Either you're not using IE (which will use the Integrated Windows Authentication to automatically log authenticate you to the web server), or the security on that directory isn't set correctly for web users.
Check the security settings in IIS. Make sure that you have Integrated Windows Authentication selected. Also, try using the FQDN in the IE address bar instead of just the machine name.
I'm not at the office but what I remember from being at the office...
Windows Authentication is set on both the IIS sites setup (one for companydomain.com and one for intranet).
Both sites point to the same content directory.
If I use the url servername/intranet then it works without prompting.
If I use servername.companydomain.com/intranet it prompts to log in.
If I use intranet.companydomain.com it prompts to log in.
DNS is setup with intranet setup in the companydomain.com zone and ALSO as its own zone so simply using intranet should work as well (assuming IIS is configured correctly and cooperates).
This is where my memory is a little fuzzy... I forget what it is called exactly but one site has simply intranet entered as the default site name while the other has both servername and servername.companydomain.com as the default site.
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