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I have some songs that are encoded in Apple Lossless on my MacBook Air. They are in iTunes Matched.

When I add the songs I get 256 kbps. I cannot add via iTunes because I have Match enabled. If I turn off Match, my songs get wiped from the iPhone.

How can I get my Apple Lossless songs to coexist with my Match library without wiping them every time I switch?

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This is not a real answer, but in short: You don't. –  Max Ried Mar 25 '12 at 18:21

3 Answers 3

To get lossless on two computers when using match you just need:

  • connect to the shared iTunes on the second computer
  • make sure that you don't have local copies of the tracks (little cloud icon by the name)
  • import tracks that are lossless.

It looks like you will create a second version of each track, but in fact ultimately iTunes sorts itself out and keeps only the lossless version

I haven't tried with a physical 256 copy of a track already downloaded to the library, only when the track is listed but showing as iCloud only

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You could use a different media player app that does not use the iPhone music library but uses it's on memory. Then you can upload your lossless music files to that app and play it. Something like AnyPlayer might be suitable.

Or, if you have a dropbox account, you might find songbox helpful.

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One workarond would be to change the media type for those files from music to podcast or video. Match would ignore them in the future.

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