Outlook credentials prompt

a b 1

Hello Everyone,

I'm having a troublesome issue with multiple outlook clients.
Our company uses L2TP over ipsec vpn's to connect to our clients networks for remote support.
For a while now, when we start a vpn connection, outlook immediately prompts for a username and password.
I can see in the prompt that its trying to connect with the username and password of the vpn adapter that is currently connected.
After some troubleshooting it became clear outlook is using the *session credentials in credential manager and not the credentials for the stored email account.

Does anyone have the same problem or know how to fix this?
I've been searching online for related problems but none come close to the description or have a viable solution.

Our environment is as follows.

Clients:
Windows10/11 latest build and updates
Outlook 365 latest build and updates

Server:
Single On Premise Exchange 2019 latest cu and build

Thanks in advance,

Aholic Liang-MSFT 13,841 Reputation points Microsoft Vendor

2022-09-15T05:22:56.027+00:00

Hi @a b ,

After some troubleshooting it became clear outlook is using the *session credentials in credential manager and not the credentials for the stored email account.

Are these computers with issue domain-joined?
I wonder whether it is still using the VPN's login credentials after troubleshooting?
If not, have you tried to remove the session credentials in Credential Manager it is using and recreate the new profile for Outlook client, is the issue persistent?
a b 1 Reputation point

2022-09-15T07:16:18.52+00:00

Hi @Aholic Liang-MSFT ,

Yes all pc's are domain joined.
Let me clarify a little more, the *session credential in the credential manager seems to be a temporary thing.
Once i remove that it or when no vpn adapter is connected it doesn't exist and outlook works fine (might need a reboot if it hangs or lost the credentials).

Once i start a vpn connection the *session gets created, outlook prompts for a password and loses its connection with exchange in the process.
Depending on if cache mode is turned on or not, outlook crashes since there is no more connection to the exchange server.

Making new outlook profiles doesn't seem to help, neither reinstalling or using a different workstation.
Aholic Liang-MSFT 13,841 Reputation points Microsoft Vendor

2022-09-16T09:44:28.96+00:00

Hi,

Thanks for your clarification!
Depending on your description, it seems to be related to network connectivity issues .
This requires some packet capture tools for more in-depth analysis, but the forum is currently unable to help in this regard.

Thank you for your understanding!

1 answer

Limitless Technology 39,586 Reputation points

2022-09-15T07:59:22.187+00:00

Hello

Thank you for your question and reaching out. I can understand you are having issues related to Outlook Password prompt.

The Exchange/Outlook Auto Discovery Settings may need to be adjusted. Because it appears that the Outlook client is now unable to identify the proper external host name for Outlook Anywhere and, consequently, the proper authentication method.

Hence Please try to troubleshoot that would be to use the "Microsoft Remote Connectivity Analyzer" (Outlook Connectivity and/or Outlook Autodiscover test).

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a b 1 Reputation point

2022-09-15T11:06:00.91+00:00

Hi, @Limitless Technology

The Microsoft Remote Connectivity seems to be alright.
The results are attached.
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