‘openssl/opensslv.h’ file not found

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Every system update is an adventure when you're a software engineer.  We do everything we can to use virtual machines so that we have (almost) complete control of the environment but sometimes you simply need to work on your host system.  Everything goes great until you update your operating system and boom: you run into an issue you thought you had fixed before.

One such issue is the 'openssl/opensslv.h' file not found problem I get when updating El Capitan.   Each OS update breaks my local dev environment and I have to scramble to get the snippet to fix everything again.  The snippet I need is:

# "'openssl/opensslv.h' file not found"
brew install openssl
brew link openssl --force

That snippet installs openssl and reestablishes the links required for access from anything that wants to use it.

Symbol not found: _BIO_new_CMS

Hand in hand with the original issue is this one whereby cryptography has a fit.  Here's how I fix the _BIO_new_CMS problem:

# Symbol not found: _BIO_new_CMS
pip uninstall cryptography
LDFLAGS="-L/usr/local/opt/openssl/lib" pip install cryptography --no-use-wheel

I found each of these snippets on the third page of a random forum so hopefully having them in one place saves someone a bunch of time!

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  1. Justin

    Thanks for the advice. This resolved missing openssl/opensslv.h

    brew install openssl
    brew link openssl --force

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