Live Updating Smart Playlist... but not live updating iPod?

I have several video files that I want to convert to iPod-compatible MP4. I have a program to do the conversion in a batch mode and then add the files to my iTunes library.
I also have a live-updating Smart Playlist (for all files where the Kind includes 'video' and the playcount is 0) to catch these files as they come in. I have this playlist as one of the ones set to be automatically updated on my iPod.
However, in my test runs, the video is properly converted and added to my iTunes library, and the Smart Playlist picks it up as well. However, it does not then send the file to my iPod (which is already in its dock) unless I first eject the iPod and reconnect it.
I'd really like to get this working, as I'm hoping to do this on a somewhat regular basis--have a selection of stuff queued up when I go to bed, and then have it waiting for me on my iPod when I wake up to go to the gym. It worked for me over the weekend, when I bought an episode of Knight Rider from the music store while the iPod was connected--it was downloaded and added to the playlist, and then copied to the iPod with no intervention from me. Unless my memory is faulty or something.

Welcome to the Discussions Steavis,
As far as I know, a sync to the iPod only occurs upon the first attachment, as long as your settings are set for such action.
The iPod will only sync after the initial attachment if you initiate the sync yourself. I believe it is in a pull-down menu, and/or CTRL-Click the iPod in the source list and select "Sync".
I am not sure if that is all correct, but in my experience, if I have connected my iPod, it syncs, then I say load in a CD to iTunes, I must re-sync the iPod before they transfer.
Not knowing what you are using for this automation to get the app that converts and adds, etc, can do, I might explore a script that runs at a specific time of day and initiates a sync to any iPod connected. That should be fairly easy to do.
Beavis2084

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