This error will present by hanging or freezing at the "Sending Waiting Files" or with the dictation log indicating a number of unsent files. If this is not the result of a loss of internet connectivity, these symptoms could be the result of an abnormally large audio file InSync is failing to process.
Stuck on Sending Waiting Files:

Dictations are Unsent:

To determine if it is a large file causing the backup we need to navigate to the folder InSync downloads audio files to.
Windows XP: C:\Documents and Settings\%userprofile%\Application Data\Emdat\InSync\DIC\NEW
Windows Vista and 7: C:\Users\%userprofile%\AppData\Roaming\Emdat\InSync\DIC\NEW
For Windows XP type %appdata% into the Run command box.

For Windows Vista and Windows 7 type %appdata% into the Start Search field.

From the Application Data folder, navigate to the Emdat\InSync\DIC\NEW folder and look for audio files that are much larger than the others, and in particular the audio file that has a matching ENC file with it. If there is a large file obstructing the upload process stop InSync either with the normal exit command, or if necessary with the Task Manager to stop an unresponsive program.

When InSync has been halted, delete the ENC version of the audio file, and copy the large obstructing file to another location, such as the desktop. In the above example, the audio file is almost 120 mb or approximately an hour and a half worth of dictation.
Restart InSync and verify the rest of the audio files upload correctly.
The user has the option to listen to the large file to determine if there are any valid portions or if the audio file does not contain a valid dictation it can be deleted. If the large file is in fact a full dictation that you do not feel needs to be re-dictated and is accurate please contact the help desk (608) 270-6400 to assist with the upload.
