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Use What If Tool to Troubleshoot Conditional Access in M365

Introduction

Conditional Access policies in Microsoft 365 help organizations enhance security by enforcing access controls based on user, device, location, and risk-based conditions. However, troubleshooting these policies can be challenging, especially when users face unexpected access denials. The 'What If' tool in Azure AD provides a powerful way to simulate user sign-in scenarios and analyze how Conditional Access policies apply. In this article, will explore how to use the 'What If' tool effectively to diagnose and resolve Conditional Access issues.

Understanding the 'What If' Tool

The 'What If' tool is part of Entra AD Conditional Access and allows administrators to.

  • Simulate a user’s sign-in attempt with specific conditions.
  • See which Conditional Access policies apply.
  • Understand why a user is granted or denied access.
  • Troubleshoot access-related issues without affecting live users.

Why Use the "What If" Tool?

  • Prevent Disruptions: Testing policies in a simulated environment ensures that legitimate users aren’t accidentally blocked from accessing critical resources.
  • Validate Policy Logic: Confirm that policies are targeting the right users, applications, and conditions.
  • Troubleshoot Access Issues: Diagnose why a user or group is experiencing access problems by replicating their scenario.
  • Optimize Security Posture: Fine-tune policies to strike the right balance between security and user experience.

Accessing the 'What If' Tool

To access the 'What If' tool.

  1. Sign in to the Microsoft Entra admin center (https://entra.microsoft.com/).
  2. Navigate to Identity > Conditional Access.
  3. Click on the What If tab.
    Conditional Access
    Microsoft

Simulating a Sign-in Scenario

Once inside the tool, follow these steps to run a simulation.

  1. Select a User: Choose the user experiencing access issues.
  2. Select a Cloud App: Pick the application for which the user is trying to authenticate.
  3. Set Conditions: Specify conditions such as:
    • IP Address: Test access from a particular location.
    • Device Platform: Choose Windows, macOS, iOS, or Android.
    • Client App Type: Browser, mobile app, or legacy authentication.
    • Sign-in Risk Level: Simulate a low, medium, or high-risk scenario.
  4. Click What If to run the simulation.
    Simulation

Interpreting the Results

The tool will display a summary of.

  • Policies that apply: Lists Conditional Access policies that are enforced.
  • Policies that do not apply: Shows policies that do not impact the scenario.
  • Access Result: Indicates whether access is granted, denied, or requires MFA.
    What If

Common Troubleshooting Scenarios

  1. Unexpected Access Denials
    • Check if a deny policy is overriding other policies.
    • Verify if the user’s location or device is restricted.
    • Look at authentication methods (e.g., legacy authentication block).
  2. Multi-Factor Authentication (MFA) Issues
    • Ensure the policy requires MFA for the selected conditions.
    • Confirm that the user has registered an MFA method.
  3. Sign-in Risk Blocking Access: If risk-based policies are blocking access, check the risk assessment from Microsoft Defender for Identity.
  4. Testing New Policies: Before rolling out a new Conditional Access policy, use the tool to ensure it behaves as expected for different user groups and scenarios.
  5. Auditing Existing Policies: Regularly test your policies to ensure they align with your organization’s security requirements and compliance standards.

Best Practices for Using the "What If" Tool

  1. Test Incrementally: Start with a small set of conditions and gradually expand to simulate more complex scenarios.
  2. Document Your Findings: Keep a record of your simulations and the resulting policy behaviors for future reference.
  3. Collaborate with Stakeholders: Work with your security and IT teams to validate policies and ensure they meet organizational goals.
  4. Monitor Policy Changes: Regularly review and update your Conditional Access policies to adapt to new threats and business requirements.

Conclusion

The "What If" tool is an indispensable resource for administrators managing Conditional Access policies in Microsoft 365. By enabling you to simulate and troubleshoot policies before they go live, the tool helps prevent disruptions, optimize security, and ensure a seamless user experience. Whether you’re rolling out new policies, troubleshooting access issues, or auditing your security posture, the "What If" tool empowers you to make informed decisions and maintain a robust defense against evolving threats.


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