How to install new OS on VPN clients

[catfeetstop]

Hey! At my office we have many users who are always connected to our network through VPN. One user is using 10.7.5 and we want to upgrade them to 10.8.5. I've been unable to connect to anyone on VPN through Casper Remote, ARD, etc... Any thoughts?

[jarednichols · Accepted solution]

The biggest suck factor is transferring 4-5 GB of data to them. Thus, two policies:

1. Caching policy on an every15 trigger that puts the OS X Install.app into the waiting room and make sure it transfers over HTTP/S. This way it'll resume the download each time it runs the policy.

2. Policy in Self Service that lights up only when the caching is complete. Perhaps walk them through it over the phone as well.

[jarednichols · Accepted solution]

The biggest suck factor is transferring 4-5 GB of data to them. Thus, two policies:

1. Caching policy on an every15 trigger that puts the OS X Install.app into the waiting room and make sure it transfers over HTTP/S. This way it'll resume the download each time it runs the policy.

2. Policy in Self Service that lights up only when the caching is complete. Perhaps walk them through it over the phone as well.

[bentoms]

Are they an admin? Can they access the App Store? Is 10.9 an option?

[catfeetstop]

Yes, 10.9 is an option. I might just suggest they do that. So will Casper Remote and ARD not work if the client is connected through VPN? Self Service and policies should still work though, right?

[jarednichols · Accepted solution]

Server-initiated connections are out, yes (Remote, ARD etc) but SS and client-triggered policies will still work fine.

[catfeetstop]

Ah, I see. Thanks for the info, guys!