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Mailbox keeps prompting for password RRS feed

  • Question

  • Hello

    I'm hoping somebody might be able to assist me in finding an issue.

    I've 2 mailboxes that, starting last month, intermittently request a password when using Outlook 2013 or 2016.

    Both these mailboxes are in addition to the users main mailboxes, which don't prompt for details.

    I've not been able to find anything wrong with the mailbox and Exchange reports the mailbox and database in good health.

    This only seems to affect users that have a second mailbox on their profile, or in our case the users are given full access to the mailbox so it appears in their folder list within Outlook.

    What's strange is, that we ignore the message or cancel it, you can still get to the mailbox.  If you decided to enter your domain credentials in, you're prompted to enter them 4 times.  Now, this could be a coincidence but we have 4 domain controllers so I wondered if it Outlook is trying to authenticate to each of those.

    I've reset the password, removed the Windows Credentials (via Control Panel) and also re-created Outlook profiles, all have no affect.

    I'm open to suggestions if anybody has any, please.  :o)

    Thanks, Richard

    Friday, April 5, 2019 4:11 PM

Answers

  • Good news!  I've finally got to the bottom of it.

    This Technet thread helped but ultimately I put in 3x registry changes to stop Outlook from prompting.

    https://social.technet.microsoft.com/Forums/en-US/76bcbc41-afb2-4789-9064-c1d18e1a122e/outlook-2016exchange-2010-keeps-prompting-for-credentials?forum=outlook

    [HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Outlook\AutoDiscover]
    "ExcludeHttpsRootDomain"=dword:00000001
    "ExcludeScpLookup"=dword:00000001
    "ExcludeExplicitO365Endpoint"=dword:00000001

    Thanks for your assistance Steve, it's much appreciated.
    Richard
    Friday, June 21, 2019 10:10 AM

All replies

  • Hi Richard,

    What version of Exchange server do you use? 

    Are you connecting to your Exchange server via Outlook Anywhere or MAPI over HTTP? Does this issue happen internally or externally?

    Do you have the 'Download Shared Folders' option enabled under Account Settings? Does it make any difference if we turn off the option?

    Are these shared mailboxes auto-mapped to the users' Outlook who are affected by this issue? Does it happen if we disable auto-mapping and then add the shared mailboxes via Account Settings > More Settings > Advanced > Add?

    Regards,
    Steve Fan


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    Monday, April 8, 2019 2:46 AM
    Moderator
  • Hi Steve

    Thanks for your reply.

    We're running Exchange 2013 CU21 and using Outlook Anywhere.
    We only see this issue on internal machine but that might be a red heron as we don't use our machines outside the office.

    The 'Download Shared Folders' option is already switched off.

    As for auto mapping, yes, the mailboxes are automatically added to the relevant users with full permission.
    I'll disable mine though, add it manually in Outlook and report back.

    Thanks again
    Richard
    Monday, April 8, 2019 9:29 AM
  • Thanks.  I'll give the Kernal-Mode auth a go this evening.

    Fingers crossed!

    Monday, April 8, 2019 11:55 AM
  • Hi Richard,

    Any progress? Have you tried giving Kernal-Mode auth a shot? We'd appreciate it if you could keep us posted at your most convenient time.

    Regards,
    Steve Fan


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    Wednesday, April 10, 2019 10:02 AM
    Moderator
  • Hi Steve

    Apologies, I made the change yesterday and only had a chance to reboot the box last night.  Unfortunately it hasn't made any difference.

    On Monday I tried the suggestion of not auto mapping the account and manually adding it but it wouldn't let me expand the mailbox so I changed it back yesterday.

    Any other ideas?

    Richard

    Wednesday, April 10, 2019 11:32 AM
  • Thank Richard for the update.

    What Authentication method do you configure? Please run the cmdlet below and provide the result to us:

    Get-OutlookAnywhere | fl Name,*auth*

    You may try setting internal authentication method to NTLM to see whether it helps.

    Regards,
    Steve Fan


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    Friday, April 12, 2019 9:37 AM
    Moderator
  • Hi Steve

    Here are the results...

    Name: Rpc (Default Web Site)
    ExternalClientAuthenticationMethod: Ntlm
    InternalClientAuthenticationMethod: Ntlm
    IISAuthenticationMethods: {Basic, Ntlm, Negotiate}

    Thanks
    Richard
    Friday, April 12, 2019 10:52 AM
  • Thanks Richard. What if we manually configure the Exchange account in Outlook 2013? 

    Besides, when the Outlook client prompts for credential, press ”Ctrl” on your keyboard and right-click the Outlook icon in the notification area of the Windows taskbar, select “Connection Status”. Capture a screenshot with the full content.

    Then, input the correct credential information, open the connection status window again. Capture the screenshot.

    Share the screenshots to us so that we can see whether there is any clue. Be sure that you have hidden the private info before you pasting the pictures.

    Regards,
    Steve Fan


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    Tuesday, April 16, 2019 9:31 AM
    Moderator
  • Hi Steve

    I'm being told the following when I try and add the pictures to the reply...  :o(

    "body text cannot contain images or links until we are able to verify your account"

    After searching, it appears it might be something a moderator has to approve.

    I try and post a link to another site, what do you think?

    Richard

    Tuesday, April 16, 2019 12:24 PM
  • Oh, I meant to say that we're using Office 2016 which doesn't give me those options to manually configure.
    Tuesday, April 16, 2019 1:42 PM
  • Thank you for the update. 

    You can share the screenshots to us via sending then to ibsofc@microsoft.com. (As this is a shared address used for collecting info purpose, please include the URL of current thread in the message so that we can easily distinguish your email)

    >>Oh, I meant to say that we're using Office 2016 which doesn't give me those options to manually configure.

    I noticed you used both Outlook 2013 or 2016 in your original post, thus I asked you to try it manually in Outlook 2013. If no Outlook 2013 client is available now, you can just forget it.

    Regards,
    Steve Fan


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    Wednesday, April 17, 2019 8:00 AM
    Moderator
  • Great, thanks Steve, I've sent the screen shots.

    It's a fairly wide window so took 2 screenshots (left and right) before and after the credentials were input and I blanked out the email addresses but they were all the same.

    Apologies re the Outlook 2013 confusion.  What I really meant to say is that I'm using Office 2016.  There is a user who has Office 2013 but he's off for the Easter break so I'm unable to get his machine.

    Thanks
    Richard
    Wednesday, April 17, 2019 8:13 AM
  • Hi Richard,

    I reviewed the screenshots you sent, it looks all connections were established even when Outlook prompted for password. What if we cancel the password prompt, does any of the connections switching to Disconnected or Connecting status?

    Besides, do you have any Load Balancer/Firewall/Proxy server between clients and Exchange server? If any, you may try to bypass these servers to force clients to connect to Exchange server directly, see if we can reproduce the issue.

    Regards,
    Steve Fan


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    Thursday, April 18, 2019 4:46 AM
    Moderator
  • Dear Richard,

    Any update here? Please don't hesitate to post back if you need further assistance on this issue.

    Regards,
    Steve Fan


    Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.


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    Monday, April 22, 2019 1:38 AM
    Moderator
  • Hi Steve

    Apologies for the delayed reply, I took Thursday off for an extended Bank Holiday break.

    No, cancelling the password prompt doesn't disconnect Outlook and the status doesn't change either.
    In fact, I usually just ignore the prompt or cancel it.  My colleges have previously been re-entering their passwords but I've since told them it doesn't make any difference, so they've stopped doing so too.

    The Exchange server is in the same building, on the same subnet, for it's internal NIC at least.
    The external NIC attached to the DMZ and is where we all connect via.  However, the Cisco ASA doesn't forward the traffic outside of itself, just re-routing it directly to the box (if that makes sense).

    I've just tried creating a new Outlook profile using the the account type 'Exchange ActiveSync', so I could enter the Exchange servers internal/local name but am told the following...
    "Log onto Exchange ActiveSync mail server (EAS): The username and password you entered isn't working. Please try typing them again."
    I've tried several variations of my username as well as trying the external server address but none of those work.  I wonder if it's related?

    Thanks
    Richard
    Tuesday, April 23, 2019 8:39 AM
  • Hi Richard,

    >>I've just tried creating a new Outlook profile using the the account type 'Exchange ActiveSync', so I could enter the Exchange servers internal/local name but am told the following...
    "Log onto Exchange ActiveSync mail server (EAS): The username and password you entered isn't working. Please try typing them again."

    It's not supported to configure an Exchange account manually in Outlook 2016 version, you have to use auto account setup to automatically configure it via autodiscover configurations. You were selecting the Exchange ActiveSync protocol instead of Exchange.

    I suggested you to set the authentication method to NTLM before, you may also try setting it to Basic to see whether it helps.

    Besides, may I know whether this happens with newly created shared mailboxes? If possible, you may try testing with a new shared mailbox to see the result.

    Regards,
    Steve Fan


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    Thursday, April 25, 2019 8:55 AM
    Moderator
  • No worries, I'll give that a go.

    I do already have another shared mailbox I connect to but I'll add a 3rd and report back next week.

    Thanks again for you help Steve and enjoy your weekend.

    Richard

    Friday, April 26, 2019 3:34 PM
  • Hi Richard,

    Any progress here? Please don't hesitate to post back if there is anything else we can do for you on this issue.

    Regards,
    Steve Fan


    Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.


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    Tuesday, April 30, 2019 6:34 AM
    Moderator
  • Hi Steve

    No joy I'm afraid.

    I connected 2 other mailboxes to my account and both have been fine since Friday but the one with the issue still prompts for my details.

    Thanks

    Richard

    Tuesday, April 30, 2019 8:54 AM
  • Thank you for the update Richard.

    Could you capture a screenshot of the password popup window and share it to us? You can send it to ibsofc@microsoft.com. (As this is a shared address used for collecting info purpose, please include the URL of current thread in the message so that we can easily distinguish your email)

    Does Outlook prompt for credential as soon as you start Outlook, or is there a specific operation (such as a Send/Receive action or opening Address Book, etc.) in Outlook which triggers the popup?

    Are these shared mailboxes on the same database with the primary mailbox? Are they hosted on the same Exchange server?

    Besides, you may try using Fiddler to capture the data when Outlook is prompting for credential, and see what Exchange services Outlook is trying to connect to. 

    Regards,
    Steve Fan


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    Wednesday, May 1, 2019 3:19 AM
    Moderator
  • Sure, no problem.  I've sent some screenshots in.

    Number 1 - Is what's shown but sometimes also has my domain details already entered.
    Number 2 - Is what's shown in Outlook when the credential prompt is shown.
    Number 3 - Is what's shown when I cancel the credential window and click on 'Need Password'.

    I can't see a pattern for Outlook asking for the credentials as it seems to happen randomly.  Sometimes I might not get it for an hour and other times it could pop up twice in an hour.

    Yes, all mailboxes are on the same database and server.

    I'll look into Fiddler next week when I return from the Bank Holiday.

    Enjoy your break.
    Richard
    Friday, May 3, 2019 4:12 PM
  • Thank you Richard. Haven't found any new clue from the updated details. You may try Fiddler when you are free and see whether it provides some clues.

    Regards,
    Steve Fan


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    Tuesday, May 7, 2019 9:53 AM
    Moderator
  • Will do.  It'll be next week before I'm likely to get a chance.

    I might even bite the bullet and create a new account then transfer the mail over.

    Thursday, May 9, 2019 3:32 PM
  • Great. Looking forward to you response.

    Regards,
    Steve Fan


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    Monday, May 13, 2019 9:54 AM
    Moderator
  • Morning Steve

    I've some news.  Creating a new mailbox didn't make any difference, however I've caught Outlook requesting the password when trying to update the address book.

    I've not always been able to catch it when the prompt box pops up but I've watched it 3 times now.

    I realise you asked me at which stage it was happening before but as I didn't see when it was happening, I didn't think it was at a certain stage.

    I've found an article about changing the permissions to allow Authenticated Users to access the OAB folder on Exchange but it hasn't made any difference.

    It may be a red herring but it's something else to check I suppose.

    Thanks

    Richard

    Tuesday, May 21, 2019 9:08 AM
  • Good news!  I've finally got to the bottom of it.

    This Technet thread helped but ultimately I put in 3x registry changes to stop Outlook from prompting.

    https://social.technet.microsoft.com/Forums/en-US/76bcbc41-afb2-4789-9064-c1d18e1a122e/outlook-2016exchange-2010-keeps-prompting-for-credentials?forum=outlook

    [HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Outlook\AutoDiscover]
    "ExcludeHttpsRootDomain"=dword:00000001
    "ExcludeScpLookup"=dword:00000001
    "ExcludeExplicitO365Endpoint"=dword:00000001

    Thanks for your assistance Steve, it's much appreciated.
    Richard
    Friday, June 21, 2019 10:10 AM