Sign-in & Login Problems

Fix Microsoft 365 Apps Keep Asking Users to Sign In

Maira Mehtab Sep 22, 2026 871 views

Question details

Users are continuously prompted to enter their login credentials multiple times a day while using Microsoft 365 applications.

Product: Microsoft 365 Apps
Device & OS: not provided
Scenario: Using desktop or web-based Microsoft 365 applications for daily workflow.
Observed behavior: The applications interrupt workflows by repeatedly demanding user authentication due to session timeouts, policy conflicts, or credential errors.

Before you start

Ensure you have administrative privileges to access the Microsoft 365 Admin Center and Microsoft Entra ID (formerly Azure AD), as adjusting authentication policies requires elevated permissions.

Solution 1Recommended

Review and Adjust Session Timeout Policies

Modify Conditional Access policies in Microsoft Entra ID to prevent overly aggressive session timeouts that force frequent logins.

Microsoft 365 uses Conditional Access policies to determine how often a user must re-authenticate. If the 'Sign-in frequency' setting is configured too strictly, users will face constant login prompts.

Access the Admin Portal

Log into the Microsoft Entra admin center as an administrator.

Navigate to Conditional Access

Go to Protection > Conditional Access > Policies.

Modify Sign-in Frequency

Select the policy affecting your users, click on 'Session' under Access controls, and adjust the 'Sign-in frequency' setting to a more appropriate timeframe (e.g., 30 or 90 days).

Save Changes

Save the updated policy and advise affected users to sign out and sign back into their Microsoft 365 apps.

Policy Application Delay: It may take up to 24 hours for new Conditional Access policies to propagate fully across all Microsoft 365 services.

Solution 2

Clear Cached Credentials

Remove outdated or corrupted Microsoft Office credentials saved locally on the device.

Solution 3

Check Network Stability and VPN Connections

Ensure that intermittent network drops or VPN software are not severing the authentication connection.

Free Microsoft Office alternative

Switch to WPS Office for a Hassle-Free Desktop Experience

If persistent authentication issues in Microsoft 365 are disrupting your productivity, consider switching to WPS Office. It provides a lightweight, highly compatible alternative that lets you edit documents offline without forced logins.

1. Download WPS Office: Visit the official WPS website and download the free installer.
2. Install and Launch: Follow the simple installation wizard and open the WPS Office suite.
3. Open Your Files: Drag and drop your existing Microsoft Word, Excel, or PowerPoint files directly into WPS to continue working.

Fully compatible with Microsoft Office formats like DOCX, XLSX, and PPTX.Work entirely offline without cloud-forced sign-in loops interrupting your flow.Lightweight application that uses fewer system resources.Familiar user interface makes migrating from Microsoft 365 seamless.

Frequently Asked Questions

Why does Outlook keep asking for my password even after I check 'Remember my credentials'?

This usually occurs because of conflicting entries in your system's Credential Manager or because your organization has a Multi-Factor Authentication (MFA) policy that overrides the 'remember me' setting.

Can clearing browser cookies fix web-based Microsoft 365 sign-in issues?

Yes. For users accessing Microsoft 365 via a web browser, corrupted cookies or overly restrictive privacy settings blocking third-party cookies can cause continuous sign-in loops. Clearing cache and cookies often resolves this.

Does having multiple Microsoft accounts logged in cause sign-in conflicts?

Yes. If you have both personal and work Microsoft accounts logged into Windows or Office apps simultaneously, the authentication token manager can get confused, leading to repeated login prompts.

Login & Account Issues