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Outlook/Exchange 2010 password prompts on server reboot even after rebooting PC.

    Question

  • Recently migrated to Exchange 2010 and have mostly Outlook 2003 with 4 Outlook 2010 users as a pilot.  Twice now on 2 different PC's...if I reboot the Exchange server for server updates and the user's Outlook is open...when the server comes back online, Outlook will prompt for a password (which I would expect)....but, I can close outlook, reboot the PC...doesn't matter...still prompts for a password every time Outlook is opened (and about every 10 mins if I leave it open).  If I cancel the password prompt, everything seems fine with the mailbox...I'm assuming it's the OAB and free/busy that's prompting.  To resolve the issue I have to create a new profile...once I do that...the prompting stops.   Does anyone know what is happening and what I might be able to do besides creating a whole new profile?  I'm deathly afraid to roll Outlook 2010 out to a couple hundred people and have this issue pop up when I do server updates.

    Tuesday, March 13, 2012 3:32 PM

Answers

  • Hi,

    Please remember the issue disappears after creating a new profile--Although the credential is prompted for OAB downloading or free/busy status, Outlook failed to provide correct credential.

    So, it is the cause of profile, no need to change virtual directories authentication.  


    Fiona Liao

    TechNet Community Support

    Thursday, March 15, 2012 3:16 AM
    Moderator
  • Hi,

    sorry for the delay response.

    It is not the profile prompt the credentials. It is the Exchnge web-based service prompt credentials, and then Outlook is supposed to be able to scratch it from Windows profile. If it is failed to scratch, or the profile could not provide the credential correctly, the prompt box will appears for user to type in.

    To know the root cause of widnows profile, you might need to pose the question in Windoes forum or Outlook forum. Your understandind would be appreciated.


    Fiona Liao

    TechNet Community Support

    Tuesday, March 27, 2012 9:36 AM
    Moderator

All replies

  • Hi,

    it can be a problem of autodiscover or OAB authentication.

    try to desactivate OAB authentication kernel mode as described here http://blogs.technet.com/b/essentialbusinessserver/archive/2009/03/20/outlook-presents-multiple-prompts-for-authentication-in-ebs.aspx

    Regards,


    Best Regards Don't forget to mark it as answer if it helps

    Wednesday, March 14, 2012 11:23 AM
  • None of the 3 virtual directories listed had that enabled.  Again though...everyone is working fine (outlook 2010 and 2003)...it's just if Outlook 2010 is open when the server is rebooted...from that point on, that particular Outlook prompts until a new profile is created even after rebooting the PC.  Everyone who had Outlook 2010 closed is fine....2003 is not affected.

    Wednesday, March 14, 2012 3:06 PM
  • Is autodiscover working correctly?

    When the prompts occur, does it say what it's trying to connect to?

    Can you insert a images?

    Check the connection status and CTRL right click OLK Icon and test auto config, untick guest & guest smart.


    Sukh

    Wednesday, March 14, 2012 3:24 PM
  • "Is autodiscover working correctly?" -  Yes...no issues externally or internally.

    "When the prompts occur, does it say what it's trying to connect to?" - Looks like it's trying to connect to the Outlook Anywhere external server address.  (if our Internal server address is internal.domain.local  and external address for the same server is outside.domain.com it's trying to connect to outside.domain.com)

    "Can you insert a images?" - Of the login prompt?   It's just a standard windows logon IE box.

    Auto config test worked fine.  Status shows Established for everything.  If I hit cancel at the login prompt...then go to Status and hit "Reconnect" an entry that says "Instance-b2f914d6-<more numbers>" connecting...if I cancel the login prompt that line disappears.

    If I hit cancel at the login prompt....trying to set the Out of Office gives me a server not available message. 

    After further testing...if I uncheck the Outlook Anywhere "Connect to Exchange via HTTP" box it works fine and doesn't prompt.  Recheck it and it prompts...BUT this is only on the profile that was open during the server reboot.  If I use the new Outlook profle...SAME outlook anywhere settings, same email settings...no prompts and works fine.  I don't get it....why is the profile that was open during reboot prompting for Outlook Anywhere credentials? 

    Wednesday, March 14, 2012 10:53 PM
  • Update after more testing...sorry if I seem all over the place with this...trying to understand what's happening.  I ran across some articles on Outlook Anywhere and when I manually set the rpc virtual directory in IIS to Windows Authentication and the client OA to NTLM, the problem Outlook profile does not prompt for a password anymore.  

    So...disregarding my not understanding of what "breaks" in the first place when the server reboots...what is the best practice for setting up Outlook 2010 clients and the 2010 Exchange server?   Is there a downside to setting the IISAuthenticationMethods to Basic and NTLM and then the ClientAuthenticationMethod to NTLM?   Is that the "standard" way to do it? 

    Wednesday, March 14, 2012 11:56 PM
  • When you specify authentication for Outlook Anywhere, you set the authentication
    method that will be used by the Outlook client. This authentication method is
    automatically provided to the client by the Autodiscover service. This
    authentication method is separate from the authentication method on the /rpc
    virtual directory that's located on your Microsoft Exchange Server 2010 Client
    Access servers. By default, the /rpc virtual directory is enabled for Basic
    authentication, and the authentication method can't be modified.

    http://technet.microsoft.com/en-us/library/bb124149.aspx

    http://technet.microsoft.com/en-us/library/gg247612.aspx

    If the
    DefaultAuthenticationMethodparameter is specified, neither the
    ClientAuthenticationMethodnor the IISAuthenticationMethods
    parameter can be used.

    Sukh

    Thursday, March 15, 2012 12:07 AM
  • Hi,

    Please remember the issue disappears after creating a new profile--Although the credential is prompted for OAB downloading or free/busy status, Outlook failed to provide correct credential.

    So, it is the cause of profile, no need to change virtual directories authentication.  


    Fiona Liao

    TechNet Community Support

    Thursday, March 15, 2012 3:16 AM
    Moderator
  • Hi,

    Please remember the issue disappears after creating a new profile--Although the credential is prompted for OAB downloading or free/busy status, Outlook failed to provide correct credential.

    So, it is the cause of profile, no need to change virtual directories authentication.  


    Fiona Liao

    TechNet Community Support

    So then is there a solution besides creating a new profile?   What is "breaking" on the bad profile when rebooting the server? 

    Thursday, March 15, 2012 11:46 AM
  • Create a batch file on the all users desktop with the following:

    NET STOP msexchangerpc
    Shutdown -r -t 15

    Always use this to restart the system. It shuts down the service that causes users to have to log back in. Worked in our case at least.


    Thursday, March 15, 2012 2:32 PM
  • Thanks...I'm assuming this will prevent the problem in the future (I can't test this right now though).  But does anyone know what in the profile would be causing OA to prompt while creating a new profile with the same settings doesn't?  
    Thursday, March 15, 2012 11:36 PM
  • Hi,

    sorry for the delay response.

    It is not the profile prompt the credentials. It is the Exchnge web-based service prompt credentials, and then Outlook is supposed to be able to scratch it from Windows profile. If it is failed to scratch, or the profile could not provide the credential correctly, the prompt box will appears for user to type in.

    To know the root cause of widnows profile, you might need to pose the question in Windoes forum or Outlook forum. Your understandind would be appreciated.


    Fiona Liao

    TechNet Community Support

    Tuesday, March 27, 2012 9:36 AM
    Moderator
  • Thanks...I'm assuming this will prevent the problem in the future (I can't test this right now though).  But does anyone know what in the profile would be causing OA to prompt while creating a new profile with the same settings doesn't?  
    I have the same issue with a mixed 2007 and 2010 environment. I have 5ish users that are having this problem and creating a new windows profile is a sloppy workaround not an answer. 

    • Edited by Glate Saturday, May 05, 2012 7:16 AM
    Saturday, May 05, 2012 7:15 AM
  • Saturday, May 12, 2012 7:23 AM