Right now: you don't according to Apple unless you update all of your devices/computers to the latest OSs. I've found this to be a crock of BS and found another workaround, although Apple won't actually tell that to you for reasons that I do not understand. There are known issues with iCloud syncing that have been plaguing me (and countless others) since I upgraded to Ventura/Monterrey. To be clear: when I say "known issues", I mean that Apple has actually acknowledges them to me on multiple occasions during my chat/phone tech support sessions.
As we're on our own, here's what I did that <<seems>> to work for me, bi-directionally. There are still a few exceptions, but those seem to only include non-Apple devices.
- Confirm I'm logged into all devices with the same AppleID
- Confirm Messages.app is set to sync via iCloud on all devices
- Do a manual sync on all devices (Settings -> AppleID -> iCloud -> Messages -> Sync Now)
- Confirm # of messages in iCloud registers the same number of messages for all devices (mine did not)
- If not, log Messages.app out of and then back into iCloud on all affected devices
- Restart all devices
At that point, you may STILL not see your messages syncing. This is when I was told that I NEED to update all of my devices to the latest OS and that OS's release. This, of course, is a lie: Apple didn't suddenly stop supporting Message syncing in iCloud for older OSs.
So, what I did to solve was this: toggled on/off the "enable messages in iCloud" button on the Mac and all of my associated iOS devices. On the Mac you'll find that toggle here, located in the preferences of the Messages.app:
On your iPhone, you'll find the toggle in Settings -> AppleID -> iCloud -> Messages and it looks like this:
[Edited by Moderator]
