Hi Mistro
From your description, Classic Outlook does not open properly, and when it does, it keeps asking for the password repeatedly.
Have you already tried the steps from Q&A Assist? If yes, what happened? To let me guide you better, could you please also confirm:
- Does Outlook fail to open at all, or does it open and then go into a password prompt loop?
- Is this a Microsoft account (Outlook.com/Hotmail) or a third-party account such as Gmail/Yahoo?
In addition, please try these:
1, Start Outlook in safe mode
- Close Classic Outlook app completely
- Press Windows + R, type
outlook.exe /safe> press Enter - If Outlook is stable in Safe Mode, disable add-ins (Go to File > Options > Add-ins > Manage: COM Add-ins > Go) and re-enable them one by one to find the culprit.
2, Try to Repair Office (Online Repair) and, if needed, create a new Outlook profile:
Please kindly follow the official troubleshooting steps here: Outlook crashes or stops responding when used with Office 365 - Microsoft Support
Feel free to let me know how it goes so I'd be happy to assist you further. I truly appreciate your time and understanding!
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