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Outlook is keep asking me to login, i am using exchange server 2019 with office 2016/2021

Meteor Tsang 20 Reputation points
2025-03-31T08:35:29.6666667+00:00

After rebooting the Exchange server.

Outlook keeps asking me to log in, I am using Exchange Server 2019 with Office 2016/2021 on the desktop and laptop machines.

But the strange thing is that not all the machines have been affected by the issue; only some of the machines keep getting the issue. I have tried to use the external network too, it works fine for me with the same laptop and the same test account which is not working in the internal network.

I also just flushed DNS and changed the DNS records to 1.1.1.1 and 8.8.8.8, but it is still not working.

Is there anything I can try to resolve the issue to normal, or any info do I need to provide?

Exchange | Exchange Server | Management
Accepted answer
  1. Sharon Zhao-MSFT 25,756 Reputation points Microsoft External Staff
    2025-04-01T05:15:14.3566667+00:00

    Hi @Meteor Tsang,

    Welcome to Q&A!

    To better understand your issue, please provide below information:

    The screenshot of the related error.

    The version of Outlook client.

     

    Additionally, here are some suggestions for your reference:

    1.Recreate the Outlook profile on affected machines and verify if it works.

    2.Clear cached credentials in Windows:

    Open Credential Manager (Control Panel > Credential Manager)

    Remove any Outlook/Exchange related credentials

    3.Update Outlook to the latest version.

    4.If the issue persists, please run the "Test Email AutoConfiguration" and check the connectivity of Autodiscover

    • Press Ctrl button and right click the Outlook icon in the system tray: User's image
    • Enter your email address and password (if prompted), select "Use AutoDiscover", then click "Test". In Results tab, we can see the related information.
    • Share the results with us (ensure sensitive data is redacted).

    If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".

     

    Note: Please follow the steps in our documentation](https://aka.ms/msftqanotifications)) to enable e-mail notifications if you want to receive the related email notification for this thread.

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  1. mkaszewiak 85 Reputation points Microsoft Employee Moderator
    2025-03-31T16:47:52.8933333+00:00

    Hi @Meteor Tsang The Open Specifications tags are related to Open Specifications documentation issues.

    The Open Specifications can be found at: https://learn.microsoft.com/en-us/openspecs/main/ms-openspeclp/3589baea-5b22-48f2-9d43-f5bea4960ddb . Your question does not appear to be related to the Open Specifications documentation set.

    I've removed the Open Specifications tag and added Exchange Server tag to provide better assistance.

    1 person found this answer helpful.
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