/usr/lib/python3/dist-packages/requests/__init__.py:87: RequestsDependencyWarning: urllib3 (1.26.12) or chardet (5.1.0) doesn't match a supported version!

I upgraded my proxy vm from Debian 11 to 12 and now I get this error:

certbot /usr/lib/python3/dist-packages/requests/__init__.py:87: RequestsDependencyWarning: urllib3 (1.26.12) or chardet (5.1.0) doesn't match a supported version!

I already tried to downgrade urllib3 with

pip install urllib3==1.21.1

but no luck

Have you tried reinstalling certbot?
If that fails, how are you installing certbot?

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I tried

apt install --reinstall certbot

but no change

But this worked:

apt remove certbot python3-urllib3
apt install certbot
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Mixing distribution packages and pip globally will almost ALWAYS eventually lead to dependency errors such as these.

It's best to stick to distribution packages without using pip and if you somehow require to use pip because you can't get some package/module otherwise, I'd recommend to ALWAYS use a virtual environment using the Python venv module. And from within the venv stick to pip packages.

That said, recommended way to install Certbot currently is using snap.

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