Nano won't recognize Apple LossLess files

So some of my music is in the Apple Lossless format and everytime I try to put those particular songs on my iPod, I get a message saying: "some of the songs from iTunes such as the file "insert name" were not copied to the iPod "insert name" because they cannot be played on this iPod". Now last time I checked Apple Lossless formats where supported by iPods, so I went and downloaded the newest iPod updater only to find that I was already up to date on my software. I would convert the songs to another format, but for some reason these few songs when converted to AAC become 2x as long and play at half speed, so I really just want to be able to put Apple LossLess files on my nano. Any one know why I can't play them on my iPod, or how to make it play them? Thanks.
-Blake

Is the podcast playlist configured to sync to your iPod from under your iPod's Podcast configuration tab?  To access this tab, plug your iPod in and when it appears in iTunes, click on its name from under the Devices section in the left hand pane.  This will bring you to the Summary tab.
Locate the podcast tab and click on it.  Here you can configure your iPod to sync podcast playlists.
B-rock

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