"Last Played" won't update on iTunes-purchased songs

I've had great joy using the variable "Least Recently Played" to create Smart Playlists. But certain things are not updating properly now, with 10.5.3.3
Here's the table:
Ripped Music, iPod Touch Gen 3: UPDATES PROPERLY.
Ripped Music, played in Win7 iTunes, UPDATES PROPERLY
Purchased Music, iPod Touch Gen 3: DOESN'T UPDATE
Purchased Music, played in Win7 iTunes: UPDATES PROPERLY.
I haven't done a full-blown matrix of experimentation of the whole library, but the one album I noticed it from is Wow 2012 Hits.
I've seen some discussion of similar problems, but not to this fine detail. Thanks for listening.
I also noted that iTunes isn't updating video podcasts correctly.

With more testing, it turns out to be just Wow Hits 2012. All my other iTunes-Store-purchased music is updating properly.
http://itunes.apple.com/us/album/wow-hits-2012/id462986937

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With more testing, it turns out to be just Wow Hits 2012. All my other iTunes-Store-purchased music is updating properly.
http://itunes.apple.com/us/album/wow-hits-2012/id462986937

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RestonMacGuy wrote:
I did something similar, but not the same: I "played" a few tracks from the iPod (fast-forwarding until about 30 seconds from the end) while the Shuffle was connected to my computer and in iTunes, which then caused the "Last Played" field to be updated.
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Plug in my iPOD, and it says its updating, and I can see the new music on the iPOD from iTunes, but its NOT ON MY IPOD when I unplug and try and play.
sounds like a drive letter confusion on your PC. see:
http://docs.info.apple.com/article.html?artnum=93499
... although, of course, you don't actually
b care
about what we might say, or fixing it ...
love, b

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"Last Played" won't update on iTunes-purchased songs

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