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If you by chance create a watch expression that will crash an iOS app in the Xamarin IDE, you will be unable to ever remove this watch, because the app will crash before you get a chance to. As soon as the app crashes, the watch entries are disabled, preventing you from removing them.
A workaround is to hack the userprefs file and manually remove the watch entries, but really this should be fixed up in the IDE. I don't see any logical reason behind disabling watch entries when the app is not running.
The reason the debugger pads (locals, watches, ...) get disabled when the debugger isn't running is because the code tries to evaluate stuff when you add/edit items.
Anyways, I agree that in the case of the Watch Window, this sucks.
Implemented in git master