Hi Aiden,
I’ve come across this issue before, and here’s what usually works to get your Microsoft account to require both a password and the Authenticator app:
Check Passwordless Sign-In in the Authenticator App:
Open the Authenticator app, find your Microsoft account, and see if there’s an option to turn off passwordless sign-in directly in the app. If it still shows as enabled, disable it—this often resyncs the app with your actual account settings.
Remove and Re-Add Your Account in Authenticator:
Try deleting the account from the Authenticator app, closing the app, and then re-adding the account. This usually forces it to sync with your account’s current security settings. Just be sure passwordless isn’t enabled during the setup.
Toggle 2FA Off and Back On:
Log into your Microsoft security settings online and temporarily turn off two-factor authentication (2FA), wait a bit, then turn it back on. This often resets the settings so both the password and Authenticator are required.
Clear App Cache or Reinstall Authenticator:
If passwordless still shows as enabled in the app, try clearing the app cache or even reinstalling the app. Sometimes a fresh start clears any setting issues.
Test on a Different Device or Browser:
After following these steps, log in from a new device or browser. If it’s working, you should see both a password prompt and an Authenticator check.
If it’s still not quite right, it might be worth a call to Microsoft Support to check for any setting misalignments on their end. These steps usually fix it so you can get the security setup you’re after!