We have purchased iPhone upgrades for a few of our users. They all came out of the box with iOS 16.X. They are setup in Jamf Pro with prestage enrollments with configurations that do not restrict using messages or having their own individual Apple ID's on the device. We have 1 user who has reset and switched phones 3 times and had their messages populate on their "new" device (which was supervised in Jamf Pro with the same configurations) successfully with the only difference we can find being that those devices were on iOS 15.x at the time. We now have 4 users who have not been able to get their messages to load on their new device and have halted the remaining users from swapping until we can figure this out. Those users all have their settings->iCloud->messages turned on (sync this iPhone) and the manage storage is showing an amount that seems reasonable to what they have with messages. They all are either under the 5GB free limit for iCloud or are paying for additional iCloud storage. Their settings->Messages have iMessage turned on. Does anyone know what setting we are missing to get the messages to download to their new devices or what might be the issue?
Solved
iMessages not populating on new device

Best answer by lfriedo
We figured it out. The end users were either not turning on sync and a few settings under messages directly or they weren't understanding that they needed to connect to WiFi and plug in their devices overnight so the sync could complete. We did lose messages for one user as we reset their phone prior to the sync being able to complete but now we know not to do that again.
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