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To use virtualenv, set the Python Executable in Project Properties to Activated Env and enter the full path to the activate or activate.bat script (without any quotes).

Looking at this, there seem to be some problems with OS Commands and virtualenvs. The venv is not being activated before running most commands. It would be for Start Terminal but that is disabled on Windows.

For now, it may make more sense to run poetry and pip outside of Wing, but you could add a command like this to OS Commands:

${WING:PYTHON} -m pip install

The special env ${WING:PYTHON} is replaced with the value of sys.executable set in the Python Executable selected in Project Properties, so the command will be run in the activated env.

We do plan to add a package management tool to Wing in the future, to make this easier to do from the IDE.