		MediaItemID: pgBookUUID,
+		UserID:      pgUserID,
+	})
+	for _, bm := range bookmarks {
+		pos0 := bm.Position.String
+		if pos0 == "" && bm.CfiPosition.Valid {
+			pos0 = bm.CfiPosition.String
+		}
+		koreaderBookmark := KOReaderBookmark{
+			Text:     bm.Title,
+			Pos0:     pos0,
+			Pos1:     pos0,
+			Datetime: bm.CreatedAt.Time.Format(time.RFC3339),
+		}
+		if bm.Notes.Valid && bm.Notes.String != "" {
+			koreaderBookmark.Notes = bm.Notes.String
+		}
+		if bm.ChapterNumber.Valid {
+			koreaderBookmark.Chapter = int(bm.ChapterNumber.Int32)
+		}
+		annotationsResponse.Bookmarks = append(annotationsResponse.Bookmarks, koreaderBookmark)
+	}
+
+	cutoff := pgtype.Timestamptz{Time: time.Now().Add(-wsync.TombstoneTTL), Valid: true}
+	tombstones, _ := h.db.GetTombstonedAnnotationsForBook(c.Request().Context(), database.GetTombstonedAnnotationsForBookParams{
+		MediaItemID: pgBookUUID,
+		UserID:      pgUserID,
+		DeletedAt:   cutoff,
+	})
+	for _, ts := range tombstones {
+		var dd map[string]interface{}
+		if len(ts.DeviceSyncData) > 0 {
+			json.Unmarshal(ts.DeviceSyncData, &dd)
+		}
+		if dd == nil {
+			dd = map[string]interface{}{}
+		}
+		dd["dedup_key"] = ts.DedupKey.String
+		if ts.AnnotationType == "highlight" {
+			annotationsResponse.DeletedHighlights = append(annotationsResponse.DeletedHighlights, dd)
+		} else if ts.AnnotationType == "bookmark" {
+			annotationsResponse.DeletedBookmarks = append(annotationsResponse.DeletedBookmarks, dd)
+		}
+	}
+
 	lastSync := "never"
 	if progress.LastSyncTimestamp.Valid {
 		lastSync = progress.LastSyncTimestamp.Time.Format(time.RFC3339)
@@ -737,6 +927,21 @@ func (h *KOReaderHandler) convertCFIToXPointer(c *echo.Context, mediaItem databa
 	}
 }
 
+func (h *KOReaderHandler) reverseConvertCFI(c *echo.Context, mediaItem database.MediaItems, epubcfi string) string {
+	if h.libraryService == nil || epubcfi == "" {
+		return ""
+	}
+	epubPath, err := h.libraryService.ResolveMediaPath(c.Request().Context(), mediaItem.LibraryID, mediaItem.FilePath)
+	if err != nil || epubPath == "" {
+		return ""
+	}
+	loc := wsync.ConvertFromCanonical(wsync.LocatorSourceKOReader, epubcfi, 0, "", mediaItem.FormatGroup, epubPath, "")
+	if loc.Position != "" && loc.Position != epubcfi {
+		return loc.Position
+	}
+	return ""
+}
+
 func (h *KOReaderHandler) GetLibrary(c *echo.Context) error {
 	device := c.Get("device").(database.Devices)
 	userID := device.UserID.Bytes
@@ -776,7 +981,7 @@ func (h *KOReaderHandler) GetLibrary(c *echo.Context) error {
 			}
 		}
 
-		annotations, _ := h.db.GetAnnotationsForBook(c.Request().Context(), database.GetAnnotationsForBookParams{
+		annotations, _ := h.db.GetActiveAnnotationsForBook(c.Request().Context(), database.GetActiveAnnotationsForBookParams{
 			MediaItemID: pgItemUUID,
 			UserID:      pgUserID,
 		})
@@ -876,15 +1081,36 @@ func (h *KOReaderHandler) SyncBookmarks(c *echo.Context) error {
 			position = fmt.Sprintf("page:%d", bookmark.Page)
 		}
 
-		_, err := h.db.CreateMediaNote(ctx, database.CreateMediaNoteParams{
-			MediaItemID: mediaItemID,
-			UserID:      pgUserID,
-			Content:     bookmark.Text,
-			Position:    pgtype.Text{String: position, Valid: position != ""},
-		})
+		if h.annotationSvc != nil {
+			deviceData, _ := json.Marshal(map[string]interface{}{
+				"datetime": bookmark.Datetime,
+				"pos0":     bookmark.Pos0,
+				"page":     bookmark.Page,
+			})
 
-		if err == nil {
-			bookmarksSynced++
+			result, err := h.annotationSvc.SaveBookmark(ctx, wsync.SaveBookmarkRequest{
+				MediaItemID:    mediaItemID,
+				UserID:         pgUserID,
+				Title:          bookmark.Text,
+				Position:       position,
+				ChapterNumber:  int32(bookmark.Chapter),
+				Source:         "koreader",
+				DeviceSyncData: deviceData,
+			})
+			if err == nil && result.Outcome != wsync.SaveOutcomeDeleted {
+				bookmarksSynced++
+			}
+		} else {
+			_, err := h.db.CreateMediaNote(ctx, database.CreateMediaNoteParams{
+				MediaItemID: mediaItemID,
+				UserID:      pgUserID,
+				Content:     bookmark.Text,
+				Position:    pgtype.Text{String: position, Valid: position != ""},
+			})
+
+			if err == nil {
+				bookmarksSynced++
+			}
 		}
 	}
 
@@ -906,15 +1132,35 @@ func (h *KOReaderHandler) SyncBookmarks(c *echo.Context) error {
 			position = fmt.Sprintf("page:%d", note.Page)
 		}
 
-		_, err := h.db.CreateMediaNote(ctx, database.CreateMediaNoteParams{
-			MediaItemID: mediaItemID,
-			UserID:      pgUserID,
-			Content:     note.Notes,
-			Position:    pgtype.Text{String: position, Valid: position != ""},
-		})
+		if h.annotationSvc != nil {
+			deviceData, _ := json.Marshal(map[string]interface{}{
+				"datetime": note.Datetime,
+				"pos0":     note.Pos0,
+				"page":     note.Page,
+			})
 
-		if err == nil {
-			notesSynced++
+			result, err := h.annotationSvc.SaveNote(ctx, wsync.SaveNoteRequest{
+				MediaItemID:    mediaItemID,
+				UserID:         pgUserID,
+				Content:        note.Notes,
+				Position:       position,
+				Source:         "koreader",
+				DeviceSyncData: deviceData,
+			})
+			if err == nil && result.Outcome != wsync.SaveOutcomeDeleted {
+				notesSynced++
+			}
+		} else {
+			_, err := h.db.CreateMediaNote(ctx, database.CreateMediaNoteParams{
+				MediaItemID: mediaItemID,
+				UserID:      pgUserID,
+				Content:     note.Notes,
+				Position:    pgtype.Text{String: position, Valid: position != ""},
+			})
+
+			if err == nil {
+				notesSynced++
+			}
 		}
 	}
 
@@ -941,17 +1187,51 @@ func (h *KOReaderHandler) SyncBookmarks(c *echo.Context) error {
 			color = highlight.Color
 		}
 
-		_, err := h.db.CreateMediaHighlight(ctx, database.CreateMediaHighlightParams{
-			MediaItemID:   mediaItemID,
-			UserID:        pgUserID,
-			SelectionText: highlight.Text,
-			StartPosition: pgtype.Text{String: startPos, Valid: startPos != ""},
-			EndPosition:   pgtype.Text{String: endPos, Valid: endPos != ""},
-			Color:         pgtype.Text{String: color, Valid: true},
-		})
+		if h.annotationSvc != nil {
+			epubcfiStart, epubcfiEnd := h.convertHighlightPositions(ctx, mediaItemID, highlight.Pos0, highlight.Pos1)
 
-		if err == nil {
-			highlightsSynced++
+			pctStart := 0.0
+			if highlight.Percentage != nil {
+				pctStart = *highlight.Percentage
+			}
+
+			deviceData, _ := json.Marshal(map[string]interface{}{
+				"datetime": highlight.Datetime,
+				"pos0":     highlight.Pos0,
+				"pos1":     highlight.Pos1,
+				"page":     highlight.Page,
+			})
+
+			result, err := h.annotationSvc.SaveHighlight(ctx, wsync.SaveHighlightRequest{
+				MediaItemID:     mediaItemID,
+				UserID:          pgUserID,
+				SelectionText:   highlight.Text,
+				StartPosition:   startPos,
+				EndPosition:     endPos,
+				Color:           color,
+				NoteText:        highlight.Notes,
+				PercentageStart: pctStart,
+				EpubcfiStart:    epubcfiStart,
+				EpubcfiEnd:      epubcfiEnd,
+				Source:          "koreader",
+				DeviceSyncData:  deviceData,
+			})
+			if err == nil && result.Outcome != wsync.SaveOutcomeDeleted {
+				highlightsSynced++
+			}
+		} else {
+			_, err := h.db.CreateMediaHighlight(ctx, database.CreateMediaHighlightParams{
+				MediaItemID:   mediaItemID,
+				UserID:        pgUserID,
+				SelectionText: highlight.Text,
+				StartPosition: pgtype.Text{String: startPos, Valid: startPos != ""},
+				EndPosition:   pgtype.Text{String: endPos, Valid: endPos != ""},
+				Color:         pgtype.Text{String: color, Valid: true},
+			})
+
+			if err == nil {
+				highlightsSynced++
+			}
 		}
 	}
 

internal/handlers/media.go

@@ -19,6 +19,7 @@ import (
 	"path/filepath"
 	"strconv"
 	"strings"
+	"time"
 
 	"github.com/google/uuid"
 	"github.com/jackc/pgx/v5"
@@ -136,6 +137,7 @@ type MediaHandler struct {
 	libraryService *services.LibraryService
 	searchService  *services.SearchService
 	progressSvc    *wsync.ProgressService
+	annotationSvc  *wsync.AnnotationService
 }
 
 func NewMediaHandler(db *database.Queries, libraryService *services.LibraryService, worker ...*services.Worker) *MediaHandler {
@@ -154,6 +156,10 @@ func (mh *MediaHandler) SetProgressService(svc *wsync.ProgressService) {
 	mh.progressSvc = svc
 }
 
+func (mh *MediaHandler) SetAnnotationService(svc *wsync.AnnotationService) {
+	mh.annotationSvc = svc
+}
+
 func (h *MediaHandler) DownloadBook(c *echo.Context) error {
 	bookUUID, err := uuid.Parse(c.Param("uuid"))
 	if err != nil {
@@ -1388,14 +1394,31 @@ func (mh *MediaHandler) CreateMediaNote(c *echo.Context) error {
 		return c.JSON(http.StatusBadRequest, map[string]string{"error": err.Error()})
 	}
 
-	note, err := mh.db.CreateMediaNote(c.Request().Context(), database.CreateMediaNoteParams{
-		MediaItemID: pgtype.UUID{Bytes: mediaUUID, Valid: true},
-		UserID:      pgtype.UUID{Bytes: userUUID, Valid: true},
-		Content:     req.Content,
-		Position:    pgtype.Text{String: req.Position, Valid: req.Position != ""},
-	})
-	if err != nil {
-		return c.JSON(http.StatusInternalServerError, map[string]string{"error": err.Error()})
+	var note database.MediaNotes
+	if mh.annotationSvc != nil {
+		result, err := mh.annotationSvc.SaveNote(c.Request().Context(), wsync.SaveNoteRequest{
+			MediaItemID: pgtype.UUID{Bytes: mediaUUID, Valid: true},
+			UserID:      pgtype.UUID{Bytes: userUUID, Valid: true},
+			Content:     req.Content,
+			Position:    req.Position,
+			Source:      "web",
+			ModifiedAt:  time.Now(),
+		})
+		if err != nil {
+			return c.JSON(http.StatusInternalServerError, map[string]string{"error": err.Error()})
+		}
+		note = result.Note
+	} else {
+		var err error
+		note, err = mh.db.CreateMediaNote(c.Request().Context(), database.CreateMediaNoteParams{
+			MediaItemID: pgtype.UUID{Bytes: mediaUUID, Valid: true},
+			UserID:      pgtype.UUID{Bytes: userUUID, Valid: true},
+			Content:     req.Content,
+			Position:    pgtype.Text{String: req.Position, Valid: req.Position != ""},
+		})
+		if err != nil {
+			return c.JSON(http.StatusInternalServerError, map[string]string{"error": err.Error()})
+		}
 	}
 
 	return c.JSON(http.StatusCreated, note)
@@ -1456,7 +1479,11 @@ func (mh *MediaHandler) DeleteMediaNote(c *echo.Context) error {
 		return c.JSON(http.StatusBadRequest, map[string]string{"error": "invalid note id"})
 	}
 
-	err = mh.db.DeleteMediaNote(c.Request().Context(), pgtype.UUID{Bytes: noteUUID, Valid: true})
+	if mh.annotationSvc != nil {
+		err = mh.annotationSvc.TombstoneNoteByID(c.Request().Context(), pgtype.UUID{Bytes: noteUUID, Valid: true})
+	} else {
+		err = mh.db.DeleteMediaNote(c.Request().Context(), pgtype.UUID{Bytes: noteUUID, Valid: true})
+	}
 	if err != nil {
 		return c.JSON(http.StatusInternalServerError, map[string]string{"error": err.Error()})
 	}
@@ -1525,9 +1552,29 @@ func (mh *MediaHandler) CreateMediaHighlight(c *echo.Context) error {
 		color = req.Color
 	}
 
+	pgMediaID := pgtype.UUID{Bytes: mediaUUID, Valid: true}
+	pgUserID := pgtype.UUID{Bytes: userUUID, Valid: true}
+
+	if mh.annotationSvc != nil {
+		result, err := mh.annotationSvc.SaveHighlight(c.Request().Context(), wsync.SaveHighlightRequest{
+			MediaItemID:    pgMediaID,
+			UserID:         pgUserID,
+			SelectionText:  req.SelectionText,
+			StartPosition:  req.StartPosition,
+			EndPosition:    req.EndPosition,
+			Color:          color,
+			Source:         "web",
+			ModifiedAt:     time.Now(),
+		})
+		if err != nil {
+			return c.JSON(http.StatusInternalServerError, map[string]string{"error": err.Error()})
+		}
+		return c.JSON(http.StatusCreated, result.Highlight)
+	}
+
 	highlight, err := mh.db.CreateMediaHighlight(c.Request().Context(), database.CreateMediaHighlightParams{
-		MediaItemID:   pgtype.UUID{Bytes: mediaUUID, Valid: true},
-		UserID:        pgtype.UUID{Bytes: userUUID, Valid: true},
+		MediaItemID:   pgMediaID,
+		UserID:        pgUserID,
 		SelectionText: req.SelectionText,
 		StartPosition: pgtype.Text{String: req.StartPosition, Valid: true},
 		EndPosition:   pgtype.Text{String: req.EndPosition, Valid: true},
@@ -1613,7 +1660,16 @@ func (mh *MediaHandler) DeleteMediaHighlight(c *echo.Context) error {
 		return c.JSON(http.StatusBadRequest, map[string]string{"error": "invalid highlight id"})
 	}
 
-	err = mh.db.DeleteMediaHighlight(c.Request().Context(), pgtype.UUID{Bytes: highlightUUID, Valid: true})
+	pgHighlightID := pgtype.UUID{Bytes: highlightUUID, Valid: true}
+
+	if mh.annotationSvc != nil {
+		if err := mh.annotationSvc.TombstoneHighlightByID(c.Request().Context(), pgHighlightID, "web"); err != nil {
+			return c.JSON(http.StatusInternalServerError, map[string]string{"error": err.Error()})
+		}
+		return c.NoContent(http.StatusNoContent)
+	}
+
+	err = mh.db.DeleteMediaHighlight(c.Request().Context(), pgHighlightID)
 	if err != nil {
 		return c.JSON(http.StatusInternalServerError, map[string]string{"error": err.Error()})
 	}