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I have multiple MacBook Airs on Mavericks that need to be updated to Yosemite. I currently have a Mac Mini Server on 10.9.5 – I'm using the Caching service to download the software to have it locally available. Is there any way I can use ARD to assist in this process so that way I don't have to click through the installer screens and automate some of the process? Thank you in advance.

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You should be able to use Apple Remote Desktop to copy the macOS Installer application to the Applications folder on every client Mac, then send the following UNIX command as root:

/Applications/Install\ OS\ X\ Yosemite/Contents/Resources/startosinstall --applicationpath /Applications/Install\ OS\ X\ Yosemite.app --agreetolicense --nointeraction

This command starts the in-place upgrade action to OS X Yosemite. It may take some time for the entire process to complete, but it doesn't require any user interaction.

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