If you need to use serial ports created by Serial-to-USB (S2U) adaptors in MacOS with your Windows apps running in Wine, you’ll need to map them so that Wine can correctly detect and use them. For the Wine version of the Bookman Desktop Manager 1.3, I needed to map the port it used to COM1:

  1. Unplug all of your S2U adapters to begin
  2. Run ls /dev/tty.usb* to list all of the devices pre-existing for your machine
  3. Plug in the S2U device you intend to use with Wine and then run the command from #2
  4. Find the new entry in the list, ex: /dev/tty.usbserial-1410
  5. Find the Wineskin / Winery / CrossOver .app file. This is the wrapper around your Windows app.
  6. Right click on the .app file and select “Show Package Contents”; the wrapper is actually a directory.
  7. Then proceed into Contents/Resources. There is a dosdevices directory here that exposes all files (including device files, such as the COM port) which Wine can access during a run of the Windows program
  8. Open a terminal window and type cd then drag the dosdevices directory from the Finder window into the terminal to get the full path. Hit Enter to go into that directory.
  9. If you type pwd into the terminal you should now see the full path of the dosdevices directory.
  10. Run ln -s MACOS_DEV_TTY com1, replacing MACOS_DEV_TTY with the result from #4; ex: ln -s /dev/tty.usbserial-1410 com1. This creates a symbolic link file inside dosdevices which maps the device file from MacOS to Wine.
  11. Run your Wine app as normal, you should now be able to select COM1 in your app and use the serial port.

As for the BDM3.1 app I was using, that now worked perfectly on MacOS through this mapping procedure and spared me the experience of relying on Windows. A great success!