On a Windows 2008 R2 server (IIS 7.5) I have configured a website with "Require SSL" and "Client certificates: Require", to always force clients to use certificates to access the site.
This works ok, the client is prompted for a cert when arriving at the site.
However, the client will be stuck on a 403.7 (invalid client cert page) if the they click "Cancel" or chooses an incorrect certificate in the selection dialog. The only way for the client to be able select a new certificate is to close the browser and access the site again. This is not browser specific, I have tried it in Chrome, IE 8 and Firefox.
On other sites with SSL w/ client cert requirements (not mine), this doesn't happen. If you choose "Cancel" in the selection dialog, and then enter the URL again you will be prompted anew. This is the behavior I want in my IIS site as well.