Some outlook clients list in the lower right corner 'needs password' after server restart this past weekend.  Server 2003 R2 64 bit with exchange 2007 and outlook 2007 on windows 7 sp1 clients.  This happens on about a dozen clients out of over 100 total.

So far I have tried

- changing authentication method of the affected clients from negotiate to NTLM or kerberos authentication

- restarting outlook client and PC and logging off, logging back in as user

- deleting and recreating ost file

- checked autodiscover settings in IIS on the exchange server, and nothing looks incorrect

cannot find anything in eventlogs of clients, exchange server, or DCs that gives more info about this problem.  What should I try next?  Thank you!

• Edited by capitan12 Monday, April 06, 2015 7:27 PM

Tried repair of office but no joy.  I have also tried

- installing all office 2007 updates

- deleting and recreating ost file

- also made sure to remove all credentials in credential manager for outlook.

I did come accross another clue, if I uncheck 'used cached exchange mode' on the clients, it no longer prompts for password.  This will help for now, but still need to fix the issue.  Thanks for your post David.

• Edited by capitan12 Monday, April 06, 2015 7:25 PM

Tried repair of office but no joy.  I have also tried

- installing all office 2007 updates

- deleting and recreating ost file

- also made sure to remove all credentials in credential manager for outlook.

I did come accross another clue, if I uncheck 'used cached exchange mode' on the clients, it no longer prompts for password.  This will help for now, but still need to fix the issue.  Thanks for your post David.

Hi,

I noticed that the issue doesn't happen when unchecking 'used Cached Exchange mode' and using Online mode in Outlook.

Generally, the difference between Online mode and Cached mode in Outlook is the Outlook profile and OAB. Please create a new profile in Cached mode instead of removing the account then adding the account back in the same profile to have a try.

Additionally, please run Test E-mail AutoConfiguration in Outlook client to check whether the autodiscover service can retrive the OAB URL from Exchange server:

Open Outlook - press CTRL key - right click on the Outlook icon from right bottom corner taskbar - Test Email AutoConfiguration. Put your email address - uncheck use guessmart and secure guessmart authentication - click Test to check your Autodiscover service.

In Exchange server side, please check and make sure all Exchange services are started and running.

Regards,

H Winnie, thank you for your reply.  I created new outlook profile on a few clients with cached mode checked and still get the password prompt.  So then I tested the email auto-config and it looks like it passed, this is the response I get on the log tab:

I checked the services on the exchange server and as far as I can tell, all necessary services are started:

This issue is still occurring, so any help is still appreciated!

Thank you Winnie.

So it turns out that adding integrated windows authentication by checking the box for this for the Offline Address Book (OAB) in IIS on the exchange server is what made this prompt go away.  I found this setting in IIS > web sites > default web site > OAB >rt. click, properties > directory security tab > authentication and access control edit button > check integrated windows authentication.

A couple hints that it was the OAB causing the problem was that it was affecting outlook clients only, not mobile devices with activesync clients.  Also, even though it kept prompting for password, it never prevented outlook clients from getting email, so I figured it was something else prompting for the password.

Thank you for all the helpful replies!

• Marked as answer by capitan12 15 hours 18 minutes ago

Tried repair of office but no joy.  I have also tried

- installing all office 2007 updates

- deleting and recreating ost file

- also made sure to remove all credentials in credential manager for outlook.

I did come accross another clue, if I uncheck 'used cached exchange mode' on the clients, it no longer prompts for password.  This will help for now, but still need to fix the issue.  Thanks for your post David.

Hi,

I noticed that the issue doesn't happen when unchecking 'used Cached Exchange mode' and using Online mode in Outlook.

Generally, the difference between Online mode and Cached mode in Outlook is the Outlook profile and OAB. Please create a new profile in Cached mode instead of removing the account then adding the account back in the same profile to have a try.

Additionally, please run Test E-mail AutoConfiguration in Outlook client to check whether the autodiscover service can retrive the OAB URL from Exchange server:

Open Outlook - press CTRL key - right click on the Outlook icon from right bottom corner taskbar - Test Email AutoConfiguration. Put your email address - uncheck use guessmart and secure guessmart authentication - click Test to check your Autodiscover service.

In Exchange server side, please check and make sure all Exchange services are started and running.

Regards,