Hybrid Exchange - Outlook Password prompt if not in VPN or LAN

Question

Hybrid Exchange - Outlook Password prompt if not in VPN or LAN

A Ska 241

Dears

We have an on-premise Exchange 2016 environment with Microsoft hybridation (AD connect services are ok).
After hybridation our users (all with on-premise mailboxes) noticed that when opening Outlook from home (nor in VPN neither in LAN), Outlook asks them to put the password.
We're using, in my case, Office 2021 but the problem occurs with 2019 too.
I verified lots of thing but there's n way to get out of this issue.
Already trying updating clients, clearing credentials cache, still same issue.
Thank in advance

Joy Zhang-MSFT 1,051 Reputation points

2022-12-02T02:54:49.79+00:00
Hi @A Ska ,

Based on the results returned by above command, you seem have configured the https:// URLs from your on-premises, you seem don't need change something on these.

For further troubleshooting, we want to confirm something with you:

Is there any error message when you run exrca to test autodiscover?

What is the result via Test E-mail AutoConfiguration?

Press and hold the Ctrl key, right-click the Outlook icon in the notification area, and then click Test E-mail AutoConfiguration.

Enter your email address and password.

Clear the checkboxes next to Use Guessmart and Secure Guessmart Authentication. Make sure that Use AutoDiscover is selected.

Click the Test button. It may take up to a minute before the test is complete

Could you try to recreate outlook profile to check if the issue continues?
A Ska 241 Reputation points

2022-12-02T09:11:27.467+00:00

Dear

I have indeed some errors
See attach266563-xml-result-testautomaticconfig.txt

See attach text of the most important part of the RCA:266519-rca-result.txt
Joy Zhang-MSFT 1,051 Reputation points

2022-12-06T05:46:21.86+00:00

Hi @A Ska ,

Could you please post the specific error messages since logs you provided above are hard to read？

In addition, have you modified something before the issue happened? Does outlook connect to exchange server successfully after you input password?

3 answers

Your answer

Joy Zhang-MSFT 1,051 Reputation points

2022-12-02T02:54:49.79+00:00

Hi @A Ska ,

Based on the results returned by above command, you seem have configured the https:// URLs from your on-premises, you seem don't need change something on these.

For further troubleshooting, we want to confirm something with you:

Is there any error message when you run exrca to test autodiscover?

What is the result via Test E-mail AutoConfiguration?

Press and hold the Ctrl key, right-click the Outlook icon in the notification area, and then click Test E-mail AutoConfiguration.

Enter your email address and password.

Clear the checkboxes next to Use Guessmart and Secure Guessmart Authentication. Make sure that Use AutoDiscover is selected.

Click the Test button. It may take up to a minute before the test is complete

Could you try to recreate outlook profile to check if the issue continues?
A Ska 241 Reputation points

2022-12-02T09:11:27.467+00:00

Dear

I have indeed some errors
See attach266563-xml-result-testautomaticconfig.txt

See attach text of the most important part of the RCA:266519-rca-result.txt
Joy Zhang-MSFT 1,051 Reputation points

2022-12-06T05:46:21.86+00:00

Hi @A Ska ,

Could you please post the specific error messages since logs you provided above are hard to read？

In addition, have you modified something before the issue happened? Does outlook connect to exchange server successfully after you input password?

Answer 1

Andy David - MVP 157.8K MVP Volunteer Moderator

Most likely its the direct connect feature in outlook which is assuming you have a mailbox in Exchange Online.
https://learn.microsoft.com/en-us/outlook/troubleshoot/profiles-and-accounts/unexpected-autodiscover-behavior

This article shows how to change that behavior:
Test it out and see with a few clients:
https://medium.com/jj365/outlook-issue-with-direct-connect-to-office365-352dd29de65

Answer 2

Dear @Andy David - MVP

I tried Resolution 1 with no luck.
Do I have to try with Resolution 2?
Disable MAPI using Exchange Online Powershell

Based on this article I noticed that on my MSOnline I miss the first link

PS C:\> Get-MsolServicePrincipal -AppPrincipalId 00000002-0000-0ff1-ce00-000000000000 | select -ExpandProperty ServicePrincipalNames

https://autodiscover.exoip.com/
https://mail.exoip.com/
00000002-0000-0ff1-ce00-000000000000/mail.exoip.com
00000002-0000-0ff1-ce00-000000000000/autodiscover.M365x877334.mail.onmicrosoft.com
00000002-0000-0ff1-ce00-000000000000/M365x877334.mail.onmicrosoft.com
00000002-0000-0ff1-ce00-000000000000/autodiscover.exoip.com
00000002-0000-0ff1-ce00-000000000000/exoip.com
00000002-0000-0ff1-ce00-000000000000/autodiscover.exoip.local
00000002-0000-0ff1-ce00-000000000000/exoip.local
00000002-0000-0ff1-ce00-000000000000/outlook.office365.com
00000002-0000-0ff1-ce00-000000000000/mail.office365.com
00000002-0000-0ff1-ce00-000000000000/outlook.com
00000002-0000-0ff1-ce00-000000000000/*.outlook.com
00000002-0000-0ff1-ce00-000000000000
https://ps.compliance.protection.outlook.com
https://outlook-sdf.office.com/
https://outlook-sdf.office365.com/
https://outlook.office365.com:443/
https://outlook.office.com/
https://outlook.office365.com/
https://outlook.com/
https://ps.protection.outlook.com/
https://outlook-tdf.office.com/
https://outlook-tdf-2.office.com/
https://ps.outlook.com

Is it needed? Al the others are the same.

Thank you

Answer 3

A Ska 241

Update

I added the first entry to the MSOl Exchange but the result is the same, Outlook keeps asking password

Any suggestion?

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Hybrid Exchange - Outlook Password prompt if not in VPN or LAN

3 answers

Your answer