I have Mac and iOS. Problem: I want to upload my Photos from iCloud. I choose to uncheck the box “Security copy only new pictures/videos” (because I want all the media stretching back many years, that´s the point…)
I activate the Automatic upload feature.
And the process starts.
But then the process stops without any explanation whatsoever by just switching ON “Security copy only new pictures/videos” with the fotnote “Only photos or videos that begin with 22 August 2025 is going to be uploaded”…
I don’t think you’re doing anything wrong, as you’ve seen, the process is simple and should just work. On Android, at times, I’ve had similar issues where uploading of photos prior to the install of the client just didn’t work. And then again, recently, on a new install, a few versions later, it suddenly did work, and perfectly.
With iOS you don’t have the same freedom to test with different versions of the client app, but if I were to take a guess, I’d say this was a client bug.
Since it isn’t an issue specific to StartOS, it could be worth posting about it on Nextcloud’s own forums. You could also take another approach, i.e. you probably have these photos synced on iCloud prior to you deleting them from there… you could download them onto your Mac, then upload them to Nextcloud from there.
