Play count not updating - Shuffle 1st gen

My 1st generation iPod shuffle is not updating the play count or last played fields properly.
I have tested it with a few tracks manually dragged into the iPod, and it seems to work if I do this. However the play counts do not update if I use Autofill from my smart playlist. And I tried limiting my smart playlist to 950 MB (It's a 1GB shuffle) and dragging the playlist manually. Again the play count does not update.
This is a pain as I use the smart playlist to pick songs for my iPod and I use play counts in my smart playlist criteria, so it's messed up the way I use my iPod and iTunes.
(It used to work fine when I had earlier versions of Windows, iTunes and iPod software. I had problems getting iTunes to recognise or sync with the iPod, but updating windows to Service Pack 3 fixed this. But have had this play count problem since. I have up to date versions of iTunes and iPod software.)
Anyone had a similar problem and managed to fix it?

I've had this problem too, since the 8.1 release? It had been failing in shuffle mode but not in "not shuffle"/"in order". As of today it failed to update play date/count after playing in the "not shuffle" mode. The songs that were played are untouched, but a like number of other random songs that had not been played show today's date.
The apparent lack of support for older hardware is really disappointing. It certainly does not motivate me to go out and buy more Apple hardware which they will soon stop supporting.

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