Bug: Messages sync to Airmessage incorrectly after Mac syncs iMessages with iCloud

[rohituteja]

After syncing the Mac the server is running on with iCloud, any messages that were downloaded from iCloud will sync to Airmessage in reverse chronological order, with many duplicated messages and “Read Dec 31, 2000” showing. I saw two reddit threads from 2 years ago where this was acknowledged as an issue, but not fixed, so I’m not entirely sure if this has been fixed by now and it’s something on my end, but this does still seem to be an issue so I figured I’d throw it in here since I can’t find anything about it outside said old reddit threads.

[tagavari]

AirMessage sorts messages by database insertion order rather than by date, since in the past sorting by date caused some messages sent soon after one another to be clearly out of order.

Unfortunately, I'm not entirely sure how to resolve this issue, so for now my best recommendation is to reset your message history by disable iCloud message syncing, quitting the Messages app, and deleting the database files at ~/Library/Messages.

If anyone has any ideas on how to get around this problem, please let me know!