SSL_connect SYSCALL returned=5 errno=0 state=SSLv3 read server hello A (OpenSSL::SSL::SSLError)

Question

I have already looked through many of the questions similar to this one on stack overflow and im asking the ruby gods for help now.

im getting this stack trace when

Answer 1

OpenSSL 0.9.8zg 14 July 2015

Don't let you fool by the recent date in the version of the OpenSSL version. Mac ships with an rotten old version of OpenSSL which is not able to do TLS 1.1 and TLS 1.2 and does not support any newer ciphers, but it applies security fixes to this old version. Given that your question lacks the details to reproduce the problem my guess is that the server simply expects a new TLS version or some of the newer ciphers.

You can check the behavior of a public https server at SSLLabs which also shows the SSL protocol versions and ciphers supported by the server. It also shows if problems are expected with various clients, including with OpenSSL version 0.9.8 which you use.