Hi Michael, it sounds like Outlook is misflagging your login attempts possibly due to cached credentials or sync conflicts. Try clearing saved credentials from Windows Credential Manager, switching browsers, and enabling 2FA via Microsoft Authenticator to bypass the passcode prompts. Also, check if your Chromebook’s sync settings are interfering with Outlook.
If it still fails, submit a formal support ticket with screenshots.
also, when the error occurs, are you logging in via the Outlook app, a browser, or both and does it happen consistently across all devices or just one?
I hope this helps you out, let me know how it goes.
Chard