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I can't reproduce this on Mac, are you sure it is an issue to all platforms?
What are the versions of the sdk tools do you have and what framework is your project targeting? I couldn't repro it after 400+ clicks with the device I was given (Nexus 5 with Android 6.0)
I managed to repro the issue and discovered that we lost the fix for bug #30994. Cherry picked the fix to the preview branch.
Fixed in 220.127.116.11 (monodevelop-5.9-branch-android-m-preview)
I have checked this issue with following builds:
Mac OS X 10.10.3
Xamarin Studio: 5.9.5 (build 20)
Mono 4.0.4 ((detached/5ab4c0d)
GTK+ 2.24.23 (Raleigh theme)
Xamarin.Android : 18.104.22.168 (Enterprise Edition)
Now I am not getting the debugger connection lost issue, I am able to deploy and debug application without any debugger connection lost.
This issue has been fixed. Hence I am closing this issue.