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I have run into an interesting problem with one of my web servers giving 404 errors on the HTTPS parts of the site.

Here is how we have it setup, we have a single website setup on it that has no host headers setup and is configured to accept any request on *. We have just installed second IP address on this server as we are going to deploy another web site and we need it to bind the new SSL to it, we have both SSL certs installed on the server but only have one of the bound to an IP as it is the current site running. We run a single code base so both sites will run in a single .Net worker process(we have it set as a web farm) and the app deals with the url request on what site to load, this is a side note to give you some back ground on how we do things. So since adding the second IP address I am now getting 404 errors from IIS HTTPAPI(it does not happens all the time its intermittent), the httperr log shows this quite clearly and none of our other servers are doing this as they only have 1 IP address at the moment.

The one thing I tired was binding the URL to the SSL cert using appcmd command which I thought would resolve the issue but it has not, I have a few other ideas but I wanted to put this out there to see if anyone else has run across this problem and what was done to resolve it. I am getting a second server setup with a second IP address to see if it does this as well and I am going to add a host header to the site and bind it to the IP address the SSL is on as well.

Any advice on this would be super!

Also why not take some time to have a listen to a classic song :)

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What's "404 errors from IIS HTTPAPI"? More information on symptoms would be useful - for example, an excerpt from those HTTPERR logs you mentioned. (404 in them? Interesting. Odd.) – TristanK Aug 31 '11 at 4:01

I have discovered the reason this was happening and have corrected the problem, once I added the host head to port 80 on the IP address we are using for the site the error stopped happening.

So in summary I would never recommend the use of 2+ IP addresses on IIS without having the host headers setup(I know this is how it should be done but some time if you let developers think to much they come up with these wacky ideas about not needing them) and I would setup the host header on the SSL cert as well. Here is a good link that explains how to do it.

And here is a song about Client Eastwood

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