It seems that since Ruby disabled the TLS 1.0 protocol, there is an issue with installing custom gems in the puppet server.
If you run puppetserver gem environment you will probably see the following output:
/opt/puppetlabs/bin/puppetserver gem environment RubyGems Environment: - RUBYGEMS VERSION: 2.4.8 - RUBY VERSION: 1.9.3 (2015-06-10 patchlevel 551) [java] - INSTALLATION DIRECTORY: /opt/puppetlabs/server/data/puppetserver/jruby-gems - RUBY EXECUTABLE: java -jar /opt/puppetlabs/server/apps/puppetserver/puppet-server-release.jar - EXECUTABLE DIRECTORY: /opt/puppetlabs/server/data/puppetserver/jruby-gems/bin - SPEC CACHE DIRECTORY: /root/.gem/specs - SYSTEM CONFIGURATION DIRECTORY: file:/opt/puppetlabs/server/apps/puppetserver/puppet-server-release.jar!/META-INF/jruby.home/etc - RUBYGEMS PLATFORMS: - ruby - universal-java-1.7 - GEM PATHS: - /opt/puppetlabs/server/data/puppetserver/jruby-gems - /root/.gem/jruby/1.9 - file:/opt/puppetlabs/server/apps/puppetserver/puppet-server-release.jar!/META-INF/jruby.home/lib/ruby/gems/shared - GEM CONFIGURATION: - :update_sources => true - :verbose => true - :backtrace => false - :bulk_threshold => 1000 - "install" => "--no-rdoc --no-ri --env-shebang" - "update" => "--no-rdoc --no-ri --env-shebang" - REMOTE SOURCES: - https://rubygems.org/ - SHELL PATH: - /usr/local/sbin - /usr/local/bin - /usr/sbin - /usr/bin - /sbin - /bin - /usr/games - /usr/local/games - /opt/puppetlabs/bin
Also if you want to install a gem you will receive:
/opt/puppetlabs/bin/puppetserver gem install toml-rb ERROR: Could not find a valid gem 'toml-rb' (>= 0), here is why: Unable to download data from https://rubygems.org/ - Received fatal alert: protocol_version (https://api.rubygems.org/specs.4.8.gz)
Short but unsafe fix for this is:
opt/puppetlabs/bin/puppetserver gem install --source "http://rubygems.org/" toml-rb Fetching: toml-rb-1.1.1.gem (100%) Successfully installed toml-rb-1.1.1 WARNING: Unable to pull data from 'https://rubygems.org/': Received fatal alert: protocol_version (https://api.rubygems.org/specs.4.8.gz) 1 gem installed
It’s not that elegant, but it does the trick. You can also include this in an puppet exec block.