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Does IIS 6 inherently support IP tunneling? I heard from a consulting group that it does not but I find that hard to believe.

If not, is there a standard way to support IP tunneling using third-party solutions?

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My understanding from talking to stevej is that he wants a URL on an IIS server which will be proxyied by IIS to a web service on another machine/port. Sort of like the Apache 'Proxy' directive... I haven't really used IIS since about 2.0, so I'm no help. – darron Jun 4 '09 at 18:55

Hmm, I'm not sure I understand your question.

IIS 6 (the Windows web server) will serve IP traffic to any host that requests it. It does not do any tunneling itself - it sits ontop of that layer of TCP/IP stack.

An IP tunnel (whether encrypted by IPSec, CHAP or whatever) should appear at the server as an IP address on an virtual adapter. If that's the case, then yes, IIS 6 can serve content to it.

If you mean IPv6, then this is another matter all together!

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OK fair enough, a better question would be does the traditional Windows environment hosting IIS6 support IP tunneling or do I need third-party support to do it. Let's say I am running XP or Vista... – stevej Jun 4 '09 at 3:11
In that case, no. IIS6 is not a VPN server. It only serves web pages. Your solution with Windows Server is Routing and Remote Access. For other OS's (XP or Vista), then there's a huge amount of options. Personally I use a program called Hamachi. It's a VPN that requires no configuration. Once you have the VPN set up, hooking IIS up to it is a doddle. – Mark Henderson Jun 4 '09 at 3:39

it's unclear what you mean by tunneling. You can set up Routing and remote access (using PPTP or L2TP) if you want to allow remote access. You can also set up IPsec and domain isolation if you are trying to restrict traffic to certain hosts. Take a look at this doc and see if this describes what you are trying to do: Server and Domain Isolation

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Take a look at this StackOverflow question:

Best reverse proxy for IIS 6

It seems to imply that IIS can't natively do it, but an ISAPI extension called 'Helicon ISAPI Rewrite 3.0' can.

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Okay, okay-- I blew all that crap away.

Assuming dblack's comment is accurate re: what you're looking for is accurate, the answer is an unfortunate "no". IIS doesn't have proxying functionality like Apache does.

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OK, right. I understand that Windows offers only partial support for IPv6. Does that include support for PPTP out-of-the-box or not? Is third-party support needed to enable that on XP, Vista, or Server 2003, might be a better question. – stevej Jun 4 '09 at 3:15
I'm such an idiot. I saw "IIS 6" as "IPv6" and wrote this rant. My apologies. I thought you were talking about mandatory features of the protocol... IIS 6 is an application server. It doesn't do tunneling protocols. I'm not sure what you mean by IIS 6 "supporting tunneling". – Evan Anderson Jun 4 '09 at 3:21
Do you mean: Can a Windows server running IIS 6 also host PPTP / L2TP / or other types of tunnels? Yes-- definitely. The Routing and Remote Access service can support PPTP and L2TP tunnels. You can also do tunnel-mode IPSEC. – Evan Anderson Jun 4 '09 at 3:22
Yes, I am getting closer to asking the right question: Can a Windows server running IIS support tunnels? You said yes. No third-party support required? XP Pro and Vista, too, or just Server 200X? – stevej Jun 4 '09 at 4:16
I really appreciate you hanging in here on the thread... – stevej Jun 4 '09 at 4:20

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