I ran into an interesting Messages issue after updating to macOS 26.5 / iOS 26.5 and wanted to see if anyone else is seeing the same thing.
Sending messages from my Macs (two separate MacBook Pros: M4 and M5) to Android/green-bubble contacts fails, even when the thread clearly says “Text Message - SMS.” In many cases the send attempt sits for about 3 minutes and then fails with “Message failed to send". . What made this especially confusing is that sending the same message from my iPhone works perfectly, and the iPhone-originated message syncs normally to all devices afterward.
One reason I do not think this is the cellular-related issue some people have reported is that both Macs were on Wi-Fi on my Comcast home network when the failures occurred. The iPhone itself can still send SMS messages normally over AT&T, so at least on the surface this does not appear to be a carrier connectivity issue.
I initially suspected the new RCS / End-to-End Encryption changes in 26.5, so I disabled all three RCS-related settings on the iPhone (RCS Messaging, End-to-End Encryption beta, and RCS Business Messaging). I also rebooted devices, reset Text Message Forwarding, deleted/recreated threads, and signed out/in of Messages on the Mac. One very interesting finding: SMS messages sent from the Mac to business shortcodes (FedEx in my case) work perfectly and replies are received normally, which suggests Continuity/Text Message Forwarding itself is functioning. The failure appears specific to person-to-person Android messaging from the Mac side.
Another clue: when a Mac-originated message is going to fail, it never immediately appears on my other Apple devices. Successful sends sync almost instantly across devices. That makes me think the failure is happening before the handoff into iCloud Messages sync fully completes. At this point I suspect there may be some stale per-contact RCS capability cache or routing issue introduced with the 26.5 messaging changes. I’ve submitted detailed feedback to Apple, but I’d be curious whether others here are seeing similar behavior with Android messaging from Macs after 26.5.
Sending messages from my Macs (two separate MacBook Pros: M4 and M5) to Android/green-bubble contacts fails, even when the thread clearly says “Text Message - SMS.” In many cases the send attempt sits for about 3 minutes and then fails with “Message failed to send". . What made this especially confusing is that sending the same message from my iPhone works perfectly, and the iPhone-originated message syncs normally to all devices afterward.
One reason I do not think this is the cellular-related issue some people have reported is that both Macs were on Wi-Fi on my Comcast home network when the failures occurred. The iPhone itself can still send SMS messages normally over AT&T, so at least on the surface this does not appear to be a carrier connectivity issue.
I initially suspected the new RCS / End-to-End Encryption changes in 26.5, so I disabled all three RCS-related settings on the iPhone (RCS Messaging, End-to-End Encryption beta, and RCS Business Messaging). I also rebooted devices, reset Text Message Forwarding, deleted/recreated threads, and signed out/in of Messages on the Mac. One very interesting finding: SMS messages sent from the Mac to business shortcodes (FedEx in my case) work perfectly and replies are received normally, which suggests Continuity/Text Message Forwarding itself is functioning. The failure appears specific to person-to-person Android messaging from the Mac side.
Another clue: when a Mac-originated message is going to fail, it never immediately appears on my other Apple devices. Successful sends sync almost instantly across devices. That makes me think the failure is happening before the handoff into iCloud Messages sync fully completes. At this point I suspect there may be some stale per-contact RCS capability cache or routing issue introduced with the 26.5 messaging changes. I’ve submitted detailed feedback to Apple, but I’d be curious whether others here are seeing similar behavior with Android messaging from Macs after 26.5.
