Why does Microsoft Outlook keep asking for Password

I have fixed this issue after looking at multiple suggestions. In Outlook 2019 Desktop app on Windows, select File->Account Settings->Account Settings-> and highlight the Outlook/Hotmail account and then Repair on the line above the accounts. Select Repair and when the next screen comes up for IMAP Account Settings, select the "Outgoing Mail" line. At the bottom, select "My outgoing (SMTP) server requires authentication" and then select "Log on using user name and password" and enter the correct information for logging on to the email account. Check the box for "Remember password". Select Next and this should fix the issue. It did for me. Hope this helps.

We are having the same issue with two of our clients using our email, not Microsoft's email. There have been several little "bugs" over the last year or so where our clients have had issues using Outlook with our email service. It's really beginning to seem that Microsoft is making it harder for people to use Outlook without using Microsoft email. We have begun to urge our clients to switch to eM Client vs Outlook. We use eM Client in our office flawlessly. The "New" Outlook won't even let us connect using EAS. Microsoft seems to be silent on this thread lately. None of the "fixes" that have been suggested by Microsoft alleviate the problem. Constantly asking for a password, and when we enter it, it just doesn't connect, it asks for it again. It's so frustrating because we have clients that have used Outlook for years and they don't want to switch. But Microsoft is throwing roadblock after roadblock.

Yeah they want us all to "drink the koolaid"

Same issue here, cannot seem to resolve. I even enter my correct password and that doesnt work, constantly says trying to connect.

Please refrain from this continued email.