diff --git a/lib/providers/download_queue_provider.dart b/lib/providers/download_queue_provider.dart
index a01b8e8..6f983bf 100644
--- a/lib/providers/download_queue_provider.dart
+++ b/lib/providers/download_queue_provider.dart
@@ -770,6 +770,37 @@ class DownloadHistoryNotifier extends Notifier<DownloadHistoryState> {
 
   /// Remove history entries where the file no longer exists on disk
   /// Returns the number of orphaned entries removed
+  /// Audio file extensions that the app commonly produces or converts between.
+  static const _audioExtensions = [
+    '.flac',
+    '.m4a',
+    '.mp3',
+    '.opus',
+    '.ogg',
+    '.wav',
+    '.aac',
+  ];
+
+  /// When the original file is missing, check whether a sibling with a
+  /// different audio extension exists (e.g. the user converted .flac → .opus).
+  /// Returns the path of the first match found, or `null` if none exist.
+  Future<String?> _findConvertedSibling(String originalPath) async {
+    // Strip the current extension to get the base path.
+    final dotIndex = originalPath.lastIndexOf('.');
+    if (dotIndex < 0) return null;
+    final basePath = originalPath.substring(0, dotIndex);
+    final originalExt = originalPath.substring(dotIndex).toLowerCase();
+
+    for (final ext in _audioExtensions) {
+      if (ext == originalExt) continue;
+      final candidatePath = '$basePath$ext';
+      try {
+        if (await fileExists(candidatePath)) return candidatePath;
+      } catch (_) {}
+    }
+    return null;
+  }
+
   Future<int> cleanupOrphanedDownloads() async {
     _historyLog.i('Starting orphaned downloads cleanup...');
 
@@ -791,7 +822,21 @@ class DownloadHistoryNotifier extends Notifier<DownloadHistoryState> {
           if (filePath == null || filePath.isEmpty) return null;
           pathById[id] = filePath;
           try {
-            return MapEntry(id, await fileExists(filePath));
+            if (await fileExists(filePath)) return MapEntry(id, true);
+
+            // Original file missing -- check for a converted sibling.
+            final sibling = await _findConvertedSibling(filePath);
+            if (sibling != null) {
+              _historyLog.i(
+                'Found converted sibling for $id: $filePath → $sibling',
+              );
+              // Update the stored path so future checks succeed immediately.
+              await _db.updateFilePath(id, sibling);
+              pathById[id] = sibling;
+              return MapEntry(id, true);
+            }
+
+            return MapEntry(id, false);
           } catch (e) {
             _historyLog.w('Error checking file existence for $id: $e');
             return MapEntry(id, false);
diff --git a/lib/utils/path_match_keys.dart b/lib/utils/path_match_keys.dart
index ace140d..0df1c02 100644
--- a/lib/utils/path_match_keys.dart
+++ b/lib/utils/path_match_keys.dart
@@ -8,6 +8,33 @@ const _androidStoragePathAliases = <String>[
   '/mnt/sdcard',
 ];
 
+/// Audio file extensions that the app commonly produces or converts between.
+/// Used to generate extension-stripped match keys so that a file converted from
+/// one format to another (e.g. .flac → .opus) is still recognised as the same
+/// track.
+const _audioExtensions = <String>[
+  '.flac',
+  '.m4a',
+  '.mp3',
+  '.opus',
+  '.ogg',
+  '.wav',
+  '.aac',
+];
+
+/// Strips a trailing audio extension from [path] if present.
+/// Returns the path without extension, or `null` if no known audio extension
+/// was found.
+String? _stripAudioExtension(String path) {
+  final lower = path.toLowerCase();
+  for (final ext in _audioExtensions) {
+    if (lower.endsWith(ext)) {
+      return path.substring(0, path.length - ext.length);
+    }
+  }
+  return null;
+}
+
 Set<String> buildPathMatchKeys(String? filePath) {
   final raw = filePath?.trim() ?? '';
   if (raw.isEmpty) return const {};
@@ -79,6 +106,18 @@ Set<String> buildPathMatchKeys(String? filePath) {
   }
 
   addNormalized(cleaned);
+
+  // Add extension-stripped variants so that a file converted from one audio
+  // format to another (e.g. Song.flac → Song.opus) still matches.
+  final extensionStrippedKeys = <String>{};
+  for (final key in keys) {
+    final stripped = _stripAudioExtension(key);
+    if (stripped != null && stripped.isNotEmpty) {
+      extensionStrippedKeys.add(stripped);
+    }
+  }
+  keys.addAll(extensionStrippedKeys);
+
   return keys;
 }