Error when running le-renew-webroot script

When running the le-renew-webroot script on my server, it fails with the following error.

Command "/root/.local/share/letsencrypt/bin/python2.7 -u -c "import setuptools, tokenize;__file__='/tmp/pip-build-Uq9O9J/cryptography/';exec(compile(getattr(tokenize, 'open', open)(__file__).read().replace('
', '
'), __file__, 'exec'))" install --record /tmp/pip-NOGsrE-record/install-record.txt --single-version-externally-managed --compile --install-headers /root/.local/share/letsencrypt/include/site/python2.7/cryptography" failed with error code 1 in /tmp/pip-build-Uq9O9J/cryptography
You are using pip version 8.0.3, however version 8.1.2 is available.
You should consider upgrading via the 'pip install --upgrade pip' command.
Reloading nginx
Job for nginx.service failed. See 'systemctl status nginx.service' and 'journalctl -xn' for details.
Renewal process finished for domain

I can see it’s complaining about the version of Python PIP I’m running, but I already have the requested version.

> sudo pip -V
pip 8.1.2 from /usr/local/lib/python2.7/dist-packages (python 2.7)

Running the suggested command confirms this:

> sudo pip install --upgrade pip
Requirement already up-to-date: pip in /usr/local/lib/python2.7/dist-packages

So I’m not sure what’s going on.

I’m on Debian 8 (Jessie).

:+1: got the same problem, anybody a clue?

The solution for me was rather simple. Upgrading to pip requires a server reboot. After that pip v8.1.2 was used and the script works fine.

Thanks, yes restarting the box fixed it for me too.
Seems odd that a pip update would need a restart, but there you go.

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