X-mas playlist only shuffling 38 of 100 songs

My problem, whenever I play my playlist on my iPhone5, the songs from the albums play in order by the song and only shuffle 38 of the 100 songs. This only just started happening. In order to get all the songs to play I have to have each song from every album play in order by artist.
I tried deleting the playlist and creating it again several times to no avail. I created the current playlist this problem is occuring on iTunes using the selected songs I wanted on the playlist.
It's obvious that the iPhone's playing the playlist I created but when I try to select "shuffle" it only plays 38 of the 100.
It's very frustrating that I can't figure out how why this is happening. Can someone please let me know how to fix this?
Thanks
Steve

I have a theory that it's tied to Snow Leapord and/or iTunes, probably something Apple did to disable Palm Pre phones from being able to sync with iTunes. I've never seen that confirmed though, so it might nto be. All I know is I've been having this problem for a long time. I just tried iTunes 9.2.1 on my Mac hoping Apple had finally fixed it, but alas they didn't.
The solution I found? Get a PC and find an old version of iTunes. You give up some of the newer so-called features, and you've got to deal with a Windows box for your library, but at least the iPod will sync.
For more info/history, see:
http://discussions.apple.com/thread.jspa?messageID=11434111#11434111
http://discussions.apple.com/thread.jspa?messageID=12060595#12060595
Message was edited by: gsyoungblood

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Message was edited by: Carolyn Samit

Shuffle only Shuffling some of my songs....

I listen to my itouch all day at work and notice that it's not selecting many of the songs I have loaded on my player, why I ask??? I don't have play lists or anything fancy just a dump pile of songs that I want to hear randomly. I don't have the replay button on or anything. My software is up to date etc. It's really annoying as I keep hearing the same group over and over.
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You're welcome.
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I am having problems getting my playlist to shuffle since I updated to itunes 11.1. When I go to shuffle, it only shows 5 or 6 songs when I have more than 200 in the playlist. Anyone have any ideas?

Are the songs that don't play set to Skip when shuffling?
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Either automatically or by allowing us to assign values to songs within playlists indicating how often we want to hear the particular song or how many times we want the song to be replayed before it is removed from the shuffle queue for a user specified amount of time.
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I would really like to see what other users have to think about this.

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I've just discovered, by accident, that if I double-click on a song in the Up Next playlist, iTunes will begin playing that song and remove the earlier ones above it from the list. So if you don't like what's coming up, double-click the first one in the list that you do like.
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and not this one:
You may have noticed, I said existing Playlist. I haven't noticed a "create new playlist" option when I'm doing this.
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Any good?

X-mas playlist only shuffling 38 of 100 songs

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