Messages on macOS is acting up. Bug?

I’ve been running into a bizarre behavior in Messages and thought I’d run it past the brilliance of TidBITS readers!

So, my son got a new iPhone, and everything got migrated from his old one, which was then wiped. His new phone is signed into his iCloud account, and he can use FaceTime, send iMessages, etc.

But now, when I use the Messages app on either of my Macs, and pull up his conversation, it defaults to trying to send an SMS text message to him – and tries to direct said SMS message to his iCloud email address! So, it fails. The workaround is to start a new message as if to someone new, type his name and then use the drop-down next to his name to select from the contact methods – email, phone, etc. Only his phone number is blue. His iCloud email address is green (SMS). If I select his phone number, the new message will go via iMessage and will be added to the existing conversation in Messages. But if I relaunch Messages later in the day, it’s back to defaulting to trying to SMS to his iCloud email address again.

If that was confusing, then for what it’s worth I’ve posted a video showing what happens.

I’ve tried deleting his Contact record and creating a fresh new one. I’ve tried deleting the Messages conversation and starting one anew. Now, I’m out of ideas. If anyone has experienced this or knows what’s up, I’d really appreciate hearing about it!

One thing to check when testing is to make sure the iPhone has a strong connection to its cellular network or is connected to Wi-Fi. A weak or non-existent data signal for a recipient can result in messages being sent over cell carriers’ SMS network, not the Apple Messages network.

Have your son check his phone. Settings / apps / messages. Under “iMessage” there is “Send & Receive” - have him tap that and make sure that his Apple ID email address has a checkmark next to it at the top under “You can receive iMessages to and reply from”.

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Did you remember to log out from Messages on the old phone before wiping it?

If iCloud still thinks that phone is registered to his account, it may be trying to direct messages at it, and then failing (with a fallback to SMS) when it can’t get a response.

If you think this is happening, it’s clearly too late to go back to the phone, but you can tell apple to deregister it here: Deregister and Turn Off iMessage - Apple Support

If the new phone has the same phone number as the old one and they’re both iPhones (as you said they are), then this shouldn’t (I think) matter, but it may still be worth trying. If the new phone has the same number as the old one, then this will disconnect it, but you should be able to sign out/in on the new phone to get it all back working.

That was it exactly! As it turns out, my son turned that checkbox off intentionally because he didn’t want friends he texted with to see his iCloud email address. I’m not sure if it really works that way, and I talked him into checking that box again, so hopefully he keeps it that way now!

They can’t unless he exposes it. Tell your son to make sure the “Caller ID” (i.e. the option labelled “Start New Conversations From”) is set to his phone number (or another, throwaway email), and he’ll be all right.