I'm having the exact same issue. Running POM 4.4.3, OS 10.15.7, MacBookPro mid-2014. I suspect the shortcuts are not being created correctly.
ETA: - log output:
Running wine- winecfg (Working directory : /Applications/PlayOnMac.app/Contents/Resources/playonlinux/python)
0094:err:plugplay:process_IOService_Device object 0x5d03
0094:err:plugplay:process_IOService_Device object 0x9d07
0094:err:plugplay:process_IOService_Device object 0x6007
0094:err:plugplay:process_IOService_Device object 0x6307
0094:err:plugplay:process_IOService_Device Unable to create plug in interface for USB deviceobject 0x630b
0094:err:plugplay:process_IOService_Device object 0x9a0b
0094:err:plugplay:process_IOService_Device object 0x9807
0094:err:plugplay:process_IOService_Device Unable to create plug in interface for USB deviceobject 0x980b
wine: Read access denied for device L"\\??\\Z:\\", FS volume label and serial are not available.
00ec:fixme:coreaudio:ca_channel_layout_to_channel_mask Unhandled channel 0xffffffff
00ec:fixme:coreaudio:ca_channel_layout_to_channel_mask Unhandled channel 0xffffffff
00ec:fixme:coreaudio:ca_channel_layout_to_channel_mask Unhandled channel 0xffffffff
00ec:fixme:coreaudio:ca_channel_layout_to_channel_mask Unhandled channel 0xffffffff
00ec:fixme:msg:pack_message msg 14 (WM_ERASEBKGND) not supported yet
00ec:fixme:msg:pack_message msg 14 (WM_ERASEBKGND) not supported yet
Edited by mdchase