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Running a IIS6 server on Windows 2003. All the websites use ASP.NET

I have a number of websites all running separate HTTP websites:

www.domain1.com www.domain2.com www.domain3.com

I have a separate HTTPS website


These websites are all running on the same server.

I now wish to intergrate the content of www.secure.com into each of the domains in a transparent way. Such that each website despite having its own SSL connection displays the same website. The complicatrion is www.secure.com needs to know which website the connection has come from to apply the appropriate branding. The idea behind this is to have only one website, and location, but it keeps the core website brand. https://domain1.com looks alot better from a marketing point of view (and avoids users getting confused about what our secure website is)

SSL www.domain1.com/secure -> displays www.secure.com (branded domain1)

SSL www.domain2.com/secure -> displays www.secure.com (branded domain2)

SSL www.domain3.com/secure -> displays www.secure.com (branded domain3)

How would the best way of achieving this, i'm open to using additional software if necessery. Would a reverse proxy be sutible for this situation?

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Not sure if i made this clear in my description of the problem, but i don't want www.secure.com to be visible to the end user. –  docflabby Aug 26 '09 at 13:23
What sort of capabilities does the software running on www.secure.com have that would allow it to serve different content? I've done something similar using Apache reverse-proxy but do not have experience with IIS and proxys. Honestly, I do not think 99% of the users even look at the domain of the website, as long as it isn't throwing up an error. –  Dave Drager Aug 26 '09 at 13:34
I'm quite willing to install apache on the server as well if that would achieve this. I'm just not very familier with how a reverse-proxy works. The software running on www.secure.com is a custom ASP.NET application we have developed. All of the websites are running on the same server. I agree with you on the 99% thing though. –  docflabby Aug 26 '09 at 14:55
Bascially we are going to change the software to server up a different "theme" depending on where it is accessed from. –  docflabby Aug 26 '09 at 14:57
Acctually to clarify further, each website is a marketing website with a link to a "secure" section, which is unique to each website. However we don't want to deploy multiple copies, and worry about keeping them all upto date as all the "secure" sections are identical (same functionality on each website), except for the branding –  docflabby Aug 26 '09 at 14:59

5 Answers 5

The cheapest and easiest way to achieve this would be to use subdomains. That way you can get a wildcard cert and use just one IP address.

For those still coming across this problem, check out this post about how to Run Multiple SSL Websites on IIS6 Using a Wildcard Certificate

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IIS 6 does allow you to do multiple SSL hosts on a single IP address, but requires the use of wildcard SSL certificates. Microsoft has a technet article here on how to set it up. Keeping this in mind, you could get a *.securedomain.com SSL certificate, and use:

  • site1.com/secure -> site1.securedomain.com
  • site2.com/secure -> site2.securedomain.com
  • site3.com/secure -> site3.securedomain.com

Your application can look at the host headers, and see the site1.. site2.. site3.. and apply the necessary branding.

Thinking about it, if you do use a wildcard SSL certificate, you don't even need to have multiple sites, assuming your website code knows how to figure out which HOST it is showing the end user (read the HOST header from the request).

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I don't actually know how to do this in IIS (or even if it is possible), but I thought I should note that you are going to need separate IP addresses for each of your domains if this is going to work. This is because the SSL handshake happens before header information is passed, so you can only have one certificate installed on a given IP address.

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Really? Perhaps you could read this article: sslshopper.com/article-ssl-host-headers-in-iis-7.html –  Dscoduc May 28 '10 at 4:10
If you look carefully at that article you will notice that it only works for domains where a single cert can cover all the domains. Like subdomains covered by a wildcard cert. That is not the scenario given by the poster. –  Catherine MacInnes May 29 '10 at 16:25

Cause the SSL handshake is done before any header information (domain names...), you can only get one https website per IP.

So what your were planning to do, is not a solution...

What you could do if you only want to have 1 SSL certificat. if to have this configuration: https://securedomain/site1 -> site1 content

https://securedomain/site2 -> site2 content

https://securedomain/site3 -> site3 content

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Additional IPs and Certifcates are going to be purchased. –  docflabby Aug 26 '09 at 14:56

If you can get multiple IP addresses, this is not a problem whatsoever. Just set it up ^^ All you need to make sure of is that the SSL bindings are set to the specific IP and not "all IP" as the default is.

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