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The XamMac addin must pass --debug for Debug builds otherwise driver.m won't be compiled with debugging support - which means including the mono runtime won't allow debugging.
Note that debugging (w/included runtime) is not working now, ref: #8268
A workaround is to provide "--debug" in the extra arguments of the advanced tab.
Perhaps we should always have debuggin support in there?
What do we save by not having the debugging feature?
As far as tooling goes we compile just a bit more code (in driver.m).
OTOH that code call inside the mono runtime to initialize debugging, so it means opening sockets, loading debugging symbols... which takes extra time/memory (never looked how much).
So yes, we need to pass --debug on Debug configs.
Looks like Jeff already fixed this: https://github.com/xamarin/md-addins/commit/e54fb52fb344f9e92f538a2a406090597446d66b