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For Outlook for Microsoft 365, a password change may not be recognized immediately because the OAuth token can continue to be used until it expires. After a password change, it usually takes about one hour for the token to expire, and then Outlook should prompt for sign-in again.

If Outlook is still not prompting and is not syncing, force a new sign-in prompt:

1. Close Outlook.
2. Open Credential Manager from the Windows Start menu. On Windows 10, this may require opening Control Panel first.
3. Select Windows Credentials.
4. Under Generic credentials, locate entries that start with MicrosoftOffice16_Data:OAUTH2.
5. Remove those OAuth2 credential entries for Outlook.
6. Open Outlook again and complete the sign-in prompt when it appears.

If the issue is specifically that Outlook continually prompts for the password while showing trying to connect, check the account profile setting:

1. Open Mail in Control Panel.
2. Select Show Profiles.
3. Select the Outlook profile, then choose Properties.
4. Select E-mail Accounts.
5. Select the email account, then choose Change.
6. Select More Settings.
7. On the Security tab, set Logon network security to Anonymous Authentication.
8. Select OK, then complete Next and Finish.

Avoid editing the registry for this unless necessary. Modifying the Outlook profile in the registry is not supported and can leave the profile in an unsupported state.

References:

• Users get errors 0x800CCC0E & 0x800CCC0F synchronizing Gmail and Yahoo accounts in classic Outlook
• Outlook continually prompts for your password when you try to connect to Microsoft 365
• Password prompt at every Outlook start or can't create profile