I've been trying to get a reply from anyone about this for ages now.
WordPress software - in this case Jetpack, but also the iOS client - will not accept the usage of self signed ssl certificates. Nobody will comment as to why, if this deliberate and by design, or a bug.
In brief: when attempting to perform the initial connection from a WordPress install to the jetpack servers, I get a "site inaccessible" and details of the cURL error produced. This error is the standard one you get when connecting to a self signed https server with peer validation switched on.
There is a separate, but related, issue with the iOS client which has been reported, unresolved and in some cases ignored, for months/years (http://ios.forums.wordpress.org/topic/user-should-be-able-to-override-ssl-certificate-warnings-1?replies=5 http://ios.trac.wordpress.org/ticket/1306)
I view this as a bug, but if it's a policy decision to not provide an admin bypass, and wordpress have no intention of supporting self signed certificates in their software products, could someone please comment?
At the very least could someone update the various FAQs so myself, and others, can stop wasting our time trying to chase this up?