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I have an iPod classic (160GB) which I sync with iTunes 10.6.0.40 using automatic syncing.

Generally, when I plug the iPod into my PC via USB, all of the Play count and Last played statistics update properly.

Yesterday I listened to 5 albums on my iPod, in the following order:

  1. The Pogues - If I should fall from grace with God
  2. Apples in Stereo - Fun trick noisemaker
  3. Joni Mitchell - Court and spark
  4. Led Zeppelin - Led Zeppelin III
  5. Underworld - Dubnobasswithmyheadman

However, when I plugged the iPod into my PC, iTunes only showed that I had played the last 2 albums (Led Zeppelin, Underworld) and it was as if the other albums hadn't played (their Last played dates were back in 2010).

Any idea what may be causing this?

Why doesn't iTunes respect my diverse taste in music?

Edit: I have since upgraded to iTunes 10.6.1.7 and I am still seeing this issue, so I am now offering a bounty to anyone who can help me solve this.

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Does the "Recently Played" list update in your iPod? –  Dante May 17 '12 at 8:09
1  
@Andrew - it's updated on the iPod after I play the albums, but once I hook the iPod up to iTunes, it's like I never played certain albums (i.e. they don't appear in the Recently Played list on either the iPod or iTunes, and the Play Count/Last Played stats don't show the albums as having played recently). –  LeopardSkinPillBoxHat May 17 '12 at 23:56
    
Try this: In the left-hand pane, right-click the name of the playlist, choose Edit Smart Playlist, and make sure that "Live Updating" is checked. –  Dante May 18 '12 at 3:17
1  
@Andrew - thanks. It is already checked. I don't think this is an issue with the "Recently played" playlist (or any playlist for that matter). As I said, the iPod/iTunes forgets that I ever played it (i.e. the Last Played date may be some date in 2010 despite the fact that I played it yesterday). And yes, the date/time on both my iPod and iTunes is accurate. –  LeopardSkinPillBoxHat May 18 '12 at 5:41
    
Does the play count update correctly when you play the same albums locally (i.e. in iTunes)? –  kopischke May 18 '12 at 19:14
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