So how do you know that are getting uploaded to iCloud? Do you check at the iCloud web site? If they are there, then you know the problem isn’t with your iPhone, as that part of the sync is working fine. So no need to mess around with your iPhone and restart it or anything. So I would check and re-check your Photos setting on your Mac.
The most recent versions of MacOS have an iCloud feature which allows the Desktop and Documents folders on a Mac to be synced to iCloud Drive. This allows a Macs desktop and documents folders to be accessed from other Macs, iOS devices, or iCloud. 1 The Basics of iCloud 1.1 Sign up for iCloud: iOS devices. 1.2 Sign up for iCloud: Mac. 1.3 Sign up for iCloud: PC. 1.4 Related Posts: You need an Apple ID to set-up an iCloud account. Either use a current Apple ID, create a new Apple ID in advance, or tap the link in Setup Assistant to get a new Apple ID.
Are you using the latest software updates? Do you have Photos, Preferences, iCloud, iCloud Photo Library turned on? And it sounds like you want “Download Originals” turned on too. I would then check your connection and make sure your Mac is connected and all is well there. You say a “desktop” so I assume you mean an iMac, Mac Pro or Mac mini. So no battery charging issues. Is it that the photos sometimes don’t sync?
Sounds like sometimes, so maybe it is in progress. Does Photos, Preferences, iCloud show any progress message, I think at the bottom? Are you using the same iCloud account?
Sometimes I take a video that is a few minutes long, which then is much much larger than a photo, and when that syncs across it takes a while, holding up any photos that come after it. Are you letting your Mac sleep instead of shutting down? When you shut down, it could make it very far behind in syncing in some cases. How fast is your Internet connection? You can rebuild your Photos library by holding down Command+Option when launching Photos. But I’m not sure this would help with syncing. That’s all I can think of.
There is no way to force syncing other than turning off iCloud Photo lIbrary and turning it on again. But that could also delay things further as it has to re-check and re-sync everything.
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