How did I get to the solution?  Well, today I decided to click the “Send to Microsoft” button on the infamous crash pop-up window.  And from it I actually got a link to a fix for the issue.  Apparently the issue is not related to Integration Services in particular, it is a much broader Visual Studio shell issue that occurs in Visual Studio 2008 with SP1 when you’ve got a combination of undocking windows and changing window layout.  And that is indeed what I usually do when debugging a package!  When the package stops executing I often execute the following scenario:

• double-click the title bar on the Output window to undock it
• enlarge the undocked Output window to almost full-screen so I can have a good look at the errors
• double-click the title bar to dock the window back to its original place
• click the “Package execution completed.” link (or hit the Stop Debugging button)

And that’s exactly the second scenario described in this Microsoft Support article because when you stop debugging, the IDE switches the window layout back from debug to design.

I have now installed the hotfix and the issue is gone.  Beware though if you also use WPF, better read through the whole article and comments on the download page first.

Hmm, this may also explain some other unexplicable crashes I’ve seen lately.  Makes you wonder doesn’t it