Outlook 2007 Autodiscover keeps asking for password

Hi All,

I am trying to setup outlook 2007 with exchange 2007 SP2 autodiscover. I know the autodiscover service is working because it is setup on other users laptops.

There is one user I can not get to setup properly. The laptop is XP SP3 with Outlook 2007. I connect locally in the LAN with the laptop and setup outlook 2007 with exchange no problem. However when I connect outside the LAN it keeps prompting for a user name and password and does not connect with even the correct u/p typed in. I have also tried turning off the Windows firewall in XP and no luck.

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RLComputingConnect With a Mentor Author Commented:
Problem was solved by following this article:


Basically, it seems to be caused by some windows updates. On the exchange server, I did the following changes to the host file (c:\windows\system32\drivers\etc)

::1 localhost

…by changing it to:

# ::1 localhost

Hope that helps someone in the future.
Jeff BeckhamEngineerCommented:
When you say connecting prompts for username and password, do you mean starting Outlook or "Test E-mail AutoConfiguration" applet from the Outlook system tray icon?
can you also share the screen-shots/results for the results/log tab of the "Test e-mail autoconfiguration"
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RLComputingAuthor Commented:
I have setup Outlook 2007 by connecting internally (LAN). When i take the laptop outside of the LAN and open Outlook it will prompt for the user name and password non-stop, even though the password is correct.

I have also tried setting up outlook externally from the LAN via autodiscover and it prompts for the u/p non-stop as well.

Autodiscover is setup on other laptops and OWA works as well.
Jeff BeckhamEngineerCommented:
Are you connecting over a proxy like ISA or are you connecting directly to the CAS server through your firewall?
RLComputingAuthor Commented:
I am connecting to a Windows SBS 2008 VPN.. Is it not true with exchange 2007 and autodiscover I don't have to connect to VPN for outlook 2007 to work?
RLComputingAuthor Commented:
Also, the laptop was previously setup and working until this past Wednesday. I am guessing Windows updates had something to do with it.
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