tlsv1 alert protocol version when connecting via SSL to OS X Server
curl 7.19.0 ... OpenSSL/0.9.8h 


This is a very old (and unsupported) version of OpenSSL you are using here which has no support for modern protocols like TLS 1.2 and modern ECDHE ciphers. Chances are high that after the upgrade your server now requires such protocol and/or cipher and thus connecting with your old OpenSSL version will fail. 


  * SSLv3, TLS handshake, Client hello (1):


This might also indicate that your client is trying to use SSL 3.0, which is usually disabled today because it is an insecure protocol. You might try to enforce to use TLS 1.0 (which is supported by OpenSSL 0.9.8) by using curl -1 or curl --tls1 in the hope that the server still supports TLS 1.0 and has ciphers configured to be usable by the old OpenSSL version.