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Sky8Blue's avatar
Sky8Blue
Copper Contributor
Feb 09, 2025

Cannot connect to an on prem 2019 Exchange mailbox

Hi,

I am having all weird issues trying to get my home laptop to configure an Outlook (M365 apps) account to connect to our work on prem Exchange. It times out as if it can't talk to the Exchange server.

I created a new computer profile then tried, it actually worked, I could see my mailbox, send and receive email. Later I deleted the profile, tried again in the same local computer profile, it failed with the same behavior as above.

When I do an 'nslookup austodiscover.mydomain.com.au' it resolves correctly to WAN IP where our server is located behind.

Other people have no issue connecting externally, so there's nothing wrong with the firewall or server communicating with external Outlook clients. My work computer connects fine on the LAN. I brought my home laptop into the LAN, it still doesn't work. DNS issue right? Well, as mentioned, the autodiscover nslookup works and I don't have any other weird DNS related issues.

There's just something really flaky going on with my computer.

 

 

11 Replies

  • LeonPavesic's avatar
    LeonPavesic
    Silver Contributor

    Hi Sky8Blue,

    Sometimes, cached credentials can cause issues. Go to Control Panel > Credential Manager and remove any stored credentials related to your Exchange server.

    Kindest regards

    Leon

    • Sky8Blue's avatar
      Sky8Blue
      Copper Contributor

      I did check it, but I'll give it a closer look.

      Thanks.

  • Moustafa-Sherif's avatar
    Moustafa-Sherif
    Copper Contributor

    this issue is related to your outlook app you can try to remove caching from application then try to add your account again 

    • Sky8Blue's avatar
      Sky8Blue
      Copper Contributor

      Remove caching? Do you mean cached exchange mode? I can't even configure the account to get to that point of the configuration.

      • MoustafaSherif's avatar
        MoustafaSherif
        Copper Contributor

         Dear Sky8Blue 
        Thanks for your replay 

        yes, I mean cached exchange mode you can get this point through control panel through the attached image 

        Best Regards
        Moustafa Sherif
        Messaging And Office365 specialist 

        www.linkedin.com/in/moustafa--sherif

         

  • VimsTech's avatar
    VimsTech
    Copper Contributor

    If it is working for other external users and Autodiscover is pointed to your Exchange Public IP, The issue is not related to your Exchange Setup. Please try with different internet connection. It may be due to the blacklisted Internet IP address.

    • Sky8Blue's avatar
      Sky8Blue
      Copper Contributor

      Yeah, I thought of that, makes no difference. It's definitely related to my PC, but running out of ideas as to how it could possibly be failing.

  • Sky8Blue's avatar
    Sky8Blue
    Copper Contributor

    By the way, I'm running a Win 11 Pro 23H2 laptop. I also installed a Win 10 Pro VM on my laptop and am experiencing the exact same behaviour.

    • ZeDWeB's avatar
      ZeDWeB
      Copper Contributor

      Got the same symptoms on random users on my domain. OWA and mobile work fine, Oulook doesn't create the profile! Different Office versions, different OS, different connections, all tests return positive results, try to add an Outlook profile, get to type of server selection "Echange" then always get "a problem ocurred! Try again" message! I've checked GPO's, disabled O365 autodiscover, etc, same results!

      • Sky8Blue's avatar
        Sky8Blue
        Copper Contributor

        Just the other day, I was having this same issue on a customer's PC and someone suggested trying the following. It worked! I then tried it on my home computer, it worked too.

        - Open ‘Mail’ in the old style control panel, create a new profile adding a profile a name then click OK. 

        - Once the Account setup page opens, instead of configuring it, click the cancel button. You’ll get a small dialog box come up asking if you want to create the profile with no email accounts. Agree by clicking OK. 

        - Click OK again to close the Mail applet, now open Outlook and go through the mail setup wizard in the usual way. 




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