Why are songs halting playback?

I'm having a regular problem in iTunes where songs will stop playing with 1 or 2 seconds left til the end. It doesn't "Stop," in that the Play button changes to the Pause or Stop buttons, it just hangs up and doesn't play any further. If I hit the forward arrow it jumps to the next song just fine, though.
As far as I can tell, it only does it in shuffle mode. What's causing this?

I left out the fact that this happens when I'm broadcasting to my Airport, and I just realized this may be the key. The playback just stopped, and when I skipped to the next song, the display window said something about connecting to the Airport network.
Could blips in my connection strength cause iTunes to stop the playback?

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https://discussions.apple.com/community/itunes/itunes_match

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If you are syncing music to the iPhone automatically, you won't be able to drag and drop tracks on to the iPhone and the music will be grayed out.
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I would include the software iTunes version number, but I don't know how to find it.
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I don't really hate Apple, I just can't afford their products and can't operate them efficiently when I get on one.
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I get the exact same behavior. It is maddening. I find if I use the "sources" function, it happens more. I ended up wresting with it via the album view and it seemed better, but much less convenient. I've had this occur on the iPod app on my iPad, as well as on my iPod touch. Editting playlists is very flaky.
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Why are songs randomly disappearing from iTunes?

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My son (a former Apple Genius) finally figured out what was happening to my movies. A recent upgrade of iTunes seems to have a new feature that determines if the movie was purchased or gotten from another source. When the Add To Library option is used, if the new purchased movie was in the Movie folder, it is added to iTunes and remains in the same folder location. A movie from another source, if in the Movie folder to begin with, is moved by iTunes into the Home Videos folder in the iTunes Library. If you prefer to keep all of your movies in the Movie folder, which seems like the logical thing to do, select the movie title in iTunes and then right click to Get Info. Then select the Options tab at the top of the window, Change the Media Type to Movies - this will change the library file folder location where the file is stored and also change the location where the file is found in your AppleTV.

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Welcome to the Apple Community.
Are they checked in iTunes.

Why are songs I bought not listed in the purchased link

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yes, they were under the same account. I am looking at my songs purchased on the itunes store and it says 21. when I click on the little little "purchased" link on the left hand side under "ping" it only has eightteen songs.

Why are songs I've accessed in the past no longer accessible?

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It's not a good idea to post images that include your account id on public forums.
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I forgot to mention that when I look at the playlist that has been tranferred to the iPhone all the ones that won't play and are greyed out have a sync symbol next to the check mark.

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Why are songs halting playback?

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