We have multiple Windows users on a single Windows 2008 R2 server (Standard edition), say 10 users. We would like each user (or program running in that user session) to utilize a separate IP address for all internet traffic. Is there a way to configure this within Windows? Or would we need to use something like OpenVPN or Squid Proxy and configure that for each user?
Under the assumption you are talking about users using Remote Desktop Services.
Windows Server 2008 R2 has a feature called Remote Desktop IP Virtualization and comes with the Remote Desktop Server Session Host role.
This feature comes with 2 options:
https://technet.microsoft.com/en-us/library/dd759263.aspx
RDS IP Virtualization is interesting, but it does not look like it allows assigning an ip per user, which is our requirement.
Until any new info comes in, it looks like the easiest way to do this is with proxies.