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winedbg.exe is missing on lib32on64. It presents for 32 and 64, but not for lib32on64:

for 64:

/Users/<user>/Applications/CrossOver.app/Contents/SharedSupport/CrossOver/lib64/wine/fakedlls/winedbg.exe
/Users/<user>/Applications/CrossOver.app/Contents/SharedSupport/CrossOver/lib64/wine/winedbg.exe.so
# PE32+ executable (console) x86-64, for MS Windows

for 32:

/Users/<user>/Applications/CrossOver.app/Contents/SharedSupport/CrossOver/lib/wine/fakedlls/winedbg.exe
/Users/<user>/Applications/CrossOver.app/Contents/SharedSupport/CrossOver/lib/wine/winedbg.exe.so
# PE32 executable (console) Intel 80386, for MS Windows

But if I'm trying to run winedbg on Big Sur (32on64) I'm getting:
wine:error: could not find 'winedbg' in '/Users/<user>/Applications/CrossOver.app/Contents/SharedSupport/CrossOver/lib32on64/wine'

I've tried to copy winedbg.exe and winedbg.exe.so from lib to lib32on64, but I'm getting:
winewrapper.exe:error: cannot execute L"Y:\\Applications\\CrossOver.app\\Contents\\SharedSupport\\CrossOver\\lib32on64\\wine\\winedbg.exe.so"

May be it is possible to compile it from source or may be somebody knows a workaround. Currently I'm using gdb, it kind of works but with some defects, so it should be possible to run winedbg on 32on64.

You can’t compile winedbg for 32-on-64 for current versions (CX19 & CX20 sources)

So, what is the problem? Is it easy or hard to patch?

Yevhenii Havrylko wrote:

So, what is the problem? Is it easy or hard to patch?

It doesn’t compile. Here’s what what I was told originally for 19.0.0

winedbg doesn't yet compile. So, you need to use --disable-winedbg

This also hold true for 20.0.x sources.

I’m not sure this will change in CX21 but due to how memory is handled in 32-on64 it would be rather difficult.

Thank you! So sad to hear it..