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check.rb

58

#!/usr/bin/env ruby

# Encoding: utf-8

if RUBY_VERSION < "2.7"

warn "!!! WARNING !!!",

"Ruby #{RUBY_VERSION} has reached end-of-life, and is unsupported.",

"This script may not work.",

end

if ARGV.include?("-h") || ARGV.include?("--help")

puts "USAGE: check.rb [HOSTNAME] [TLS_VERSION] [VERIFY]"

puts " default: check.rb rubygems.org auto VERIFY_PEER"

puts " example: check.rb github.com TLSv1_2 VERIFY_NONE"

exit 0

end

host = ARGV.shift || "rubygems.org"

require 'uri'

require 'net/http'

begin

require 'openssl'

rescue LoadError

abort "Oh no! Your Ruby doesn't have OpenSSL, so it can't connect to #{host}. " \

"You'll need to recompile or reinstall Ruby with OpenSSL support and try again."

end

begin

# Some versions of Ruby need this require to do HTTPS

require 'net/https'

# Try for RubyGems version

require 'rubygems'

# Try for Bundler version

require 'bundler'

require 'bundler/vendor/uri/lib/uri'

rescue LoadError

end

uri = URI("https://#{host}")

ssl_version = ARGV.shift

verify_mode = ARGV.any? ? OpenSSL::SSL.const_get(ARGV.shift) : OpenSSL::SSL::VERIFY_PEER

ruby_version = RUBY_VERSION.dup

ruby_version << "p#{RUBY_PATCHLEVEL}" if defined?(RUBY_PATCHLEVEL)

ruby_version << " (#{RUBY_RELEASE_DATE} revision #{RUBY_REVISION})"

ruby_version << " [#{RUBY_PLATFORM}]"

puts "Here's your Ruby and OpenSSL environment:"

puts

puts "Ruby: %s" % ruby_version

puts "RubyGems: %s" % Gem::VERSION if defined?(Gem::VERSION)

puts "Bundler: %s" % Bundler::VERSION if defined?(Bundler::VERSION)

puts "Compiled with: %s" % OpenSSL::OPENSSL_VERSION

puts "Loaded version: %s" % OpenSSL::OPENSSL_LIBRARY_VERSION if defined?(OpenSSL::OPENSSL_LIBRARY_VERSION)

puts "SSL_CERT_FILE: %s" % OpenSSL::X509::DEFAULT_CERT_FILE

puts "SSL_CERT_DIR: %s" % OpenSSL::X509::DEFAULT_CERT_DIR

puts

puts "With that out of the way, let's see if you can connect to #{host}..."

puts

def error_reason(error)

case error.message

when /certificate verify failed/

"certificate verification"

when /read server hello A/

"SSL/TLS protocol version mismatch"

when /tlsv1 alert protocol version/

"requested TLS version is too old"

else

error.message

end

begin

b_uri = defined?(Bundler::URI) ? Bundler::URI(uri.to_s) : uri

Bundler::Fetcher.new(Bundler::Source::Rubygems::Remote.new(b_uri)).send(:connection).request(b_uri)

bundler_status = "success ✅"

rescue => error

bundler_status = "failed ❌ (#{error_reason(error)})"

end

puts "Bundler connection to #{host}: #{bundler_status}"

begin

require 'rubygems/remote_fetcher'

Gem::RemoteFetcher.fetcher.fetch_path(uri)

rubygems_status = "success ✅"

rescue => error

rubygems_status = "failed ❌ (#{error_reason(error)})"

end

puts "RubyGems connection to #{host}: #{rubygems_status}"

begin

# Try to connect using HTTPS

Net::HTTP.new(uri.host, uri.port).tap do |http|

http.use_ssl = true

if ssl_version

if http.respond_to? :min_version=

vers = ssl_version.sub("v", "").to_sym

http.min_version = vers

http.max_version = vers

else

http.ssl_version = ssl_version.to_sym

end

http.verify_mode = verify_mode

end.start

puts "Ruby net/http connection to #{host}: success ✅"

puts

rescue => error

puts "Ruby net/http connection to #{host}: failed ❌"

puts

puts "Unfortunately, this Ruby can't connect to #{host}. 😡"

case error.message

# Check for certificate errors

when /certificate verify failed/

abort "Your Ruby can't connect to #{host} because you are missing the certificate " \

"files OpenSSL needs to verify you are connecting to the genuine #{host} servers."

# Check for TLS version errors

when /read server hello A/, /tlsv1 alert protocol version/

if ssl_version == "TLSv1_3"

abort "Your Ruby can't connect to #{host} because #{ssl_version} isn't supported yet."

else

abort "Your Ruby can't connect to #{host} because your version of OpenSSL is too old. " \

"You'll need to upgrade your OpenSSL install and/or recompile Ruby to use a newer OpenSSL."

end

else

puts "Even worse, we're not sure why. 😕"

puts

puts "Here's the full error information:"

puts "#{error.class}: #{error.message}"

puts " " << error.backtrace.join("\n ")

puts

puts "You might have more luck using Mislav's SSL doctor.rb script. You can get it here:"

puts "https://github.com/mislav/ssl-tools/blob/8b3dec4/doctor.rb"

puts "Read more about the script and how to use it in this blog post:"

puts "https://mislav.net/2013/07/ruby-openssl/"

abort

end

guide_url = "http://ruby.to/ssl-check-failed"

if bundler_status =~ /success/ && rubygems_status =~ /success/

# Whoa, it seems like it's working!

puts "Hooray! This Ruby can connect to #{host}. You are all set to use Bundler and RubyGems. 👌"

elsif rubygems_status !~ /success/

puts "It looks like Ruby and Bundler can connect to #{host}, but RubyGems itself cannot. You can likely solve this by manually downloading and installing a RubyGems update. Visit #{guide_url} for instructions on how to manually upgrade RubyGems. 💎"

elsif bundler_status !~ /success/

puts "Although your Ruby installation and RubyGems can both connect to #{host}, Bundler is having trouble. The most likely way to fix this is to upgrade Bundler by running `gem install bundler`. Run this script again after doing that to make sure everything is all set. If you're still having trouble, check out the troubleshooting guide at #{guide_url} 📦"

else

puts "For some reason, your Ruby installation can connect to #{host}, but neither RubyGems nor Bundler can. The most likely fix is to manually upgrade RubyGems by following the instructions at #{guide_url}. After you've done that, run `gem install bundler` to upgrade Bundler, and then run this script again to make sure everything worked. ❣️"

end

def tls12_supported?

ctx = OpenSSL::SSL::SSLContext.new

if ctx.methods.include?(:min_version=)

ctx.min_version = ctx.max_version = OpenSSL::SSL::TLS1_2_VERSION

true

else

OpenSSL::SSL::SSLContext::METHODS.include?(:TLSv1_2)

end

rescue

end

# We were able to connect, but perhaps this Ruby will have trouble when we require TLSv1.2

unless tls12_supported?

puts

puts "WARNING: Although your Ruby can connect to #{host} today, your OpenSSL is very old! 👴"

puts "WARNING: You will need to upgrade OpenSSL before January 2018 in order to keep using #{host}."

abort

end

exit 0

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