iPad Sync Problem - Please Help

[legaleye3000]

I have the latest iPad Pro 11 inch on the latest iOS 13.5.1 trying to sync with an iMac running latest Catalina 10.15.5 Supplemental.

I plug in and Finder recognizes the iPad; however, when I click on the iPad, a message comes up saying if you are experiencing a problem with my ipad, I can restore to its original settings and just see a greyed out button to update or a button to restore.

The iPad works perfectly fine. I tried using AnyTrans to transfer a video and syncing worked fine in AnyTrans. Help appreciated. Thank you!

 

[0128672]

Is your iPad plugged into your iMac directly or via a hub? Have you tried testing with a different cable? It sounds like the trust handshake worked because the Finder recognizes your iPad, but just a guess, try resetting the Location & Privacy setting on your iPad to initiate the trust handshake again.

 

[legaleye3000]

I reset location and privacy and its directly connected. No difference. Thanks for your reply.

 

[0128672]

I'm wondering if the buttons are grayed out because (1) you're on the latest version of iPadOS, and (2) you haven't created a backup saved to your iMac. Are the Sync and Backup buttons active? A screenshot might be helpful.

 

[legaleye3000]

Actually- very weird thing just happened. I completely wiped my iOS and DID NOT restore from backup. Everything worked. I then wiped again and restored from backup and its not working.