IPod (Mini) refuse to sort smart playlists

Hello helpful ones.
I've got a rather annoying problem. I have a few smart playlists on my iPod Mini, like most people. I've set my iTunes to NOT autosync with the iPod. This is because the iPod does not have enough storage space for this feature.
Anyway, take the "recently added"-playlist for example. I've set it up to return the 50 newest songs, and sort them by their title/name. Whenever I drag-n-drop a new file onto the iPod, it appears in the playlist but allways ends up at the bottom. The iPod is totally disregarding my sorting instructions.
Playlist details, roughly translated from Norwegian:
Match the following criteria:
<Date added> <is in the last> <3> <months>
Limit to <50> <songs> selected/sorted by <most recently added>
<auto update>
iTunes on the other hand, sorts the playlist just fine. I seems like iTunes won't bother to update the playlist on the iPod, for some reason (I guess this is how it works, as it seems that the iPod itself aren't capable of much database handling).
I'm using an iPod Mini with firmware version 1.4 (all though it seems like this problem has been there with previous versions, but I can't really remember) and iTunes version 6.0.1.3 (Norwegian).
Does anyone have a clue what I'm doing wrong, or why my iPod is acting up?
Thanks for taking the time to read this

I read most of that thread before posting my question. It seems like the problems mentioned in that scenario gets solved when connecting the iPod to a computer.
That's what I can't understand here. When browsing the playlist on the iPod from within iTunes, everything seems updated and ok. But when I'm accessing the same playlist on the iPod itself after disconnecting it from the computer, the newly added songs just gets appended to the bottom of the list. I.e. no sorting of titles.
Just for the record, I completly restored both the iPod firmware (erasing everything) and the iTunes installation on my computer. I also reinstalled the ipodservice-thing that runs when you connect the device.

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