Why are some of my songs not syncing in my playlist when most of them are?

I am syncing playlists and a few of my songs are not syncing when the rest of them are. I have checked that they have been downloaded (and purchased!) and have a check mark in front of them. They are in the playlist lineup...

Do the songs play in iTunes?
Do you have any Restrictions (Settings>General>Restrictions) set that would prevent syncing those songs? (iTunes purchases only)

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Hello igho234,
Thank you for contacting Apple Support Communities. You don't mention how those songs got onto your playlist, but this article may address your issue, if they were imported from a third-party application or CD.
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http://support.apple.com/kb/TS3159
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Why are some of my songs not downloading to my ipod from iTunes?

I had downloaded all my albums from iTunes onto my iPod and then went a deleted the songs that I didn't like from the album. Later, I deleted all songs of my iPod Touch (4th Gen) and I was going to reload them all back on.
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All music is syncing across from my purchased items to my phone... However, some are missing from the 'purchased' playlist and I can only come across them when scrolling through the 'Artist' or 'Song' menu. I then have to manually add them back to my purchased playlist.
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Why are some of my songs not syncing in my playlist when most of them are?

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