The DEA has figured out that getting a wiretap order for an iPhone, executed at the phone company, doesn’t get them iMessage content. It’s pretty obvious the various TLAs engaged in law enforcement will use this as a concrete example to push the “Going Dark” initiative to get CALEA reinterpreted (or legislated) to cover various internet based communication services. And designing a service to use end-to-end protection will be right out.
iMessage is a special case here, since it inserts itself into the normal text message user interface. It’s the phone’s preferred way to send messages, and from the user’s (and law enforcement’s) perspective, it’s a native feature of the phone rather than an app.
I’m worried this will bring up yet another concern–even if they get what they want with CALEA, they are going to discover that they have execute multiple, maybe even many, wire tap orders to track a single subject. How long until we require each ISP to be able to MiTM attach every TLS connection? Or another clipper chip initiative?