diff --git a/allstarr/Controllers/JellyfinController.cs b/allstarr/Controllers/JellyfinController.cs
index 2e43adc..790b2c7 100644
--- a/allstarr/Controllers/JellyfinController.cs
+++ b/allstarr/Controllers/JellyfinController.cs
@@ -2973,12 +2973,13 @@ public class JellyfinController : ControllerBase
             }
             
             // ONLY if no local track exists, check for external match
-            var matched = orderedTracks.FirstOrDefault(t => t.SpotifyId == spotifyTrack.SpotifyId);
+            // First check pre-matched cache
+            var matched = orderedTracks?.FirstOrDefault(t => t.SpotifyId == spotifyTrack.SpotifyId);
             if (matched != null)
             {
                 finalTracks.Add(matched.MatchedSong);
                 externalUsedCount++;
-                _logger.LogInformation("📥 #{Pos} '{Title}' by {Artist} → EXTERNAL: {Provider}/{Id}", 
+                _logger.LogInformation("📥 #{Pos} '{Title}' by {Artist} → EXTERNAL (cached): {Provider}/{Id}", 
                     spotifyTrack.Position, 
                     spotifyTrack.Title, 
                     spotifyTrack.PrimaryArtist,
@@ -2987,9 +2988,65 @@ public class JellyfinController : ControllerBase
             }
             else
             {
-                skippedCount++;
-                _logger.LogWarning("❌ #{Pos} '{Title}' by {Artist} → NO MATCH (not in Jellyfin, not in external cache)", 
-                    spotifyTrack.Position, spotifyTrack.Title, spotifyTrack.PrimaryArtist);
+                // No cached match - search external providers on-demand
+                try
+                {
+                    var query = $"{spotifyTrack.Title} {spotifyTrack.PrimaryArtist}";
+                    var searchResults = await _metadataService.SearchSongsAsync(query, limit: 5);
+                    
+                    if (searchResults.Count > 0)
+                    {
+                        // Fuzzy match to find best result
+                        var bestExternalMatch = searchResults
+                            .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 * 0.6) + (x.ArtistScore * 0.4)
+                            })
+                            .OrderByDescending(x => x.TotalScore)
+                            .FirstOrDefault();
+                        
+                        if (bestExternalMatch != null && bestExternalMatch.TotalScore >= 60)
+                        {
+                            finalTracks.Add(bestExternalMatch.Song);
+                            externalUsedCount++;
+                            _logger.LogInformation("📥 #{Pos} '{Title}' by {Artist} → EXTERNAL (on-demand): {Provider}/{Id} (score: {Score:F1}%)", 
+                                spotifyTrack.Position, 
+                                spotifyTrack.Title, 
+                                spotifyTrack.PrimaryArtist,
+                                bestExternalMatch.Song.ExternalProvider, 
+                                bestExternalMatch.Song.ExternalId,
+                                bestExternalMatch.TotalScore);
+                        }
+                        else
+                        {
+                            skippedCount++;
+                            _logger.LogWarning("❌ #{Pos} '{Title}' by {Artist} → NO MATCH (best external score: {Score:F1}%, need 60%)", 
+                                spotifyTrack.Position, spotifyTrack.Title, spotifyTrack.PrimaryArtist,
+                                bestExternalMatch?.TotalScore ?? 0);
+                        }
+                    }
+                    else
+                    {
+                        skippedCount++;
+                        _logger.LogWarning("❌ #{Pos} '{Title}' by {Artist} → NO MATCH (no external results)", 
+                            spotifyTrack.Position, spotifyTrack.Title, spotifyTrack.PrimaryArtist);
+                    }
+                }
+                catch (Exception ex)
+                {
+                    skippedCount++;
+                    _logger.LogError(ex, "❌ #{Pos} '{Title}' by {Artist} → ERROR searching external providers", 
+                        spotifyTrack.Position, spotifyTrack.Title, spotifyTrack.PrimaryArtist);
+                }
             }
         }