There are recent builds of OpenSSL for OpenVMS:
http://polarhome.com/openssl/ http://www.openvms.org/stories.php?story=14/04/11/6422157
HP's version is a bit older:
http://h71000.www7.hp.com/openvms/products/ssl/ssl.html
Free OpenVMS accounts:
Is there anything except resources that prevent you from moving to a more modern platform? Of course, "it works" is a valid argument there, too. But you seem to be writing new code, too.
OpenVMS has some really good ideas baked into the OS that we've had to reimplement or find off-the-shelf solutions for our new platform (for example a distributed key-value store (called "logicals"), a job queue system, and a clustered filesystem) but nothing so earth-shattering that it would keep us on VMS.
The biggest downsides are expensive hardware (OpenVMS is designed around clusters of a few beefy boxes, rather than many commodity boxes), lack of community knowledge, and lack of new software available for the platform. (End of life is also looming: http://h71000.www7.hp.com/openvms/openvms_supportchart.html .)