Posting to this thread with hopes of getting some kind of response from people.
SSL self signed certificates are currently not supported on Jetpack or the iOS client (the latter used to work but it has been broken for several releases now, bug report was opened some months ago by someone else but at time of writing hasn't had any acknowledgement).
Requests for comment from myself and others have been made on numerous threads and have all gone unanswered.
Could someone give a definitive answer as to whether this is a deliberate choice or a bug? If it's a bug, are there any plans to fix it? The fix should be fairly simple - a config option to disable peer verification would be enough for IOS, but I admit you might need a bit more of a handshake/override for Jetpack.
I appreciate that people are busy, and I really don't want to be a pain, but I've been trying to get a comment from someone - even if that's a "We have no plans to support it, go away" - for ages now and the silence is most frustrating!