Outlook constantly asking for password. New SBS 2008 network

Posted on 2010-01-08
Last Modified: 2012-05-08
Im coming towards the end of building a brand new SBS 2008 Premium network with about 20 computers.

On all of the workstations, outlook keeps asking for a username and password. A box comes up and says "connection to".

If I try and enter a password it rejects whatever I enter.

If I leave it blank and click cancel outlook connects for 30seconds, downloads some emails and then asks the user for the username and password again.

Workstations are a mixture of Vista and Windows XP

They are all connected to the domain via the http://connect wizard. Everything else seems fine (internet, network drives etc).

Any ideas?

Thanks for any input.

Question by:SM17CH
    LVL 14

    Accepted Solution

    Make sure you install exchange rollout 9 update.
    LVL 3

    Assisted Solution

    This could be because of missing OAB rights (outlook tries to download the OAB every minute or so).
    Please ensure that "Authenticated Users" have read-access to the following folder on your front-end:
    C:\program files\microsoft\Exchange\client access\oab

    You can check if it really is because of the OAB by trying the following in Outlook:
    Tools -> Send/Recieve -> Download Address Book -> OK.

    If you are unable to download the OAB and the popup appears, then thats the problem.
    LVL 14

    Expert Comment

    I mispelled it. It is Exchange Rollup 9 for Exchange 2007. Here is the link
    LVL 21

    Expert Comment

    Hello SM17CH,

    is the correct cert correctly binded to the sbs web appz site in IIS?
    make sure port 443 is binded to in the bindings of that site.
    btw, did you ran the certificate wizard?
    You could also install exchange SP2


    LVL 15

    Expert Comment

    After Following MCSA2003 and Kyosh check the follwoing settings:

    Make sre you have valid SAN certificate, Run Test EmailAutoconfiguartion on the Client machine and see if you get the valid URLs see below article to set the URl.

    Check below Authentication methods on virtual directories in IIS :

    SBS Web Application Should have annonymous and no SSL

    1) Autodiscover: Basic and Integrated authentication SSLOptional
    2) EWS : Integrated authentication NO SSL
    3) Exadmin : Basic and Integrated authentication NO SSL
    4) Exchange : Basic and Integrated authentication SSL optional
    5) Exchweb : Basic and Integrated authentication NO SSL
    6) Microsoft-Server-ActiveSync: Basic authentication SSLOptional
    7) OAB : Integrated authentication NO SSL
    8) OWA : Basic authentication SSL Optional
    9) Public : Basic and Integrated authentication SSL Optional
    LVL 2

    Author Comment

    Hey guys,
    I think it was the exchange rollout that fixed it. Although the permissions on the OAB folder didnt have authenticated users added to the security either.
    Thanks for the help.

    Expert Comment

    I wanted to add to this thread since I was having the same issue on a SBS 2008 with prompts for username and password. The answer here by MCSA2003 is correct, rollup 9 will fix this problem.

    The reason I am posting is to provide a bit of help with installing rollup 9.
    I found that simply downloading and trying to apply the patch does not always work as smoothly as you will think, so if you are having problems installing the update here is a solution I found posted by Mark Raborn on

    And just in case this ever goes down I will summaries it.
    1. you need to make sure that the administrator group has full control to C:\Program Files\Microsoft\Exchange Server\RelNotes.htm

    2. you need to run the update from an elevated command prompt

    These 2 things helped me install the rollup and solved the problem.


    Featured Post

    Maximize Your Threat Intelligence Reporting

    Reporting is one of the most important and least talked about aspects of a world-class threat intelligence program. Here’s how to do it right.

    Join & Write a Comment

    Set up iPhone and iPad email signatures to always send in high-quality HTML with this step-by step guide.
    Sometimes drives fill up and we don't know why.  If you don't understand the best way to use the tools available, you may end up being stumped as to why your drive says it's not full when you have no space left!  Here's how you can find out...
    To efficiently enable the rotation of USB drives for backups, storage pools need to be created. This way no matter which USB drive is installed, the backups will successfully write without any administrative intervention. Multiple USB devices need t…
    This tutorial will walk an individual through configuring a drive on a Windows Server 2008 to perform shadow copies in order to quickly recover deleted files and folders. Click on Start and then select Computer to view the available drives on the se…

    731 members asked questions and received personalized solutions in the past 7 days.

    Join the community of 500,000 technology professionals and ask your questions.

    Join & Ask a Question

    Need Help in Real-Time?

    Connect with top rated Experts

    18 Experts available now in Live!

    Get 1:1 Help Now