I’m fairly new to SRM, but even so this one seemed like a real head-scratcher! If you happen to be using CA signed certificates on your “protected site” vCenter and “recovery site” vCenter servers, when you come to linking the two SRM sites you encounter SSLHandShake errors – basically SRM assumes you want to use certificates for authentication because you’re using signed certificates. If you use the default self-signed certificates, SRM will default to using password authentication (see SRM Authentication).
The process of requesting certificates for vSphere 5.1 is a fairly grim, manual process. It’s repetitive and easy to make a mistake on any step of the way. Since I’ve got to do this for quite a few VirtualCenter Servers, I thought I’d script the certificate generation if nothing else. I am following the excellent documentation provided in Implementing CA signed SSL certificates with vSphere 5.1 and more specifically in Creating certificate requests and certificates for vCenter Server 5.