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I think you can run the following as an equivalent to 'django-admin makemigrations myadd' on the command line:

/path1/to/python /path2/to/django-admin.py makemigrations myadd

Of course you have to replace both /path1/to and /path2/to with the actual paths to those files. For Python you can see its path in the Python Shell in Wing by typing this:

import sys
sys.executable

Note that if you try this on the command line outside of Wing you only need the full path to Python if you're running outside of an activated environment.

Assuming that does work, you can open django-admin.py in Wing, right click on the editor to select Properties, and then enter the run args under the Debug/Execute tab:

makemigrations myadd

Then you can start debug for that file in Wing.

Note that you can also create and debug named entry points if you have several different command lines you want to debug. These are described in https://wingware.com/doc/debug/named-entry-points