I just figured out a similar workflow using PyCharm Pro. I set up a Deployment mapping from my Windows laptop to my Linux workstation which deploys code whenev

I just figured out a similar workflow using PyCharm Pro. I set up a Deployment mapping from my Windows laptop to my Linux workstation which deploys code whenever I save. Then the Linux folder is volume-mounted into the Docker container. I set up a Remote Debugging configuration, and then after the Docker container is brought up, it will attach via SSH to the Python instance running in the remote Docker container. (Your code needs only have the pydevd_pycharm library installed.) From there you can breakpoint, watch variables, interact at the console, etc. It was a bit of bear to set up, but now I find it very tractable to run and immensely useful.