In brief: Neither jetpack nor the ios app work if you have a self signed certificate.
In the former, you get a SSL error generated and jetpack complains that your site can't be contacted. In iOS, you get a fatal error. Annoyingly, earlier versions of the ios app used to work, but now don't.
I appreciate the need for security, but in both cases a "Yes, I really know what I'm doing, please ignore the error" option would save me massive headaches.
I've previously tried to raise @wordpress.org on a number of channels, but have had nothing back.
Any developments planned to sort this out?