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App crashes when trying to access USB device

I'm trying to use a windows app that communicates over USB with a serial device. The app crashes a few seconds after launching. The error messages in the log are:

0094:err:plugplay:process_IOService_Device object 0x9c03
0094:err:plugplay:process_IOService_Device object 0x9c07
0094:err:plugplay:process_IOService_Device object 0x9c0b
0094:err:plugplay:process_IOService_Device object 0x9c0f
0094:err:plugplay:process_IOService_Device object 0x9c13
0094:err:plugplay:process_IOService_Device Unable to create plug in interface for USB deviceobject 0x9c17
0094:err:plugplay:process_IOService_Device Unable to create plug in interface for USB deviceobject 0x9c1b
0094:err:plugplay:process_IOService_Device object 0x9c1f
0094:err:plugplay:process_IOService_Device object 0x9c23
0094:err:plugplay:process_IOService_Device object 0x9c27
0024:fixme:exec:SHELL_execute flags ignored: 0x00000100
0024:fixme:exec:SHELL_execute flags ignored: 0x00004100
00ec:fixme:comm:set_queue_size insize 2050 outsize 2050 unimplemented stub
00b0:fixme:imm:ImeSetActiveContext (0x1721d8, 0): stub
00b0:fixme:imm:ImmReleaseContext (00010022, 001721D8): stub
00ec:fixme:imm:ImeSetActiveContext (0x1a7cd8, 1): stub
00ec:fixme:imm:ImmReleaseContext (00010092, 001A7CD8): stub
wine: Assertion failed at address 068B100E (thread 00f8), starting debugger...
00f8:err:seh:start_debugger Couldn't start debugger L"winedbg --auto 232 220" (2)
Read the Wine Developers Guide on how to set up winedbg or another debugger

I followed the instructions on how to set up a new key. Before I did that, the app wouldn't see the USB port. After I installed the key, the app would open and see the USB port but shortly thereafter would crash. Any recommendations how to handle this?

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