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I've managed to attach the wingide debugger to the script running in the container. However, I'm not sure of the necessary steps to reproduce it and probably many of the things I tried are not necessary:

So initially I was getting the Value = [Errno 110] Connection timed out

In another terminal I run a bash in the same container where the example was running and tried to ping my host and ssh my host and I could do both from inside the container. Then I find out what the container ip adrress was from within the container and add it to the "Allowed Hosts" and "Common Attach Hosts" in wingide preferences. I also played with enabling and disabling the port 50005 in host machine with ufw, but I think this is not necessary.

At some point I started to get a different error 'Value = [Errno 111] Connection refused'

Then I added -p 50005:50005 to the docker run command and I started to get a different error Value = [Errno 104] Connection reset by peer'

Then after repeating the same run command a few time I got the error Error starting userland proxy: listen tcp 0.0.0.0:50005: bind: address already in use.

I removed the -p 50005:50005 . Then I saw the debug icon in the bottom left of wingide to turn green but still get the Value = [Errno 104] Connection reset by peer' I added a Location Map for the /app corresponding folder in my host. Then the debugger could attach to the script but not the callback function hello()

in the terminal it keep complaining that:

No valid wingdebugpw file found in the following directories: ['/wingide6', '$<winguserprofile>']

I copied wingdebugpw to /usr/lib/wingide6 and finally the breakpoints worked both in the body and the callback function.