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Since upgrading the Mono for Android SDK to any version following 4.1.7 breakpoints in Visual Studio are not getting resolved any more, whilst the debugged app itself is running fine.
This particular issue has already been discussed on the Mono for Android mailing list , ,  and also over here , but does not seem to be resolved.
From my point of view it looks like the **.mdb** files necessary for debugging with breakpoints are missing in the generated (and signed) .apk, because they can not be found in either the directory **\obj\Debug\assemblies** or the directory **\obj\Debug\android\assets**. The .mdb files are being generated besides the .pdb files in the \bin\Android directory, but do not make their way onto the device.
I'm not sure if there's something broken in the build process and if the issue could be resolved configuration-wise.
-  http://mono-for-android.1047100.n5.nabble.com/debugging-in-Visual-Studio-w-1-9-1-td4899373.html
-  http://mono-for-android.1047100.n5.nabble.com/Breakpoints-suddenly-stopped-working-td5126366.html
-  http://mono-for-android.1047100.n5.nabble.com/debugger-breakpoints-4-4-41-td5712641.html
-  http://stackoverflow.com/questions/8853313/breakpoints-not-being-hit-mono-for-android-monodroid
Tried another Monodroid mailist post from Sep 2011.
Seems as if it's the linking. I switched linking "Sdk only" to "None" and debug symbols are in the .apk again (*.dll + *.mdb from the \bin\Android directory).
Debugging using breakpoints works, but it would be interesting to have clarified under which circumstances Linking breaks the deployment of a debuggable configuration.
I think this is the same issue as
which is now fixed
*** This bug has been marked as a duplicate of bug 9433 ***