The support for OpenSSL 1.1.0+ should be already available in upcoming Ruby 2.4 [1], but it is question, if upstream will be able to backport OpenSSL 1.1.0+ support into stable releases [2]. [1] http://bugs.ruby-lang.org/issues/12324 [2] http://bugs.ruby-lang.org/issues/12830
This was actually resolved by upgrade to Ruby 2.4, which supports OpenSSL 1.1.0+ just fine.