Password Protect a directory using IIS 7 Digest Authentication

This may just be my misunderstanding of the subject, but I would hope to find a simple answer.

I run a web server for my own use, among many reasons just so I have a domain name to reference my network at home.

I just deployed Sever 2008 Enterprise thanks to acquiring a MS charity license. It’s so much better than the IIS 5 on XP setup I had before.

I’m still toying around with AD groups and users, but right now I just want to password protect a couple of folders on the web side of this box.

Say I go to, no problem. I want public access there, and it works just fine. But if I go to, I want that to come up with a user/pass box. I achieved this before by using a cheap program called IISPassword that used .htaccess/.htpasswd files.

While reading up on the capabilities of IIS7, I became interested in Digest Authentication. Knowing that basic auth would transmit passwords in clear text, I decided this would be a far superior option.

I’ve set permissions on the /private folder to disable all other methods ( anon, basic ), and only enable Digest in IIS MMC. I have not modified the folder permissions on an NTFS level ( just domain groups, IUSR has no entry ). All I get in response when viewing the page is an error 500.

I’ll admit I’m still new to this level of administration, and would very much appreciate any help I can get to enable this level of protection. I’d be fine using AD authentication, but I think I’m still stuck at ‘why do I get a 500 instead of a credentials prompt’


Password Protect a directory using IIS 7 Digest Authentication