"Not enough free space" for my music. But there is.

Long time iPod/iPhone user here, but first time encountering this.
Until now I've always had iPods with sufficient memory to hold my entire music library, but this time (to save money) I bought the 16GB iPhone 4S and for the first time I'm having to pick and choose what I want to carry around with me. So I created a playlist in iTunes and have selected to only sync that playlist.
But here's an oddity: the capacity bar on the screen in iTunes suggests I can put that playlist on with 1.43GB to spare. But when I try to sync the iPhone it tells me ther's not enough space. See screenshot below.
Any ideas?
Posted to both iPhone and iTunes forums.

Hmm, changing the drive letter usually works if the ipod is reporting available space incorrectly.
http://support.apple.com/kb/TS1493
+iTunes and Windows Explorer report the wrong amount of available space on iPod.+
Your music library portion might only have 20GB, but what about podcasts, music, & photos? That could be the other 20GB it is saying it doesn't have room for.
Try syncing selected playlists and get it down to under 40 GB. You're right, you can't ignore it, but you can work around it.

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