I've only been using an iphone for the last 6 months or so, after a successful ~7 years in a mixed marriage of OSX and Android. I'm not sure if this odd discrepancy has been around since my day 1 with my current iphone 7, but I finally got around to some screenshot proof. I always upload my photos/videos via lightning cable, and sometimes I see this header: Which, if I remember correctly, was similar to every time I uploaded from Android phones in that I had the option to delete items after importing. Sometimes however, I see this header on the Photos import window: Same thing, except no delete option. I haven't seen any difference in settings or whatnot when I plug in to upload, although it could be something quite obvious that I'm missing. I prefer the auto-delete option. Any ideas? If it matters, I'm using Photos 1.5 on El Cap and clinging to 10.3.3 as long as I can.