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Apple, I like you but you're pissing me off.
December 16, 2012 1:48 PM   Subscribe

How do I get iTunes to give me a different random selection of music from my library every time I sync my iPhone.

It seems like this shouldn't be this hard...

I have a dinky 2GB iPhone and a lot of music in my library. I like to change up what's on my phone frequently, say once per week. But it seems like every time I sync my phone it gives me the same damn albums and songs over and over again, even though I do not have these items checked.

Walk me through it like I'm an idiot. What arcane combination of boxes do I need to check to get an automatic random selection of music on my phone.

I'm using the newest version of iTunes but I had been having this problem with older versions as well.
posted by Jess the Mess to Technology (4 answers total) 7 users marked this as a favorite
 
Does this help?
posted by axiom at 1:57 PM on December 16, 2012


http://support.apple.com/kb/PH12113 - specifically, scroll down to the section titled "Use Autofill to add songs". Note steps 4 & 5 particularly.

Also, I think that only works if you have “Manually manage music” turned on.
posted by Pinback at 2:00 PM on December 16, 2012


There is a relatively easy way to do this. Easy, but completely illogical. You will end up with a Smart Playlist that you sync to your iPhone. Every time you sync your phone, if you want to change the selection of albums / songs in the list, you will have to 'edit' the Smart Playlist, flip an option, flip it back, and save it again.

It's an ass pain, but it results in a random selection of albums every time.
1. Go to 'Controls' menu anywhere in iTunes
2. Scroll down to 'Shuffle', change setting to 'by Albums'
(you've done the important, completely illogical bit)
3. Make a new Smart Playlist.
4. Set the conditions to whatever you want. Personally, I have it choose from another, hand-built playlist containing many hundreds of albums I particularly like to have at random intervals. I also have some settings checked like "Last Played is Not in the Last 1 Month".
5. Limit the list size at the bottom to 2gb, or whatever, and (this bit is important) choose to "Select by Random".
6. Save the list
7. Add this list to the automatic sync settings on your iPhone, or drag it manually onto the phone (if you use manual syncing).
8. Every time you want to refresh the list, Edit the Smart Playlist, change the "Select by Random" to "Select by Album", then change it back to "Select by random". Your list should be refreshed. If you want to randomize again, do that flip again.
You can jazz this up with loads of extra settings. For instance, I have a normal playlist called "Ignore". In the Smart Playlist I have a setting that says if an album is in "Ignore" then, well, Ignore it. If the random selection is 99% good, but it has one album on it I am not interested in hearing, I drag this album to the Ignore list and the Smart Playlist will add something else instead. Later, if you delete the album from your Ignore list, it will be added to the possible list of random albums.

I am pretty sure this would also work with just random songs, rather than albums. Just change Controls to "Shuffle by Song". Sweet

These options are super convoluted, and it's odd that Apple haven't added some more clever/simple rule setting. Are you listening Apple?
posted by 0bvious at 2:28 PM on December 16, 2012


(p.s. the way above can be done automatically, rather than merely manually, and is the only way I have come across to sync albums at random, rather than merely a selection of songs)
posted by 0bvious at 2:42 PM on December 16, 2012


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