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Sign-in & Login Problems

How to Fix Microsoft 365 Keeps Asking for Password After Sign-In

Steve KSteve K Sep 25, 2026 869 views

Question details

The user experiences a continuous login loop where Microsoft 365 services repeatedly prompt for a password after choosing not to stay signed in.

How to Fix Microsoft 365 Repeatedly Asking for a Password
Product
Microsoft 365
Device & OS
not provided
Scenario
Accessing Microsoft 365 services like Planner via a web browser and selecting the sign-in preference.
Observed behavior
The authentication system fails to register the user's preference and repeatedly requests the password instead of loading the application.
Before you start

Ensure you know your account passwords for other frequently visited websites, as clearing your general browser cookies may sign you out of other active sessions.

Solution 1Recommended

Clear Browser Cache and Authentication Cookies

Removing corrupted or conflicting cached authentication data forces the browser to establish a fresh, clean connection with Microsoft 365 servers.

Sign-in preferences are stored in your browser's cookies. If these files become corrupted or if there is a conflict in cached authentication data, Microsoft 365 will fail to recognize your active session and prompt you for a password repeatedly.

1
Open browser settings

Click the three-dot menu in the upper-right corner of your browser (such as Google Chrome or Microsoft Edge) and select Settings.

2
Navigate to privacy options

Select 'Privacy and security' from the left-hand menu, then click on 'Clear browsing data'.

3
Select data to clear

Set the time range to 'All time'. Check the boxes next to 'Cookies and other site data' and 'Cached images and files'.

4
Clear data and restart

Click the 'Clear data' button. Once completed, close the browser entirely, restart your device, and attempt to sign in to Microsoft 365 again.

Clear Browser Cache and Authentication Cookies
Targeted Cookie Clearing: If you prefer not to clear cookies for all websites, search your browser's cookie settings for 'microsoft', 'office', and 'live', and delete only those specific entries.
Free Microsoft Office alternative

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Tired of constant web login prompts and authentication loops? WPS Office offers a seamless, lightweight, and free alternative for creating and editing your documents locally without forced web logins or complicated browser cache issues.

  1. 1. Download the installer: Visit the official WPS Office website and click the free download button for your operating system.
  2. 2. Install the software: Run the downloaded installation file and follow the straightforward on-screen instructions.
  3. 3. Open your files: Launch WPS Office and directly open your existing Microsoft Office files without worrying about online sign-in loops.
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Frequently Asked Questions

Why does Microsoft 365 keep asking me to sign in?

This usually happens when your browser's cache or cookies are corrupted, preventing the authentication server from storing your login session correctly. It can also occur if your browser is set to strictly block third-party cookies.

Can I clear cookies only for Microsoft 365 to avoid signing out of other sites?

Yes. In most modern browsers, you can go to the specific site settings or cookie management section, search for Microsoft and Office related URLs, and delete only the site data related to those specific domains.

What should I do if clearing the cache doesn't fix the password loop?

If the issue persists, try accessing Microsoft 365 in an Incognito or Private browsing window. If it works there, a browser extension might be interfering. Alternatively, check your device's credential manager to remove any outdated saved passwords.