Renaming the ebuild and add ruby19 works. * Running test phase for ruby19 ... Ruby v1.9.3 (ruby), Pry v0.9.10, method_source v0.8.1, CodeRay v1.0.6, Slop v2.4.4 ....................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................... 759 tests, 1096 assertions, 0 failures, 0 errors ebuild pry-0.9.10.ebuild digest clean test 6.38s user 1.19s system 101% cpu 7.480 total The failing testcase described in the wiki http://wiki.gentoo.org/wiki/Project:Ruby/Pending_Bumps#pry_0.9.10 just happens with ruby18. I think ruby18 isn't supported by pry anymore (maybe it is also related to https://github.com/pry/pry/wiki/FAQ#wiki-source_location )
It would be nice if upstreams would clearly advertise whether they still support ruby18. I've taken the remark you mentioned in the FAQ and the mysterious crashes in the test case to mean that they don't. pry 0.9.11.4 is now in the tree as ruby19 only, in a separate slot.
