diff --git a/Controllers/Managers/SongManager.cs b/Controllers/Managers/SongManager.cs
index b743d8c..b9ed3ae 100644
--- a/Controllers/Managers/SongManager.cs
+++ b/Controllers/Managers/SongManager.cs
@@ -170,7 +170,7 @@ public class SongManager : BaseManager
             dirMgr.CreateDirectory();
 
             var tempPath = song.SongPath();
-            song.Filename = song.GenerateFilename(1);
+            song.Filename = song.GenerateFilename(true, AudioFileExtensionsType.WAV);
             var filePath = $"{dirMgr.SongDirectory}{song.Filename}";
 
             _logger.Info($"Absolute song path: {filePath}");
@@ -205,7 +205,7 @@ public class SongManager : BaseManager
 
         if (string.IsNullOrEmpty(song.Filename))
         {
-            song.Filename = song.GenerateFilename(1);
+            song.Filename = song.GenerateFilename(true, AudioFileExtensionsType.WAV);
         }
 
         _logger.Info($"Temporary directory: {_tempDirectoryRoot}");
@@ -254,7 +254,6 @@ public class SongManager : BaseManager
         var coverMgr = new CoverArtManager(_config);
         var coverArt = coverMgr.SaveCoverArt(coverArtData, song);
 
-
         var meta = new Utilities.MetadataRetriever();
         meta.UpdateMetadata(song, song);
 
@@ -264,6 +263,7 @@ public class SongManager : BaseManager
         var tempPath = song.SongPath();
 
         song.SongDirectory = dirMgr.SongDirectory;
+        song.Filename = song.GenerateFilename(true, AudioFileExtensionsType.FLAC);
 
         var filePath = song.SongPath();
         _logger.Info($"Absolute song path: {filePath}");
@@ -340,7 +340,7 @@ public class SongManager : BaseManager
     {
         _logger.Info("Assigning song filename");
         var song = new Song { SongDirectory = this._tempDirectoryRoot };
-        var filename = await song.GenerateFilenameAsync(0) + "-" + songFile.FileName;
+        var filename = await song.GenerateFilenameAsync(false) + "-" + songFile.FileName;
         song.Filename = filename;
         var songPath = song.SongPath();
 
diff --git a/Models/Song.cs b/Models/Song.cs
index fd303a8..d0d7a8b 100644
--- a/Models/Song.cs
+++ b/Models/Song.cs
@@ -88,26 +88,43 @@ public class Song
         return fullPath;
     }
 
-    public string GenerateFilename(int flag = 0)
+    public string GenerateFilename(bool includeExtension = false, AudioFileExtensionsType flag = AudioFileExtensionsType.Default)
     {
         int length = Constants.DirectoryPaths.FILENAME_LENGTH;
         string chars = Constants.DirectoryPaths.FILENAME_CHARACTERS;
         var filename = this.Generate(length, chars);
-        var extension = Icarus.Constants.FileExtensions.DEFAULT_AUDIO_EXTENSION;
+        // var extension = Icarus.Constants.FileExtensions.DEFAULT_AUDIO_EXTENSION;
+        var extension = this.DetermineFileExtension(flag);
 
-        return flag == 0 ? filename : $"{filename}{extension}";
+        return includeExtension ? $"{filename}{extension}" : filename;
     }
-    public async Task<string> GenerateFilenameAsync(int flag = 0)
+    public async Task<string> GenerateFilenameAsync(bool includeExtension = false, AudioFileExtensionsType flag = AudioFileExtensionsType.Default)
     {
         int length = Constants.DirectoryPaths.FILENAME_LENGTH;
         string chars = Constants.DirectoryPaths.FILENAME_CHARACTERS;
-        var extension = Icarus.Constants.FileExtensions.DEFAULT_AUDIO_EXTENSION;
+        // var extension = Icarus.Constants.FileExtensions.DEFAULT_AUDIO_EXTENSION;
+        var extension = this.DetermineFileExtension(flag);
         var filename = await Task.Run(() =>
         {
             return this.Generate(length, chars);
         });
 
-        return flag == 0 ? filename : $"{filename}{extension}";
+        return includeExtension ? $"{filename}{extension}" : filename;
+    }
+
+    private string DetermineFileExtension(AudioFileExtensionsType flag)
+    {
+        switch (flag)
+        {
+            case AudioFileExtensionsType.Default:
+                return Constants.FileExtensions.DEFAULT_AUDIO_EXTENSION;
+            case AudioFileExtensionsType.WAV:
+                return Constants.FileExtensions.WAV_EXTENSION;
+            case AudioFileExtensionsType.FLAC:
+                return Constants.FileExtensions.FLAC_EXTENSION;
+            default:
+                return "";
+        }
     }
 
     private string Generate(int length, string chars)
@@ -119,3 +136,10 @@ public class Song
     }
     #endregion
 }
+
+public enum AudioFileExtensionsType
+{
+    Default = 0,
+    WAV = 1,
+    FLAC = 2
+}