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Error 50 when trying to add app to library

Been using an older version of iTunes on High Sierra to manage my iTunes library, mainly to manage apps that are no longer on the store or are 32 bit for my older devices. I’m ready to upgrade to Mojave and don’t want to loose this functionality. Did some reading around and been experimenting with using a virtual machine and pointing it at my host’s iTunes library. Everything works fine, even purchased music, but have the problem is when trying to add apps. Error -50 appears and the app will not add to the library. Searched far and wide and found solutions for this error for other types of media but not apps specifically. I have tried using iMazing but doesn’t quite work for me after going back and forth with tech support. I am willing to use a commercial product if it works the way I want to. Any one have any ideas or suggestions? Thanks for any help or advice.

VMware, macOS 10.13

Posted on Mar 25, 2019 3:47 PM

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Mar 26, 2019 10:38 AM in response to Mr_dOObla

Got it working, but have one more question.


Solved the problem by opening finder to the mobile applications library under iTunes. This is where the apps reside, did a secondary click, and chose open with, and choose iTunes. After that all the apps transferred without incident into the library. Guessing some sort of permissions issue?


The question is hopefully an easier one. Any ideas how to transfer the media keys (next track, pause, etc.) from the host OS to the guest? Both OS’s are running High Sierra. When pressing the media keys on the host, they work fine. When using them on the guest they open various applications on the host. Probably mapped them as a shortcut long ago and forgot about it. Any ideas? Thanks again for any help.

Error 50 when trying to add app to library

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