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I would like to be able to step through an application deployed to a remote location which as yet has nothing bar version 3.5 of the .Net framework.
What steps do I need to go through to achieve this and how long would you envisage this taking?
If you have unrestricted TCP/IP access to the remote location, this will be very easy (as in, 5 minutes tops to get it to work): see How to: Set Up Remote Debugging and How to: Run the Remote Debugging Monitor for the steps involved.
If your development machine is separated from the remote server by firewalls, routers, etc., things get a bit more difficult. Since remote debugging requires Windows authentication, DCOM and other things that are usually (and quite sensibly) blocked by security policies, you’ll most likely require some kind of VPN access to the remote network in order to get things to work.
Setting up a Routing and Remote Access service on the target server is a quick way to get PPTP dial-in access to it, but there are significant security implications to doing this. So, this is most likely the step that will take up most of your time (and, depending on the organization that manages the target network, lots of discussions with their network/security people…).
My advice would be to start testing with remote debugging using a test machine on your local LAN first, and deal with the connectivity issues once you’re comfortable with the basics.