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I recently upgraded the system image associated with my account to the latest image, but pip and pip3 seem to be tied to the old version corresponding to the state prior to the image upgrade (Python 3.6), specifically the one residing in my home folder:

21:02 ~ $ pip --version
pip 21.1.3 from /home/azin/.local/lib/python3.6/site-packages/pip (python 3.6)
21:02 ~ $ pip3 --version
pip 21.1.3 from /home/azin/.local/lib/python3.6/site-packages/pip (python 3.6)
21:02 ~ $ pip3.9 --version
pip 21.1.2 from /usr/local/lib/python3.9/site-packages/pip (python 3.9)

I upgraded to the Glastonbury system image under the Account tab and have every option set to Python 3.9.

What am I missing here?

I fixed the issue by deleting my .cache/ and .virtualenvs/ folders.

Glad you solved that -- we heard about that behaviour and advise the same thing.