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Playlists in iTunes and Syncing with the iPhone

Forgive me if this gets long, but I want to get all the facts out there…I’ve had trouble understanding exactly how syncing music to the iPhone works and it’s beginning to bug me.

I like to only sync about 600-songs to my iPhone from my iTunes library at any given time. To grab a random selection I do the following: (1) create a playlist named Shuffle to iPhone, (2) with all the songs in my iTunes library in the playlist I select the Shuffle button, (3) scroll down to about song number 601 and select it and all the ones below, (4) uncheck them.

In the syncing options for the iPhone I have it set to only sync checked songs and to only pull from the above-named playlist.

While this system works in terms of getting the requested songs onto my iPhone it fails back in iTunes in that my Music library now only has 600 checked songs and I always have to select the entire library and recheck them. (I like to listen to my iTunes library in its entirety when I’m at the Mac, but I listen to them shuffled).

Is there something I am missing so that I do not have to select the whole library and recheck them after I sync to my iPhone? Or better yet, is there a way to Save the playlist so that I don’t have to recreate one every time I go to sync my phone. While the playlist is always there once I go back to the Music library and recheck everything the playlist also becomes completely checked and I don’t want all those songs transferring.

I hope this made sense.


— forkboy1965

Comments: 3 Responses to “Playlists in iTunes and Syncing with the iPhone”

    11 years ago

    Why not do this:
    Create a smart playlist. Have it pick random songs. Limit it to 600. Sync just that playlist. Then forget about the checkmarks.

    11 years ago

    I’ll give that a try, but I seem to recall previously having problems with this approach. But maybe it did it incorrectly.

    Thanks Gary.

    11 years ago


    Thanks for the great advice. I hadn’t quite understood how to appropriately set-up the smart playlist so I wasn’t getting the results I wanted. A review of the procedure led to the sort of success you indicated I should have.

    Thanks again.

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