I really need this feature as well. Itunes has it and foo_dop (foobar plugin) has it as well. I switched to MM because foo_dop does not work with iOS 5 and am really disappointing to see this feature not existing here.

That's ridiculous - it's an "urgent" feature bug that's been open since 2005.

As you can see here: http://www.ventismedia.com/mantis/view.php?id=2312 no, this feature hasn't been added yet.

Has this been fixed? Don't want to spend $30 for the Gold version if it's not up to iTunes quality

I have just started using Media Monkey to sync my iPod Classic and have noticed the same problem. I am also very annoyed by this. The auto-playlists and having them update themselves on the iPod is incredibly important to me.
Is there any updated info or help for this problem?

I'm pretty sure the problem lies with Apple as no documentation is made available on the workings of iDevices and they're constantly changed to keep third party developers guessing and catching up.

Wow, that sucks. That pretty much kills my main usage of MM. Guess I'll be making use of the 30-day money back guarantee on the gold license. I didn't think my usage/expectations of Auto Playlists to be that out of the norm.

Smart playlists aren't supported. See http://www.ventismedia.com/mantis/view.php?id=2312

I have a 3rd generation iPod nano and am trying to fully switch away from iTunes. An issue I just realized I'm running into is that it appears like Auto-playlists are being sync'd to the iPod as a static list. With iTunes, if all the criteria of the auto-playlist will exist on the iPod, the auto-playlist will update itself on the iPod without having to be sync'd again. For a concrete example of what I'm talking about, here's my situation:

I have a static playlist ("Main Selection") and an Auto-playlist ("Rarely Played"). The criteria of "Rarely Played" is that the songs are in the "Main Selection" playlist and the Last Played date is greater than 28 days ago. It appears that MM is syncing both lists to the iPod as static lists. When I had this same set up in iTunes (although specifying 4 weeks instead of 28 days), I could listen to part of "Rarely Played" on the iPod, listen to another another playlist for awhile, and then come back to "Rarely Played" and the list would be reduced to those songs that still have a Last Played date greater than 28 days ago.

I'm hoping there's just a configuration option I don't have checked or something to make this happen. Or is this the intended functionality?