iMessage and Voice Memos not syncing properly across devices

[Fontane]

I've been having sync issues between my iphone and macbook for a long time (several years) and have not been able to solve it. I'm running the latest software on both devices. There's a couple issues i've been trying to figure out:

1) The biggest issue is photo thumbnails do not display in iMessage on my Mac. instead, I get a general thumbnail like the image below. This happens for all videos and pictures.

2) I get iMessages on both devices, but deleted messages do not sync. In other words, if I delete a message on my MacOS, the message is not deleted on my iphone/iOS.

3) I just discovered last night that voice memos are not syncing between the two devices.

I have icloud enabled for everything. I've checked multiple times, disabled, reenabled, rebooted a hundred times, and nothing works to fix these issues. The problem started happening after I disabled iCloud for a brief period over a year ago. I've been having issues since then.

Appreciate any thoughts or help to figure this out. I'm at the point that I want to wipe my Mac and start fresh, but that's a huge effort and I'm not sure it will fix the problem.

 

[Sheepish-Lord]

I've been having sync issues between my iphone and macbook for a long time (several years) and have not been able to solve it. I'm running the latest software on both devices. There's a couple issues i've been trying to figure out:

1) The biggest issue is photo thumbnails do not display in iMessage on my Mac. instead, I get a general thumbnail like the image below. This happens for all videos and pictures.

View attachment 2084981

2) I get iMessages on both devices, but deleted messages do not sync. In other words, if I delete a message on my MacOS, the message is not deleted on my iphone/iOS.

3) I just discovered last night that voice memos are not syncing between the two devices.

I have icloud enabled for everything. I've checked multiple times, disabled, reenabled, rebooted a hundred times, and nothing works to fix these issues. The problem started happening after I disabled iCloud for a brief period over a year ago. I've been having issues since then.

Appreciate any thoughts or help to figure this out. I'm at the point that I want to wipe my Mac and start fresh, but that's a huge effort and I'm not sure it will fix the problem.

Common, syncing still is hit or miss across devices

 

[Fontane]

Common, syncing still is hit or miss across devices

But we're talking about basic sync functionality.

 

[Fontane]

Update: I just solved the voice memos issue by deleting and reinstalling the iOS app. Don't think I can do the same thing for the iMessages app on the MacOS so still cant figure out how to fix it.

 

[Sheepish-Lord]

But we're talking about basic sync functionality.

Trust me I know. One of the reasons I’ve vastly reduced my Apple ecosystem because they still can’t get basic things right but since nobody else really offers a similar experience people don’t make a big deal about it.

 

[Fontane]

Just wanted to bump this thread to see if anyone else has come across this issue and solved it. My imessages on MacOS is still not downloading thumbnails for pictures/videos. iMessage also does not sync deleted items across devices. So if I delete a message on any device, I have to then delete it on all the other devices, which makes central management of iMessages a high-maintenance headache.