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I have access to a secure VPN (VyprVPN via Giganews) and want to use this for only some applications; not all.

For example: If I connect to a VPN I want only the applications Opera and Newsbin to use that VPN connection. All other applications, like f.e. Outlook, should use the normal internet connection (while the VPN is connected/open).

Afaik this isn't possible, but I'm not totally sure. So therefore my question: is is doable?

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related: Disable VPN for a given process/application –  slhck Jun 7 '11 at 12:54

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No it isn't. Well not using normal means. Routing is routing. Routing operates lower down the OSI model. What you need to happen is for it to be aware at the applicaion level (higher up) so it can detect what program you are using etc. NORMAL routers do not allow you to configure routes based on applications or port numbers.

I think it is possible though. Routers can see ports so you can filter them by port number and send the traffic out different routes. i am sure i read something a while ago with Cisco routers that can do this. They don't come cheap though and they are business routers which require a lot of config and I'm guessing you want something simple for home use.

In summary it is the router that would need this feature and your bog standard ones for home use, even business don't support these features. Only the advanced line of Cisco and Sonicwalls offer these capabilities.

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It is possible to accomplish this, at least on Linux (and I'm thinking on BSD and OS X as well). You can do so by:

  • Create an exra user for all VPN traffic.
  • Create an extra routing table with 1 default route via the VPN.
  • Configure Netfilter through Iptables to use the other routing table for all traffic originating from a specific User ID.
  • Run the applications that should use the VPN under their own user. For example with 'sudo'.

The steps can also be found here.

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You could use the Windows Firewall to accomplish this (provided you are using Win 7 or Vista) - I wrote a guide on this

  1. Connect to your VPN as you normally would.

  2. Open the Network and Sharing Center - right-click on the Internet connection icon in the taskbar and choose "Open Network and Sharing Center" (see below)

  3. You should see (at least) two networks listed under "View Your Active Networks" - your VPN connection and one called "Network" - a.k.a. your ISP Connection. Ensure that your VPN is a "Public Network", and your ISP connection is "Home Network". If you need to change either connection, click it and an option window will appear (see below).

  4. Go to the Control Panel and click System and Security (see below).

  5. In the resulting window, click Windows Firewall (see below).

  6. In the Windows Firewall window, click Advanced Settings on the left pane (see below). Note: You must be logged in as an Adminstrator to make changes to the Firewall Settings.

  7. You should see a window titled Windows Firewall with Advanced Security. In this window, click Inbound Rules (see below).

  8. On the right pane, you will see an option for a New Rule. Click it (see below).

  9. In the New Inbound Rule Wizard (which should appear), do the following:

    • Choose Program and click Next.

    • Choose the program you wish to block all traffic to except on the VPN connection, and click next.

    • Choose Block the Connection.

    • Tick Domain and Private. Make sure Public is left unticked.

  10. Repeat Step 9 for Outbound Rules.

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