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There are several ways to do this, but I've done this before via intergrating to LDAP. Ask if you are allowed to access your AD (Active Directory) where you can get users credentials and authenticate users based on that.. you can then write an ASP code that gets user id from network (NTLM) , translates the given non-APEX URL to an APEX URL along with the user name and some encrypted passcode to confirm that the given link/URL is generated by the current user ( not copied over to another machine for example) and then have your custom authentication scheme check if that userid is allowed to have access to your app.. I know there are too many details, but I gave you the key points that you need to research to make this happen.
In addition to APEX, we also use Microsoft SharePoint at my company.Sounds like you are using a lot of Microsoft server products, if so then why not run Apex through Microsoft IIS, which gives you Integrated Windows Authentication "for free":
I have access to our active directory server
I'm just not sure how to retrieve the OS user from a webpage and automatically log them into the APEX application without requiring a password.