SQL Server – How to Disable ‘Completion Time’ in Messages Window

In 2005 at least, hit F5 to re-run your query. SSMS will determine it is no longer connected and then prompt you to reconnect. If I recall correctly, 2005 will put you back into the same database while 2008 puts you into your default catalog. A second execution of F5 will actually run the command. I've never had a semaphore timeout but it works for other disconnect scenarios.

Well, you shouldn't ever be using DBCC SHRINKDATABASE, IMHO - if you need to shrink files at all, you should think twice, maybe even three times, and even in the odd case where it really is warranted (hint: this should be rare), you should target each file individually using DBCC SHRINKFILE. Please read every single word on this page.

Anyway, you can see the progress using:

SELECT percent_complete, estimated_completion_time
  FROM sys.dm_exec_requests
  WHERE session_id = <spid running the shrink>;

Documentation for sys.dm_exec_requests.