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So I'm about ready to upgrade my mac (which is on the other side of the United States) to El Capitan. I'll only have access to the computer via Chrome Remote Desktop and SSH while this happens.

Has anyone tried this before, and is there anything I should be worried about happening or any need to have physical access to the computer?

I will have some physical access, but it will be either a couple of days away or will be very unskilled labor.

The reason I'm doing this at all is that I actually do a significant amount of work on this computer remotely, but I'm away from it long-term (I do development on it over SSH from my chromebook).

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I personally would recommend staying away from anything that requires a restart of a remote computer you don't have easy access to. First I would hope that you have a backup of your computer since it sounds like it's important (aka more than just a web browser to you) whether or not you decide to proceed with this update. However why I recommend against you doing any restarts let alone an update is you are unable to control your computer from the moment you log off to the moment you log back on. If the update were to fail for some reason and the computer is unable to boot/log in you will be out of contact with it till someone can see what the issue is and fix anywhere from needing to type in a password to worst being go through a Time Machine restore of before the update. So basically to keep it simple if the worst case scenario of being unable to use your computer till someone can tend to it is not that bad of a thing to you, go ahead, a remote desktop connection does not put the computer at higher risk of something bad happening. If that is a bad thing then try to hold off till you have some safe down time. Hope this helps!

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  • These are solid suggestions and great general guidelines for dealing with remote upgrades. With CRD and SSH I can control my computer at the login screen, but it is very much dependent on my getting the timing right when I restart. So it's definitely not something I want to do without being able to handle extended downtime. – Roger Filmyer Nov 2 '15 at 20:19

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