Digest and AD

Have a 10.4.10 server bound to AD and trying to set up website for AD users to access files via http.
When I set the realm authentication to "basic" both AD users and Local Users can authenticate.
When I set the realm authentication to "digest" only local users can authenticate.
I don’t receive any error it just keeps asking for my username and password.

In the error log I see:
Apple Digest: Unable to authenticate for URI "/" from user "xxx" for realm "xxxx" at location "/Active Directory/xxx.xxx" from the directory (error = -14091).

In the access log I see:
"GET / HTTP/1.1" 401 492


I don't just want to fling clear text passwords around.
Has anyone gotten this to work?
Any help or hints would be appreciated.