diff --git a/allstarr/Services/Spotify/SpotifyTrackMatchingService.cs b/allstarr/Services/Spotify/SpotifyTrackMatchingService.cs
index 399c0f4..c130734 100644
--- a/allstarr/Services/Spotify/SpotifyTrackMatchingService.cs
+++ b/allstarr/Services/Spotify/SpotifyTrackMatchingService.cs
@@ -2,6 +2,7 @@ using allstarr.Models.Domain;
 using allstarr.Models.Settings;
 using allstarr.Models.Spotify;
 using allstarr.Services.Common;
+using allstarr.Services.Jellyfin;
 using Microsoft.Extensions.Options;
 using System.Text.Json;
 
@@ -146,6 +147,7 @@ public class SpotifyTrackMatchingService : BackgroundService
     /// <summary>
     /// New matching mode that uses ISRC when available for exact matches.
     /// Preserves track position for correct playlist ordering.
+    /// Only matches tracks that aren't already in the Jellyfin playlist.
     /// </summary>
     private async Task MatchPlaylistTracksWithIsrcAsync(
         string playlistName,
@@ -163,25 +165,84 @@ public class SpotifyTrackMatchingService : BackgroundService
             return;
         }
         
+        // Get the Jellyfin playlist ID to check which tracks already exist
+        var playlistConfig = _spotifySettings.Playlists
+            .FirstOrDefault(p => p.Name.Equals(playlistName, StringComparison.OrdinalIgnoreCase));
+        
+        HashSet<string> existingSpotifyIds = new();
+        
+        if (!string.IsNullOrEmpty(playlistConfig?.JellyfinId))
+        {
+            // Get existing tracks from Jellyfin playlist to avoid re-matching
+            using var scope = _serviceProvider.CreateScope();
+            var proxyService = scope.ServiceProvider.GetService<JellyfinProxyService>();
+            
+            if (proxyService != null)
+            {
+                try
+                {
+                    var (existingTracksResponse, _) = await proxyService.GetJsonAsync(
+                        $"Playlists/{playlistConfig.JellyfinId}/Items", 
+                        null, 
+                        null);
+                    
+                    if (existingTracksResponse != null && 
+                        existingTracksResponse.RootElement.TryGetProperty("Items", out var items))
+                    {
+                        foreach (var item in items.EnumerateArray())
+                        {
+                            if (item.TryGetProperty("ProviderIds", out var providerIds) &&
+                                providerIds.TryGetProperty("Spotify", out var spotifyId))
+                            {
+                                var id = spotifyId.GetString();
+                                if (!string.IsNullOrEmpty(id))
+                                {
+                                    existingSpotifyIds.Add(id);
+                                }
+                            }
+                        }
+                        _logger.LogInformation("Found {Count} tracks already in Jellyfin playlist {Playlist}, will skip matching these", 
+                            existingSpotifyIds.Count, playlistName);
+                    }
+                }
+                catch (Exception ex)
+                {
+                    _logger.LogWarning(ex, "Could not fetch existing Jellyfin tracks for {Playlist}, will match all tracks", playlistName);
+                }
+            }
+        }
+        
+        // Filter to only tracks not already in Jellyfin
+        var tracksToMatch = spotifyTracks
+            .Where(t => !existingSpotifyIds.Contains(t.SpotifyId))
+            .ToList();
+        
+        if (tracksToMatch.Count == 0)
+        {
+            _logger.LogInformation("All {Count} tracks for {Playlist} already exist in Jellyfin, skipping matching", 
+                spotifyTracks.Count, playlistName);
+            return;
+        }
+        
+        _logger.LogInformation("Matching {ToMatch}/{Total} tracks for {Playlist} (skipping {Existing} already in Jellyfin, ISRC: {IsrcEnabled})", 
+            tracksToMatch.Count, spotifyTracks.Count, playlistName, existingSpotifyIds.Count, _spotifyApiSettings.PreferIsrcMatching);
+        
         // Check cache - use snapshot/timestamp to detect changes
         var existingMatched = await _cache.GetAsync<List<MatchedTrack>>(matchedTracksKey);
-        if (existingMatched != null && existingMatched.Count == spotifyTracks.Count)
+        if (existingMatched != null && existingMatched.Count >= tracksToMatch.Count)
         {
             _logger.LogInformation("Playlist {Playlist} already has {Count} matched tracks cached, skipping", 
                 playlistName, existingMatched.Count);
             return;
         }
 
-        _logger.LogInformation("Matching {Count} tracks for {Playlist} (ISRC: {IsrcEnabled})", 
-            spotifyTracks.Count, playlistName, _spotifyApiSettings.PreferIsrcMatching);
-
         var matchedTracks = new List<MatchedTrack>();
         var isrcMatches = 0;
         var fuzzyMatches = 0;
         var noMatch = 0;
 
         // Process tracks in batches for parallel searching
-        var orderedTracks = spotifyTracks.OrderBy(t => t.Position).ToList();
+        var orderedTracks = tracksToMatch.OrderBy(t => t.Position).ToList();
         for (int i = 0; i < orderedTracks.Count; i += BatchSize)
         {
             if (cancellationToken.IsCancellationRequested) break;
@@ -293,7 +354,7 @@ public class SpotifyTrackMatchingService : BackgroundService
             
             _logger.LogInformation(
                 "✓ Cached {Matched}/{Total} tracks for {Playlist} (ISRC: {Isrc}, Fuzzy: {Fuzzy}, No match: {NoMatch})", 
-                matchedTracks.Count, spotifyTracks.Count, playlistName, isrcMatches, fuzzyMatches, noMatch);
+                matchedTracks.Count, tracksToMatch.Count, playlistName, isrcMatches, fuzzyMatches, noMatch);
         }
         else
         {