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Sync multiple iTunes music libraries with one iPhone iPhone
I'm a bit of an audiophile, and I like to have all my music in Lossless format. I keep a separate library of Lossless files on an external drive, while my internal drive contains my AAC/MP3 library.

I often want to add a Lossless version of a song to my iPhone, for use in my car or with better headphones. So what I did was copy the iTunes Library file from my AAC/MP3 library into my Lossless iTunes Library folder. The AAC/MP3 Library was synced to my iPhone with 'Manually Manage Music' checked.

I then opened the Lossless library by holding Option while opening iTunes. I selected my lossless folder. I then deleted all items from the library with iTunes, careful to make sure not to send the files to the trash. I then added all the music in my Lossless library.

Now I can add music from both libraries to my iPhone without a hitch. In theory you could do this with as many libraries as you wanted, as long as the original library file was synced to your iPhone.
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Sync multiple iTunes music libraries with one iPhone | 4 comments | Create New Account
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Sync multiple iTunes music libraries with one iPhone
Authored by: blubalu on Tue, Nov 25 2008 at 7:52AM PST
I then deleted all items from the library with iTunes,...
I guess this gets rid of all your ratings in that library? Useless to me then.

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Sync multiple iTunes music libraries with one iPhone
Authored by: DocMan on Tue, Nov 25 2008 at 12:14PM PST
And you've pretty much always been able to do this if you're willing to Manually Manage the music on your device.

Some would say that because you are Manually Managing music, you are NOT syncing.

Not much of a hint either way.

Doc

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Sync multiple iTunes music libraries with one iPhone
Authored by: mrmobius on Tue, Nov 25 2008 at 1:33PM PST
Manully managing doesn't work with the iPhone. You can't add music to an iPhone from another library even when that option is enabled. This is an iPhone only hint. Regular iPods don't have this limitation.

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Sync multiple iTunes music libraries with one iPhone
Authored by: zane on Tue, Nov 25 2008 at 2:03PM PST
This is a hint, and a rather good one at that.

As the OP just mentioned, you cannot add music to an iPhone from two separate libraries, even with the "Manually manage…" option checked. If you have this option checked in your main library, then quit and relaunch iTunes opening your secondary library, the "Manually manage…" option will appear as unchecked, and dragging of music onto the iPhone from the secondary library is disabled. Re-checking the option with the secondary library open and hitting "Apply" results in a "The iPhone Blah is synced with another library…" dialog, with only a "Cancel" or "Erase and Sync option" available.

I will try this hint out a litter later, re-linking my 100gb or so external library after switching the library files will take some time I think.

It's annoying that copying music from separate libraries under a "Manually manage…" scenario is not available for the iPhone by default.

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