SOLVED - Why I couldn't transfer using TiVo Desktop

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Long story short: I had similar symptoms as most people with Tivo Desktop: Couldn't transfer files to/from DVR. I was specifically looking to serve my .mp4 movie library from my media-dedicated pc so anyone in the house can transfer/watch. All settings were correct and the "Now Playing from PC" was not showing up in the My Shows screen on the TiVo.

As it turns out (in my case at least) the problem was that when I installed the Tivo Desktop software it picked the wrong Network adapter to communicate with the DVR.

In my case, I have VMWare Workstation installed on this PC and so it creates some VM network adapters. Well the TivoDesktop software picked one of the VMNet adapters which obviously is wrong so it could never connect to the location of the shared videos. As soon as I made the change to the ACTUAL NIC of the PC and re-started the Tivo Server **BOOM** it showed up in my Roamio.

Hope this helps others having this issue although I know that not many people have additional NICs or even Virtual NICs installed.