diff --git a/allstarr/Services/Spotify/SpotifyMissingTracksFetcher.cs b/allstarr/Services/Spotify/SpotifyMissingTracksFetcher.cs
index 0143fee..3d46347 100644
--- a/allstarr/Services/Spotify/SpotifyMissingTracksFetcher.cs
+++ b/allstarr/Services/Spotify/SpotifyMissingTracksFetcher.cs
@@ -146,12 +146,13 @@ public class SpotifyMissingTracksFetcher : BackgroundService
             .AddMinutes(settings.SyncStartMinute);
         var syncEnd = syncStart.AddHours(settings.SyncWindowHours);
 
-        if (now < syncStart || now > syncEnd)
+        // Only run after the sync window has passed
+        if (now < syncEnd)
         {
             return;
         }
 
-        _logger.LogInformation("Within sync window, fetching missing tracks...");
+        _logger.LogInformation("Sync window passed, searching last 24 hours for missing tracks...");
 
         foreach (var kvp in _playlistIdToName)
         {
@@ -175,46 +176,106 @@ public class SpotifyMissingTracksFetcher : BackgroundService
         var jellyfinUrl = _jellyfinSettings.Value.Url;
         var apiKey = _jellyfinSettings.Value.ApiKey;
         var httpClient = _httpClientFactory.CreateClient();
-        var today = DateTime.UtcNow.Date;
-        var syncStart = today
+        
+        // Start from the configured sync time (most likely time)
+        var now = DateTime.UtcNow;
+        var todaySync = now.Date
             .AddHours(settings.SyncStartHour)
             .AddMinutes(settings.SyncStartMinute);
-        var syncEnd = syncStart.AddHours(settings.SyncWindowHours);
+        
+        // If we haven't reached today's sync time yet, start from yesterday's sync time
+        var syncTime = now >= todaySync ? todaySync : todaySync.AddDays(-1);
 
-        _logger.LogInformation("Searching for missing tracks file for {Playlist}", playlistName);
+        _logger.LogInformation("Searching ±12 hours around {SyncTime} for {Playlist}", 
+            syncTime, playlistName);
 
-        for (var time = syncStart; time <= syncEnd; time = time.AddMinutes(5))
+        var found = false;
+        
+        // Search forward 12 hours from sync time
+        for (var minutesAhead = 0; minutesAhead <= 720; minutesAhead++) // 720 minutes = 12 hours
         {
             if (cancellationToken.IsCancellationRequested) break;
 
-            var filename = $"{playlistName}_missing_{time:yyyy-MM-dd_HH-mm}.json";
-            var url = $"{jellyfinUrl}/Viperinius.Plugin.SpotifyImport/MissingTracksFile" +
-                     $"?name={Uri.EscapeDataString(filename)}&api_key={apiKey}";
-
-            try
+            var time = syncTime.AddMinutes(minutesAhead);
+            if (await TryFetchMissingTracksFile(playlistName, time, jellyfinUrl, apiKey, httpClient, cancellationToken))
             {
-                _logger.LogDebug("Trying {Filename}", filename);
-                var response = await httpClient.GetAsync(url, cancellationToken);
-                if (response.IsSuccessStatusCode)
-                {
-                    var json = await response.Content.ReadAsStringAsync(cancellationToken);
-                    var tracks = ParseMissingTracks(json);
-                    
-                    if (tracks.Count > 0)
-                    {
-                        await _cache.SetAsync(cacheKey, tracks, TimeSpan.FromHours(24));
-                        _logger.LogInformation(
-                            "✓ Cached {Count} missing tracks for {Playlist} from {Filename}",
-                            tracks.Count, playlistName, filename);
-                        break;
-                    }
-                }
+                found = true;
+                break;
             }
-            catch (Exception ex)
+            
+            // Small delay every 60 requests
+            if (minutesAhead > 0 && minutesAhead % 60 == 0)
             {
-                _logger.LogDebug(ex, "Failed to fetch {Filename}", filename);
+                await Task.Delay(TimeSpan.FromSeconds(1), cancellationToken);
             }
         }
+        
+        // Then search backwards 12 hours from sync time
+        if (!found)
+        {
+            for (var minutesBehind = 1; minutesBehind <= 720; minutesBehind++)
+            {
+                if (cancellationToken.IsCancellationRequested) break;
+
+                var time = syncTime.AddMinutes(-minutesBehind);
+                if (await TryFetchMissingTracksFile(playlistName, time, jellyfinUrl, apiKey, httpClient, cancellationToken))
+                {
+                    found = true;
+                    break;
+                }
+                
+                // Small delay every 60 requests
+                if (minutesBehind % 60 == 0)
+                {
+                    await Task.Delay(TimeSpan.FromSeconds(1), cancellationToken);
+                }
+            }
+        }
+        
+        if (!found)
+        {
+            _logger.LogWarning("Could not find missing tracks file for {Playlist} in ±12 hour window", playlistName);
+        }
+    }
+
+    private async Task<bool> TryFetchMissingTracksFile(
+        string playlistName,
+        DateTime time,
+        string jellyfinUrl,
+        string apiKey,
+        HttpClient httpClient,
+        CancellationToken cancellationToken)
+    {
+        var filename = $"{playlistName}_missing_{time:yyyy-MM-dd_HH-mm}.json";
+        var url = $"{jellyfinUrl}/Viperinius.Plugin.SpotifyImport/MissingTracksFile" +
+                 $"?name={Uri.EscapeDataString(filename)}&api_key={apiKey}";
+
+        try
+        {
+            _logger.LogDebug("Trying {Filename}", filename);
+            var response = await httpClient.GetAsync(url, cancellationToken);
+            if (response.IsSuccessStatusCode)
+            {
+                var json = await response.Content.ReadAsStringAsync(cancellationToken);
+                var tracks = ParseMissingTracks(json);
+                
+                if (tracks.Count > 0)
+                {
+                    var cacheKey = $"spotify:missing:{playlistName}";
+                    await _cache.SetAsync(cacheKey, tracks, TimeSpan.FromHours(24));
+                    _logger.LogInformation(
+                        "✓ Cached {Count} missing tracks for {Playlist} from {Filename}",
+                        tracks.Count, playlistName, filename);
+                    return true;
+                }
+            }
+        }
+        catch (Exception ex)
+        {
+            _logger.LogDebug(ex, "Failed to fetch {Filename}", filename);
+        }
+        
+        return false;
     }
 
     private List<MissingTrack> ParseMissingTracks(string json)