Updating pip problem

i'm trying to update octoprint and plugin via the UI and got

2023-03-13 00:06:00,816 /home/pi/OctoPrint/octo2/bin/python3 -m pip --disable-pip-version-check install https://github.com/OctoPrint/OctoPrint/archive/1.8.7.zip --no-cache-dir
2023-03-13 00:06:01,489 ! /home/pi/OctoPrint/octo2/bin/python3: No module named pip

but i have pip, previous update did work just fine

2022-12-19 16:18:30,977 /home/pi/OctoPrint/octo2/bin/python3 -m pip --disable-pip-version-check install https://github.com/OctoPrint/OctoPrint/archive/1.8.6.zip --no-cache-dir
2022-12-19 16:18:34,427 > Collecting https://github.com/OctoPrint/OctoPrint/archive/1.8.6.zip
2022-12-19 16:18:34,428 > Downloading https://github.com/OctoPrint/OctoPrint/archive/1.8.6.zip (6.6 MB)
2022-12-19 16:18:35,433 > ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ 6.6/6.6 MB 7.3 MB/s eta 0:00:00
2022-12-19 16:18:37,439 > Preparing metadata (setup.py): started
2022-12-19 16:18:39,554 > Preparing metadata (setup.py): finished with status 'done'

dude@3dee:~$ pip --version

pip 20.3.4 from /usr/lib/python3/dist-packages/pip (python 3.9)

it's a debian system on atom cpu, i think the only thing i change since then is installing unattented-upgrades
so maybe not a octoprint problem but more a debian update problem but i don't know much where or what to ask. pretty much every search return something about pip not being install by default and just apt-get it.

systeminfo.txt
env.python.pip: 22.1
env.python.version: 3.7.3
env.python.virtualenv: True

Can you share a systeminfo bundle (the whole zip)?

octoprint-systeminfo-20230313175501.zip (28.7 KB)

oh i'm running two octoprint on the same computer. same problem with both.
here the other systeminfo
octoprint-systeminfo-20230313195845.zip (31.7 KB)
.

i try reboot, now octoprint doesn't start

File "/home/pi/OctoPrint/octo1/bin/octoprint", line 5, in <module>
from octoprint import main
ModuleNotFoundError: No module named 'octoprint'

Ok it running again by reinstalling. Once running i had to reselect 3rd party plugin. It seems to have kept all the settings

su pi
source octo1/bin/activate
python -m ensurepip
python -m pip install --upgrade pip
pip install --no-cache-dir octoprint
python -m pip install wheel
pip install psycopg2
sudo service octoprint@1 start

source octo2/bin/activate
python -m ensurepip
python -m pip install --upgrade pip
pip install --no-cache-dir octoprint
python -m pip install wheel
pip install psycopg2
sudo service octoprint@2 start

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