Xamarin: Could not connect to debugger - iOS

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If you run into a Xamarin Studio 6.x error while trying to debug an app on an iOS device and you get the "Could not connect to debugger" dialog, read on...

  1. Try to clean and rebuild then attempt to debug
  2. Debug an app using Xcode on the same device.
#2 Was the fix for me, because I updated my iOS version, but never told Xcode. When I attempted to debug another app directly from Xcode, it download the debug symbols. Afterwards Xamarin device debugging worked perfect.

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