diff --git a/MEMORY_OPTIMIZATION_RECOMMENDATIONS.md b/MEMORY_OPTIMIZATION_RECOMMENDATIONS.md
new file mode 100644
index 0000000..a9a3b27
--- /dev/null
+++ b/MEMORY_OPTIMIZATION_RECOMMENDATIONS.md
@@ -0,0 +1,191 @@
+# Memory Optimization Recommendations for Allstarr
+
+## Current Implementation Status
+
+✅ **COMPLETED**: Mark-for-deletion system with 24-hour delay
+✅ **COMPLETED**: Persistent favorites tracking using JSON files
+✅ **COMPLETED**: Cache-first copying for favorites (avoids re-downloads)
+✅ **COMPLETED**: Dependency injection for CacheCleanupService to process pending deletions
+
+## Memory Optimization Strategies
+
+### 1. Collection Optimizations
+
+**Current Issues:**
+- Multiple `List<Song>`, `List<Album>`, `List<Artist>` collections created during searches
+- Large `Dictionary<string, object?>` objects for Jellyfin metadata
+- Concurrent collections like `ConcurrentDictionary<string, SessionInfo>` for sessions
+
+**Recommendations:**
+```csharp
+// Use ArrayPool for temporary collections
+private static readonly ArrayPool<Song> SongArrayPool = ArrayPool<Song>.Shared;
+
+// Use Span<T> for temporary operations
+ReadOnlySpan<Song> ProcessSongs(ReadOnlySpan<Song> songs) { ... }
+
+// Use IAsyncEnumerable for streaming large results
+IAsyncEnumerable<Song> SearchSongsStreamAsync(string query);
+```
+
+### 2. JSON Serialization Optimizations
+
+**Current Issues:**
+- Heavy use of `JsonSerializer.Deserialize<Dictionary<string, object?>>()` 
+- Multiple serialization/deserialization cycles for caching
+
+**Recommendations:**
+```csharp
+// Use System.Text.Json source generators for better performance
+[JsonSerializable(typeof(List<Song>))]
+[JsonSerializable(typeof(Dictionary<string, FavoriteTrackInfo>))]
+public partial class AllstarrJsonContext : JsonSerializerContext { }
+
+// Use JsonDocument for read-only scenarios instead of Dictionary
+JsonDocument.Parse(json).RootElement.GetProperty("Items")
+```
+
+### 3. Caching Strategy Improvements
+
+**Current Issues:**
+- File-based caching creates multiple copies of data
+- Redis and file caches can contain duplicate data
+
+**Recommendations:**
+```csharp
+// Implement cache eviction policies
+public class LRUCache<TKey, TValue> where TKey : notnull
+{
+    private readonly int _maxSize;
+    private readonly Dictionary<TKey, LinkedListNode<CacheItem>> _cache;
+    private readonly LinkedList<CacheItem> _lruList;
+}
+
+// Use weak references for large objects
+private readonly WeakReference<List<Song>> _cachedSongs = new(null);
+```
+
+### 4. String Interning and Optimization
+
+**Current Issues:**
+- Many duplicate strings (artist names, album titles) across collections
+- Path strings created repeatedly
+
+**Recommendations:**
+```csharp
+// Use string interning for common values
+private static readonly ConcurrentDictionary<string, string> InternedStrings = new();
+public static string Intern(string value) => InternedStrings.GetOrAdd(value, v => v);
+
+// Use StringBuilder for path construction
+private static readonly ThreadLocal<StringBuilder> PathBuilder = 
+    new(() => new StringBuilder(256));
+```
+
+### 5. Background Service Optimizations
+
+**Current Issues:**
+- Multiple background services running simultaneously
+- Potential memory leaks in long-running services
+
+**Recommendations:**
+```csharp
+// Implement proper disposal patterns
+public class CacheCleanupService : BackgroundService, IDisposable
+{
+    private readonly SemaphoreSlim _semaphore = new(1, 1);
+    
+    protected override async Task ExecuteAsync(CancellationToken stoppingToken)
+    {
+        using var _ = await _semaphore.WaitAsync(stoppingToken);
+        // ... cleanup logic
+    }
+    
+    public override void Dispose()
+    {
+        _semaphore?.Dispose();
+        base.Dispose();
+    }
+}
+```
+
+### 6. HTTP Client Optimizations
+
+**Current Issues:**
+- Multiple HTTP clients for different services
+- Large response buffers
+
+**Recommendations:**
+```csharp
+// Use HttpClientFactory with proper configuration
+builder.Services.AddHttpClient<DeezerMetadataService>(client =>
+{
+    client.DefaultRequestHeaders.Add("User-Agent", "Allstarr/1.0");
+    client.Timeout = TimeSpan.FromSeconds(30);
+})
+.ConfigurePrimaryHttpMessageHandler(() => new HttpClientHandler
+{
+    MaxConnectionsPerServer = 10,
+    PooledConnectionLifetime = TimeSpan.FromMinutes(15)
+});
+
+// Stream large responses instead of loading into memory
+using var stream = await response.Content.ReadAsStreamAsync();
+using var reader = new StreamReader(stream);
+```
+
+### 7. Container Memory Limits
+
+**Docker Configuration:**
+```dockerfile
+# Set memory limits in docker-compose.yml
+services:
+  allstarr:
+    deploy:
+      resources:
+        limits:
+          memory: 512M
+        reservations:
+          memory: 256M
+```
+
+**Runtime Configuration:**
+```csharp
+// Configure GC for container environments
+GCSettings.LatencyMode = GCLatencyMode.Batch;
+GC.Collect(2, GCCollectionMode.Optimized);
+```
+
+## Immediate Actions (Priority Order)
+
+1. **Enable GC monitoring** - Add memory usage logging to identify hotspots
+2. **Implement cache size limits** - Prevent unbounded growth of in-memory caches
+3. **Use object pooling** - For frequently allocated objects like Song/Album/Artist
+4. **Stream large responses** - Instead of loading entire JSON responses into memory
+5. **Optimize JSON serialization** - Use source generators and reduce Dictionary usage
+
+## Monitoring Recommendations
+
+```csharp
+// Add memory monitoring to Program.cs
+builder.Services.AddHostedService<MemoryMonitoringService>();
+
+public class MemoryMonitoringService : BackgroundService
+{
+    protected override async Task ExecuteAsync(CancellationToken stoppingToken)
+    {
+        while (!stoppingToken.IsCancellationRequested)
+        {
+            var memoryUsage = GC.GetTotalMemory(false);
+            var gen0 = GC.CollectionCount(0);
+            var gen1 = GC.CollectionCount(1);
+            var gen2 = GC.CollectionCount(2);
+            
+            _logger.LogInformation("Memory: {Memory:N0} bytes, GC: Gen0={Gen0}, Gen1={Gen1}, Gen2={Gen2}",
+                memoryUsage, gen0, gen1, gen2);
+                
+            await Task.Delay(TimeSpan.FromMinutes(5), stoppingToken);
+        }
+    }
+}
+```
\ No newline at end of file
diff --git a/allstarr/Controllers/JellyfinController.cs b/allstarr/Controllers/JellyfinController.cs
index b102518..bf15e4c 100644
--- a/allstarr/Controllers/JellyfinController.cs
+++ b/allstarr/Controllers/JellyfinController.cs
@@ -3460,6 +3460,13 @@ public class JellyfinController : ControllerBase
     {
         try
         {
+            // Check if already favorited (persistent tracking)
+            if (await IsTrackFavoritedAsync(itemId))
+            {
+                _logger.LogInformation("Track already favorited (persistent): {ItemId}", itemId);
+                return;
+            }
+
             // Get the song metadata first to build paths
             var song = await _metadataService.GetSongAsync(provider, externalId);
             if (song == null)
@@ -3481,6 +3488,8 @@ public class JellyfinController : ControllerBase
                 if (existingFiles.Length > 0)
                 {
                     _logger.LogInformation("Track already exists in kept folder: {Path}", existingFiles[0]);
+                    // Mark as favorited even if we didn't download it
+                    await MarkTrackAsFavoritedAsync(itemId, song);
                     return;
                 }
             }
@@ -3529,6 +3538,7 @@ public class JellyfinController : ControllerBase
             if (System.IO.File.Exists(keptFilePath))
             {
                 _logger.LogInformation("Track already exists in kept folder (race condition): {Path}", keptFilePath);
+                await MarkTrackAsFavoritedAsync(itemId, song);
                 return;
             }
 
@@ -3546,6 +3556,9 @@ public class JellyfinController : ControllerBase
                     _logger.LogDebug("Copied cover art to kept folder");
                 }
             }
+
+            // Mark as favorited in persistent storage
+            await MarkTrackAsFavoritedAsync(itemId, song);
         }
         catch (Exception ex)
         {
@@ -3560,63 +3573,241 @@ public class JellyfinController : ControllerBase
     {
         try
         {
-            // Get the song metadata to build paths
-            var song = await _metadataService.GetSongAsync(provider, externalId);
-            if (song == null)
+            // Mark for deletion instead of immediate deletion
+            await MarkTrackForDeletionAsync(itemId);
+            _logger.LogInformation("✓ Marked track for deletion: {ItemId}", itemId);
+        }
+        catch (Exception ex)
+        {
+            _logger.LogError(ex, "Error marking external track {ItemId} for deletion", itemId);
+        }
+    }
+
+    #region Persistent Favorites Tracking
+
+    private readonly string _favoritesFilePath = "/app/cache/favorites.json";
+
+    /// <summary>
+    /// Checks if a track is already favorited (persistent across restarts).
+    /// </summary>
+    private async Task<bool> IsTrackFavoritedAsync(string itemId)
+    {
+        try
+        {
+            if (!System.IO.File.Exists(_favoritesFilePath))
+                return false;
+
+            var json = await System.IO.File.ReadAllTextAsync(_favoritesFilePath);
+            var favorites = JsonSerializer.Deserialize<Dictionary<string, FavoriteTrackInfo>>(json) ?? new();
+            
+            return favorites.ContainsKey(itemId);
+        }
+        catch (Exception ex)
+        {
+            _logger.LogWarning(ex, "Failed to check favorite status for {ItemId}", itemId);
+            return false;
+        }
+    }
+
+    /// <summary>
+    /// Marks a track as favorited in persistent storage.
+    /// </summary>
+    private async Task MarkTrackAsFavoritedAsync(string itemId, Song song)
+    {
+        try
+        {
+            var favorites = new Dictionary<string, FavoriteTrackInfo>();
+            
+            if (System.IO.File.Exists(_favoritesFilePath))
             {
-                _logger.LogWarning("Could not find song metadata for {ItemId}", itemId);
-                return;
+                var json = await System.IO.File.ReadAllTextAsync(_favoritesFilePath);
+                favorites = JsonSerializer.Deserialize<Dictionary<string, FavoriteTrackInfo>>(json) ?? new();
             }
 
-            // Build kept folder path: /app/kept/Artist/Album/
+            favorites[itemId] = new FavoriteTrackInfo
+            {
+                ItemId = itemId,
+                Title = song.Title,
+                Artist = song.Artist,
+                Album = song.Album,
+                FavoritedAt = DateTime.UtcNow
+            };
+
+            // Ensure cache directory exists
+            Directory.CreateDirectory(Path.GetDirectoryName(_favoritesFilePath)!);
+            
+            var updatedJson = JsonSerializer.Serialize(favorites, new JsonSerializerOptions { WriteIndented = true });
+            await System.IO.File.WriteAllTextAsync(_favoritesFilePath, updatedJson);
+            
+            _logger.LogDebug("Marked track as favorited: {ItemId}", itemId);
+        }
+        catch (Exception ex)
+        {
+            _logger.LogWarning(ex, "Failed to mark track as favorited: {ItemId}", itemId);
+        }
+    }
+
+    /// <summary>
+    /// Removes a track from persistent favorites storage.
+    /// </summary>
+    private async Task UnmarkTrackAsFavoritedAsync(string itemId)
+    {
+        try
+        {
+            if (!System.IO.File.Exists(_favoritesFilePath))
+                return;
+
+            var json = await System.IO.File.ReadAllTextAsync(_favoritesFilePath);
+            var favorites = JsonSerializer.Deserialize<Dictionary<string, FavoriteTrackInfo>>(json) ?? new();
+            
+            if (favorites.Remove(itemId))
+            {
+                var updatedJson = JsonSerializer.Serialize(favorites, new JsonSerializerOptions { WriteIndented = true });
+                await System.IO.File.WriteAllTextAsync(_favoritesFilePath, updatedJson);
+                _logger.LogDebug("Removed track from favorites: {ItemId}", itemId);
+            }
+        }
+        catch (Exception ex)
+        {
+            _logger.LogWarning(ex, "Failed to remove track from favorites: {ItemId}", itemId);
+        }
+    }
+
+    /// <summary>
+    /// Marks a track for deletion (delayed deletion for safety).
+    /// </summary>
+    private async Task MarkTrackForDeletionAsync(string itemId)
+    {
+        try
+        {
+            var deletionFilePath = "/app/cache/pending_deletions.json";
+            var pendingDeletions = new Dictionary<string, DateTime>();
+            
+            if (System.IO.File.Exists(deletionFilePath))
+            {
+                var json = await System.IO.File.ReadAllTextAsync(deletionFilePath);
+                pendingDeletions = JsonSerializer.Deserialize<Dictionary<string, DateTime>>(json) ?? new();
+            }
+
+            // Mark for deletion 24 hours from now
+            pendingDeletions[itemId] = DateTime.UtcNow.AddHours(24);
+
+            // Ensure cache directory exists
+            Directory.CreateDirectory(Path.GetDirectoryName(deletionFilePath)!);
+            
+            var updatedJson = JsonSerializer.Serialize(pendingDeletions, new JsonSerializerOptions { WriteIndented = true });
+            await System.IO.File.WriteAllTextAsync(deletionFilePath, updatedJson);
+            
+            // Also remove from favorites immediately
+            await UnmarkTrackAsFavoritedAsync(itemId);
+            
+            _logger.LogDebug("Marked track for deletion in 24 hours: {ItemId}", itemId);
+        }
+        catch (Exception ex)
+        {
+            _logger.LogWarning(ex, "Failed to mark track for deletion: {ItemId}", itemId);
+        }
+    }
+
+    /// <summary>
+    /// Information about a favorited track for persistent storage.
+    /// </summary>
+    private class FavoriteTrackInfo
+    {
+        public string ItemId { get; set; } = "";
+        public string Title { get; set; } = "";
+        public string Artist { get; set; } = "";
+        public string Album { get; set; } = "";
+        public DateTime FavoritedAt { get; set; }
+    }
+
+    /// <summary>
+    /// Processes pending deletions (called by cleanup service).
+    /// </summary>
+    public async Task ProcessPendingDeletionsAsync()
+    {
+        try
+        {
+            var deletionFilePath = "/app/cache/pending_deletions.json";
+            if (!System.IO.File.Exists(deletionFilePath))
+                return;
+
+            var json = await System.IO.File.ReadAllTextAsync(deletionFilePath);
+            var pendingDeletions = JsonSerializer.Deserialize<Dictionary<string, DateTime>>(json) ?? new();
+            
+            var now = DateTime.UtcNow;
+            var toDelete = pendingDeletions.Where(kvp => kvp.Value <= now).ToList();
+            var remaining = pendingDeletions.Where(kvp => kvp.Value > now).ToDictionary(kvp => kvp.Key, kvp => kvp.Value);
+
+            foreach (var (itemId, _) in toDelete)
+            {
+                await ActuallyDeleteTrackAsync(itemId);
+            }
+
+            if (toDelete.Count > 0)
+            {
+                // Update pending deletions file
+                var updatedJson = JsonSerializer.Serialize(remaining, new JsonSerializerOptions { WriteIndented = true });
+                await System.IO.File.WriteAllTextAsync(deletionFilePath, updatedJson);
+                
+                _logger.LogInformation("Processed {Count} pending deletions", toDelete.Count);
+            }
+        }
+        catch (Exception ex)
+        {
+            _logger.LogError(ex, "Error processing pending deletions");
+        }
+    }
+
+    /// <summary>
+    /// Actually deletes a track from the kept folder.
+    /// </summary>
+    private async Task ActuallyDeleteTrackAsync(string itemId)
+    {
+        try
+        {
+            var (isExternal, provider, externalId) = _localLibraryService.ParseSongId(itemId);
+            if (!isExternal) return;
+
+            var song = await _metadataService.GetSongAsync(provider!, externalId!);
+            if (song == null) return;
+
             var keptBasePath = "/app/kept";
             var keptArtistPath = Path.Combine(keptBasePath, PathHelper.SanitizeFileName(song.Artist));
             var keptAlbumPath = Path.Combine(keptArtistPath, PathHelper.SanitizeFileName(song.Album));
             
-            if (!Directory.Exists(keptAlbumPath))
-            {
-                _logger.LogInformation("Track not in kept folder (album folder doesn't exist): {ItemId}", itemId);
-                return;
-            }
+            if (!Directory.Exists(keptAlbumPath)) return;
 
-            // Find and remove the track file
             var sanitizedTitle = PathHelper.SanitizeFileName(song.Title);
             var trackFiles = Directory.GetFiles(keptAlbumPath, $"*{sanitizedTitle}*");
             
-            if (trackFiles.Length == 0)
-            {
-                _logger.LogInformation("Track not found in kept folder: {ItemId}", itemId);
-                return;
-            }
-
             foreach (var trackFile in trackFiles)
             {
                 System.IO.File.Delete(trackFile);
-                _logger.LogInformation("✓ Removed track from kept folder: {Path}", trackFile);
+                _logger.LogInformation("✓ Deleted track from kept folder: {Path}", trackFile);
             }
 
             // Clean up empty directories
             if (Directory.GetFiles(keptAlbumPath).Length == 0 && Directory.GetDirectories(keptAlbumPath).Length == 0)
             {
                 Directory.Delete(keptAlbumPath);
-                _logger.LogDebug("Removed empty album folder: {Path}", keptAlbumPath);
                 
-                // Also remove artist folder if empty
                 if (Directory.Exists(keptArtistPath) && 
                     Directory.GetFiles(keptArtistPath).Length == 0 && 
                     Directory.GetDirectories(keptArtistPath).Length == 0)
                 {
                     Directory.Delete(keptArtistPath);
-                    _logger.LogDebug("Removed empty artist folder: {Path}", keptArtistPath);
                 }
             }
         }
         catch (Exception ex)
         {
-            _logger.LogError(ex, "Error removing external track {ItemId} from kept folder", itemId);
+            _logger.LogWarning(ex, "Failed to delete track {ItemId}", itemId);
         }
     }
 
+    #endregion
+
     /// <summary>
     /// Loads missing tracks from file cache as fallback when Redis is empty.
     /// </summary>
diff --git a/allstarr/Program.cs b/allstarr/Program.cs
index 1d37077..fdb7d3d 100644
--- a/allstarr/Program.cs
+++ b/allstarr/Program.cs
@@ -388,6 +388,9 @@ if (backendType == BackendType.Jellyfin)
     builder.Services.AddSingleton<JellyfinSessionManager>();
     builder.Services.AddScoped<JellyfinAuthFilter>();
     builder.Services.AddScoped<allstarr.Filters.ApiKeyAuthFilter>();
+    
+    // Register JellyfinController as a service for dependency injection
+    builder.Services.AddScoped<allstarr.Controllers.JellyfinController>();
 }
 else
 {
diff --git a/allstarr/Services/Common/CacheCleanupService.cs b/allstarr/Services/Common/CacheCleanupService.cs
index 218f5b0..e62e71a 100644
--- a/allstarr/Services/Common/CacheCleanupService.cs
+++ b/allstarr/Services/Common/CacheCleanupService.cs
@@ -1,5 +1,6 @@
 using Microsoft.Extensions.Options;
 using allstarr.Models.Settings;
+using allstarr.Controllers;
 
 namespace allstarr.Services.Common;
 
@@ -11,16 +12,19 @@ public class CacheCleanupService : BackgroundService
 {
     private readonly IConfiguration _configuration;
     private readonly SubsonicSettings _subsonicSettings;
+    private readonly IServiceProvider _serviceProvider;
     private readonly ILogger<CacheCleanupService> _logger;
     private readonly TimeSpan _cleanupInterval = TimeSpan.FromHours(1);
 
     public CacheCleanupService(
         IConfiguration configuration,
         IOptions<SubsonicSettings> subsonicSettings,
+        IServiceProvider serviceProvider,
         ILogger<CacheCleanupService> logger)
     {
         _configuration = configuration;
         _subsonicSettings = subsonicSettings.Value;
+        _serviceProvider = serviceProvider;
         _logger = logger;
     }
 
@@ -41,6 +45,7 @@ public class CacheCleanupService : BackgroundService
             try
             {
                 await CleanupOldCachedFilesAsync(stoppingToken);
+                await ProcessPendingDeletionsAsync(stoppingToken);
                 await Task.Delay(_cleanupInterval, stoppingToken);
             }
             catch (OperationCanceledException)
@@ -160,4 +165,30 @@ public class CacheCleanupService : BackgroundService
 
         await Task.CompletedTask;
     }
+
+    /// <summary>
+    /// Processes pending track deletions from the kept folder.
+    /// </summary>
+    private async Task ProcessPendingDeletionsAsync(CancellationToken cancellationToken)
+    {
+        try
+        {
+            // Create a scope to get the JellyfinController
+            using var scope = _serviceProvider.CreateScope();
+            var jellyfinController = scope.ServiceProvider.GetService<JellyfinController>();
+            
+            if (jellyfinController != null)
+            {
+                await jellyfinController.ProcessPendingDeletionsAsync();
+            }
+            else
+            {
+                _logger.LogWarning("Could not resolve JellyfinController for pending deletions processing");
+            }
+        }
+        catch (Exception ex)
+        {
+            _logger.LogError(ex, "Error processing pending deletions");
+        }
+    }
 }