I’ve been getting this error when I try to install a gem: ERROR: Could not find a valid gem 'pry' (>= 0), here is why: Unable to download data from https://rubygems.org/ - SSL_connect returned=1 errno=0 state=SSLv3 read server certificate B: certificate verify failed (https://s3.amazonaws.com/production.s3.rubygems.org/latest_specs.4.8.gz) My solution was to reinstall my ruby instances via: $ rvm list # to get the list of ruby versions $ rvm reinstall 2.0.0 --with-openssl-dir=$rvm_path/usr