I’m using an iphone SE3 and M1 MBP. At some point in the last few iOS updates, I lost the ability to send pictures or video via text to Android phones. There were no issues sending messages to iphones. This applied both to the phone and the MBP. I reviewed settings in excruciating detail, and followed every suggestion found online, including Apple support (one Apple genius actually suggested that I tell my Android user recipients to use WhatsApp in order to share pics.) This issue occurred whether using cellular or wifi calling, and VPN on or off. I’m quite confident I eliminated all the usual troubleshooting steps. The one I didn’t try was updating. So, although I am a very late adopter especially of OS updates, I updated the phone to 17.7, and it seemed to cure the issue; I was finally able to reliably send pics via text on my phone. Although I eliminated the issue, I wasn’t entirely satisfied because the function should have worked anyway. No other iphone users that I knew had this problem.
Sounds great, right? The problem now, is that since updating the iOS, I can no longer send text messages with or without attachments via the messages app on my MBP. I made no other change to any setting beside the iOS update. The MBP is running Ventura 13.6.3 (and basic texting to Androids has always worked on the mac). From what I can tell, this is not a widespread issue with other users, which leads me to believe that there is a problem with my settings (or machine) that can be rectified without updating the OS - something I won’t do until at least the x.1 update. And like many power users / nerds, I find that OS replacement isn’t a satisfying fix, anymore than replacing the phone and the mac would be.
Any ideas outside of the obvious I should look into? Something in icloud or…?
Try restarting your iPhone and Mac.
Also erase current conversations with android users and start a new one verifying that you you using yours and the other party phone number.
I have found that Messages can be more sensitive than other apps to a “mismatch” between operating systems. Usually people update their iPhones more frequently than their Macs, so the Mac lags several versions “behind” the iPhone. Updating the Mac often fixes it when other methods have failed.
Sometimes I think the problem isn’t actually in the operating system itself, but rather that something gets out of sync after an update on the iPhone. By updating the Mac’s operating system, some cache gets cleared or some security token gets re-synced, etc. Thus, I have sometimes been able to fix problems by resetting something on the iPhone.
First as @MacExpert suggested, restarting everything is worth a try.
Next, I’d try resetting the network settings on your iPhone. This will affect your phone’s carrier settings, so maybe it will help the MMS problem. Here’s where it’s found:
Settings > General > Transfer or Reset iPhone > Reset > Reset Network Settings
Actually that was the suggestion from Dave Hamilton at Mac Geek Gab (yes I’ve been asking everyone for help on this issue!) While it was a good idea, it didn’t help in this case. The only thing that made any difference was updating OS on the phone. And while that solved one problem (sending pics to androids from iPhone) it started another (messages on Mac can’t send anything to androids). So I’ll keep slogging away, accepting the unfortunate reality that there is probably no logical reason with a sensible solution, e.g., a setting is incorrectly switched.
I understand that text messaging requires multiple companies to play well together, but it is supremely frustrating because there’s never a clear path to solving it, as you said.
Right now I’m battling with my Messages on my mother’s computer. For whatever reason, it will not update messages marked as read when they’re read on another device (her iPhone, mainly). They get delivered just fine, but the read status doesn’t sync. She’s been ignoring it, and there are now over 300 “unread” messages. That leads her to just ignore it on the Mac, so she keeps missing new messages that arrive when she’s using her Mac. I’ve tried everything except updating her operating system, and that’s next on the list.