iCloud message syncing troubles

My Macbook Air will not sync messages seemingly no matter how hard I try. I can click the 'Sync Now' button, but nothing happens (stuck in Not synced) - I'm not sure if I have to wait awhile or what... I've gone into settings, and tried turning iCloud messages back on and off for it, I've made sure my vpn isn't on. I even updated my computer to the new Golden Gate 27.0.1 to no avail, and have restarted it a couple times as well. Everything works fine on my phone's end.

Posted on Oct 9, 2026 5:23 PM

1 reply

WheelieNick

Level 9 (74,110 points)

Nov 6, 2026 7:30 AM in response to skycandybrowni3

Hi there

Please try this

Toggling Messages in iCloud settings often isn't enough because the core authentication token remains cached. Logging out of the application container itself forces macOS to pull a completely fresh token from Apple.

Open Messages on your Mac.
Click Messages in the top menu bar, then choose Settings (or Preferences).
Go to the iMessage tab.
Click Sign Out and confirm.
Restart your Mac one more time to clear out the active processes.
Re-open Messages, Sign In with your Apple ID, and try clicking Sync Now again.