Github release update hangs in OSX with many OpenSSL warnings

Okay, I confirmed the following workaround to work:

before_deploy:
  - |
    if [[ $TRAVIS_OS_NAME == "osx" ]]; then
      sudo chown -R "$USER:$(id -g)" /Users/travis/.rvm/rubies/
      rvm $(travis_internal_ruby) do gem uninstall openssl --all
    fi

The deployment logic is at https://github.com/travis-ci/dpl/blob/master/lib/dpl/providers/releases.rb. You can fork that project, create a topic branch with debug logic and use it in your build by specifying the following in the deploy: entry:

edge:
  source: your_github_name/dpl
  branch: your_topic_branch

In this case, however, the warnings and ruby - Fresh install of Rails and getting OpenSSL errors: "already initialized constant OpenSSL" - Stack Overflow suggest that Travis’ openssl gem is incompatible with Homebrew’s OpenSSL – looks like the same general problem as Ruby Openssl: Python deployment fails on osx image. The incompatible gem happened to be not the default one so it was enough to uninstall it, rebuilding Ruby wasn’t needed.