A Complete Guide to Microsoft Entra Conditional Access

today’s world, organizations face ever-evolving security threats. Protecting sensitive data while ensuring users have seamless access to business resources is a challenge. Microsoft Entra Conditional Access provides a solution by allowing organizations to enforce adaptive policies based on real-time signals. This guide explores the history, features, setup, and latest updates in Conditional Access to help businesses strengthen their security posture.

This article will be bit longer than the other articles. Because I need to summarize all the details about Microsoft Entra Conditional Access Policies within a single post. So, I highly recommend you to read the complete article to get a solid understanding about Entra CA policies.

History of Conditional Access

Security started with simple username-password authentication, but as cyber threats grew, businesses needed stronger access control mechanisms. Role-Based Access Control (RBAC) and Single Sign-On (SSO) were introduced to simplify and secure authentication, but they were not enough to stop sophisticated attacks. With the rise of cloud computing and remote work, organizations required dynamic security measures that adjusted based on context. in order to fulfill this requirement, Microsoft introduced Conditional Access to address these challenges by evaluating risk signals in real-time before granting access.

What is Microsoft Entra Conditional Access?

Microsoft Entra Conditional Access is a policy-driven security framework that enables organizations to control access to corporate resources. It considers signals such as user identity, device status, location, and application sensitivity to determine whether access should be granted, denied, or require additional authentication steps.

Entra ID Security Defaults

Since October 2019, Microsoft has been implementing Entra ID security defaults for newly created tenants. These defaults consist of pre-configured settings designed to defend against prevalent identity-based threats such as phishing and password spraying.

Security defaults are primarily intended for free-tier Entra ID tenants or those without access to Conditional Access features. Organizations with a P1 or P2 Entra ID licenses are advised to use Conditional Access policies instead of using security defaults. as it offers fully customizable security policies, whereas security defaults have fixed configurations.

How to check Entra ID’s Security Defaults

To enable Entra ID security defaults:

1. Sign in to the Microsoft Entra Admin Center as a security or higher level Admin.
2. Navigate to Identity > Overview> Properties.
3. Select Security Defaults and toggle it ON or OFF as per your need.
4. Save changes to apply baseline security policies.

Types of Conditional Access Policies

1. User-based policies – Applied based on user groups or roles.
2. Device-based policies – Enforced depending on device compliance and trust level.
3. Location-based policies – Access is allowed or restricted based on geographic location.
4. Application-based policies – Protects access to specific applications based on sensitivity.

Features of Conditional Access Policies

• Adaptive authentication - to enhance security while reducing friction.
• Granular access controls - for different users and applications.
• Integration with risk-based authentication - to block suspicious logins.
• MFA enforcement - for added security layers.

Why You Should Adopt Conditional Access?

Conditional Access enhances security by ensuring that only legitimate users and devices are access business applications or any other corporate resources. It helps to prevent unauthorized access, secures remote work, and ensures compliance with industry regulations. So, let's talk about a real-life scenario...!!

Imagine you’re responsible for identity and access management in a Sri Lakan Company with 300 employees across various departments and places.

• R&D (some are working remotely).
• Sales (some are working in Australia).
• Accounting (some are working locally).

The company also outsources key services, such as:

• Security Operations Center.
• Marketing.
• IT and Cloud consulting.

Its infrastructure is a mix of on-premises and cloud environments, including:

• An on-premises Active Directory.
• Legacy on-premises applications.
• An Entra ID tenant synchronized with the on-prem AD.
• Workloads hosted on a major IaaS provider like Microsoft Azure.
• Cloud services and SaaS applications, including:
  • Microsoft 365 (Email, SharePoint, Office, Teams, Office 365 Apps)
  • Salesforce, Jira.
  • GitHub.
  • Accounting and finance SaaS solutions (Sage, Dynamics BC).

Given this setup, your challenge is to design a secure authentication strategy that balances security and usability, keeping in mind the following principles:

• Flexibility: Apply strict security measures only when absolutely necessary.
• Remote Work Support: Ensure every department can function remotely.
• Seamless Access: On-premises users should have Single Sign-On (SSO) across the hybrid environment.
• Role-Based Access Control: Employees should only access services relevant to their role.
• Least Privilege Principle: Grant minimal necessary permissions for each user.

This scenario reflects the reality of modern businesses, where employees work remotely across different locations with varying access levels. Strong authentication security is essential if an administrator or a user logs in from an unfamiliar location, their authentication process should be more stringent than when logging in from the office.

To achieve both flexibility and robust security, Conditional Access is key. It allows you to tailor security policies based on user roles, locations, and applications, creating a dynamic and secure authentication framework that meets your organization’s needs.

How Do Conditional Access Policies Work?

Conditional Access dynamically controls access to applications and resources based on specific conditions. It evaluates access requests in real-time, considering various factors like user identity, device compliance, location, risk level, and application sensitivity before granting or denying access.

When a user attempts to access a resource, Conditional Access follows a structured process.

Before making an access decision, Conditional Access gathers signals such as:

• User Identity: Who is trying to log in? What is their role?
• Device Health: Is the device compliant with security policies?
• Location: Is the login coming from a trusted or unfamiliar region?
• Application Access: Which application is being accessed?
• Risk Level: Does this login show signs of potential compromise (e.g., unusual location, multiple failed attempts)?

Once the contextual signals are collected, Conditional Access evaluates them against the organization's pre-configured policies. These policies define rules based on:

• Who is trying to access (users/groups).
• Which applications or services are being accessed.
• The conditions under which access is requested (location, device, risk level).
• The security controls required for access (MFA, device compliance, etc.).

After evaluating the request, Conditional Access enforces one of the following actions:

• Grant Access: If the request meets all security conditions, access is granted.
• Require Additional Authentication: If the login is from an unfamiliar location or an untrusted device, Multi-Factor Authentication (MFA) may be required.
• Block Access: If the request poses a high security risk (e.g., logging in from a known malicious IP address, multiple sign failures, MFA failure), access will be denied.

Example Scenario

An employee attempts to access Microsoft 365 from an unknown device in a different country. Conditional Access would:

1. Detect that the user is logging in from an unfamiliar location.
2. Check if the device is compliant with security policies.
3. Require MFA as an extra layer of security before granting access.

If this were an administrator logging in from an unusual location, stricter policies might apply, such as blocking access altogether or enforcing more advanced security measures.

How to Configure a Conditional Access Policy

Okay, now let's take a look on how to set up conditional access policies in your environment.

Here is the step-by-step guidance.

1. Access the Microsoft Entra Admin Center

• Sign in to the Microsoft Entra admin center (entra.microsoft.com).
• Navigate to Identity > Protection > Conditional Access > Policies.

2. Create a New Policy

• Click + New policy and give it a descriptive name (e.g., "MFA for External Users").

3. Define Policy Conditions

• Assign Users or Groups: Select users, groups, or roles the policy applies to (e.g., all users, specific departments, or guest users).
• When assigning users or groups, please make sure to exclude a breakglass admin account which having enough admin permissions to the conditional access policy configuration to rollback the settings to previous to avoid unnecessary lockdowns.
• Select Target Resouces: Choose the resources that you want to protect (e.g., All Cloud Apps, Global Secure Access, Specific App, User Action, Etc.).
• Set Conditions, Network (Optional):
• Device Platform (Windows, macOS, iOS, Android).
• Locations (Block access from high-risk countries).
• Risk Level (Enforce stricter rules for suspicious sign-ins).

4. Configure Access Controls

• Under Access Controls, choose whether to:
• Block access (e.g., deny access from unknown locations).
• Grant access with conditions (e.g., require Multi-Factor Authentication, a compliant device, or a trusted location, require to be marked as compliant, require approved client app, Require app protection policy).

5. Choose Policy Mode

• Report-only: Test the policy without enforcing it.
• On: Enable the policy immediately.
• Off: Disable the policy while keeping it saved for future use.

6. Save and Deploy

• Click Create to save and apply the policy.
• Monitor Sign-in logs to analyze how the policy affects users and make adjustments if needed.

By following these steps, administrators can create effective Conditional Access policies that enhance security while maintaining a seamless user experience.

What is Conditional Access Used For?

Now that we know which controls are configurable, it’s time to put them to use. Here’s how you can use Conditional Access controls to achieve your security and compliance goals.

• Preventing Unauthorized Access: To minimize the risk of account compromise, restrict access to only those using passwordless or phishing-resistant multi-factor authentication (MFA) methods.
• Location-Based Access Control: Manage access permissions based on where the authentication request originates. You can define trusted and untrusted zones with specific access rules. For instance, require MFA for users to log in from home while allowing seamless access from the company’s headquarters.
• Compliance-Based Access Control: Control access based on the device used for authentication. Different compliance conditions can be applied depending on the device’s status. For example, if a device is marked as compliant in Entra ID and is domain-joined, it can have more lenient controls compared to a Zero Trust-enforced policy.
• Session Management Controls: Adjust session duration based on user roles. By default, Entra ID sets reauthentication intervals at 90 days, but you can enforce stricter reauthentication requirements for specific roles. For example, administrators might be required to verify their identity more frequently than standard users.
• Granular Identity and Application Policies: Define highly specific access policies tailored to individual applications or users. For example, create a policy that grants access to an emergency administrator only under certain conditions, or enforce stricter authentication for critical applications like the Entra admin portal compared to other cloud services.

"What If" Feature in Conditional Access Policy?

The "What If" tool in Microsoft Entra Conditional Access is a powerful feature that allows administrators to simulate and test the impact of Conditional Access policies before enforcing them. It helps IT teams predict how specific users, groups, or sign-in conditions would be affected by existing policies, reducing the risk of unintended disruptions. So, lets see how it works.

How It Works

1. Access the Tool: Navigate to the Microsoft Entra admin center → Identity → Protection → Conditional Access → Policies → What If.
2. Enter Test Parameters: Select a specific user, application, device, location, and other conditions to simulate an access scenario.
3. Run the Simulation: The tool evaluates existing Conditional Access policies and displays which policies would apply, whether access would be granted or denied, and if additional authentication (like MFA) would be required.
4. Analyze Results: IT admins can review the expected enforcement outcomes and adjust policies if needed before applying them to real users.

Why Use the "What If" Tool?

• Prevents Lockouts: Ensures that legitimate users are not accidentally blocked.
• Speeds Up Troubleshooting: Helps diagnose why a policy is or isn’t applying as expected.
• Refines Policies: Allows fine-tuning of policies to achieve the right balance between security and usability.

In short, the "What If" feature provides a risk-free way to evaluate Conditional Access policies, making it an essential tool for managing access control effectively

Latest Features of Conditional Access Policy

Microsoft continuously improves Conditional Access with features such as:

• AI-driven risk assessments.
• Enhanced session controls for cloud apps.
• New integrations with Microsoft Defender for threat protection.

Testing and Troubleshooting

If a Conditional Access policy isn’t working as expected—blocking legitimate users, not applying correctly, or causing unexpected authentication issues, here are some effective troubleshooting methods.

1. Use the 'What If' Tool

The "What If" analysis tool helps simulate access scenarios and predict which policies will apply to a specific user.

• Go to Microsoft Entra admin center → Protection → Conditional Access → Policies → What If.
• Enter user details, location, application, and device info.
• Review which policies apply and adjust as necessary.

2. Review Sign-In Logs

Sign-in logs provide real-time insights into why a Conditional Access policy is enforced or blocked.

• Navigate to Microsoft Entra admin center → Identity → Monitoring & Health → Sign-in Logs.
• Select a user sign-in attempt and review:
• Authentication details
• Applied Conditional Access policies
• Reasons for access denial or MFA prompts
• Use the "Conditional Access" tab in the logs to see which policies affected the sign-in.

3. Check Policy Settings

Misconfigured policies can cause unexpected behavior. Review:

• User Assignments: Ensure the right users/groups are included or excluded.
• Application Selection: Verify that the correct apps are covered by the policy.

Conditions & Controls: Check if location, device compliance, or risk-based settings are too restrictive

4. Enable Report-Only Mode Before Enforcing Policies

• Instead of applying a policy immediately, use Report-Only mode to test its impact without enforcement.
• Go to Conditional Access policies, edit the policy, and set the Enable Policy option to Report-only.
• Monitor sign-in logs to see how the policy behaves before enabling enforcement.

5. Check for Conflicting Policies

Multiple Conditional Access policies may overlap and cause conflicts.

• Review all active policies to ensure there’s no contradiction between different rules.
• Use policy precedence to determine which policy takes priority.

6. Verify MFA and Device Compliance Settings

If users are unexpectedly blocked or prompted for MFA, check:

• Entra ID Security Defaults: If enabled, they might conflict with Conditional Access MFA policies.
• Device Compliance Policies: Ensure the correct compliance settings are applied for managed devices.

7. Test with Different User Scenarios

• Try logging in from different locations, devices, and network conditions to see how policies behave.
• Use a test account to safely experiment with policy changes.

8. Use Conditional Access Insights & Reporting.

• In Microsoft Entra admin center, navigate to Workbooks → Conditional Access Insights and Reporting.
• Analyze the data to identify policy misconfigurations, failed sign-ins, and risk-based decisions.

9. Temporarily Disable or Modify the Policy.

If a policy is too restrictive, consider:

• Disabling it temporarily to test whether it’s causing the issue.
• Adjusting conditions to make access rules more appropriate.

10. Seek Microsoft Support

If all troubleshooting steps fail, consult Microsoft documentation or open a support ticket with Microsoft.

Conclusion

Now we went through a fully detailed walkthrough about Microsoft Entra Conditional Access policies. This is a powerful tool for securing business resources while ensuring a seamless user experience. By implementing well-structured policies, organizations can strengthen security, enhance compliance, and embrace a Zero Trust security model. Ready to implement Conditional Access? Start configuring your policies today and take your security to the next level.

If you want to have a deep dive into Microsoft SSE. refer these official Microsoft documentation and guides:

Microsoft Entra Conditional Access documentation - Microsoft Entra ID | Microsoft Learn

Have thoughts or questions? I'd love to hear from you! Drop a comment below, and let's discuss more…!!!

Also, I would like to invite you to read my other articles as well:

Cloud Computing
How to Guides
Tech News
Microsoft Intune
Microsoft Entra ID

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