iOS 16

Hello donofmonroe,

Have you been able to confirm that Messages in iCloud is enabled? Per Use Messages in iCloud - Apple Support

1. Go to the Settings app.
2. Tap your name.
3. Tap iCloud.
4. Turn on Messages.

Thanks!

I have this exact same issue. Messages deleted from iPhone delete on iPad & Mac, but not the other way. Tried all fixes with no success.

Have spent hours with Tier 2 support answering question and waiting for the "Engineers" to get back to Tier 2 to get in contact with me and NOTHING!!! A very expensive device to not work or be able to get help with. Very frustrating.

There is also another thread with the same issue:

iOS 16 iMessage bug- not update/sync - Apple Community

Hello again donofmonroe,

If both the iPhone and Mac still have Messages in iCloud enabled, then for further assistance you'll want to reach out to Contact Apple Support. They can help look into this further with you.

Thanks for using Apple Support Communities!

I am having the exact same issue with the addition of iPad. When I delete from iPhone, messages are deleted across all devices. If I delete from iPad, messages are deleted on iPad and MacBook but not iPhone. If I delete from MacBook, messages are deleted on MacBook and iPad but not iPhone.

Unfortunately not for me. My iPhone does not sync and when I delete a message on my NEW iPhone 14 pro it syncs to all devices. BUT still when I delete on my iPad it does not delete on my iPhone.

STILL waiting on a fix....Very frustrated.

It seems like iOS 16.1 has solved this issue for me.