SSL connect issue to RubyGems - worked through troubleshooting guide

[robinjfisher]

I'm having a problem. The specific error message is:

Unable to download data from https://rubygems.org/ - SSL_connect returned=1 errno=0 state=error: certificate verify failed (https://api.rubygems.org/specs.4.8.gz)

I am using rbenv to manage my Ruby installations. I have a working project using Ruby 2.2.0 and there are no issues in this project. I would like to install and use Rails 5 which requires 2.2.2 or later.

I installed Ruby 2.3.0 using rbenv and created a new project directory, setting 2.3.0 as the local version for that directory. I execute gem install bundler or any gem install command and receive the above error. I have followed the steps in this guide.

Here are my environment details for the project folder set to use Ruby 2.3.0:

$ gem env
RubyGems Environment:
  - RUBYGEMS VERSION: 2.5.1
  - RUBY VERSION: 2.3.0 (2015-12-25 patchlevel 0) [x86_64-darwin14]
  - INSTALLATION DIRECTORY: /Users/robinjfisher/.rbenv/versions/2.3.0/lib/ruby/gems/2.3.0
  - USER INSTALLATION DIRECTORY: /Users/robinjfisher/.gem/ruby/2.3.0
  - RUBY EXECUTABLE: /Users/robinjfisher/.rbenv/versions/2.3.0/bin/ruby
  - EXECUTABLE DIRECTORY: /Users/robinjfisher/.rbenv/versions/2.3.0/bin
  - SPEC CACHE DIRECTORY: /Users/robinjfisher/.gem/specs
  - SYSTEM CONFIGURATION DIRECTORY: /Users/robinjfisher/.rbenv/versions/2.3.0/etc
  - RUBYGEMS PLATFORMS:
    - ruby
    - x86_64-darwin-14
  - GEM PATHS:
     - /Users/robinjfisher/.rbenv/versions/2.3.0/lib/ruby/gems/2.3.0
     - /Users/robinjfisher/.gem/ruby/2.3.0
  - GEM CONFIGURATION:
     - :update_sources => true
     - :verbose => true
     - :backtrace => false
     - :bulk_threshold => 1000
     - "gem" => "--no-document\\n"
  - REMOTE SOURCES:
     - https://rubygems.org/
  - SHELL PATH:
     - /Users/robinjfisher/.rbenv/versions/2.3.0/bin
     - /Users/robinjfisher/.rbenv/libexec
     - /Users/robinjfisher/.rbenv/plugins/ruby-build/bin
     - /Users/robinjfisher/.rbenv/plugins/rbenv-vars/bin
     - /Users/robinjfisher/.rbenv/shims
     - /Users/robinjfisher/.rbenv/bin
     - /usr/local/bin
     - /usr/bin
     - /bin
     - /usr/sbin
     - /sbin
     - /usr/local/openssl/bin
     - /Users/robinjfisher/.rbenv/shims
     - /Users/robinjfisher/.rbenv/bin

$ ruby -ropenssl -e 'puts OpenSSL::OPENSSL_LIBRARY_VERSION'
OpenSSL 1.0.2p  14 Aug 2018

$ rbenv --version
rbenv 0.4.0-129-g7e0e85b

I will abide by the code of conduct.

[robinjfisher]

$ ruby -ropen-uri -e 'eval open("https://git.io/vQhWq").read'

Here's your Ruby and OpenSSL environment:

Ruby:           2.3.0p0 (2015-12-25 revision 53290) [x86_64-darwin14]
RubyGems:       2.5.1
Compiled with:  OpenSSL 1.0.2p  14 Aug 2018
Loaded version: OpenSSL 1.0.2p  14 Aug 2018
SSL_CERT_FILE:  /Users/robinjfisher/.rbenv/versions/2.3.0/openssl/ssl/cert.pem
SSL_CERT_DIR:   /Users/robinjfisher/.rbenv/versions/2.3.0/openssl/ssl/certs

With that out of the way, let's see if you can connect to rubygems.org...

Bundler connection to rubygems.org:       failed  ❌  (uninitialized constant Bundler)
RubyGems connection to rubygems.org:      failed  ❌  (certificate verification)
Ruby net/http connection to rubygems.org: failed  ❌

Unfortunately, this Ruby can't connect to rubygems.org. 😡
Your Ruby can't connect to rubygems.org because you are missing the certificate files OpenSSL needs to verify you are connecting to the genuine rubygems.org servers.

[robinjfisher]

OK, after plugging away at this today, I reached a solution. Might not be ideal but worked for me.

$ gem sources -r https://rubygems.org/
$ gem sources -a http://rubygems.org/
$ gem update --system
$ gem sources -a https://rubygems.org/
$ gem sources -r http://rubygems.org/

Basically, running RubyGems update over an insecure link then reinstating the secure URL once everything had updated. Seems to have worked OK.