Why is iTunes not syncing photos from library after a certain date into my iOS device? I have an iPad mini (1st gen) I want to give it to a family member, so I operated a full system backup and reset. I have all the photos from the iPad inside of my library on OSX (in the Photos app).

I now want to put all these photos back into the iPad, so I did this (selected "Copy photos from photos" and checked "all the photos" with "include video") and synced:



However, there are more than 1.808 photos/videos in my library. Indeed, this is what my library looks like on Mac OSX. Please note the presence of items after the date "21 set 2015":



All the items after "21 set 2015" are not synced. This is what the photos app looks like on the iPad:





Why is this happening? What can I do to automatically sync photos which are newer than 21 september 2015?
Simply restarting iTunes made it work. Somehow, he didn't see the newly imported photos and had to be restarted. Not very intuitive, but it works: