Sign-in & Login Problems

Fix Microsoft 365 Connected Services Asking for Sign-in After Restart

Emma Brown Sep 28, 2026 869 views

Question details

The user needs Microsoft 365 to remember the authentication status for multiple connected accounts (work, school, personal) across application and system restarts.

How to Fix Microsoft 365 Connected Services Asking for Sign-in After Restart

Product: Microsoft 365
Device & OS: Windows
Scenario: Managing multiple accounts in Office Connected Services for school, work, and personal use.
Observed behavior: Office applications prompt for authentication every time the application or device restarts, failing to keep the user signed in.

Before you start

Ensure you have the passwords for all your connected Microsoft accounts available, and save any open documents before clearing credentials or repairing Office.

Solution 1Recommended

Clear Credentials and Reconnect Accounts

Removing cached credentials and reconnecting your accounts helps resolve conflicting authentication tokens in Windows.

Windows stores login tokens in the Credential Manager. When these tokens become corrupted or conflict with one another, Office applications fail to recognize your active sessions and prompt for sign-in repeatedly.

Disconnect the work or school account

Go to Windows Settings > Accounts > Access work or school, select your affected work or school account, and click 'Disconnect'.

Open Windows Credential Manager

Click the Windows Start button, type 'Credential Manager' in the search bar, and press Enter to open it.

Clear Office credentials

Select 'Windows Credentials' and scroll down to the 'Generic Credentials' section. Click on any entries containing 'MicrosoftOffice', 'OneDrive', or 'Teams' and select 'Remove'.

Sign in to Office again

Restart your computer, open any Microsoft Office application like Word, go to File > Account, and sign back into your Connected Services.

Clear Credentials and Reconnect Accounts

Files Remain Safe: Clearing credentials only removes saved passwords and authentication tokens. Your local files and documents stored in OneDrive are completely safe and will not be deleted.

Solution 2

Run an Online Repair of Office

Use the built-in Microsoft Online Repair tool to fix underlying software issues preventing Office from saving your login state.

Solution 3

Test with a New Windows User Profile

Creating a new user profile helps determine if the recurring sign-in issue is caused by a corrupted local Windows user profile rather than the Microsoft 365 tenant.

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Frequently Asked Questions

Why does Microsoft Office keep asking me to sign in?

This usually happens due to corrupted cached credentials in the Windows Credential Manager, conflicting accounts registered in Windows Settings, or an outdated Office installation.

What are Office Connected Services?

Connected Services in Office allow you to link external cloud storage and accounts, such as personal OneDrive, OneDrive for Business, or SharePoint, directly to your Office applications for easy file access and sharing.

How do I remove a connected service in Office?

Open any Office app like Word, go to File > Account, look under the 'Connected Services' section, select the service you want to disconnect, and click 'Remove'.

Will I lose my Office activation if I clear credentials?

No. Clearing generic credentials logs you out of the current session, but your subscription status remains tied to your Microsoft account. You will simply need to sign in again to reactivate the session.

Login & Account Issues