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The last time I updated iTunes on my Mac OSX Lion, I was unable to transfer projects from garage band directly to iTunes. I ended up having to save them as a file on my desktop then drag them to iTunes. I now have a Mac OSX High Sierra 10.13.6. I purchased it in November of 2015 so it is already outdated as far as computers are concerned. Will I have a similar problem?

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    The question as written is rather broad. Are you looking into upgrading just iTunes (while keeping macOS and GarageBand on whatever version they are), or upgrading your whole setup to the newest version possible? Also, please add the version numbers of all relevant software involved. – nohillside May 28 at 14:08

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