outlook modern authentication issue while setting upon in windows 2022 server

Question

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.

Answer 1

Hello,

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

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)

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.

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?

Answer 2

Hi sokhi,

sorry for the late reply, I was trying to open the registry path as provided but i can only able to get through till Microsoft folder and can't find any office sub-folder under it (see attached picture).

please assist in resolving this

Note: Additionally , I have added key under Computer\HKEY_CURRENT_USER\Software\Microsoft\Office\Outlook , but it still throws the same cert error (dont think ,this is rigth path add)

Answer 3

Hi there,

we still looking for solution,

Also, we noticed, when we tried to login from browser to OutLook in windows servers it works perfectly. wandering, if the copied office enterpsie desktop version is corrupted and causing the modern auth issue (security cert).