MFA & Verification Issues

How to Fix Microsoft Passwordless Sign-In and Security Key Issues

Huda Qurayshi Oct 7, 2026 869 views

Question details

Users are experiencing missing prompts when trying to use registered security keys for Microsoft passwordless sign-in, and want to understand recovery options if their primary authentication device is lost.

How to Fix Microsoft Passwordless Sign-In and Security Key Issues

Product: Microsoft Account
Device & OS: not provided
Scenario: Attempting to sign in to a Microsoft account without a password using a security key, or attempting account recovery when the Authenticator app is unavailable.
Observed behavior: The system defaults to prompting for SMS or Authenticator instead of security keys, which can trigger an account recovery process rather than allowing immediate sign-in.

Before you start

Ensure you are using a FIDO2 or WebAuthn compatible web browser, such as Microsoft Edge or Google Chrome, as outdated browsers will not display the security key prompt.

Solution 1Recommended

Access the Security Key Sign-In Option

Use this solution to manually trigger the physical security key prompt when Microsoft defaults to asking for an Authenticator app approval.

By default, Microsoft may prioritize the Authenticator app if it is set as your primary passwordless method. You can manually switch to your registered security key during the login flow.

Enter your email address

Navigate to the Microsoft login page and type in your Microsoft account email address, then click Next.

Select More sign-in options

On the screen asking you to approve the request in your Authenticator app, click the link that says 'Other ways to sign in' or 'More choices'.

Choose the Security Key

From the list of available methods, select 'Use a security key'.

Authenticate with your key

Insert your FIDO2 security key (such as a YubiKey) into your device's USB port and tap it when the browser prompts you.

Browser Compatibility: If you do not see the 'Use a security key' option, verify that your browser supports WebAuthn and that your security key is properly registered in your account's Advanced Security Options.

Solution 2

Generate a Recovery Code to Prevent Lockouts

Create a persistent backup code to ensure you can regain access to your account immediately if you lose your phone or security keys.

Free Microsoft Office alternative

Looking for a Hassle-Free Office Suite? Try WPS Office

If managing complex Microsoft account security settings and cloud sign-ins is slowing down your workflow, WPS Office offers a lightweight, secure, and user-friendly alternative. Create, edit, and manage your documents effortlessly.

Free and lightweight office suite with a familiar interfaceSeamlessly open and edit Microsoft Office formats like DOCX, XLSX, and PPTXSecurely manage local documents without mandatory complex cloud authenticationBuilt-in PDF editing and comprehensive formatting tools

microsoft office alternative - wps office

Frequently Asked Questions

Why am I not prompted to use my security key during Microsoft sign-in?

If you are not prompted, you may be using a browser that does not support FIDO2/WebAuthn. Alternatively, Microsoft defaults to the Authenticator app; you must click 'Other ways to sign in' or 'More choices' on the login screen to manually select your security key.

What happens to my passwordless account if I lose my phone?

If you lose the phone hosting your Authenticator app, you can still sign in using a registered FIDO2 security key, Windows Hello on a trusted device, or a 25-character backup recovery code. If you only have SMS backup, selecting it might trigger a 30-day account recovery period.

Which security keys work with Microsoft passwordless sign-in?

Microsoft accounts support any FIDO2 certified physical security key. Popular options include YubiKey by Yubico and security keys from Feitian or Google Titan.

Can I switch back to using a standard password?

Yes. You can reactivate your password at any time by logging into your Microsoft account, going to 'Security' > 'Advanced security options', and turning off the 'Passwordless account' feature.

Login & Account Issues