https://bugs.winehq.org/show_bug.cgi?id=21483
--- Comment #9 from Roberto Viola cagnulein@gmail.com --- i achieve to debug a managed .NET 4.0 application on wine.
1) get from https://www.microsoft.com/en-us/download/details.aspx?id=2282 (i don't know if i can link M$ stuff) the mdbg for .NET 4.0 2) run mdbg from winedbg in this way: "wine winedbg mdbg.exe" 3) when winedbg starts, run "cont" command 4) in the mdbg shell debug your .NET 4.0 executable!
I don't know why mdbg works from winedbg and doesn't from wine directly.