Outlook / Exchange Authentication Issue – Troubleshooting Required

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Category: IT Services

User is on Exchange On-Premises using Outlook Classic .
User also has a Microsoft account using the same email address .
After setting up Outlook on a new computer , Microsoft login prompts appeared.
We bypassed the Microsoft account sign-in, but Outlook now repeatedly prompts the user to enter their password.
Mailbox access is intermittent due to continuous credential prompts.

Exchange On-Premises administration
Outlook Classic troubleshooting
Windows credential management
Microsoft account and Office authentication troubleshooting
Autodiscover and profile configuration
Please provide your experience with similar Outlook/Exchange authentication issues and your estimated time to resolve.
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