Pip Fails Due To Ssl Cert Tlsv1.0

Apologies for another pip issue, but I've tried almost every other thread and nothing so far works. So I am having the issue that pip doesn't install any package due to using TLSv1

Solution 1:

$ brew upgrade openssl
Error: openssl 1.0.2o_2 already installed

This shows that a newer version of openssl is indeed installed on your system.

python2 -c "import ssl; print(ssl.OPENSSL_VERSION)"
OpenSSL 0.9.8zh14 Jan 2016

But this shows that Python's ssl module was compiled against an older version.

I am unfamiliar with Homebrew, but according to this issue on Homebrew's Github page, Homebrew now uses its own version of openssl by default.

Based on this, the full steps to fix this issue would be:

brew uninstall python2
brew update
brew upgrade openssl
brew install python2