ruby install gems - SSL connect returned certificate verify failed

Question

I am working on a rails project. I have been working with rails for a while, and use an old MacBook Pro (2012) that has seen ruby/rails development since 2014. In that time, I have both RVM, RBENV, rails versions from 3.2 to 5.1.0, ruby versions from 2.0.0 to 2.2.3 on my machine.

Recently, I have been able to get around the error

SSL_connect returned=1 errno=0 state=SSLv3 read server certificate B: certificate verify failed (https://api.rubygems.org/specs.4.8.gz)

with installing gems via http and using source 'http://rubygems.org' in my gemfiles.

However, I would like to finally get rid of this issue. I have taken steps to improve this issue doing the following:

1. following this guide https://gist.github.com/luislavena/f064211759ee0f806c88
2. which lead to this link https://guides.rubygems.org/ssl-certificate-update/#installing-using-update-packages
3. which lead to this link https://bundler.io/v1.16/guides/rubygems_tls_ssl_troubleshooting_guide.html#troubleshooting-certificate-errors

The steps I have currently taken were to do the following: brew update

brew install openssl-osx-ca

brew tap raggi/ale

brew upgrade openssl

However, the result of running gem update --system returned the same error

SSL_connect returned=1 errno=0 state=SSLv3 read server certificate B: certificate verify failed (https://api.rubygems.org/specs.4.8.gz)

The #3 solution, suggested using rvm implode , forcing brew uninstall openssl --force and starting over. I am very hesitant to do this, because I use rails in my day job and I don't want to show up (i use my machine) with a machine that cannot even turn on a rails server.

Has anyone had to perform something similar? Any actionable steps I could take to fix this SSL issue for once?

Answer 1

Try this manual install instruction https://github.com/rubygems/rubygems/blob/master/UPGRADING.rdoc#manual-install

OR

1. Download latest rubygem package https://rubygems.org/gems/rubygems-update-2.7.7.gem

2. Then install it

    gem install rubygems-update-2.7.7.gem 

This worked for me and for my colleagues.