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Try using Windows Media Player. I found it is so much easier than to use the program that came with the player. Just make sure you have the most up to date version for your operating system. According to the Microsoft website, Windows XP is version 10, Vista is version 11, and Windows 7 is version 11 or 12. You can also download the current version from their website as well. I have used Windows Media Player to upload music and audio books to my MP3 player and it is so much easier.
For me, having upgraded Windows Media Player to version 11 caused the problem you are experiencing. Find a computer with Windows Media Player Version 10, then use iRiver's firmware update tool to install new firmware (version 1.77), then your T10 will work fine even with Media Player Version 11.
If you are already using Media Player 10, this problem could also be caused by corrupt firmware on the player.
make sure you have Philips Device Manager installed, from the product CD.
Run Philips Device Manager, and select the restore or repair option, then follow the on-screen prompts.
This will format the player and re-flash the corrupt firmware. All tracks on the player will be deleted.
Your problem sounds different from the one I had, but you might try the solution that worked for my problem: Go to a computer that has Windows Media Player Version 10 (not version 11), use iRiver's firmware update tool to install firmware version 1.77. Then, for me at least, my T10 worked on Windows Media Player Version 11 computers.
Follow the process on the Philips website -FAQ, "I have upgraded my Windows Media Player from 10 to 11 and encountered problem with synchronization and detection of unit by PC? What could be the problem?"
-skip over the part about updating the device drivers if you wish
Just find the songs details, and unclick skip when shuffle!! OR Windows media player 10 and 11, are almost the same, I use both, and I don't really know the difference. Go to start, click contrl panel, then change or remove programmes. Go to windows media player 11, and press delete! It won't delete it, it will change it back to windows media 10!!