I have to agree with the "timing" related thing to a degree.  Here has been my experience with this issue.  1. This issue happens whether I try and download on my local network, or externally. For example if I am connected to Emby through my reverse proxy and a download is "Ready to Transfer" I can take a totally different device connected to my LAN and try to download the same thing and that, too, "ready to transfer". I've even gone as far as setting up a wireshark tunnel to my LAN on