So, I just started turning on iMessages in iCloud so that all my devices stay in sync. I honestly think the capabilities is sub par and just doesn’t work.
Basically, when I first turned it on, everything that was on my computer was instantly synced to my iOS devices. This was a pain since I had thousands of messages on Messages on OSX since I didn’t delete them. This I considered a minor issue, since Apple never asked me “What Device” should be the default system of record for iMessages.
However, after I deleted all the messages, I assumed that any message that is deleted on my iPhone is automatically deleted on my computer.
On my iPhone right now, I have 21 messages in Messages. The earliest message was 6/24/18
On my Work Mac OSX, I have about 350 messages all the ways back to 2017
On my iPad Pro, I have about 75 message and the earliest is 4/11/18
Hmm… I’d log out from iCloud on all devices, reboot all devices, and then log-in on the iPhone first, enable Messages in iCloud and wait for the iPhone to finish sync.
Then I would do the same on the iPad, and then the MacBook.
I have always had issues with storing messages and it’s stability since the announcement.
Responses are not in sync, messages disappearing.
Best example that I have so far. I have a group message with my family. Every few days it says “I left the conversation” and have difficulty finding the message thread on my iPhone, because of this.
I have another group thread that magically duplicated and I have messages scattered across 2 groups.
Yeah, I would deactivate all iCloud sync services, before logging out, so you’re sure that it’s a “fresh” start when you log in to iCloud on your devices.
Word of caution: always take a backup of any data that you just can’t afford to lose (sometimes things that shouldn’t happen actually happens - so better to be safe than sorry)
I’ve had absolutely no luck with messages in iCloud. My devices remain out of sync despite the usual trouble shooting - sign out, sign in etc. The iPad and iPhone are marginally more in sync but the MacBook is all over the place.
I found that some of my devices in the Messages settings were set to email addresses. Once I made sure that all my devices were set to my phone number and only my phone number, the syncing has been perfect between my devices.