Not Automatically Syncing iTunes Playlists

So I recently upgraded from a 4th Gen Nano to an iPhone 4 and I'm having one minor problem. On my Nano, iTunes would automatically update every playlist on it when it synced as soon as I hooked it up. With my iPhone, I need to delete the old playlist on the phone in iTunes, drag the updated playlist from the library to the phone and THEN sync. Simply dragging the new playlist to the phone without deleting the old one creates a playlist that's 99% duplicates.
This is kind of minor, but it's getting to be a nuisance. I'm sure someone's asked it before, but I can't seem to find it anywhere. Thanks.

First of all, This has nothing to do with iCloud, this is all iTunes. To enable songs to sync in iTunes you will need to goto your device > Music > Sync Music, and iTunes should sync all the music you specify and new songs you purchased.

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