diff --git a/allstarr/Controllers/JellyfinController.cs b/allstarr/Controllers/JellyfinController.cs
index bbb096c..b64655b 100644
--- a/allstarr/Controllers/JellyfinController.cs
+++ b/allstarr/Controllers/JellyfinController.cs
@@ -2860,20 +2860,26 @@ public class JellyfinController : ControllerBase
         var userId = _settings.UserId;
         if (string.IsNullOrEmpty(userId))
         {
-            _logger.LogWarning("No UserId configured - attempting to fetch existing playlist tracks may fail");
+            _logger.LogError("❌ JELLYFIN_USER_ID is NOT configured! Cannot fetch playlist tracks. Set it in .env or admin UI.");
+            return null; // Fall back to legacy mode
         }
         
-        var playlistItemsUrl = $"Playlists/{playlistId}/Items";
-        if (!string.IsNullOrEmpty(userId))
-        {
-            playlistItemsUrl += $"?UserId={userId}";
-        }
+        var playlistItemsUrl = $"Playlists/{playlistId}/Items?UserId={userId}";
         
-        var (existingTracksResponse, _) = await _proxyService.GetJsonAsync(
+        _logger.LogInformation("🔍 Fetching existing tracks from Jellyfin playlist {PlaylistId} with UserId {UserId}", 
+            playlistId, userId);
+        
+        var (existingTracksResponse, statusCode) = await _proxyService.GetJsonAsync(
             playlistItemsUrl, 
             null, 
             Request.Headers);
         
+        if (statusCode != 200)
+        {
+            _logger.LogError("❌ Failed to fetch Jellyfin playlist items: HTTP {StatusCode}. Check JELLYFIN_USER_ID is correct.", statusCode);
+            return null;
+        }
+        
         var existingTracks = new List<Song>();
         var existingBySpotifyId = new Dictionary<string, Song>(); // SpotifyId -> Song
         var existingByIsrc = new Dictionary<string, Song>(); // ISRC -> Song
@@ -2894,7 +2900,7 @@ public class JellyfinController : ControllerBase
                     if (!string.IsNullOrEmpty(spotifyId))
                     {
                         existingBySpotifyId[spotifyId] = song;
-                        _logger.LogDebug("Indexed local track by Spotify ID: {SpotifyId} -> {Title}", spotifyId, song.Title);
+                        _logger.LogDebug("  📌 Indexed local track by Spotify ID: {SpotifyId} -> {Title}", spotifyId, song.Title);
                     }
                 }
                 
@@ -2902,15 +2908,16 @@ public class JellyfinController : ControllerBase
                 if (!string.IsNullOrEmpty(song.Isrc))
                 {
                     existingByIsrc[song.Isrc] = song;
-                    _logger.LogDebug("Indexed local track by ISRC: {Isrc} -> {Title}", song.Isrc, song.Title);
+                    _logger.LogDebug("  📌 Indexed local track by ISRC: {Isrc} -> {Title}", song.Isrc, song.Title);
                 }
             }
-            _logger.LogInformation("Found {Count} existing tracks in Jellyfin playlist ({SpotifyIds} with Spotify IDs, {Isrcs} with ISRCs)", 
+            _logger.LogInformation("✅ Found {Count} existing tracks in Jellyfin playlist ({SpotifyIds} with Spotify IDs, {Isrcs} with ISRCs)", 
                 existingTracks.Count, existingBySpotifyId.Count, existingByIsrc.Count);
         }
         else
         {
-            _logger.LogWarning("No existing tracks found in Jellyfin playlist {PlaylistId} - may need UserId parameter", playlistId);
+            _logger.LogError("❌ No existing tracks found in Jellyfin playlist {PlaylistId} - Jellyfin Spotify Import plugin may not have run yet", playlistId);
+            return null;
         }
         
         // Get the full playlist from Spotify to know the correct order
@@ -2930,7 +2937,7 @@ public class JellyfinController : ControllerBase
         {
             Song? localTrack = null;
             
-            // Try to find local track by Spotify ID first (fastest)
+            // Try to find local track by Spotify ID first (fastest and most reliable)
             if (existingBySpotifyId.TryGetValue(spotifyTrack.SpotifyId, out var trackBySpotifyId))
             {
                 localTrack = trackBySpotifyId;
@@ -2945,6 +2952,34 @@ public class JellyfinController : ControllerBase
                 _logger.LogDebug("#{Pos} {Title} - Found LOCAL by ISRC: {Isrc}", 
                     spotifyTrack.Position, spotifyTrack.Title, spotifyTrack.Isrc);
             }
+            // Fallback: Match by title + artist name (like Jellyfin Spotify Import plugin does)
+            else
+            {
+                var bestMatch = existingTracks
+                    .Select(song => new
+                    {
+                        Song = song,
+                        TitleScore = FuzzyMatcher.CalculateSimilarity(spotifyTrack.Title, song.Title),
+                        ArtistScore = FuzzyMatcher.CalculateSimilarity(spotifyTrack.PrimaryArtist, song.Artist)
+                    })
+                    .Select(x => new
+                    {
+                        x.Song,
+                        x.TitleScore,
+                        x.ArtistScore,
+                        TotalScore = (x.TitleScore * 0.7) + (x.ArtistScore * 0.3) // Weight title more
+                    })
+                    .OrderByDescending(x => x.TotalScore)
+                    .FirstOrDefault();
+                
+                // Only use if match is good enough (>75% combined score)
+                if (bestMatch != null && bestMatch.TotalScore >= 75)
+                {
+                    localTrack = bestMatch.Song;
+                    _logger.LogDebug("#{Pos} {Title} - Found LOCAL by fuzzy match: {MatchTitle} (score: {Score:F1})", 
+                        spotifyTrack.Position, spotifyTrack.Title, bestMatch.Song.Title, bestMatch.TotalScore);
+                }
+            }
             
             // If we found a local track, use it
             if (localTrack != null)