When docking multiple tool windows to each other and ending Debug mode or launching the IDE, Visual Studio 2008 will crash.
I use a mult-monitor setup where on the second monitor contains many tool windows (Task List, Bookmarks, Error List, Output, etc). In Debug mode, I have a whole new set of windows (Call Stack, Autos, Locals, Watches, etc). When all the tool windows are separate, to maximize space, each window has to be sized and placed and each window has a title bar. To get rid of the title bar on each window, I docked every tool window into one giant window with just one title bar. Docking all the windows together also helps with not having to reposition each one when system settings change which sometimes cause the windows to shift between both monitor displays. Docking works except the fact I cannot keep it this way as Visual Studio 2008 crashes when exiting debug mode or relaunching the IDE.