How to create a self-signed wildcard SSL certificate for IIS 6?

Question

I'm trying to create a self-signed wildcard SSL certificate for use on a number of development and test servers running IIS 6. Following various guides has led to a couple ways of generating the certificates, but I haven't had any luck getting it to work. The most successful ways I've had were following this OpenSSL guide and using makecert.exe like so:

makecert.exe -r -b 01/01/2009 -e 01/01/2042 -sr LocalMachine -ss MY -a sha1 -n CN="*.example.com" -sky exchange -pe -eku 1.3.6.1.5.5.7.3.1 -sy 12 -sp "Microsoft RSA SChannel Cryptographic Provider" wildcard.cer

 

Both of which generate certificates that IIS 6 will accept, but when I actually try to view the site I get the following error in firefox:

Data Transfer Interrupted

The connection to dev.example.com was interrupted while the page was loading.

IE just gives:

Internet Explorer cannot display the webpage

Most likely causes:

• You are not connected to the Internet.
• The website is encountering problems.
• There might be a typing error in the address.

This error happens whether I try to access it by domain name, machine name, localhost, local ip, or loopback ip.

So...how can I create a self-signed wildcard cert that IIS 6 will work with? Or how can I fix the problems I'm experiencing with the ones I've already created?

Answer 1

Did you realize that you would need to change from "example.com" to some thing more appropriate to your situation ("localhost" might be one of them during testing).

Answer 2

For IIS 7 - there is a wzard to do this. It takes about 30 seconds to setup.

For IIS 6 - it's a bit trickier. It takes about 30 minutes to setup.

Which one are you using?

I strongly recommend moving to IIS 7 - it is very foreign at first, but they've made a lot of improvements.

Given that you probably can't upgrade to IIS 7, I had to do the following to implement what you want in IIS 6.

1) create certificate server 2) generate request 3) grant request 4) install certificate

It's a bit of a pain to setup the certificate authority server, but it comes with Windows Server and the walkthrough is pretty straight forward.

Answer 3

You can use the IIS 6 Resource Kit provided by MS, an command line app called SelfSSL. It can generate the SSL key and import it into your IIS installation.

IIS 6 Resource Kit

Answer 4

We discovered that the Certificate Authority wasn't being trusted because of domain settings and was causing the errors. We ended up deploying a star cert generated by a trusted CA and that cleared up the problems.

Answer 5

For IIS 7 - there is a wzard to do this. It takes about 30 seconds to setup.

IIS 7 wizard does not allow wildcards certificates. For example when I set the name in the wizard as *.example.com then it issues the certificate to servername.example.com