Checking email from server box multiple accounts help

Due to some weird problems i have to have SPA and or Windows authentication on in order for my smtp server to send mail to all domains. I know wierd! But when i check mail this happens:

Since SPA (or windows authentication i don't know which) is enabled when i put in my password to authenticate with SPA i only get the mail for the primary mailbox and the secondary mailbox's mail stays on the server and isn't downloaded.

For example if i have two accounts set up in outlook or outlook express. When i click on send and receive i get the password authentication box for SPA (or windows authentication i don't know which) Then i enter the password for the primary account. then the primary account's email is downloaded and the secondary account remains unchecked. Why do i have so many problems... Yes i know i should just use exchange but do you have a couple thousand to throw down for a stupid mail program? cuz i don't.

Andy just to give you the cool diagram feel i'll spell it out here.

Joe (primary account)
Bob (secondary account)

Send/Receive ->

Logon - server

Information
Username:Joe
Password:blahblah
Domain:

then i press okay and get the mail for joe but the same authentication box never comes up for bob and i never get the email for him unless i make him the primary account. HELP

P.S. I am running the standard windows 2003 server pop3/smtp built-in application to server my email stuff.

I'm wondering if you defined the send and recieve groups if that might prompt for a login for the other users mailbox. Worth a shot anyways.

Or what happens when you try open other users folder instead of opening other mailboxes when the main profile is opened. Does that prompt?