Index: banshee-2.0.1/src/Dap/Banshee.Dap/Banshee.Dap/DapSource.cs
===================================================================
--- banshee-2.0.1.orig/src/Dap/Banshee.Dap/Banshee.Dap/DapSource.cs	2011-05-19 10:39:02.871913607 -0400
+++ banshee-2.0.1/src/Dap/Banshee.Dap/Banshee.Dap/DapSource.cs	2011-05-19 10:39:17.308128443 -0400
@@ -324,14 +324,19 @@
 
         private void AttemptToAddTrackToDevice (DatabaseTrackInfo track, SafeUri fromUri)
         {
+            Log.DebugFormat ("Trying to add file ({0})", fromUri.ToString ());
+
             if (!Banshee.IO.File.Exists (fromUri)) {
                 throw new FileNotFoundException (Catalog.GetString ("File not found"), fromUri.ToString ());
             }
 
+            Log.DebugFormat ("Bytes available ({0}), file size ({1}), track file size ({2})", BytesAvailable, Banshee.IO.File.GetSize (fromUri), track.FileSize);
+
             // Ensure there's enough space
             if (BytesAvailable - Banshee.IO.File.GetSize (fromUri) >= 0) {
                 // Ensure it's not already on the device
                 if (ServiceManager.DbConnection.Query<int> (track_on_dap_query, DbId, track.MetadataHash) == 0) {
+                    track.FileSize (Banshee.IO.File.GetSize (fromUri));
                     AddTrackToDevice (track, fromUri);
                 }
             }
@@ -397,6 +402,7 @@
                     "File format conversion support is not available"));
             }
 
+            Log.DebugFormat ("Enqueuing track to transcoder ({0})", track);
             transcoder.Enqueue (track, PreferredConfiguration, OnTrackTranscoded, OnTrackTranscodeCancelled, OnTrackTranscodeError);
         }
 
