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I ran into the same problem with my Sansa when listening to legally downloaded audio books from the local library. This is what I found:
" Are you sure the player is in MTP(plays for sure) mode when you transfer it? You
can check by going to settings>usb mode on the player itself. I
think it needs to be for you to use library files like that. " (This worked for me)
"are you copy and pasting the files? if so you will need to use WMP to
sync the files. copy and paste might not be transferring the license." (didn't try this -- didn't need to)
first you must format the player using msc mode then after that retransfer the songs to the player. If you are receiving this message it means that the songs on the player have expired. This is normal if you download the songs off rhapsody, napster or any online music stores and if you have ripped songs iwht copy protect music on it if you ripped them using windows media player 10.
"Syncronize to continue your music subscription"
is normally an indicator of the following causes, depending on the source and type of the music that you have on your M240:
(1) If your music files came from a subscription music service provider
(Napster,Yahoo, Rhapsody for example):
This would mean that the licenses for these subscription songs need to be updated. They must be updated at least once every 30 days. You must use your subscription music service's software to resync the songs (the process varies depending on the service). Also, you would get that "sync" notice if you've cancelled your subscription.
(2) If your music files were ripped from an audio CD:
The best solution would be to once again "Rip" these audio CD files using Windows Media Player, version 10 or 11. Before ripping, ensure that the "Copy Protect Music" option is unchecked by going to Windows Media Player's "Tools", then "Options", then selecting the "Rip Music" tab.
If all else fails, the best "last resort" would be by setting the M240 to MSC mode and formatting it in Windows Explorer or "Disk Management"
I hope this proves useful. I know it's quite a bummer when you have a whole bunch of songs just sitting in your player with a "Sync" error.