Laptop asks to be reauthorized every time I play certain songs

Laptop asks to be reauthorized each time I play certain songs even thoug ther were purchased from iTune

Dittos here. I've had my iPod since May. Everything worked fine until the most recent iPod Firmware update.
Specifically, MP3 podcast files from Manager-Tools.com cause reboot of the IPOD when in UNREAD state. If played (even 3 sec.) in iTunes prior to sync, they play fine; if reset in iTunes to UNREAD they again cause the a reboot in my iPod! Other podcast MP3 files are fine. All downloaded and administered via iTunes 7 (latest release). iPod debugger shows no errors. BTW: I have been unable to restore to the prior update.
Suggestions?
HP dv4000   Windows XP Pro  

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