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Offline Files, VPN, non-domain computers

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The CEO of our non-profit has a workstation in our office where he creates and modifies his networked files in a personal folder on our server, the majority of his work time.

At home, he uses a personal laptop and unhappily (due to perceived speed of opening, closing and saving docs) uses the VPN client (AnyConnect) so he can get access to his remote files.

But the man travels a lot and finds the downtime in airports and the like quite productive, provided he has access to his files. He uses his pesonal laptop when he travels.

In truth, this is the simplest scenario as he uses machines at a university office, a desktop or two at home as well as his work desktop. And he wants fast access to his file on the net and off.

The scenario I envision I'm not sure can work: install the vpn client on the non-domain laptop, enable offline files on his personal drive on the server and then sync offline files through the VPN tunnel.

I'm interested to know if this is doable or what other suggestions there might be. Thanks.


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