Exchange 2019 promting passwords

Иван Галашов 0

Good afternoon!

Outlooks 2010, 2013, 2016 constantly ask for a password. Some users today, others tomorrow. I tried to add registry entries about Autodiscover, I tried to clean saved credentials in Windows- it doesn't help. Could there be a problem on the server side ?

1 answer

Yuki Sun-MSFT 41,051 Reputation points Microsoft Vendor

2023-08-30T02:54:03.0233333+00:00
Hi @Иван Галашов ,

Outlook password prompting issues could be caused by various factors, so it might be hard and time consuming to troubleshoot.

With that being said, since from the description, multiple versions of Outlook clients are affected, it indeed could be an issue on the Exchange server side. Could you please provide more details so that we can better understand the situation?

Does this issue affect all users in your organization? Any difference inside or outside the organization's network?

What are users doing when the password prompts, launching Outlook or doing any particular task in Outlook?

Will the password pop up stop if the user input the correct credentials?

Could you try to catch a screenshot of the Connection Status in Outlook when the issue occurs? Do remember to remove all personal information like domain name, email addresses involved when posting the image.
While Outlook is running, click the CTRL key and then right-click the Outlook icon in the system tray, select “Connection Status”.

Besides, it's recommended to patch both Outlook clients and Exchange server to the latest build. This can make sure we are not troubleshooting an issue here that has already been solved.

By the way, Outlook 2010 and Outlook 2013 have already reached the end of lifecycle. Actually, according to this document, Outlook 2010 is not listed as the supported clients for Exchange 2019. So, it's highly recommended to upgrade to the supported versions of Outlook as soon as possible.

If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".

Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.
Please sign in to rate this answer.
Yuki Sun-MSFT 41,051 Reputation points Microsoft Vendor

2023-09-04T08:50:54.9633333+00:00

Hi @Иван Галашов ,

I'm writing to check if your issue has been resolved. If the problem is successfully resolved, you can share your solution or accept post you find helpful as answer. This can be beneficial to others who reading this thread. If you need further assistance on this, please feel free to post back. Thanks!

Иван Галашов 0 Reputation points

2023-09-11T08:20:56.0933333+00:00

Hello, Yuki!

Yes, all users in the organization are affected.

The password request occurs when Outlook starts. And randomly during work day.

When you enter a correct password, Outlook does not accept it, and requests it endlessly. If you click cancel, an exclamation mark will appear on Outlook with a message that there is no connection to the server. At the same time, the emails both go and come. If you click on the label "Password needed", you will connect to the Exchange server without requesting a password

Yuki Sun-MSFT 41,051 Reputation points Microsoft Vendor

2023-09-11T09:21:04.12+00:00

Hi @Иван Галашов ,

How does the Connection Status look like when it's working?

Could you check it on some more users' side when the issue occurs to them and see if all they have a line similar like below in Connection Status?

By the way, do you have any workaround now which can temporarily solve the issue?

Иван Галашов 0 Reputation points

2023-09-11T10:21:32.2666667+00:00

When it's warking status looks like this:

Yes, all other users have similar status when promting password

Yuki Sun-MSFT 41,051 Reputation points Microsoft Vendor

2023-09-13T07:16:31.0333333+00:00

Hi @Иван Галашов ,

Is "Testbox" a shared mailbox? If so, do all the affected users have access to it?

And as aforementioned, is there any way to temporarily solve this issue now?

Galashov Ivan 0 Reputation points

2023-09-13T07:27:23.02+00:00

Hello! Yes, this is shared box and only one user has access to it. No, we have no any workarounds to temporary fix it. We noticed that Outlook 2010 practically does not suffer from such a problem. Maybe some authorization or encryption settings? I checked - both 2010 and 2013 clients use the negotiation method. Also, our Exchange 2019 server is CU5

Yuki Sun-MSFT 41,051 Reputation points Microsoft Vendor

2023-09-14T09:02:27.31+00:00

Exchange 2019 server is CU5

Hi! CU5 is quite a couple of CUs behind for Exchange 2019, the most recent one is CU13. It's highly recommended to apply the latest CU to stay in the supported configuration and also make sure it's not an issue that has already been solved.

Galashov Ivan 0 Reputation points

2023-09-19T05:31:14.15+00:00

Good day!

I upgraded Exchange to CU13 and changed the authentication method from Negotiation to NTLM. During the day, the password prompt window stopped popping up, but when Outlook starts, it still pops up and does not accept the correct password. You have to click "Cancel", after which Outlook starts without connecting to the server. If you click on the "Password required" button, the client connects to the server without requesting a password

Galashov Ivan 0 Reputation points

2023-09-19T05:35:17.3766667+00:00

It feels like Outlook is starting correctly, connecting to the server. It is unclear from what he asks for a password. If you do not touch this window, the client works fine.

Galashov Ivan 0 Reputation points

2023-09-25T04:50:18.8633333+00:00

Do you have any other ideas? This error is terribly annoying. I read that changing encryption helped someone, but I didn't figure out where to configure it.

Иван Галашов 0 Reputation points

2023-09-29T05:58:19.6266667+00:00

What is the difference between NTLM and NTLM* in connection status? After reinstalling Outlook, the status is NTLM and everything works fine. However, after restarting the PC, the status may change to NTLM* and starts asking for a password again
Sign in to comment

Use comments to ask for clarification, additional information, or improvements to the question.

Share via

Exchange 2019 promting passwords

1 answer

Your answer