My certificates expire in a few days and I haven't had any luck updating them with letsencrypt-auto or certbot-auto. As fas as I can tell, everything is up to date but I get a:

Running setup.py install for cryptography: finished with status 'error'

every time. I've run sudo with the -H flag like the output suggests but no change. I've looked at a bunch of posts both here and other sites and none of the suggestions seem to have helped. Anyone have any ideas?

My operating system is Ubuntu 16.04.

sudo ./letsencrypt-auto renew
sudo ./certbot-auto renew


Running setup.py install for cryptography: finished with status 'error'
Command "/home/colby/.local/share/letsencrypt/bin/python2.7 -u -c "import setuptools, tokenize;file='/tmp/pip-build-STzmW5/cryptography/setup.py';exec(compile(getattr(tokenize, 'open', open)(file).read().replace(' ', ' '), file, 'exec'))" install --record /tmp/pip-nBBkFY-record/install-record.txt --single-version-externally-managed --compile --install-headers /home/colby/.local/share/letsencrypt/include/site/python2.7/cryptography" failed with error code 1 in /tmp/pip-build-STzmW5/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.

The full output is here since it's pretty long.

  • I have no idea what's wrong. Maybe check the link to the full output? Everything is pasted there. – colby Oct 11 '16 at 1:28
  • Hmm. It appears your system has a local copy of OpenSSL installed in addition to the system OpenSSL. This local copy is what it's choking on. Why is it there in the first place? – Michael Hampton Oct 11 '16 at 1:44
  • I'm not sure why it's there. Where are you seeing the local copy installed? – colby Oct 11 '16 at 1:46
  • Searching the log for error turns up the compiler error as the third result. That was easy. If you don't know why it's there, I would recommend you find whoever installed it and ask him or her what it's doing there. – Michael Hampton Oct 11 '16 at 1:49
  • 1
    Thanks Michael. Turns out I installed it a while ago while trying to fix a different issue. I've gotten rid of it and everything is working. – colby Oct 11 '16 at 18:47

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