Forum Discussion
Sky8Blue
Feb 09, 2025Copper Contributor
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.
- LeonPavesicSilver 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- Sky8BlueCopper Contributor
I did check it, but I'll give it a closer look.
Thanks.
- Moustafa-SherifCopper Contributor
this issue is related to your outlook app you can try to remove caching from application then try to add your account again
- Sky8BlueCopper Contributor
Remove caching? Do you mean cached exchange mode? I can't even configure the account to get to that point of the configuration.
- MoustafaSherifCopper Contributor
Dear Sky8Blue
Thanks for your replayyes, 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
- VimsTechCopper 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.
- Sky8BlueCopper 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.
- Sky8BlueCopper 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.