If you're like me, you wonder why that Outlook 2003 Authentication box doesn't remember your password when using Outlook via the Internet (also known as RPC over HTTP).
I was frustrated by this, so I wanted to find out why. Turns out it was pretty simple reasoning.
If you follow the instructions on the Remote Web Workplace for your Small Business Server 2003 box, you'll probably be setting the Proxy Authentication Settings to Basic Authentication. Basic Authentication will send the password in clear text over the internet. Don't fret! you're still SSL encrypted, so it's not really clear text!. Basic Authentication is not remembered via the system, (since it would also store the password in clear text). This could give hackers or Spyware that runs on your system a chance to get this password and send it out to another source.
The other option in this drop down is NTLM Authentication. This type of password is encrypted, and hence can be stored by the system. The problem is, NTLM authentication isn't good at passing through firewalls. Seeing as there are a lot of firewalls on the Internet (chances are if you're running XP SP2, and your server is SBS your going through at least 2 firewalls, possibly 3 or even 4!).
So while Basic can work through any number of firewalls that it may encounter, it cannot store this on the system (for security reasons), NTLM has the exact opposite problem. In many cases, NTLM won't even connect, so it doesn't matter it can save your credentials.
So that's why you can't save your password in the Outlook 2003 RPC/HTTP dialog box.