diff --git a/allstarr/Controllers/JellyfinController.cs b/allstarr/Controllers/JellyfinController.cs
index c6e8dbd..d4abc15 100644
--- a/allstarr/Controllers/JellyfinController.cs
+++ b/allstarr/Controllers/JellyfinController.cs
@@ -3096,6 +3096,54 @@ public class JellyfinController : ControllerBase
         return Ok(results);
     }
     
+    /// <summary>
+    /// Manually trigger track matching for all Spotify playlists.
+    /// GET /spotify/match?api_key=YOUR_KEY
+    /// </summary>
+    [HttpGet("spotify/match", Order = 1)]
+    [ServiceFilter(typeof(ApiKeyAuthFilter))]
+    public async Task<IActionResult> TriggerSpotifyMatch([FromServices] IEnumerable<IHostedService> hostedServices)
+    {
+        if (!_spotifySettings.Enabled)
+        {
+            return BadRequest(new { error = "Spotify Import is not enabled" });
+        }
+
+        _logger.LogInformation("Manual Spotify track matching triggered");
+        
+        // Find the SpotifyTrackMatchingService
+        var matchingService = hostedServices
+            .OfType<allstarr.Services.Spotify.SpotifyTrackMatchingService>()
+            .FirstOrDefault();
+        
+        if (matchingService == null)
+        {
+            return StatusCode(500, new { error = "SpotifyTrackMatchingService not found" });
+        }
+        
+        // Trigger matching asynchronously
+        _ = Task.Run(async () =>
+        {
+            try
+            {
+                await matchingService.TriggerMatchingAsync();
+            }
+            catch (Exception ex)
+            {
+                _logger.LogError(ex, "Error during manual track matching");
+            }
+        });
+        
+        return Ok(new 
+        { 
+            status = "started",
+            message = "Track matching started in background. Check logs for progress.",
+            playlists = _spotifySettings.PlaylistNames.Count > 0 
+                ? _spotifySettings.PlaylistNames 
+                : _spotifySettings.PlaylistIds
+        });
+    }
+    
     private List<allstarr.Models.Spotify.MissingTrack> ParseMissingTracksJson(string json)
     {
         var tracks = new List<allstarr.Models.Spotify.MissingTrack>();
diff --git a/allstarr/Services/Spotify/SpotifyMissingTracksFetcher.cs b/allstarr/Services/Spotify/SpotifyMissingTracksFetcher.cs
index 85a8235..97ff395 100644
--- a/allstarr/Services/Spotify/SpotifyMissingTracksFetcher.cs
+++ b/allstarr/Services/Spotify/SpotifyMissingTracksFetcher.cs
@@ -72,28 +72,19 @@ public class SpotifyMissingTracksFetcher : BackgroundService
         }
         _logger.LogInformation("========================================");
 
-        // Run once on startup if we haven't run in the last 24 hours
+        // Always run once on startup to ensure we have missing tracks
         if (!_hasRunOnce)
         {
-            var shouldRunOnStartup = await ShouldRunOnStartupAsync();
-            if (shouldRunOnStartup)
+            _logger.LogInformation("Running initial fetch on startup");
+            try
             {
-                _logger.LogInformation("Running initial fetch on startup (bypassing sync window check)");
-                try
-                {
-                    await FetchMissingTracksAsync(stoppingToken, bypassSyncWindowCheck: true);
-                    _hasRunOnce = true;
-                }
-                catch (Exception ex)
-                {
-                    _logger.LogError(ex, "Error during startup fetch");
-                }
-            }
-            else
-            {
-                _logger.LogInformation("Skipping startup fetch - already have recent cache");
+                await FetchMissingTracksAsync(stoppingToken, bypassSyncWindowCheck: true);
                 _hasRunOnce = true;
             }
+            catch (Exception ex)
+            {
+                _logger.LogError(ex, "Error during startup fetch");
+            }
         }
 
         while (!stoppingToken.IsCancellationRequested)
diff --git a/allstarr/Services/Spotify/SpotifyTrackMatchingService.cs b/allstarr/Services/Spotify/SpotifyTrackMatchingService.cs
index f00f2c5..edc2ee4 100644
--- a/allstarr/Services/Spotify/SpotifyTrackMatchingService.cs
+++ b/allstarr/Services/Spotify/SpotifyTrackMatchingService.cs
@@ -44,6 +44,17 @@ public class SpotifyTrackMatchingService : BackgroundService
         // Wait a bit for the fetcher to run first
         await Task.Delay(TimeSpan.FromMinutes(2), stoppingToken);
 
+        // Run once on startup to match any existing missing tracks
+        try
+        {
+            _logger.LogInformation("Running initial track matching on startup");
+            await MatchAllPlaylistsAsync(stoppingToken);
+        }
+        catch (Exception ex)
+        {
+            _logger.LogError(ex, "Error during startup track matching");
+        }
+
         while (!stoppingToken.IsCancellationRequested)
         {
             try
@@ -60,6 +71,15 @@ public class SpotifyTrackMatchingService : BackgroundService
         }
     }
 
+    /// <summary>
+    /// Public method to trigger matching manually (called from controller).
+    /// </summary>
+    public async Task TriggerMatchingAsync()
+    {
+        _logger.LogInformation("Manual track matching triggered");
+        await MatchAllPlaylistsAsync(CancellationToken.None);
+    }
+
     private async Task MatchAllPlaylistsAsync(CancellationToken cancellationToken)
     {
         _logger.LogInformation("=== STARTING TRACK MATCHING ===");
@@ -103,7 +123,7 @@ public class SpotifyTrackMatchingService : BackgroundService
         var existingMatched = await _cache.GetAsync<List<Song>>(matchedTracksKey);
         if (existingMatched != null && existingMatched.Count > 0)
         {
-            _logger.LogDebug("Playlist {Playlist} already has {Count} matched tracks cached, skipping", 
+            _logger.LogInformation("Playlist {Playlist} already has {Count} matched tracks cached, skipping", 
                 playlistName, existingMatched.Count);
             return;
         }
@@ -112,7 +132,7 @@ public class SpotifyTrackMatchingService : BackgroundService
         var missingTracks = await _cache.GetAsync<List<MissingTrack>>(missingTracksKey);
         if (missingTracks == null || missingTracks.Count == 0)
         {
-            _logger.LogDebug("No missing tracks found for {Playlist}, skipping matching", playlistName);
+            _logger.LogInformation("No missing tracks found for {Playlist}, skipping matching", playlistName);
             return;
         }
 
@@ -158,7 +178,7 @@ public class SpotifyTrackMatchingService : BackgroundService
                         
                         if (matchCount % 10 == 0)
                         {
-                            _logger.LogDebug("Matched {Count}/{Total} tracks for {Playlist}", 
+                            _logger.LogInformation("Matched {Count}/{Total} tracks for {Playlist}", 
                                 matchCount, missingTracks.Count, playlistName);
                         }
                     }