[lokie]

I am trying to figure out the easiest way to import songs from an (PC laptop) external HD to my 14 Gig Iphone 4.

With Iphone connected to Itunes and my Iphone showing up under devices...

I have the following relevant options checked:

under Summary: Convert higher bit rate songs to 128 kbps ACC
under Music: Selected Playlists, artists, albums, and genres

The Playlists  checked has 6300 songs in ALAF format.

Obviously all these songs won't fit on my phone and when I try to sync I get this message:

The Iphone cannot be synced because there is not enough free space to hold all of these slected items (additional 14.37GB required)

Is there someway to auto fill songs that would fit and just leave the rest off? 

[saisunil]

I'd just manually deselect what I can live without and sync ...

[skunark]

I typically make playlists in two forms:
1) smart playlists by filtering on a year or decade.
2) genius playlists on favorite songs.

From that I will select as many as I can for the iPhone/iPod Touch and for the other iPods I would also select the checkbox to auto-fill remaining space.