How do I apply SSL certificates to multiple websites?

Box 1 is a Win 2003 server with DC, DNS, AD
Box 2 is a Win 2003 server with IIS.  It has a single NIC with IPs,,

In DNS I have 2 Host (A) entries: for for

In IIS I have 2 webs:

Both webs use port 80 and port 443.
App1 is assigned for both ports
App2 is assigned for both ports

I generated the following certificate with selfssl as follows:
selfssl /t / /v:365 /s:67793743
selfssl /t / /v:365 /s:74919743

My problem:  Both apps work at all time without SSL (http://...) But with SSL (https://...) only one of my web apps will work at a time.  To fix the broken one, I remove its SSL certificate then recreate it with selfssl.  However, this breaks the other app.  The IE error I get is: Internet Explorer cannot display the webpage.

I have limited experience with SSL certificates.  What I am doing wrong?  Thanks in advance.
Who is Participating?

[Product update] Infrastructure Analysis Tool is now available with Business Accounts.Learn More

I wear a lot of hats...

"The solutions and answers provided on Experts Exchange have been extremely helpful to me over the last few years. I wear a lot of hats - Developer, Database Administrator, Help Desk, etc., so I know a lot of things but not a lot about one thing. Experts Exchange gives me answers from people who do know a lot about one thing, in a easy to use platform." -Todd S.

Are you generating two SSL certs - one for the app1 and one for app2?

What is the exact error message you are getting?
acb55Author Commented:
Yes I am generating two SSL certs.

The full error text from IE is:

  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.
   What you can try:
     Check your Internet connection. Try visiting another website to make sure you are connected.  
     Retype the address.  
     Go back to the previous page.
     More information

This problem can be caused by a variety of issues, including:

Internet connectivity has been lost.
The website is temporarily unavailable.
The Domain Name Server (DNS) is not reachable.
The Domain Name Server (DNS) does not have a listing for the website's domain.
If this is an HTTPS (secure) address, click tools, click Internet Options, click Advanced, and check to be sure the SSL and TLS protocols are enabled under the security section.  
acb55Author Commented:
With Google Chrome, I get the following error:

Error 104 (net::ERR_CONNECTION_FAILED): The attempt to connect to the server failed.
acb55Author Commented:

I replaced my 2 certificates with a single wild card certificate.  I followed these instructions:

Note sure if this SSL bug was a factor but I though I would mention for the benefit of someone else with similar issues.

Experts Exchange Solution brought to you by

Your issues matter to us.

Facing a tech roadblock? Get the help and guidance you need from experienced professionals who care. Ask your question anytime, anywhere, with no hassle.

Start your 7-day free trial
It's more than this solution.Get answers and train to solve all your tech problems - anytime, anywhere.Try it for free Edge Out The Competitionfor your dream job with proven skills and certifications.Get started today Stand Outas the employee with proven skills.Start learning today for free Move Your Career Forwardwith certification training in the latest technologies.Start your trial today

From novice to tech pro — start learning today.