How to remove authorization request in outlook?

Question

Windows

Friends! How about a little brainstorming?

Given: Two Exchange 2013 servers are running in a DAG cluster.

Recently, we decided to upgrade the servers to version 2019. To do this, we rolled out the latest updates and security updates. We also implemented the third Exchange 2019
server. The third server was just set up, nothing else was done. It cannot be implemented in the DAG, since the 2013 version is not compatible with 2019, we are going to transfer mailboxes to new servers, but so far there has been a problem.
Users complain that when starting Outlook, an authorization request window pops up. And not at all, but somehow randomly.
It does not depend on the version of outlook. There are requests for both 2013 and 2019 outlook.
It also does not depend on whether the computer is in the domain or not. Remotely via VPN or in the office.
Tell me where to dig? Who is guilty? Latest updates or new server?

Tried shutting down the new server for a few days. Authorization requests still appear.
Enter your password and you're good to go. But users are annoyed, and why do we need extra attention? ))

Answer 1

Does the checkmark under the password "Remember credentials" hint at anything?