http://bugs.winehq.org/show_bug.cgi?id=58742
--- Comment #4 from Zowie zowie+wine@vandillen.io --- I've tried to compile with and without optimization flags on my laptop just now and optimization flags are definitely the source of the problems. I've attached the logs of building Wine with and without the flags. Winedbg only crashes when building Wine with -Og.
Checking ntdll.dll on the one that crashes, ntdll.dll indeed has the DEBUG_STRIPPED characteristic, and `winedump -j debug ./ntdll.dll` dumps pretty much nothing. I've attached the printouts. The DLL only has 11 sections, as opposed to 19 sections when building without the optimization flags. The difference is the ".debug" sections, which aren't in the DLL with -Og.