MFA & Verification Issues

Fix Mac Microsoft 365 Sign-In Loop After Two-Factor Authentication

Steven Parker Oct 21, 2026 869 views

Question details

The user is trapped in an infinite sign-in loop on Microsoft applications despite entering correct credentials and the verification code.

How to Fix Mac Microsoft 365 Sign-In Loop After Two-Factor Authentication

Product: Microsoft 365
Device & OS: macOS Ventura on MacBook Air
Scenario: Signing into Microsoft 365 desktop applications using a school or organizational account that requires MFA.
Observed behavior: The application accepts the username, password, and two-factor authentication code, but then immediately loops back to the sign-in screen displaying an incorrect user ID or password error.

Before you start

Verify that your Mac is connected to a stable internet connection and try logging into the Microsoft 365 web portal in Safari to confirm your account credentials are valid.

Solution 1Recommended

Verify Organization Device Compliance and Contact IT Support

School and work accounts often have hidden device-compliance policies that block desktop app access, resulting in authentication loops.

Even when your password and 2FA code are correct, an organization's conditional access policies might prevent macOS desktop apps from connecting if the device is not registered in their system.

Test Web Access

Open your browser and navigate to portal.office.com. Sign in to see if you can access your web apps without entering a loop.

Document the Issue

Take screenshots of the entire login flow, including the initial credential prompt, the 2FA screen, and the final error message. Crop out any personal phone numbers or email addresses.

Contact the Administrator

Send these screenshots to your school's IT department or organization administrator. Ask them to verify if your MacBook Air requires specific device enrollment or management profiles to use the desktop applications.

Verify Organization Device Compliance and Contact IT Support

Alternative Access: While waiting for IT support, you can often continue your work by using the web-based versions of Word, Excel, and PowerPoint.

Solution 2

Clear Cached Microsoft Credentials in Keychain Access

Removing outdated or corrupted Microsoft tokens from your Mac's Keychain can stop the application from supplying conflicting login data during the 2FA process.

Free Microsoft Office alternative

Bypass Sign-In Frustrations with WPS Office for Mac

If Microsoft 365 sign-in loops are preventing you from finishing urgent assignments, switch to WPS Office. It provides a lightweight, offline-ready suite that doesn't force complex organizational authentication just to edit a document.

1. Download the App: Visit the official WPS Office website and download the macOS version to your MacBook.
2. Install WPS Office: Open the downloaded file and drag the WPS Office icon to your Applications folder.
3. Open Files Instantly: Launch the app and open your existing school or work documents directly without worrying about network loops.

No mandatory organizational sign-ins or complex 2FA loops to edit basic offline documents.Seamlessly compatible with Microsoft Word, Excel, and PowerPoint formats (.docx, .xlsx, .pptx).Highly optimized for macOS Ventura and Apple Silicon, running smoothly on MacBook Air.Completely free basic version with a familiar, easy-to-use interface.

microsoft office alternative - wps office

Frequently Asked Questions

Why does Microsoft 365 return to the login screen after I enter my 2FA code?

This sign-in loop typically occurs because of corrupted authentication tokens in the Mac Keychain or strict organizational policies that deny desktop application access to unenrolled devices.

Can I bypass my school's two-factor authentication requirement?

No, you cannot bypass security requirements set by an organization's administrator. However, you can check if the web version of the apps allows access, as web versions sometimes bypass strict device-compliance rules.

Does macOS Ventura have compatibility issues with Microsoft 365?

While macOS Ventura is fully compatible with Microsoft 365, strict OS privacy settings or background task blockers can sometimes prevent Microsoft apps from successfully saving their authentication tokens.

Login & Account Issues