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I currently have two IIS websites with windows authentication turned on. Internally on my network when you connect to them you're authenticated seamlessly and logged on. Externally you are prompted to login. This is all fine and expected.

However the two sites reference assets on each other, so going to site A causes not only a prompt to login for site A but also a prompt to login for site B as well.

Is there any kind of server that I can stick in front of the two websites so that the user will only have to authenticate once against that server and then all subsequent authentication is handled by it?

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I think kerberos is the system which handles user authentication across multiple machines in a domain. Don't know enough about the MS implementation to give you more detail though. All I know is that if kerberos is enabled a token is given when a user logs in with domain credentials, and that this token is valid to another machine on the domain. –  jackweirdy Aug 3 '12 at 22:42
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What about setting virtual directory for the domain. Say you are creating virtual directory for website A which points to a folder for website B.

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