upgrade jruby-openssl (due regression) #3053
https://travis-ci.org/jruby/jruby/jobs/72430858#L3412 is the problem that the prerelease is not used as default gem. though on other such integrity tests the same thing should go red (or you fixed it there ;)
just release the gem and all will be green again.
the tomcat error is a timing issue when tomcat shutsdown and probably some classloaders get closed before tomcat is finished (or so).