Funny enough, I had a similar issue last night. I daily drive a Windows machine and wanted to send some clips of me gaming to a buddy via iMessage. Apparently y

Funny enough, I had a similar issue last night. I daily drive a Windows machine and wanted to send some clips of me gaming to a buddy via iMessage. Apparently you can't simply drag and drop files onto an iPhone once it's plugged in. You must use iTunes or some other program. iTunes took 20 tries to finally see my iPhone, and once it did it froze trying to sync it. Finally, I was able to drag my clips into iTunes and sync them over to my phone (a transfer that should've taken 1/10 the time it did given I was using USB 3). Great, the files are now on my phone and I can send them to my buddy. Nope, they are only available in my "TV" app and cant be exported or shared.