On a hunch that maybe it has to do with some strange assembly version or mono version mismatch, I used monodis/ilasm to roundtrip the assembly, reassembling it against the dependencies provided in the git repo. It still exhibits the same breakpoint issue, so something is the code itself must be different.

On Friday, 10 January 2014 at 00:39:36 UTC, Alexander Bothe wrote:
Anyway, you can set logGdb
(https://github.com/llucenic/MonoDevelop.Debugger.Gdb.D/blob/master/Gdb/GdbSession.cs#L84)
to be true to let it dump every interaction between Mono-D and
gdb - might be good to know what's wrong with the
breakpoints..I'd be happy if it was MonoDevelop-related, but
well, gotta check it, too.

Since recompiling from source fixes the problem, this is difficult to test. However, since I've successfully roundtripped the broken dll, I can try to find and set that value in the IL itself. My IL knowledge is a bit rusty, but I did a LOT of work with it years ago, so hopefully this won't be too hard.

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