once VPNed into pfSense, unable to hit the public URLs of my websites - they are routed to the pfSense box

Posted by Sean on Server Fault See other posts from Server Fault or by Sean
Published on 2011-02-13T22:39:28Z Indexed on 2011/02/13 23:26 UTC
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Filed under:

dns

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vpn

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pptp

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pfsense

I have a pfSense box setup as the firewall/router/VPN appliance at my colo.

Once I VPN into the colo (either pptp or openvpn, pptp preferred due to multiple clients and ease of configuration), I am able to hit all my servers by their private 10.10.10.x ip and am able to browse the public internet without issue.

When I try and hit the URL of a domain hosted by one of my servers, I am prompted for credentials. If I login using the pfSense credentials, I'm connected to pfSense as if I'd used it's internal IP. If I hack my hosts file to point url -> server private IP it works fine, but this is obviously not a good solution.

To recap: not connected to VPN -> www.myurl.com works connected to VPN -> www.myurl.com never makes it to the correct server, but is sent only to the pfSense box

I'm sure it's something small that I've missed in the pfSense config.

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