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Something is screwy with my itunes setup... I can play multiple songs after each other from the Music Library, but if I want to play several songs in a row from a playlist, it doesn't seem to work. It plays one and then stops. Any suggestions?

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ARGH -- never mind, I figured it out -- you have to have songs checked; it only plays the checked songs automatically, and skips the unchecked songs.

I wish iTunes handled some of these things a little more intuitively or at least gave you feedback if you're not doing things the way it likes.

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You shouldn't have to select songs in a playlist to get them to play. – ridogi Dec 13 '09 at 18:18
Yeah there's something else going on here because that's not normal behavior. – phoebus Dec 13 '09 at 18:57
sorry, meant checked, not selected. – Jason S Dec 13 '09 at 19:56
Smarty pants I thought I was when I wanted to use the option "Only sync checked tunes to ipod" as a means to make my ipod playlist on the fly using checkmarks in iTunes without playlists, until I found out that it affected playback behavior in iTunes. Back then sent feedback to the Void, erm I mean to Apple, to tell them this feature had overlapping functionality and should be customizable. – mtone Jan 12 '10 at 20:21
As a workaround for that, try the manually manage songs option, then click and drag the ones you want to the iPod. – TuxRug Aug 9 '10 at 18:39
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