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

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