Tried this today on a Debian Buster system:
$ bundle exec rake test rake aborted! NoMethodError: undefined method `<<' for nil:NilClass /home/godog/src/wikimedia/puppet/vendor/bundle/ruby/2.5.0/gems/puppet-4.8.2/lib/puppet/util/monkey_patches.rb:104:in `<class:SSLContext>' /home/godog/src/wikimedia/puppet/vendor/bundle/ruby/2.5.0/gems/puppet-4.8.2/lib/puppet/util/monkey_patches.rb:98:in `<top (required)>' /home/godog/src/wikimedia/puppet/vendor/bundle/ruby/2.5.0/gems/puppet-4.8.2/lib/puppet/util.rb:16:in `require' /home/godog/src/wikimedia/puppet/vendor/bundle/ruby/2.5.0/gems/puppet-4.8.2/lib/puppet/util.rb:16:in `<module:Util>' /home/godog/src/wikimedia/puppet/vendor/bundle/ruby/2.5.0/gems/puppet-4.8.2/lib/puppet/util.rb:15:in `<module:Puppet>' /home/godog/src/wikimedia/puppet/vendor/bundle/ruby/2.5.0/gems/puppet-4.8.2/lib/puppet/util.rb:14:in `<top (required)>' /home/godog/src/wikimedia/puppet/vendor/bundle/ruby/2.5.0/gems/puppet-4.8.2/lib/puppet.rb:12:in `require' /home/godog/src/wikimedia/puppet/vendor/bundle/ruby/2.5.0/gems/puppet-4.8.2/lib/puppet.rb:12:in `<top (required)>' /home/godog/src/wikimedia/puppet/vendor/bundle/ruby/2.5.0/gems/puppet-syntax-2.4.1/lib/puppet-syntax/templates.rb:2:in `require' /home/godog/src/wikimedia/puppet/vendor/bundle/ruby/2.5.0/gems/puppet-syntax-2.4.1/lib/puppet-syntax/templates.rb:2:in `<top (required)>' /home/godog/src/wikimedia/puppet/vendor/bundle/ruby/2.5.0/gems/puppet-syntax-2.4.1/lib/puppet-syntax.rb:3:in `require' /home/godog/src/wikimedia/puppet/vendor/bundle/ruby/2.5.0/gems/puppet-syntax-2.4.1/lib/puppet-syntax.rb:3:in `<top (required)>' /home/godog/src/wikimedia/puppet/rake_modules/taskgen.rb:9:in `require' /home/godog/src/wikimedia/puppet/rake_modules/taskgen.rb:9:in `<top (required)>' /home/godog/src/wikimedia/puppet/Rakefile:38:in `require' /home/godog/src/wikimedia/puppet/Rakefile:38:in `<top (required)>' /home/godog/src/wikimedia/puppet/vendor/bundle/ruby/2.5.0/gems/rake-12.0.0/exe/rake:27:in `<top (required)>' (See full trace by running task with --trace)
The problem seems to be ruby 2.5 and puppet monkey patching ruby ssl, fixed upstream at https://github.com/puppetlabs/puppet/commit/8b112c4bea7f33b98f0753c2d2e09bc231201684 so using puppet gem >= 4.10.2 fixes this