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DNS Failover - Outlook RRS feed

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    We have DNS Made Easy for failover. We finally got it running. However, when the failover occurred, Outlook disconnected and prompted for a password. I entered the password and it connected, still on the failover DNS. What is causing Outlook to disconnect and password prompt? Is it DNS record I am missing related, Windows10/Outlook related? Firewall/NAT related? Can it be fixed or does it need a load balancer?
    Friday, May 8, 2020 10:53 PM

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    i added a autodiscover record in the registry. plus our barracuda spam system didnt have the backup wan ip added. once i did both of those, i dont see the disconnect
    • Marked as answer by Dan732 Thursday, May 21, 2020 9:51 PM
    Thursday, May 21, 2020 9:51 PM

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    Hi

    Im guessing you are using dns round robin so that the same record points to different servers as no load balancer in-between?

    Outlook will disconnect and then after a few min, try connect again and should. If it is connecting to server 2 and you getting asked for password, also check your config on that server compared to server 1 that is working.

    Hope this helps. Please remember to click “Mark as Answer” on the post that helps you, and to click “Unmark as Answer” if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread.

    Saturday, May 9, 2020 1:19 PM
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    Hi,

    What's the detailed version of your Exchange server? You can check with the following command:

    Get-ExchangeServer | Format-List Name,Edition,AdminDisplayVersion

    Do you use Outlook Anywhere or MAPI/HTTP in your organization?

    As Edward mentioned, do you use DNS load balancing? 

    If so, you can use the following command to check your authentication method for Outlook Anywhere or MAPI/HTTP according to your configuration:

    Get-MapiVirtualDirectory|fl identity,*auth*
Get-OutlookAnywhere|fl identity,*auth*

    In general, since the Outlook can re-connect the Exchange successfully, it should be normal that the client need to be authenticated to connect to another Exchange server.

    Regards,

    Lydia Zhou

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

    Monday, May 11, 2020 5:48 AM
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    Edition             : Standard
    AdminDisplayVersion : Version 15.1 (Build 1531.3)

    Identity                      : MyServer\mapi (Default Web Site)
    IISAuthenticationMethods      : {Ntlm, Negotiate}
    InternalAuthenticationMethods : {Ntlm, Negotiate}
    ExternalAuthenticationMethods : {Ntlm, Negotiate}

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

    No, load balancing.

    Do I need Split DNS?

    Monday, May 11, 2020 3:54 PM
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    Do you only have one Exchange server in your organization?

    I did some research, and found that DNS Made Easy can automatically updates A record for your Exchange server. Am I right? If I misunderstand, please point out or provide more information about your DNS record configuration. If this is the case, it's normal that the clients need to re-connect Exchange with the backup IP address, and have to enter the password again to be authenticated.

    For "I entered the password and it connected, still on the failover DNS", do you mean you still connects with the primary IP address instead of the backup one? Since this is a third-party tool, you can contact the vendor for the detailed working process of the DNS Failover. This can help us know what happens for clients when DNS failover performs.

    Regards,

    Lydia Zhou

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

    Wednesday, May 13, 2020 7:00 AM
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    Yes, DNS will update the record if the primary IP goes down. The A record points to the primary IP. The failover A record does not exist for the backup IP until the primary goes offline and failover occurs.

    I contacted DNSMadeEasy and they basically told me they have never seen this issue before and do not support it.

    When Outlook clients are external and the failover occurs, Outlook disconnects and prompts for password.

    Today, I manually added a autodiscover registry key for my domain (autodiscover@mydomain.com)  to [HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Outlook\AutoDiscover\RedirectServers]

    I was hoping this would fix the issue of Outlook disconnecting during failover.

    Please do let me know any thoughts

    Wednesday, May 13, 2020 5:47 PM
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    You can use Fiddler to know more about the process of Outlook connectivity. It may also help to know what happens to the Outlook client when DNS failover occur. For your reference: Using Fiddler for Autodiscover troubleshooting scenarios.

    Note: Microsoft is providing this information as a convenience to you. The sites are not controlled by Microsoft. Microsoft cannot make any representations regarding the quality, safety, or suitability of any software or information found there. Please make sure that you completely understand the risk before retrieving any suggestions from the above link.

    Regards,

    Lydia Zhou

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

    Friday, May 15, 2020 5:47 AM
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    Any updates so far? If you have solved your problem, could you share with us? Maybe it will help more people with similar problems. 

    Regards,

    Lydia Zhou

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

    Wednesday, May 20, 2020 8:58 AM
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    i added a autodiscover record in the registry. plus our barracuda spam system didnt have the backup wan ip added. once i did both of those, i dont see the disconnect
    • Marked as answer by Dan732 Thursday, May 21, 2020 9:51 PM
    Thursday, May 21, 2020 9:51 PM
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    It's great that your issue is solved and thanks for your sharing. Here is a brief summary about this thread.

    Issue Symptom:

    We have DNS Made Easy for failover. We finally got it running. However, when the failover occurred, Outlook disconnected and prompted for a password. I entered the password and it connected, still on the failover DNS. What is causing Outlook to disconnect and password prompt? 

    Cause:

    Barracuda spam system didn't have the backup when ip added.

    Solution:

    I added a autodiscover record in the registry. plus our barracuda spam system didnt have the backup wan ip added. once i did both of those, i dont see the disconnect.

    Regards,

    Lydia Zhou

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

    Monday, May 25, 2020 1:25 AM