diff --git a/lib/db/photo_db.dart b/lib/db/photo_db.dart
index 2027f5a65..cae5bad6d 100644
--- a/lib/db/photo_db.dart
+++ b/lib/db/photo_db.dart
@@ -133,14 +133,21 @@ class PhotoDB {
     return _convertToPhotos(results);
   }
 
-  Future<Photo> getMatchingPhoto(String localId, String title,
-      String deviceFolder, int createTimestamp) async {
+  Future<Photo> getMatchingPhoto(
+      String localId, String title, String deviceFolder, int createTimestamp,
+      {String alternateTitle}) async {
     final db = await instance.database;
     final rows = await db.query(
       table,
-      where:
-          '$columnLocalId=? AND $columnTitle=? AND $columnDeviceFolder=? AND $columnCreateTimestamp=?',
-      whereArgs: [localId, title, deviceFolder, createTimestamp],
+      where: '''$columnLocalId=? AND ($columnTitle=? OR $columnTitle=?) AND 
+          $columnDeviceFolder=? AND $columnCreateTimestamp=?''',
+      whereArgs: [
+        localId,
+        title,
+        alternateTitle,
+        deviceFolder,
+        createTimestamp
+      ],
     );
     if (rows.isNotEmpty) {
       return _getPhotoFromRow(rows[0]);
diff --git a/lib/face_search_manager.dart b/lib/face_search_manager.dart
index 6e6692b9d..cbf14c1d4 100644
--- a/lib/face_search_manager.dart
+++ b/lib/face_search_manager.dart
@@ -5,6 +5,7 @@ import 'package:logging/logging.dart';
 
 import 'package:photos/models/face.dart';
 import 'package:photos/models/photo.dart';
+import 'package:photos/utils/file_name_util.dart';
 
 class FaceSearchManager {
   final _logger = Logger("FaceSearchManager");
@@ -48,7 +49,8 @@ class FaceSearchManager {
     for (Photo photo in result) {
       try {
         photos.add(await PhotoDB.instance.getMatchingPhoto(photo.localId,
-            photo.title, photo.deviceFolder, photo.createTimestamp));
+            photo.title, photo.deviceFolder, photo.createTimestamp,
+            alternateTitle: getHEICFileNameForJPG(photo)));
       } catch (e) {
         // Not available locally
         photos.add(photo);
diff --git a/lib/photo_sync_manager.dart b/lib/photo_sync_manager.dart
index 418973694..8af5418c1 100644
--- a/lib/photo_sync_manager.dart
+++ b/lib/photo_sync_manager.dart
@@ -10,9 +10,9 @@ import 'package:photos/events/user_authenticated_event.dart';
 import 'package:photos/photo_repository.dart';
 import 'package:path_provider/path_provider.dart';
 import 'package:photo_manager/photo_manager.dart';
+import 'package:photos/utils/file_name_util.dart';
 import 'package:shared_preferences/shared_preferences.dart';
 import 'package:dio/dio.dart';
-import 'package:path/path.dart';
 import 'package:photos/models/photo.dart';
 
 import 'package:photos/core/configuration.dart';
@@ -166,8 +166,7 @@ class PhotoSyncManager {
   }
 
   Future<void> _downloadDiff(SharedPreferences prefs) async {
-    int lastSyncTimestamp = _getLastSyncTimestamp(prefs);
-    var diff = await _getDiff(lastSyncTimestamp, _diffLimit);
+    var diff = await _getDiff(_getLastSyncTimestamp(prefs), _diffLimit);
     if (diff != null && diff.isNotEmpty) {
       await _storeDiff(diff, prefs);
       PhotoRepository.instance.reloadPhotos();
@@ -209,12 +208,15 @@ class PhotoSyncManager {
     for (Photo photo in diff) {
       try {
         var existingPhoto = await _db.getMatchingPhoto(photo.localId,
-            photo.title, photo.deviceFolder, photo.createTimestamp);
+            photo.title, photo.deviceFolder, photo.createTimestamp,
+            alternateTitle: getHEICFileNameForJPG(photo));
         await _db.updatePhoto(existingPhoto.generatedId, photo.uploadedFileId,
             photo.remotePath, photo.updateTimestamp, photo.thumbnailPath);
       } catch (e) {
         await _db.insertPhoto(photo);
       }
+      // _logger.info(
+      //     "Setting update timestamp to " + photo.updateTimestamp.toString());
       await prefs.setInt(_lastSyncTimestampKey, photo.updateTimestamp);
     }
   }
@@ -241,9 +243,7 @@ class PhotoSyncManager {
   }
 
   Future<Photo> _uploadFile(Photo localPhoto) async {
-    var title = extension(localPhoto.title) == ".HEIC"
-        ? basenameWithoutExtension(localPhoto.title) + ".JPG"
-        : localPhoto.title;
+    var title = getJPGFileNameForHEIC(localPhoto);
     var formData = FormData.fromMap({
       "file": MultipartFile.fromBytes((await localPhoto.getBytes()),
           filename: title),
diff --git a/lib/utils/file_name_util.dart b/lib/utils/file_name_util.dart
new file mode 100644
index 000000000..6661694b8
--- /dev/null
+++ b/lib/utils/file_name_util.dart
@@ -0,0 +1,14 @@
+import 'package:photos/models/photo.dart';
+import 'package:path/path.dart';
+
+String getJPGFileNameForHEIC(Photo photo) {
+  return extension(photo.title) == ".HEIC"
+      ? basenameWithoutExtension(photo.title) + ".JPG"
+      : photo.title;
+}
+
+String getHEICFileNameForJPG(Photo photo) {
+  return extension(photo.title) == ".JPG"
+      ? basenameWithoutExtension(photo.title) + ".HEIC"
+      : photo.title;
+}