Microsoft 365 Keeps Asking for Password — Permanent Solution (2025)

Does Microsoft 365 keep asking for your password every few minutes, even after signing in successfully? You’re not alone. This is one of the most frustrating Office 365 authentication issues on Windows 10 and 11. The good news — it’s fixable. In this 2025 guide, we’ll walk you through proven methods to stop the repetitive login prompts and restore smooth syncing for Outlook, OneDrive, and other Microsoft 365 apps.

🧭 Why Microsoft 365 Keeps Asking for Password

• Corrupted Windows Credentials — Stored credentials clash with updated authentication tokens.
• Modern Authentication Disabled — Legacy protocols force re-authentication loops.
• Outdated Office Build — Old builds may reject new Microsoft login endpoints.
• Misconfigured Cached Mode — Outlook cache corruption interrupts credential validation.
• Third-party Security Software — Some antivirus tools block Microsoft Authentication Broker.

🛠 Permanent Fixes for Microsoft 365 Password Loop

1️⃣ Clear Saved Windows Credentials

Outdated or duplicate credentials can cause infinite login prompts. Here’s how to clear them:

1. Open Control Panel → Credential Manager → Windows Credentials.
2. Locate entries starting with MicrosoftOffice16 or Outlook.
3. Click Remove for each one.
4. Restart your PC and sign in again with your Microsoft account.

2️⃣ Enable Modern Authentication

If your Office 365 tenant still uses basic authentication, upgrade to modern auth:

1. Go to Admin Center → Settings → Org Settings → Modern Authentication.
2. Check “Enable Modern Authentication” for Exchange Online and Skype for Business.

This enables secure token-based login and stops password prompts.

3️⃣ Reset Office 365 Sign-in Settings

Corrupted sign-in files cause authentication conflicts. To reset:

• Press Win + R, type %localappdata%\Microsoft\IdentityCache → delete all files.
• Next, delete %localappdata%\Microsoft\Office\16.0\Licensing.
• Restart your computer and reopen Office apps.

4️⃣ Reconnect Microsoft Account via Settings

On Windows 11:

1. Open Settings → Accounts → Email & Accounts.
2. Remove any existing Microsoft work or school account.
3. Click Add Account and sign in again.

This refreshes your authentication tokens and clears conflicting sessions.

5️⃣ Update Office 365 to the Latest Version

Go to File → Account → Update Options → Update Now. Latest versions include updated credential manager and authentication APIs.

6️⃣ Turn Off “Always Prompt for Login Credentials” in Outlook

If this setting is enabled, Outlook will request passwords every session. To disable:

• In Outlook, go to File → Account Settings → Account Settings → Email.
• Select your account → click Change → More Settings → Security.
• Uncheck “Always prompt for logon credentials.”

💡 Additional Tips

• Ensure correct date and time zone settings — incorrect time can cause token mismatch.
• Temporarily disable third-party antivirus/firewall and test login again.
• Clear browser cache if you’re using web apps for Microsoft 365.

🔗 Related Articles

• Fix Office 365 Login Problems
• Office 365 Search Not Working After Update
• Microsoft 365 Apps Crashing After Update