outlook modern authentication issue while setting upon in windows 2022 server

Bezawada, Ravi Kumar 0 Reputation points
2024-06-18T15:25:45.93+00:00

I am trying to set up Outlook on my Windows 2022 server (prod server). I have installed the Microsoft office 365 proplus-16.0.12527.22286 version

It keeps asking for certificates that are not trusted, despite having installed them and allowing it to automatically choose their position. I am still facing issues because of this. I tried to troubleshoot with SARA as it prompts the issue is with modern authentication issue and i let SARA to the update outlook settings but still the issue persists. please assist me in resolving the issue.

I have same sign-in with other office products login as well (Excel) but when i tried to login with browser it works well only the issue with office desktop applications

Please help me resolve this.

Outlook Management
Outlook Management
Outlook: A family of Microsoft email and calendar products.Management: The act or process of organizing, handling, directing or controlling something.
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  1. Bezawada, Ravi Kumar 0 Reputation points
    2024-06-20T15:46:15.42+00:00

    Hello,

    Initially, it ask for certs Install (below screenshot). I let the certs and install but its still asking the certs again and again.

    Capture1

    I tried to troubleshoot with SARA as it prompts the issue is with modern authentication issue and i let SARA to the update outlook settings (screenshot: capture-3)

    Capture3

    Capture2

    Apparently, updated settings doesn't work if i run the troubleshooting again it shows below error, but if turn off api proxy as SARA suggest(internet) i can't able to connect.

    Capture1

    please help us in resolving in issue. what if we allow autodiscover through the firewall ? does it helps ? or the issue with the office app version itself?