I wanted to be able to transparently proxy Windows Integrated Authentication. I made a 
small change to squid that seems to let it
work. I altered the hash key used for the persistent server connection list so it 
includes the IP and port of the client, as well as
the host name and port of the origin server. So when a lookup is done for an idle file 
descriptor to use to connect to an origin
server, only a FD that has previously been used for a connection from the same client 
port will be used. Before I made this change,
in my test setup using IIS with Integrated Windows Authentication, I was getting 
multiple popups while trying to use Outlook Web
Access and also my test web server. After making the change, I got only one popup per 
session as hoped.

I don't understand why this seems to work, as the documentation, including from 
Microsoft says that the authentication method
requires end-to-end HTTP state, and this change is not sufficient to guarantee that. 
Perhaps others could try this and report on
what they find. Contact me directly for the source code I used.

Gary Price
Intelligent Compression Technologies

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