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Is there any way to manage an external USB drive in iTunes as if it was an iPod? Specifically, have it appear as a device in iTunes, and be able to specify which playlists, etc., should be synced to it.

The use case is managing a USB stick that I use in my car. Currently, I have a smart playlist that I want synced to it, and every time I want to make an update, I delete all the files on the USB stick and then copy the playlist over, which is far from ideal.

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The venerable Doug’s Scripts for iTunes has many AppleScript to export and export/convert songs in case you wanted them to be MP3 or re-encoded when you export them. Also available is an inexpensive app to automate this even better than the scripts:

  • This is cool, but doesn't quite do what I want, because it doesn't keep track of the stuff on the device vs new stuff in the library, meaning you still have to keep track manually. – houbysoft Oct 16 '17 at 0:58
  • Yup @houbysoft - it works one way - blow away what you had and write what you want. For true syncing, you might have to adapt the script or use Apple devices that can use Apple Music or iTunes Match to sync all songs and playlists. At some point, USB storage might grow enough to hold your whole library? – bmike Oct 16 '17 at 1:35
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In the end I wrote my own solution for this, FlashTunes, which is now available on the app store.

It'll keep track of everything for you automatically, so you can just set it up once, and then every time you reconnect the device it'll figure out what to sync automatically, much like iTunes does for iPods.

See the demo here.

  • Wow - 15 days from "I need this" to a published app. Pretty cool. – bmike Oct 16 '17 at 1:36

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