feat(db): add annotation sync schema, queries, and tombstone support

Add migration columns to media_highlights, media_notes, and media_bookmarks
for cross-device annotation sync:

- dedup_key: SHA-1 of normalized selection text + bucketed position, used
  as the stable cross-device identity for annotations
- last_modified_at / last_modified_source: edit clock for LWW resolution
  and cross-source conflict detection
- deleted / deleted_at: sticky tombstone columns for delete-wins semantics
  with a 30-day TTL before rows are physically purged
- note_text on highlights: stores attached notes from KOReader entries that
  have both selected text and a user note
- Location columns on bookmarks (cfi_position, percentage_location,
  epubcfi_location, chapter_reference, paragraph_reference)
- device_sync_data JSONB on all three tables: stores per-device native
  identifiers (e.g. KOReader pos0/datetime, Kobo bookmark_id) so each
  device can locate and manipulate its own copy of an annotation

Add partial unique indexes on (user_id, media_item_id, dedup_key) where
deleted = FALSE to enforce one active annotation per dedup key.

Add tombstone purge indexes on (deleted, deleted_at) for efficient GC.

New queries:
- GetByDedupKey for all three tables (returns active or most-recent tombstone)
- CreateFull / UpdateForSync for all three tables (populate sync columns)
- TombstoneByDedupKey / TombstoneByID for all three tables
- PurgeExpired* for all three tables (GC past TTL)
- GetActiveAnnotationsForBook (filtered union of highlights + notes)
- GetTombstonedAnnotationsForBook (union of all 3 deleted within TTL)
- GetMediaBookmarks with deleted filter
- GetMediaBookmark (singular) with deleted filter
- Added deleted=FALSE filter to GetMediaHighlights, GetAnnotationsForBook
- CreateAutoResolvedSyncConflict (INSERT with resolution_status='auto_resolved')

database/schema/schema.sql

@@ -1312,3 +1312,48 @@ CREATE TABLE IF NOT EXISTS media_bookmarks (
 
 CREATE INDEX IF NOT EXISTS idx_media_bookmarks_media ON media_bookmarks(media_item_id);
 CREATE INDEX IF NOT EXISTS idx_media_bookmarks_user ON media_bookmarks(user_id);
+
+-- ============================================
+-- ANNOTATION SYNC MIGRATIONS
+-- Adds dedup_key, LWW timestamps, soft-delete,
+-- and device_sync_data to annotation tables.
+-- ============================================
+
+ALTER TABLE media_highlights ADD COLUMN IF NOT EXISTS dedup_key VARCHAR(40);
+ALTER TABLE media_highlights ADD COLUMN IF NOT EXISTS last_modified_at TIMESTAMPTZ;
+ALTER TABLE media_highlights ADD COLUMN IF NOT EXISTS last_modified_source VARCHAR(30);
+ALTER TABLE media_highlights ADD COLUMN IF NOT EXISTS note_text TEXT;
+ALTER TABLE media_highlights ADD COLUMN IF NOT EXISTS deleted BOOLEAN DEFAULT FALSE;
+ALTER TABLE media_highlights ADD COLUMN IF NOT EXISTS deleted_at TIMESTAMPTZ;
+
+ALTER TABLE media_notes ADD COLUMN IF NOT EXISTS dedup_key VARCHAR(40);
+ALTER TABLE media_notes ADD COLUMN IF NOT EXISTS last_modified_at TIMESTAMPTZ;
+ALTER TABLE media_notes ADD COLUMN IF NOT EXISTS last_modified_source VARCHAR(30);
+ALTER TABLE media_notes ADD COLUMN IF NOT EXISTS deleted BOOLEAN DEFAULT FALSE;
+ALTER TABLE media_notes ADD COLUMN IF NOT EXISTS deleted_at TIMESTAMPTZ;
+
+ALTER TABLE media_bookmarks ADD COLUMN IF NOT EXISTS dedup_key VARCHAR(40);
+ALTER TABLE media_bookmarks ADD COLUMN IF NOT EXISTS last_modified_at TIMESTAMPTZ;
+ALTER TABLE media_bookmarks ADD COLUMN IF NOT EXISTS last_modified_source VARCHAR(30);
+ALTER TABLE media_bookmarks ADD COLUMN IF NOT EXISTS device_sync_data JSONB;
+ALTER TABLE media_bookmarks ADD COLUMN IF NOT EXISTS percentage_location FLOAT;
+ALTER TABLE media_bookmarks ADD COLUMN IF NOT EXISTS epubcfi_location TEXT;
+ALTER TABLE media_bookmarks ADD COLUMN IF NOT EXISTS chapter_reference INTEGER;
+ALTER TABLE media_bookmarks ADD COLUMN IF NOT EXISTS deleted BOOLEAN DEFAULT FALSE;
+ALTER TABLE media_bookmarks ADD COLUMN IF NOT EXISTS deleted_at TIMESTAMPTZ;
+
+CREATE UNIQUE INDEX IF NOT EXISTS idx_media_highlights_dedup
+    ON media_highlights (user_id, media_item_id, dedup_key)
+    WHERE dedup_key IS NOT NULL AND deleted = FALSE;
+
+CREATE UNIQUE INDEX IF NOT EXISTS idx_media_notes_dedup
+    ON media_notes (user_id, media_item_id, dedup_key)
+    WHERE dedup_key IS NOT NULL AND deleted = FALSE;
+
+CREATE UNIQUE INDEX IF NOT EXISTS idx_media_bookmarks_dedup
+    ON media_bookmarks (user_id, media_item_id, dedup_key)
+    WHERE dedup_key IS NOT NULL AND deleted = FALSE;
+
+CREATE INDEX IF NOT EXISTS idx_media_highlights_deleted_at ON media_highlights(deleted_at) WHERE deleted = TRUE;
+CREATE INDEX IF NOT EXISTS idx_media_notes_deleted_at ON media_notes(deleted_at) WHERE deleted = TRUE;
+CREATE INDEX IF NOT EXISTS idx_media_bookmarks_deleted_at ON media_bookmarks(deleted_at) WHERE deleted = TRUE;

internal/database/db.go

@@ -1,6 +1,6 @@
 // Code generated by sqlc. DO NOT EDIT.
 // versions:
-//   sqlc v1.31.1
+//   sqlc v1.30.0
 
 package database
 

internal/database/models.go

@@ -1,6 +1,6 @@
 // Code generated by sqlc. DO NOT EDIT.
 // versions:
-//   sqlc v1.31.1
+//   sqlc v1.30.0
 
 package database
 
@@ -165,6 +165,15 @@ type MediaBookmarks struct {
 	Position           pgtype.Text        `db:"position" json:"position"`
 	Notes              pgtype.Text        `db:"notes" json:"notes"`
 	CreatedAt          pgtype.Timestamptz `db:"created_at" json:"created_at"`
+	DedupKey           pgtype.Text        `db:"dedup_key" json:"dedup_key"`
+	LastModifiedAt     pgtype.Timestamptz `db:"last_modified_at" json:"last_modified_at"`
+	LastModifiedSource pgtype.Text        `db:"last_modified_source" json:"last_modified_source"`
+	DeviceSyncData     []byte             `db:"device_sync_data" json:"device_sync_data"`
+	PercentageLocation pgtype.Float8      `db:"percentage_location" json:"percentage_location"`
+	EpubcfiLocation    pgtype.Text        `db:"epubcfi_location" json:"epubcfi_location"`
+	ChapterReference   pgtype.Int4        `db:"chapter_reference" json:"chapter_reference"`
+	Deleted            pgtype.Bool        `db:"deleted" json:"deleted"`
+	DeletedAt          pgtype.Timestamptz `db:"deleted_at" json:"deleted_at"`
 }
 
 type MediaHighlights struct {
@@ -189,6 +198,12 @@ type MediaHighlights struct {
 	ParagraphEnd       pgtype.Int4        `db:"paragraph_end" json:"paragraph_end"`
 	PanelNumber        pgtype.Int4        `db:"panel_number" json:"panel_number"`
 	DeviceSyncData     []byte             `db:"device_sync_data" json:"device_sync_data"`
+	DedupKey           pgtype.Text        `db:"dedup_key" json:"dedup_key"`
+	LastModifiedAt     pgtype.Timestamptz `db:"last_modified_at" json:"last_modified_at"`
+	LastModifiedSource pgtype.Text        `db:"last_modified_source" json:"last_modified_source"`
+	NoteText           pgtype.Text        `db:"note_text" json:"note_text"`
+	Deleted            pgtype.Bool        `db:"deleted" json:"deleted"`
+	DeletedAt          pgtype.Timestamptz `db:"deleted_at" json:"deleted_at"`
 }
 
 type MediaItemFormats struct {
@@ -304,6 +319,11 @@ type MediaNotes struct {
 	ChapterReference   pgtype.Int4        `db:"chapter_reference" json:"chapter_reference"`
 	ParagraphReference pgtype.Int4        `db:"paragraph_reference" json:"paragraph_reference"`
 	DeviceSyncData     []byte             `db:"device_sync_data" json:"device_sync_data"`
+	DedupKey           pgtype.Text        `db:"dedup_key" json:"dedup_key"`
+	LastModifiedAt     pgtype.Timestamptz `db:"last_modified_at" json:"last_modified_at"`
+	LastModifiedSource pgtype.Text        `db:"last_modified_source" json:"last_modified_source"`
+	Deleted            pgtype.Bool        `db:"deleted" json:"deleted"`
+	DeletedAt          pgtype.Timestamptz `db:"deleted_at" json:"deleted_at"`
 }
 
 type MediaRatings struct {

internal/database/querier.go

@@ -1,6 +1,6 @@
 // Code generated by sqlc. DO NOT EDIT.
 // versions:
-//   sqlc v1.31.1
+//   sqlc v1.30.0
 
 package database
 
@@ -34,6 +34,7 @@ type Querier interface {
 	// Count unlinked books for a device
 	CountUnlinkedBooks(ctx context.Context, deviceID pgtype.UUID) (int64, error)
 	CountUserDevices(ctx context.Context, userID pgtype.UUID) (int64, error)
+	CreateAutoResolvedSyncConflict(ctx context.Context, arg CreateAutoResolvedSyncConflictParams) (SyncConflicts, error)
 	// COLLECTIONS QUERIES
 	// Create collection
 	CreateCollection(ctx context.Context, arg CreateCollectionParams) (Collections, error)
@@ -55,8 +56,10 @@ type Querier interface {
 	// Libraries queries
 	CreateLibrary(ctx context.Context, arg CreateLibraryParams) (Libraries, error)
 	CreateMediaBookmark(ctx context.Context, arg CreateMediaBookmarkParams) (MediaBookmarks, error)
+	CreateMediaBookmarkFull(ctx context.Context, arg CreateMediaBookmarkFullParams) (MediaBookmarks, error)
 	// Media Highlights queries
 	CreateMediaHighlight(ctx context.Context, arg CreateMediaHighlightParams) (MediaHighlights, error)
+	CreateMediaHighlightFull(ctx context.Context, arg CreateMediaHighlightFullParams) (MediaHighlights, error)
 	// Media Items queries
 	CreateMediaItem(ctx context.Context, arg CreateMediaItemParams) (MediaItems, error)
 	// MEDIA ITEM FORMATS QUERIES
@@ -64,6 +67,7 @@ type Querier interface {
 	CreateMediaItemFormat(ctx context.Context, arg CreateMediaItemFormatParams) (MediaItemFormats, error)
 	// Media Notes queries
 	CreateMediaNote(ctx context.Context, arg CreateMediaNoteParams) (MediaNotes, error)
+	CreateMediaNoteFull(ctx context.Context, arg CreateMediaNoteFullParams) (MediaNotes, error)
 	CreateMediaRating(ctx context.Context, arg CreateMediaRatingParams) (MediaRatings, error)
 	// OPDS TOKENS QUERIES
 	// Create OPDS token
@@ -126,6 +130,10 @@ type Querier interface {
 	DeleteUser(ctx context.Context, id pgtype.UUID) error
 	DeleteUserSystemCollection(ctx context.Context, arg DeleteUserSystemCollectionParams) error
 	GenerateKoboEntitlementId(ctx context.Context) (interface{}, error)
+	// ============================================
+	// ANNOTATION SERVE QUERIES
+	// ============================================
+	GetActiveAnnotationsForBook(ctx context.Context, arg GetActiveAnnotationsForBookParams) ([]GetActiveAnnotationsForBookRow, error)
 	// Get all system config
 	GetAllSystemConfig(ctx context.Context) ([]SystemConfig, error)
 	GetAllSystemSettings(ctx context.Context) ([]GetAllSystemSettingsRow, error)
@@ -197,8 +205,17 @@ type Querier interface {
 	// LIBRARY WITH TYPE INFO QUERIES
 	// ============================================================================
 	GetLibraryWithType(ctx context.Context, id pgtype.UUID) (GetLibraryWithTypeRow, error)
+	GetMediaBookmark(ctx context.Context, id pgtype.UUID) (MediaBookmarks, error)
+	// ============================================
+	// ANNOTATION SYNC QUERIES (bookmarks)
+	// ============================================
+	GetMediaBookmarkByDedupKey(ctx context.Context, arg GetMediaBookmarkByDedupKeyParams) (MediaBookmarks, error)
 	GetMediaBookmarks(ctx context.Context, arg GetMediaBookmarksParams) ([]MediaBookmarks, error)
 	GetMediaHighlight(ctx context.Context, id pgtype.UUID) (MediaHighlights, error)
+	// ============================================
+	// ANNOTATION SYNC QUERIES (highlights)
+	// ============================================
+	GetMediaHighlightByDedupKey(ctx context.Context, arg GetMediaHighlightByDedupKeyParams) (MediaHighlights, error)
 	GetMediaHighlights(ctx context.Context, arg GetMediaHighlightsParams) ([]MediaHighlights, error)
 	GetMediaItem(ctx context.Context, id pgtype.UUID) (MediaItems, error)
 	GetMediaItemByFilePath(ctx context.Context, arg GetMediaItemByFilePathParams) (MediaItems, error)
@@ -221,6 +238,10 @@ type Querier interface {
 	// Get media item formats
 	GetMediaItemFormats(ctx context.Context, mediaItemID pgtype.UUID) ([]MediaItemFormats, error)
 	GetMediaNote(ctx context.Context, id pgtype.UUID) (MediaNotes, error)
+	// ============================================
+	// ANNOTATION SYNC QUERIES (notes)
+	// ============================================
+	GetMediaNoteByDedupKey(ctx context.Context, arg GetMediaNoteByDedupKeyParams) (MediaNotes, error)
 	GetMediaNotes(ctx context.Context, arg GetMediaNotesParams) ([]MediaNotes, error)
 	GetMediaRating(ctx context.Context, arg GetMediaRatingParams) (MediaRatings, error)
 	GetMediaRatings(ctx context.Context, mediaItemID pgtype.UUID) ([]GetMediaRatingsRow, error)
@@ -258,6 +279,7 @@ type Querier interface {
 	// System Settings queries
 	GetSystemSetting(ctx context.Context, settingKey string) (string, error)
 	GetSystemTimezone(ctx context.Context) (string, error)
+	GetTombstonedAnnotationsForBook(ctx context.Context, arg GetTombstonedAnnotationsForBookParams) ([]GetTombstonedAnnotationsForBookRow, error)
 	// Get universal progress for a book
 	GetUniversalProgress(ctx context.Context, arg GetUniversalProgressParams) (GetUniversalProgressRow, error)
 	// Get unlinked book by ContentId
@@ -304,6 +326,9 @@ type Querier interface {
 	// List unresolved unlinked books with pagination
 	ListUnresolvedUnlinkedBooks(ctx context.Context, arg ListUnresolvedUnlinkedBooksParams) ([]ListUnresolvedUnlinkedBooksRow, error)
 	ListUsers(ctx context.Context) ([]ListUsersRow, error)
+	PurgeExpiredBookmarkTombstones(ctx context.Context, deletedAt pgtype.Timestamptz) error
+	PurgeExpiredHighlightTombstones(ctx context.Context, deletedAt pgtype.Timestamptz) error
+	PurgeExpiredNoteTombstones(ctx context.Context, deletedAt pgtype.Timestamptz) error
 	// Query media items by multiple identifiers with confidence scoring
 	QueryMediaItemsByIdentifiers(ctx context.Context, arg QueryMediaItemsByIdentifiersParams) ([]QueryMediaItemsByIdentifiersRow, error)
 	ReassignLibraries(ctx context.Context, arg ReassignLibrariesParams) error
@@ -334,6 +359,12 @@ type Querier interface {
 	// Set system config
 	SetSystemConfig(ctx context.Context, arg SetSystemConfigParams) (SystemConfig, error)
 	SyncLibraryTypeExtensions(ctx context.Context, arg SyncLibraryTypeExtensionsParams) error
+	TombstoneMediaBookmarkByDedupKey(ctx context.Context, arg TombstoneMediaBookmarkByDedupKeyParams) error
+	TombstoneMediaBookmarkByID(ctx context.Context, id pgtype.UUID) error
+	TombstoneMediaHighlightByDedupKey(ctx context.Context, arg TombstoneMediaHighlightByDedupKeyParams) error
+	TombstoneMediaHighlightByID(ctx context.Context, id pgtype.UUID) error
+	TombstoneMediaNoteByDedupKey(ctx context.Context, arg TombstoneMediaNoteByDedupKeyParams) error
+	TombstoneMediaNoteByID(ctx context.Context, id pgtype.UUID) error
 	// Update collection
 	UpdateCollection(ctx context.Context, arg UpdateCollectionParams) (Collections, error)
 	UpdateDashboardPreferences(ctx context.Context, arg UpdateDashboardPreferencesParams) (UserDashboardPreferences, error)
@@ -357,7 +388,9 @@ type Querier interface {
 	UpdateKoboShelfCollection(ctx context.Context, arg UpdateKoboShelfCollectionParams) (KoboShelves, error)
 	UpdateLibrary(ctx context.Context, arg UpdateLibraryParams) (Libraries, error)
 	UpdateMediaBookmark(ctx context.Context, arg UpdateMediaBookmarkParams) (MediaBookmarks, error)
+	UpdateMediaBookmarkForSync(ctx context.Context, arg UpdateMediaBookmarkForSyncParams) (MediaBookmarks, error)
 	UpdateMediaHighlight(ctx context.Context, arg UpdateMediaHighlightParams) (MediaHighlights, error)
+	UpdateMediaHighlightForSync(ctx context.Context, arg UpdateMediaHighlightForSyncParams) (MediaHighlights, error)
 	UpdateMediaItem(ctx context.Context, arg UpdateMediaItemParams) (MediaItems, error)
 	UpdateMediaItemChapterMetadata(ctx context.Context, arg UpdateMediaItemChapterMetadataParams) (MediaItems, error)
 	// Update media item format
@@ -375,6 +408,7 @@ type Querier interface {
 	UpdateMediaItemIdentifiers(ctx context.Context, arg UpdateMediaItemIdentifiersParams) (MediaItems, error)
 	UpdateMediaItemKoboMetadata(ctx context.Context, arg UpdateMediaItemKoboMetadataParams) (MediaItems, error)
 	UpdateMediaNote(ctx context.Context, arg UpdateMediaNoteParams) (MediaNotes, error)
+	UpdateMediaNoteForSync(ctx context.Context, arg UpdateMediaNoteForSyncParams) (MediaNotes, error)
 	UpdateMediaRating(ctx context.Context, arg UpdateMediaRatingParams) (MediaRatings, error)
 	UpdatePassword(ctx context.Context, arg UpdatePasswordParams) error
 	UpdateReadingProgress(ctx context.Context, arg UpdateReadingProgressParams) (ReadingProgress, error)

internal/database/queries/queries.sql

@@ -696,7 +696,7 @@ RETURNING *;
 SELECT * FROM media_notes WHERE id = $1;
 
 -- name: GetMediaNotes :many
-SELECT * FROM media_notes WHERE media_item_id = $1 AND user_id = $2 ORDER BY created_at DESC;
+SELECT * FROM media_notes WHERE media_item_id = $1 AND user_id = $2 AND COALESCE(deleted, FALSE) = FALSE ORDER BY created_at DESC;
 
 -- name: UpdateMediaNote :one
 UPDATE media_notes SET
@@ -719,7 +719,7 @@ RETURNING *;
 SELECT * FROM media_highlights WHERE id = $1;
 
 -- name: GetMediaHighlights :many
-SELECT * FROM media_highlights WHERE media_item_id = $1 AND user_id = $2 ORDER BY created_at DESC;
+SELECT * FROM media_highlights WHERE media_item_id = $1 AND user_id = $2 AND COALESCE(deleted, FALSE) = FALSE ORDER BY created_at DESC;
 
 -- name: UpdateMediaHighlight :one
 UPDATE media_highlights SET
@@ -735,6 +735,251 @@ RETURNING *;
 -- name: DeleteMediaHighlight :exec
 DELETE FROM media_highlights WHERE id = $1;
 
+-- ============================================
+-- ANNOTATION SYNC QUERIES (highlights)
+-- ============================================
+
+-- name: GetMediaHighlightByDedupKey :one
+SELECT * FROM media_highlights
+WHERE user_id = $1 AND media_item_id = $2 AND dedup_key = $3
+ORDER BY deleted ASC, deleted_at DESC NULLS LAST
+LIMIT 1;
+
+-- name: CreateMediaHighlightFull :one
+INSERT INTO media_highlights (
+    media_item_id, user_id, selection_text,
+    start_position, end_position, color, note_text,
+    percentage_start, percentage_end,
+    epubcfi_start, epubcfi_end,
+    chapter_reference,
+    dedup_key, last_modified_at, last_modified_source,
+    device_sync_data
+) VALUES (
+    $1, $2, $3, $4, $5, $6, $7, $8, $9, $10, $11, $12, $13, $14, $15, $16
+) RETURNING *;
+
+-- name: UpdateMediaHighlightForSync :one
+UPDATE media_highlights SET
+    selection_text = $2,
+    start_position = $3,
+    end_position = $4,
+    color = $5,
+    note_text = $6,
+    percentage_start = $7,
+    percentage_end = $8,
+    epubcfi_start = $9,
+    epubcfi_end = $10,
+    chapter_reference = $11,
+    last_modified_at = $12,
+    last_modified_source = $13,
+    device_sync_data = $14,
+    updated_at = NOW()
+WHERE id = $1
+RETURNING *;
+
+-- name: TombstoneMediaHighlightByDedupKey :exec
+UPDATE media_highlights SET
+    deleted = TRUE,
+    deleted_at = NOW(),
+    last_modified_at = NOW()
+WHERE user_id = $1 AND media_item_id = $2 AND dedup_key = $3 AND deleted = FALSE;
+
+-- name: TombstoneMediaHighlightByID :exec
+UPDATE media_highlights SET
+    deleted = TRUE,
+    deleted_at = NOW(),
+    last_modified_at = NOW()
+WHERE id = $1;
+
+-- name: PurgeExpiredHighlightTombstones :exec
+DELETE FROM media_highlights WHERE deleted = TRUE AND deleted_at < $1;
+
+-- ============================================
+-- ANNOTATION SYNC QUERIES (notes)
+-- ============================================
+
+-- name: GetMediaNoteByDedupKey :one
+SELECT * FROM media_notes
+WHERE user_id = $1 AND media_item_id = $2 AND dedup_key = $3
+ORDER BY deleted ASC, deleted_at DESC NULLS LAST
+LIMIT 1;
+
+-- name: CreateMediaNoteFull :one
+INSERT INTO media_notes (
+    media_item_id, user_id, content, position,
+    percentage_location, character_start, character_end,
+    epubcfi_location, chapter_reference, paragraph_reference,
+    dedup_key, last_modified_at, last_modified_source,
+    device_sync_data
+) VALUES (
+    $1, $2, $3, $4, $5, $6, $7, $8, $9, $10, $11, $12, $13, $14
+) RETURNING *;
+
+-- name: UpdateMediaNoteForSync :one
+UPDATE media_notes SET
+    content = $2,
+    position = $3,
+    percentage_location = $4,
+    character_start = $5,
+    character_end = $6,
+    epubcfi_location = $7,
+    chapter_reference = $8,
+    paragraph_reference = $9,
+    last_modified_at = $10,
+    last_modified_source = $11,
+    device_sync_data = $12,
+    updated_at = NOW()
+WHERE id = $1
+RETURNING *;
+
+-- name: TombstoneMediaNoteByDedupKey :exec
+UPDATE media_notes SET
+    deleted = TRUE,
+    deleted_at = NOW(),
+    last_modified_at = NOW()
+WHERE user_id = $1 AND media_item_id = $2 AND dedup_key = $3 AND deleted = FALSE;
+
+-- name: TombstoneMediaNoteByID :exec
+UPDATE media_notes SET
+    deleted = TRUE,
+    deleted_at = NOW(),
+    last_modified_at = NOW()
+WHERE id = $1;
+
+-- name: PurgeExpiredNoteTombstones :exec
+DELETE FROM media_notes WHERE deleted = TRUE AND deleted_at < $1;
+
+-- ============================================
+-- ANNOTATION SYNC QUERIES (bookmarks)
+-- ============================================
+
+-- name: GetMediaBookmarkByDedupKey :one
+SELECT * FROM media_bookmarks
+WHERE user_id = $1 AND media_item_id = $2 AND dedup_key = $3
+ORDER BY deleted ASC, deleted_at DESC NULLS LAST
+LIMIT 1;
+
+-- name: CreateMediaBookmarkFull :one
+INSERT INTO media_bookmarks (
+    media_item_id, user_id, page_number, chapter_number,
+    cfi_position, title, position, notes,
+    percentage_location, epubcfi_location, chapter_reference,
+    dedup_key, last_modified_at, last_modified_source,
+    device_sync_data
+) VALUES (
+    $1, $2, $3, $4, $5, $6, $7, $8, $9, $10, $11, $12, $13, $14, $15
+) RETURNING *;
+
+-- name: UpdateMediaBookmarkForSync :one
+UPDATE media_bookmarks SET
+    page_number = $2,
+    chapter_number = $3,
+    cfi_position = $4,
+    title = $5,
+    position = $6,
+    notes = $7,
+    percentage_location = $8,
+    epubcfi_location = $9,
+    chapter_reference = $10,
+    last_modified_at = $11,
+    last_modified_source = $12,
+    device_sync_data = $13,
+    created_at = created_at
+WHERE id = $1
+RETURNING *;
+
+-- name: TombstoneMediaBookmarkByDedupKey :exec
+UPDATE media_bookmarks SET
+    deleted = TRUE,
+    deleted_at = NOW(),
+    last_modified_at = NOW()
+WHERE user_id = $1 AND media_item_id = $2 AND dedup_key = $3 AND deleted = FALSE;
+
+-- name: TombstoneMediaBookmarkByID :exec
+UPDATE media_bookmarks SET
+    deleted = TRUE,
+    deleted_at = NOW(),
+    last_modified_at = NOW()
+WHERE id = $1;
+
+-- name: PurgeExpiredBookmarkTombstones :exec
+DELETE FROM media_bookmarks WHERE deleted = TRUE AND deleted_at < $1;
+
+-- ============================================
+-- ANNOTATION SERVE QUERIES
+-- ============================================
+
+-- name: GetActiveAnnotationsForBook :many
+SELECT
+    mh.id,
+    mh.selection_text,
+    mh.start_position,
+    mh.end_position,
+    mh.color,
+    mh.created_at,
+    mh.updated_at,
+    'highlight' as annotation_type,
+    mh.percentage_start,
+    mh.percentage_end,
+    mh.epubcfi_start,
+    mh.epubcfi_end,
+    mh.note_text,
+    mh.dedup_key,
+    mh.last_modified_at,
+    mh.last_modified_source
+FROM media_highlights mh
+WHERE mh.media_item_id = $1 AND mh.user_id = $2 AND mh.deleted = FALSE
+UNION ALL
+SELECT
+    mn.id,
+    mn.content,
+    mn.position,
+    NULL as end_position,
+    NULL as color,
+    mn.created_at,
+    mn.updated_at,
+    'note' as annotation_type,
+    mn.percentage_location as percentage_start,
+    NULL as percentage_end,
+    mn.epubcfi_location as epubcfi_start,
+    NULL as epubcfi_end,
+    NULL as note_text,
+    mn.dedup_key,
+    mn.last_modified_at,
+    mn.last_modified_source
+FROM media_notes mn
+WHERE mn.media_item_id = $1 AND mn.user_id = $2 AND mn.deleted = FALSE
+ORDER BY created_at DESC;
+
+-- name: GetTombstonedAnnotationsForBook :many
+SELECT
+    mh.id,
+    mh.dedup_key,
+    'highlight' as annotation_type,
+    mh.device_sync_data,
+    mh.deleted_at
+FROM media_highlights mh
+WHERE mh.media_item_id = $1 AND mh.user_id = $2 AND mh.deleted = TRUE AND mh.deleted_at > $3
+UNION ALL
+SELECT
+    mn.id,
+    mn.dedup_key,
+    'note' as annotation_type,
+    mn.device_sync_data,
+    mn.deleted_at
+FROM media_notes mn
+WHERE mn.media_item_id = $1 AND mn.user_id = $2 AND mn.deleted = TRUE AND mn.deleted_at > $3
+UNION ALL
+SELECT
+    mb.id,
+    mb.dedup_key,
+    'bookmark' as annotation_type,
+    mb.device_sync_data,
+    mb.deleted_at
+FROM media_bookmarks mb
+WHERE mb.media_item_id = $1 AND mb.user_id = $2 AND mb.deleted = TRUE AND mb.deleted_at > $3
+ORDER BY deleted_at DESC;
+
 -- Refresh Tokens queries
 -- name: CreateRefreshToken :one
 INSERT INTO refresh_tokens (user_id, token, expires_at)
@@ -1126,6 +1371,11 @@ INSERT INTO sync_conflicts (media_item_id, user_id, conflict_type, conflict_data
 VALUES ($1, $2, $3, $4)
 RETURNING *;
 
+-- name: CreateAutoResolvedSyncConflict :one
+INSERT INTO sync_conflicts (media_item_id, user_id, conflict_type, conflict_data, resolution_status, resolution_data, resolved_at)
+VALUES ($1, $2, $3, $4, 'auto_resolved', $5, NOW())
+RETURNING *;
+
 -- name: GetSyncConflict :one
 SELECT * FROM sync_conflicts WHERE id = $1;
 
@@ -1225,7 +1475,7 @@ SELECT
     mh.epubcfi_start,
     mh.epubcfi_end
 FROM media_highlights mh
-WHERE mh.media_item_id = $1 AND mh.user_id = $2
+WHERE mh.media_item_id = $1 AND mh.user_id = $2 AND COALESCE(mh.deleted, FALSE) = FALSE
 UNION ALL
 SELECT
     mn.id,
@@ -1241,7 +1491,7 @@ SELECT
     mn.epubcfi_location as epubcfi_start,
     NULL as epubcfi_end
 FROM media_notes mn
-WHERE mn.media_item_id = $1 AND mn.user_id = $2
+WHERE mn.media_item_id = $1 AND mn.user_id = $2 AND COALESCE(mn.deleted, FALSE) = FALSE
 ORDER BY created_at DESC;
 
 -- name: UpdateDeviceSyncTimestamp :one
@@ -2112,9 +2362,12 @@ RETURNING *;
 
 -- name: GetMediaBookmarks :many
 SELECT * FROM media_bookmarks
-WHERE media_item_id = $1 AND user_id = $2
+WHERE media_item_id = $1 AND user_id = $2 AND COALESCE(deleted, FALSE) = FALSE
 ORDER BY created_at DESC;
 
+-- name: GetMediaBookmark :one
+SELECT * FROM media_bookmarks WHERE id = $1;
+
 -- name: CreateMediaBookmark :one
 INSERT INTO media_bookmarks (media_item_id, user_id, page_number, chapter_number, cfi_position, title, position, notes)
 VALUES ($1, $2, $3, $4, $5, $6, $7, $8)