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Exchange 2010 with Outlook 2010 Continous Password prompt

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  • Exchange 2010 with Outlook 2010 Continous Password prompt

    Hi Experts,

    I have just inherited the environment and current going on with investigation on this issue.

    Issue sounds quiet common where Outlook is continuously prompting for password even entering correct username/password or click 'save password'

    This environment has:
    - 3 different sites configured in DAG.
    - all three sites are CAS/HUB/Mailbox
    - three CAS array has been created, one per site for best practise
    - 1 site is main location, 1 site is DR, 1 site is remote office
    - main location has Outlook anywhere configured
    - remote office doesn't have Outlook anywhere configured
    - SAN Certificates has been purchased with correct names

    So the problem is only occurring at the remote office where there is not Outlook anywhere configured, all the outlook has been configured NOT to use Outlook Anywhere (unticked "Connect to Microsoft Exchange using HTTP")

    I have checked with autodiscover checker on the exchange, no issue
    I have checked credential manager on the local PCs, no issue
    "Always prompt for logon credentials" is turned off

    Interesting this was if I try to login to the local owa link on the remote office exchange, after the successful login it shows the page to go to the main office owa link (I thought regardless of outlook anywhere configured or not it should let me in locally if you're on the sever).

    It would be great if any of you could provide me a clue to solving this issue.

    Kind Regards

  • #2
    You get prompt for user/password when connecting with outlook inside the organization?


    • #3
      Hi moshiko,

      Yes that's correct.

      When the users open the Outlook it requests for the username/password.

      However they can ignore/click cancel to continue working on the Outlook, as it connects to Exchange server 'fine'.

      When I get the users to enter the credentials it reappears again even when it's correct and click save password.


      • #4
        Oh and I forgot to mention there seems to be office 365 sitting in front of the exchange for email filtering