Can't play shows uploaded from PC

After giving up on my old Roamio per the discussion in the
Unable to play certain shows thread, I purchased a refurbished Roamio from Weaknees. Now I can play the shows recorded on the new Roamio.

However, I can't play anything that is uploaded from my computer. This is a problem I was also having with the old Tivo. I've tried using Tivo Desktop, pyTivo...

Can't play shows uploaded from PC

Can't play shows uploaded from PC