What is your network setup? Do most files transfer OK? Is your transfer speed greater than real time? Does the problem file have a glitch at the same place when played in a software player? I would try rebooting the TiVo again -- only takes a few minutes. Run pyTivo as a program and turn the debug config item on while you transfer the problem file. In the past I've had this same kind of problem as have others. The pyTivo version and the TiVo software version can both impact it, unfortunately not in any predictable way AFAIK. Version 208 is getting a little old now -- you might want to try the latest version. Although most of the bug fixes since 208 have affected Windows versions only.