Previous messages not syncing from iPhone 17 to Apple Watch 11 Series

I recently upgraded to the I phone 17 and Watch 11 Series with GPS. I setup and upgraded my apple watch and phone both to OS27. I have been having problems syncing my messages with my watch. All of my photos, contacts and apps have synced correctly.

There are a few contacts where my text messages go back about two years plus. Almost 20k messages. When I send or receive a new message to that contact it shows up on my watch. However all the previous conversations on my I Phone aren't syncing over.

I Have tried resetting both devices. Toggling Bluetooth and wifi on and off. Adjusting the mirroring and custom settings on my phone. Even unpaired and repaired my phone twice.

I upgraded from watch series 9 and never had any issues. I am not sure what other steps I can try?

Posted on Sep 20, 2026 6:54 AM

1 reply

WheelieNick

Level 9 (74,110 points)

Sep 20, 2026 2:22 PM in response to Erockk02

Hi there

Please try this

Open the Settings app on your iPhone 17.
Tap your Name / Apple ID at the top.
Tap iCloud, then choose Show All (or look under Apps Using iCloud) and tap Messages.
Make sure Sync this iPhone is turned ON.
If it is already on, toggle it Off and back On, or tap Sync Now if available to force the database to push past conversations to your connected devices.