It is not possible to do this at the moment if you do not establish a VPN connection yourself, and then start the Octopus deployment using Octo.exe, and then disconnect.
In the future, it would be nice to have support for opening a VPN connection in Octopus. Is your VPN session established using the components of the Windows remote access server (i.e., can this tool, for example http://dotras.codeplex.com/ open a connection?) Or is it through some special software?
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