We have the CRM addin for outlook 8.2.0005.0004 installed with the Version 2 update. Every time we open outlook it prompts for credentials. Checked all the settings in this article:

Prompted for credentials when opening CRM for Outlook - Dynamics CRM | Microsoft Learn

However none of them fix this issue.

We are using an ADFS setup for authentication. This only started happening. If we enter our credentials then the addin works for 1 day and then on reboot the following day it prompts for credentials again.