There's 2 sides to this coin: They're referring to a wiretap warrant, which only allows them get in the middle and listen to/capture data as it's being passed along. This is an easy warrant to obtain and no real evidence is needed first, just probable cause and only applies to telecom providers. It's used to get the additional evidence needed so that a search warrant can then be obtained (they want to catch drug dealers with real drugs, not words talking about drugs-message content as evidence for conviction only applies to charges like racketeering or conspiracy). Since the encryption keys are only known by the sending/receiving devices, the data can't be decoded. Apple servers just look at it's header file which identifies what device it's from/to for routing, appleID (unencrypted and easy to capture) and also includes a auth token to verify it as a genuine Apple device which is new enough to run iMessage (this is why the Lion Beta version no longer works). The encryption key handshake is no different in practice than a VPN connection, and DEA would have same "frustrations" since unencrypted data can only exist at the two endpoints, and not in between. However, if the DEA can still get enough evidence to be able to obtain a search warrant for the person in question, iMessage and iPhone is then DEA's best friend. History of every iMessage the user sent and received is saved locally on all their Apple device, even those from before they ever got a wiretap warrant going. iPhone will also have recorded the users geographical location allowing them to also know where they have been and when they were there. So I'm sure they would have no problem with drug dealers iMessaging like crazy at every "business" location or kingpin's honeycomb hideout they may visit. What may or may not be available on Apple's servers doesn't really matter. There'd be no benefit for them to get a warrant to obtain info from Apple direct because it wouldn't qualify as a wiretap warrant and there's probably no drugs inside their servers, so at that point in the investigation they could just get even more/better info by searching the suspects devices instead, at which point even if no drugs are found, they can still use all that info to start working on whoever the dealer's dealer is, and so on.