fix ruby ssl error after brew ssl updates

fix_ruby_openssl.md

problem description

Ruby and Python stopped working after brew ssl update. You'll likely have to do this for all rubies.

Possible manifestations of the error in ruby:

LoadError: library not found for class Digest::SHA1 -- digest/sha1

Library not loaded: /usr/local/opt/openssl/lib/libcrypto.1.0.0.dylib (LoadError)

In python/gcloud stuff:

ERROR: gcloud failed to load: 'module' object has no attribute 'sha256'

ERROR:root:code for hash sha1 was not found.

fixes

Make sure your ruby-build is up to date. It was changed to pull down it's own ssl rather than using homebrew's copy. That's what makes this solution work.

rm -fr /Users/travis/.gem/ruby/2.3.8/gems
rm -fr ~/.rubies/2.3.8
ruby-build 2.3.8 ~/.rubies/2.3.8

Then you can try bundling but mysql2 gem might bork on sql too. I installed that thusly:

gem install mysql2 -v '0.3.21' -- --with-ldflags=-L/usr/local/opt/openssl/lib --with-cppflags=-I/usr/local/opt/openssl/include

Obviously adjust versions and paths.

other details

Homebrew will output the following when updating ruby-build:

ruby-build installs a non-Homebrew OpenSSL for each Ruby version installed and these are never upgraded. To link Rubies to Homebrew's OpenSSL 1.1 (which is upgraded) add the following to your ~/.bash_profile: export RUBY_CONFIGURE_OPTS="--with-openssl-dir=$(brew --prefix openssl@1.1)" Note: this may interfere with building old versions of Ruby (e.g <2.4) that use OpenSSL <1.1.