A couple of years ago I started using Exchange hosted email service. The primary motivation for me was the ability to synchronize all the contacts, calendar and task with my new PDA as well as have the instant email push service.
My Exchange server is part of a different domain and I am always connecting to it through the internet. Therefore every time I start Outlook it always asks for the credentials to the Exchange server. I could not find any option to remember the password so I kind of started living with it and supplied the password each time Outlook asked me to.
Yesterday, for some reason, I started figuring out how to get rid of this. And I found a solution.
Basically, there are two types of authentication - a Basic authentication and an NTLM authentication. If your Exchange provider supports only the Basic authentication, there is actually no way of forcing Outlook to remember the credentials. The only workaround I have found is to create an application that would fill in the password for you once the credentials dialog shows up. Cumbersome, but it works. When searching the web, I found a couple of such programs, so you can use those if you like.
If you can use the NTLM authentication, you are a bit closer to a “cleaner” solution. When you use it, you will notice that the credentials dialog has the Remember password option. There is no such option with Basic authentication. Nevertheless, it does not work as one would expect. If you enter your credentials, tick the Remember password option, Outlook will prompt you again next time you start Outlook anyway.
Why? Well, the explanation lies with the fact, that the exchange server basically has two sides. It is the front-end server side, communicating with its clients over the internet and the back-end server side, being in the internal domain. You have to have to be authenticated to both, but sadly, the credentials you entered, and Windows saved, belonged only to the back-end server.
So, now, when we know where the problem is, how do we fix it? To force Windows to remember the password for both servers, you have to enter them manually. Just go to the Control panel -> Users and there you should see an option Manage network passwords (sorry for not being exact, I am translating from Czech Windows).
Once you get there, remove the previously remembered password for the back-end server and add a new entry. The entry should look as *.domain.com, DOMAIN\UserName, yourpassword. Now, if the domain of your back-end and front-end servers is the same, that is domain.com, Outlook will never ask for your credentials again!
You can find more information about this issue on http://support.microsoft.com/default.aspx?scid=kb;en-us;820281.
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