rubygem-pry was broken with commit 399570, which made it accept slop 4.2.0: https://svnweb.freebsd.org/ports/head/devel/rubygem-pry/files/patch-gemspec?revision=399570&view=co pry uses slop 3.x only and does not work with slop 4: > % pry > /usr/local/lib/ruby/gems/2.1/gems/pry-0.10.3/lib/pry/cli.rb:100:in `<top (required)>': undefined method `new' for Slop:Module (NoMethodError) > from /usr/local/lib/ruby/site_ruby/2.1/rubygems/core_ext/kernel_require.rb:54:in `require' > from /usr/local/lib/ruby/site_ruby/2.1/rubygems/core_ext/kernel_require.rb:54:in `require' > from /usr/local/lib/ruby/gems/2.1/gems/pry-0.10.3/lib/pry.rb:150:in `<top (required)>' > from /usr/local/lib/ruby/site_ruby/2.1/rubygems/core_ext/kernel_require.rb:54:in `require' > from /usr/local/lib/ruby/site_ruby/2.1/rubygems/core_ext/kernel_require.rb:54:in `require' > from /usr/local/lib/ruby/gems/2.1/gems/pry-0.10.3/bin/pry:9:in `<top (required)>' > from /usr/local/bin/pry:23:in `load' > from /usr/local/bin/pry:23:in `<main>' > % The correct freebsd fix is to add a slop3 port and make the pry port depend on devel/rubygem-slop3. I've just submitted bug #204338 for this.
A commit references this bug: Author: mmoll Date: Sun Nov 8 00:09:07 UTC 2015 New revision: 401029 URL: https://svnweb.freebsd.org/changeset/ports/401029 Log: devel/rubygem-pry: use devel/rubygem-slop3 PR: 204339 Changes: head/devel/rubygem-pry/Makefile head/devel/rubygem-pry/files/
Should be fixed now, thanks for reporting!