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If a corporate laptop user connects to the LAN via VPN, can an IT support engineer use Remote Desktop to shadow the user's session?

Thanks, Rob.

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You can not shadow a session with Remote Desktop. You can shadow a session with Remote Assistance. You will need to enable Remote Assistance on the target workstations.

As for the VPN portion, the answer is yes, so long as the machines can see each other, and there's nothing silly going on with firewalls.

Enable Remote Assistance

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+1 for Remote Assistance. The VPN doesn't matter, as long as both machines involved can see each other. – dmoisan Sep 1 '09 at 15:24
I realise that's more the question - does remote assistance work across VPN what with all the private IP addressing going on, NAT, routers et al – Rob Nicholson Sep 1 '09 at 15:54
Updated-------- – Izzy Sep 1 '09 at 16:07

Remote Assistance will work as long as there is not a firewall in the way. On a VPN if anything it should work better, as often times VPNs are set up such that once you're in, you have full network access to everything else that is inside the VPN.

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