Help with remote debugging on macOS with Parallels VM

I am having issues trying to get remote debugging functioning correctly from macOS Mojave to Windows 10 running in a Parallels VM. The process always hangs on the development machine (macOS) at “Launching application”. I’ve tried a few things (noted below) to no avail and am hoping someone who has been successful at getting this to work in a similar setup can give some advice.

  • I have tried both shared networking and bridged networking on the VM (obviously reconfiguring the development system each time)
  • The Windows firewall has been turned off, although I have also tried it by opening up a pinhole at port 44553j
  • If the Remote Debugger Desktop is not running, I get a completely different error: “Failed to connect properly…”, so it seems like the two sides are at least communicating.
  • I have tried a few different download locations, the latest being C:\Temp, but the debug file never finds its way to the remote machine (obviously this is the problem).

Anyone have ideas of what I can do next?


-bill k

Does your application unpack on the VM? If so, try double-clicking to manually start it, just as a test.

Kem, nothing get’s sent over to the remote OS, so I suspect it’s a network firewall issue. I will break out another actual Windoze laptop and try with that.

Is the firewall on the Mac side turned on?

I’ve tried it both ways. Using a separate laptop over the network seems to work, so I’m able to debug for now, but it’s not ideal. I’ll let you know if I ever solve the original problem.

I had a very similar issue using 2018R4 and the newest remote debuggers. I ran DebugView (a very useful tool - see ) to see the log messages, and it was clear that the file was transferring but not launching.

I was just about to report this as a bug, but then I re-launched the remote debugger a few times and re-set the Data folder, and then suddenly it started working.

My recommendations:

  • use DebugView to see log messages
  • try quitting/relaunching / re-choosing the data folder a few times in Remote Debugger.