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.
Best Answer
Debugger is deprecated in SSMS18 as @LowlyDBA said in his answer.
For those who look for an alternative, you can use SQL Server Data Tools (SSDT)/Visual Studio to debug a query.
From the SQL menu
From the Drop down list next to the execute icon in the query window
From the context menu in the query wondow