Welcome to the wonderful world of bug reporting on a Microsoft product. I hope you don't struggle with substance abuse, and if you do please contact your sponsor before reading further.
Microsoft Connect is one way to communicate with the product teams for various Microsoft titles. However, IIS does not appear to be one that accepts bug reports.
The IIS.net forums are a place that you can apparently, if you're lucky and the tides are just right, have your bug report seen by a Microsoft employee. Witness this example.
What you might be able to to is track down the contact information for one of the product evangelists for IIS (I found one so far, but won't post his info here) and send an email/tweet/smoke signal about your concern. The evangelists that I've dealt with are pretty nice people and will work to get your feedback to the proper people. That's not a guarantee though.
Another option us the Microsoft Support main site and snoop around for some means of contacting Microsoft concerning the product. From there you can drill down into the IIS family.
You might also want to go to the Microsoft Connect feedback page and request an IIS Connect program.
If by this time you've come to the conclusion that you're going to have a tough time directly reporting an IIS bug - you are correct. Remember, the first stage in healing is to recognize that there is a problem. Apparently Microsoft doesn't want to recognize problems with IIS... ?