Outlook prompt for username and password on MS Exchange 2010 DAG & CAS Servers

Posted on 2010-08-26
Last Modified: 2013-05-01
I have 2 Exchange 2010 DAG servers and 1 CAS/HUB role on single server on windows 2008  Server and Windows 2008 Domain infrastructure. Users on my network using Outlook MAPI client for emails. Some of users in the network gets username and password prompt everyday. If user open the outlook first time, their is no password prompt. But it suddenly occurs while outlook is running.  I search for the solution, but there is nothing on exchange 2010. The same problem occurs on one of another exchange 2010 DAG servers running on different domain and different LAN. I think their is an issue on exchange 2010 for password prompt. Please help me to resolve this. Thanks
Regards, Shahzeb Asif
Question by:shahzebasif
Welcome to Experts Exchange

Add your voice to the tech community where 5M+ people just like you are talking about what matters.

  • Help others & share knowledge
  • Earn cash & points
  • Learn & ask questions
LVL 21

Expert Comment

by:Hendrik Wiese
ID: 33529437
Hi, Exchange uses integrated authentication so that will only happen if the users account is locked or otherwise not accessible.

Scan your network and ensure that you don't have any viruses causing the issue, also check any additional applications on the users machines that might try to use their credentials for some reason and either remove the applications or ensure that the username and password that the applications use, are correct.

Let me know if this helps.
LVL 21

Expert Comment

by:Hendrik Wiese
ID: 33529488

Expert Comment

ID: 33529493
Another thought is that on slow network connections outlook falls back to connecting over http

Verify this is not set by looking into the settings of the account in outlook - look in more settings and under connection "connect to microsoft exchage over http" must be unchecked

The only reason you will be receiving a username password prompt is when outlook falls back to negotiating with xchange over the web service.

hope this helps
Free learning courses: Active Directory Deep Dive

Get a firm grasp on your IT environment when you learn Active Directory best practices with Veeam! Watch all, or choose any amount, of this three-part webinar series to improve your skills. From the basics to virtualization and backup, we got you covered.

LVL 21

Expert Comment

by:Hendrik Wiese
ID: 33529499
Or you could try the following and let me know if it worked:

Author Comment

ID: 33547633
I have tried all the options but still there is no luck. For one of the user's outlook, I have changed the logon network security settings to Password Authentication NTLM. I leave this client and will see the result tomorrow. If anybody have any other suggestion, please share with me. Thanks

Author Comment

ID: 33565700
Can anyone response to my question. The problem is not resolve yet. Any other solution? thanks

Author Comment

ID: 33602352
Dear All,
The problem is resolved now. I would like to share this with you all. It was related to Outlook Anywhere configuration. Actually some of my client's  outlook was configured using autodiscovery feature locally on network and Exchange proxy was automatically configured using exchange 2010 settigs for outlook anywhere. My Exchange 2010 Outlook Anywhere was configured with Basic Authentication. This was the only cause for password prompt. For testing I tried to restart MS Exchange RPC service, as it restart, the user gets password prompt. To resolve this issue, I changed my Outlook Anywhere Authentication Settings from Basic to NTLM Authentication and reconfirgured outlook client's exchange proxy settings to use NTLM. After this I never gets password prompt for any user. I think there is some issue with Basic Authentication on Outlook Anywhere Settings in Exchange 2010. Thanks

Khurram Khan

Accepted Solution

khurram008 earned 500 total points
ID: 33972507
Please Check with your IIS Settings for SSL Certificate. By default, it is configured as Ignore Certificate in IIS, Try to change the settings to Accept Certificate and check if outlook or OWA is prompting for username and password.

Featured Post

Industry Leaders: We Want Your Opinion!

We value your feedback.

Take our survey and automatically be enter to win anyone of the following:
Yeti Cooler, Amazon eGift Card, and Movie eGift Card!

Question has a verified solution.

If you are experiencing a similar issue, please ask a related question

A list of top three free exchange EDB viewers that helps the user to extract a mailbox from an unmounted .edb file and get a clear preview of all emails & other items with just a single click on mailboxes.
This article will help to fix the below errors for MS Exchange Server 2013 I. Certificate error "name on the security certificate is invalid or does not match the name of the site" II. Out of Office not working III. Make Internal URLs and Externa…
In this video we show how to create a mailbox database in Exchange 2013. We show this process by using the Exchange Admin Center. Log into Exchange Admin Center.: First we need to log into the Exchange Admin Center. Navigate to the Servers >> Data…
In this Micro Video tutorial you will learn the basics about Database Availability Groups and How to configure one using a live Exchange Server Environment. The video tutorial explains the basics of the Exchange server Database Availability grou…

729 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