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I currently have a VPN server running and I am attached to it as a client. The current setup is such that only routes 10.0.0.0/16 are tunnelled through the VPN. Additionally, I push Amazon's internal DNS server (10.0.0.2) to the client so if I hit any of my private hosted zones then Route 53 will take care of the redirection.

My question is, how can I route a specific URL to tunnel through the VPN? For example:

google.com -> local wifi

abc.com -> vpn

where abc.com is my specified URL that I want to make sure gets tunneled.

closed as off-topic by Ron Maupin Apr 27 '18 at 11:18

This question appears to be off-topic. The users who voted to close gave this specific reason:

  • "NE is a site for to ask and provide answers about professionally managed networks in a business environment. Your question falls outside the areas our community decided are on topic. Please visit the help center for more details. If you disagree with this closure, please ask on Network Engineering Meta." – Ron Maupin
If this question can be reworded to fit the rules in the help center, please edit the question.

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    Do you have control over the VPN server? What kind is it? – Ron Trunk Nov 18 '15 at 22:26
  • Yes, it is OpenVPN. – Liam Horne Nov 19 '15 at 2:59
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    Unfortunately, questions about protocols above OSI layer-4, and questions about host/server configurations, are off-topic here. You could try to ask this question on Server Fault for a business network, or on Super User for a personal network. – Ron Maupin Apr 27 '18 at 11:17
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You have to have the IP of abc.com included in the tunnel policy.

  • My issue is that abc.com maps to multiple, possibly frequently changing IP addresses. – Liam Horne Nov 20 '15 at 15:37
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    You have a problem :) Your VPN client routes traffic based on network layer information (IP addresses), but you want it to route based on information contained in the http data. Furthermore, you want to do this based on a DNS query that can resolve to an arbitrary IP address. I can't think of how this would be possible without writing a custom client. – Ron Trunk Nov 20 '15 at 15:42
  • That's what I was afraid of, and okay fair enough, I will look into possible solutions that can help me out here. – Liam Horne Nov 20 '15 at 19:31
  • How about running a script in crontab that updates the IP route table? I have two NICs and I want to route some IPs to a specific connection. – Alexis_FR_JP May 14 at 9:48

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