[Spooky23]

You nailed it. I stopped reading and started laughing when iMessage was hailed as a successful platform addressing these issues. The only thing securing iMessage is the procedure for processing law enforcement requests.

PGP is a tool that requires expertise to operate effectively. That isn't good or bad, it just is.

[matthewdgreen]

I think if you read it that way you probably didn't click the link to the extensive criticism I've written about iMessage's key distribution. Saying something is better than plaintext is not the same as saying it's good enough to send secret documents.

http://blog.cryptographyengineering.com/2013/06/can-apple-re...

[Spooky23]

I'm not terribly familiar with your writing, but I disagree that plaintext is inferior to ineffective crypto. The problem with convenient things is that you are giving up control in exchange for expediency.

In my professional life, I've provided communications solutions to a variety of true VIPs in key executive and other roles. The advice that their counsel gave on most occasions was simple: exchange secrets orally, and in person.

That means don't use the courthouse wifi, don't conduct critical deliberations via email or public telephone networks. If you google around, you can see plenty of referenced to US state governors only communicating via Blackberry text or obscure phone lines, mostly to control short term leaks and keep deliberations out of the public record.

The point of all of this is that keeping secrets is hard, and if you must exchange them electronically, you need a strong set operational protocols to keep those secrets.