iMessage Downgrading

Glenn Fleishman:

The odds of this change in standards causing a security breach and your messages being exposed seem unlikely, at least right now. But after scrolling through conversations and seeing what’s going on, I feel Apple has omitted important signals for users when iMessage suddenly stops being used during a conversation. The impact of that hit me while revising my book: when iMessage isn’t available, Apple tells you only inline. Despite all the information Messages displays about iMessage being encrypted, the inverse state is faint. This kind of negative knowledge, or information about something not happening, can often be as important as something that does happen. A warning about a fuel tank approaching empty is the kind of information every driver (or pilot) needs, for instance. If you think end-to-end encryption—or Apple-based encryption—is critical for you, then a pop-up message or other warning is what you would expect. If you’d like to prevent Messages from downgrading security, you have options, although they may not be fully desirable. All of these are managed on an iPhone at Settings: Apps: Messages. You can’t control these message settings from an iPad or Mac.

This recently happened to my mother, and it was very confusing for her. For unknown reasons, while at home on Wi-Fi, she got signed out of iMessage. But it was not clear to her that this had happened or that she should try to sign back in. She was not aware that the Messages app supports multiple protocols or what the different bubble colors mean. All she noticed was that certain messages (e.g. ones sharing files) would no longer send and that she was not receiving some of the messages that people were sending to her. She saw the inline warning about encryption and interpreted it as that the sender was using a newer form of encryption that her phone didn’t support, so maybe she needed to upgrade.

I went over to take a look and quickly figured out that she was signed out of iMessage, but I couldn’t fix it. I kept getting errors that iMessage couldn’t be activated, even after rebooting the phone. Eventually, much later and again for unknown reasons, activation succeeded.