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I just installed PlayOnMac 4.4.2 under Catalina and am unable to run 64 bit apps.  The steps are:

1. click on "install a non-listed program"

2. click on "Install a program in a new virtual drive"

3. select 64 bit wine

4. select a 64 bit .Net 5.0 exe

I get error "Error in POL_Wine Starting 64-bit process /Users/philipg/publish/soundjar.exe is not supported in 32-bit virtual drives" even though I selected 64 bit wine in the setup wizrd.

Also, it seems there is a bug which also causes "Tools -> Manage Wine Versions does not work" to now show any installable version of wine.  Both the left and right lists are empty there and I cannot install any Wine versions there

 

Cheers

Philip