EDIT: Just realized this post is in the wrong place, but if anyone has any help regardless that would be much appreciated! So I'll get straight into it. iTunes hates me. Every time I plug in my iPad it wipes all my most recent photos. This is due too it being set too replace them with photos contained in folders on the computer. So the simple solution is too just drag photos from my phone, into those folders and then sync. Then problem is, since upgrading to a iPhone 6 Plus from a iPhone 5, many of the photos share the same name and trying to keep them in the same folder results in the deletion of old photos it views as duplicates. So what I am asking is, does anyone know of software which I can use to have all the photos renamed to the date taken and time taken, or something along those lines? Once on the iPad its fine, it sorts them by the date and time held within the Meta data, its just getting them there! Alternately if anyone has another suggestion that would be great. These are all memories, you see, I don't want to lose them (I already permanently lost months of Summer photos by trying to use iCloud Photo Library. Wiped everything and I had foolishly not created a backup! I wont try that again!) Thank you in advanced, Alexandros. P.S. I also have a folder (mostly videos) that do not have meta data and thus when they go on the iPad they are placed at the date they were transferred. This is really annoying and this I don't put them on. IF anyone knows a way I can add my own Metadata I would be very thankful. I can guess at most as I have pictures with Metadata to go along with them.