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I was working on TiVoToGo for my Series 3, too. I have the feeling that the TiVo Desktop software might be doing something funky with that directory. Try sharing a different directory and see if you can upload the files to it. Not that that will get your files to the TiVo, but it will take the TiVo Desktop software out of the picture altogether so you can see if it's the culprit.

Bitt, how much luck have you had, if any, with "Tivo to Come Back"? Getting content ONTO the Tivo is extremely hit or miss (mostly miss). I've had three different errors for one file on three different attempts. The most frustrating is when I'll set it up to transfer, it starts, and I can even play the file while it's going, but then right at the end it'll claim there's an error. Argh.

I've been having better luck with Tivo to Go and using VideoReDo to edit out commercials, though (then transfer them back to the Tivo).
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Matt