IPod Library in iTunes different from iPod Library on actual device

Sorry for the cryptic header - I can't seem to get iTunes to match with the iPod. When you connect your iPod to your computer and open up iTunes, you can check your iPod's music library by clicking the Music tab under the icon for your iPod. My problem is that when I disconnect the iPod from the computer, certain songs that iTunes said were in my iPod's library don't show up when I look for them with the iPod. Any ideas?

When you connect the iPod, you should see your Summary page... it has a picture of the iPod, next to its name, serial number, software version, capacity, and format. Down towards the bottom of this page is a section entitled Options. Below this there is an option that says "manually manage music and videos." Is this option selected?
If so, iTunes is expecting you to manually click and drag songs to the iPod. If you'd rather iTunes & iPod match, you can uncheck this option, as well as the one that says "enable disk use" and then click Apply. This should make the two match.
If this option is not selected, check to make sure the songs that are not transferring to the iPod play in iTunes.
CG

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