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If you have a Philips HDD Series, it will not work with Windows Vista or Windows Media Player 11 except for briefly, then the player will stop working one day. Your only hope is to use it with Windows XP and Windows Media Player 10 - it is, basically, an obsolete player at this point in time.
The Philips Device Manager has a strange feature - it only properly updates your device if you have the newest version of the Device Manager: Download the newest version of the Philips Device Manager: www.usasupport.philips.com - change your country/language as needed Enter in your exact model # Click on the link for your exact model # Click on the Software & Drivers section Click on "Firmware Upgrade Software" Install the new Device Manager Open and run the "Update" tab -Tha Mp3 Doctor
Try transferring with Windows Media Player instead - see if the GoGear icon appears on the left hand side of the WMP screen (while the GoGear isp lugged in). If it does, then you can transfer and delete songs through Windows Media Player.