Baffling authentication problem in Outlook as an Exchange 2007 client running on SBS 2008

Question

I recently configured my new SBS-2008 box. The Outlook 2007 client on the first desktop client I am setting up receives and sends email, but Outlook keeps pestering me for the password to connect to www.mydomain.com (I changed the default prefix from "remote" to "www"). It refuses to accept the password, while I am fully able to logon to the desktop using it! Connecting through owa gives no problem either. What is going on??

Answer 1

What Farseeker says is true, but ALSO make sure you've applied Update Rollup 9 for Exchange 2007 sp1. Your problem, presuming it's the same one, hit my box a few weeks back and it was because I did not have this update applied. WSUS in SBS2008 had downloaded it, but it was marked an an optional update.

Here's a blog post about it. When you follow the link on that page to the newsgroup page, look further down for the message from "Joshua Tu" at Microsoft. (Sorry, I'm a new user and can only offer you one hyperlink!!)

Sure hope this helps. I was banging my head on my keyboard for a few days over this one. A recent update triggers this problem if you don't have the rollup installed, likely this one: 973917.

Answer 2

You need to use the format:

DOMAIN\username

For example:

SERVERFAULT\jeff.attwood

If your domain was serverfault.local, and the username was jeff.attwood

You will also need to check to see if the user in question is a member of a group that has access to the IIS website for www.example.com. But as far as I am aware, the root of the IIS should have anonymous access enabled to it, becuase opening it in the browser should bring up the SBS Remote Workplace login screen.

Thirdly, try this website: https://www.testexchangeconnectivity.com/. When it first surfaced about 6 months ago I was very suspicious as to who it was owned by and if it was safe to use, but since then they've updated it drastically and it's pretty clear that it is owned and operated by Microsoft for tracking exchange issues. I've used it on a few depoloyments to find out-of-the-way RPC configuration issues.