Sorry I was out of town. Just got back to test this. Here are the plexamp logs you requested, @elan . I just downloaded two smart playlists and the order in the download is randomized.
53427581738992.zip (356.8 KB)
And to be honest, the sorting in the smart playlist on the web interface is not 100% correct. It is mostly correct, but there are a couple songs not sorted correctly. But in the plexamp download, they are completely wrong. Here are the plex server logs after the download if that helps.
