Outlook asking password

Question

Outlook asking password

Franck 196

We have several servers, base Proxmox, 2 or 3 VMs : Windows Server 2019 / 2022 : 1 for AD / DNS / ... one for FileServer / SQL the last one for RDS.

RDS using the "basic" install UDP disk on the same server.

Office is installed, Pro or Business version (don't know what is the damn difference).

Each users has a "local" email (office 365 for the client) and another email from government (******@NO-NAME-SERVICE.be). The MFA is ON for gov email and for 50% of email using client name.

On each server, we have SOME with Outlook asking password once a day, or 3 TIMES A DAY, or once every 3 months.

WHY ?

Sometimes we try to add / remove key like (enableAdal, DisableAADWAM, DisableADALaptopWAMOverride), remove entire outlook profile, clear (empty) identification manager, disconnect Office entirely, delete HKCU\Software\Microsoft\Office\16.0\Common\Identity, delete %localappdata%\Microsoft\Office\16.0\Licensing, delete HKCU\Software\Microsoft\Office\16.0\Registration, reboot RDS server, problem still the same..since march I think.
Please, help.

SokiGuo-MSFT 31,536 Reputation points Microsoft External Staff

2023-10-26T05:09:47.17+00:00
Hi @Franck

For our better research, please provide more information about this case:

What does the password prompt popup look like? Can you provide a screenshot (please be careful to cover your personal privacy information.)

Do you have the same problem when logging in to another account?

Can you log in normally using Outlook for Web?

In some cases, the Outlook password prompt issues could be resolved by enabling modern authentication for Outlook clients using registry keys.

If you are using Outlook 2016 or later, Modern authentication is usually already enabled by default. You can follow the recommended way to force Outlook to use Modern Authentication by setting the DWORD value of the following registry key to 1 and see if it can help:

HKEY_CURRENT_USER\Software\Microsoft\Exchange\AlwaysUseMSOAuthForAutoDiscover

(Important: Follow the steps in this section carefully. Serious problems might occur if you modify the registry incorrectly. Before you modify it, back up the registry for restoration in case problems occur.)
SokiGuo-MSFT 31,536 Reputation points Microsoft External Staff

2023-10-31T08:21:05.05+00:00

Hi @Franck

Haven't received your message for a long time.

Do you have any further issue on this topic? I look forward to your kind response.
Franck 196 Reputation points

2023-10-31T08:43:23.5033333+00:00

After opening Outlook we have this :

We have the same issue with multiple accounts.
I will try with the regedit you gave me.

Note : one user it was solved with adding EnableADAL @ 1, same exact method didn't change for other, another was fine, I change in privacy to allow all macro and suddenly outlook start asking passwords...
Franck 196 Reputation points

2023-10-31T08:51:17.05+00:00

Sorry didn't answer for OWA : connection is working, but OWA disable in admin center so only display the generic error can't connect.
SokiGuo-MSFT 31,536 Reputation points Microsoft External Staff

2023-11-02T09:15:12.48+00:00

Hi

I change in privacy to allow all macro and suddenly outlook start asking passwords...

Did you do anything that would pop up for other users?

Is there the same problem if you don't use a virtual machine?
SokiGuo-MSFT 31,536 Reputation points Microsoft External Staff

2023-11-07T09:38:32.9833333+00:00

Hi

Haven't received your message for a long time.

Is there any update on this case?
Franck 196 Reputation points

2023-11-07T09:48:52.98+00:00

Did you do anything that would pop up for other users?

I only change this one option, so no reason it will do anything for other users.

Is there the same problem if you don't use a virtual machine?

The servers are installed on a Proxmox server. No way to use it to connect them. We have few Windows Server with Hyper-V but manager doesn't like it. We can't ask users to work on the Hyper-V server directly (need to install all tools for them to work) and we don't have access to users mailbox because it need the MFA to connect.
Franck 196 Reputation points

2023-11-07T17:02:49.73+00:00
HKEY_CURRENT_USER\Software\Microsoft\Exchange\AlwaysUseMSOAuthForAutoDiscover

Last week for mostly off (1st of November to Sunday).

I leave Monday & Tuesday to end and I can confirm now, after users working 2 entires days with Office that, no this key alone didn't solve the issue.
SokiGuo-MSFT 31,536 Reputation points Microsoft External Staff

2023-11-09T05:16:37.87+00:00
Hi

Thanks for your reply. Try creating a new profile to check if there are any differences.

Open Control Panel > Mail > Show Profiles>Click Add.

Type a name for the profile, and then click OK.

Follow the Add Account wizard to add user account as Exchange Online/365 (not POP or SMTP). When you're done, click Finish.

Then open Outlook on new profile and check if issue persists.
Franck 196 Reputation points

2023-11-14T12:00:59.16+00:00

This problem is the same since April / March. We have the same issue with every new servers.
We already tried to make new profil (in param > Emails and Windows profiles too).

We Always pick Exchange / 365 if needed, usually just entering email address when starting Outlook.

The option to select the type of server only come if he can not connect automatically to address.
SokiGuo-MSFT 31,536 Reputation points Microsoft External Staff

2023-11-16T08:39:26.7766667+00:00

Hi

Do you still have the problem of re-adding the profile?

Try running diagnostics to identify issues that may be causing the error. Diagnostics will perform automated checks and provide possible solutions to resolve the detected issues. Select Diagnostics: Outlook keeps asking for a password to start diagnostics.

Diag: Outlook keeps asking for my password.
Franck 196 Reputation points

2023-11-17T16:14:14.9066667+00:00

We have no issue adding the profile, I just reply we have (only exceptional times) this message to select the type of server.

I will try to use the tool you send, we already tried 2 of them. The problem is we can enter the password and it connect correctly (except some 1001), the problem is not the connection, only the fact it can't stay logged.
SokiGuo-MSFT 31,536 Reputation points Microsoft External Staff

2023-11-21T02:01:45.4033333+00:00

Hi @Franck

Thanks for your reply!

Is '1001' an error message when you check your account?

This diagnostic can't detect issues with all accounts at once.
Franck 196 Reputation points

2023-11-21T08:37:58.42+00:00

Good morning,

We may receive the 1001 error when we re-enter password. It's only a few times and not a real problem for us.
The main issue is the fact that Outlook may ask the password every time a user reconnect is UDP disk or sometimes when Outlook ask password 3 times a day even if user is active on Outlook during the entire day. I will check your tool (from msg Nov 16, 2023, 9:39 AM) this week-end.
Franck 196 Reputation points

2023-11-28T11:40:58.7966667+00:00

I tried to use the tool several times.
I select Outlook then "Keep asking password", seems to be the more similar to my issue.

It says "Outlook is not configured to used advanced authentication but the tenant is" (more or less, I use the french version).

I select to "fix" Outlook (without asking admin credential on a RDS server so maybe user modification)...and we closing the tool and starting again I have the same message like the previous 'fix' didn't do anything.

After few hours the user receive again a message to connect in his account. It didn't worked.