Have a iPhone XR, a 2015 Macbook Pro, 2015 Macbook Air. Photos, contacts etc were in sync, take a pic on the phone, it shows up in the macbook's, same with contacts etc. 2 days ago, I noticed pics not showing up in the mac's, same with new contact's. Played with settings for iCloud, signed out of iCloud account on all devices, and back in with same account, no change.
Called for support today. I spoke with one agent in Alabama who was unable to resolve, he then patched me through to advanced support and chatted with her for a bit until she escalated me to the next level which seems to be one step down from the engineers?
I was told I need to update the OS on mac's and IOS on the phone, I declined. My experience with both mac's, but mostly iPhone's, newer system software on older devices has negative effects on the operation of the machine's
If anyone has had luck with resolving syncing issues from iPhone to mac, I would be grateful to hear any advice.