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I'm tired of always having to click "Autofill" in iTunes to put new songs and podcasts on my second generation iPod shuffle so I'm looking for a way to automate this with a keyboard shortcut, AppleScript, etc.

According to Apple's iPod shuffle FAQ, what I want to do isn't possible. . .

How do I make Autofill automatic—like how automatic syncing works on other iPods?

Autofill actually requires some action. You can manually click on Autofill each time you insert iPod shuffle, or you can use the "Keep this iPod in the source list" option to click Autofill any time and then connect iPod shuffle.

. . . but surely there is some way to improve my current workflow, which is to plug in my iPod shuffle, click it in the device list, and then click "Autofill". Any suggestions?

p.s. Apparently that "Keep this iPod in the source list" option went away with iTunes 7; I don't have any such option in iTunes 10.

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3 Answers

My ipod shuffle has an option to "fill available free space with music" or something like that. It's in the first options screen when my ipod is plugged in. Does this not accomplish what you want?

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No, I don't have that option. I have a second generation iPod shuffle. My first option is "Open iTunes when this iPod is attached", which I do have checked. –  Philip Durbin Oct 20 '10 at 11:59
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Click on your shuffle under "Devices."
Turn off “Manually manage music” on the iPod Summary tab.
Go to the Music tab, check Sync Music.
The checkbox for "Automatically fill free space with songs" will then appear.
Check it and click "Apply" or "Sync".

I don't have a shuffle but I can't imagine iTunes being that much different for any other iPod. I hope that works for you.

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Yeah, I don't see "Manually manage music". Sorry. I dunno, I really only use this thing for podcasts. Maybe I'll try to figure out some non-iTunes podcatcher/sync solution. –  Philip Durbin Oct 22 '10 at 1:28
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up vote 1 down vote accepted

I best way I've found to avoid having to click the Autofill button is use AppleScript to delete the contents of your iPod shuffle and then copy new content in its place. This is obviously slower than the Autofill mechanism, but once you start the process it's complete unattended and you can assign shortcut key to it like I have if you want. Here's the script I'm now using, thanks to http://www.eahanson.com/2009/03/16/applescripts-for-creating-podcast-playlists-in-itunes/

(* iPodShuffleAutofill.applescript *)
tell application "iTunes"

    repeat with thisSource in sources
        if the name of thisSource = "Phil Durbin's iPod" then set myIpod to thisSource
    end repeat

    set destinationPlaylist to the first playlist in myIpod
    set allTracks to every track of destinationPlaylist
    (* for testing/debugging
    repeat with this_track in every track in destinationPlaylist
        display dialog "Deleting " & name of this_track
    end repeat
    *)
    delete tracks in destinationPlaylist

    delay 3

    set sourcePlaylist to playlist "00podcasts"
    if the number of tracks in sourcePlaylist is greater than 0 then
        set shufflable of (every track of sourcePlaylist) to true
        duplicate every track of sourcePlaylist to destinationPlaylist
    end if

    reveal destinationPlaylist

end tell
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