How to Safely Pilot Conditional Access for Privileged Users Without Lockouts

When deploying Conditional Access, high-risk users like admins, finance, or executives are both the most urgent and sensitive targets. If a policy is misconfigured and locks them out, it can disrupt critical operations, break workflows, and damage trust quickly. Microsoft’s report-only mode allows these policies to be tested safely in production, showing how they behave without enforcing them.

This guide gives MSPs a simple pilot framework to:

• Validate Conditional Access policies in audit mode.
• Spot potential access issues before enforcement.
• Safely roll out policies to privileged users without disruption.

While NinjaOne doesn’t control CA directly, it adds support by giving visibility into user/system states, device conditions, and reporting, all of which work alongside the Entra-based pipeline.

Steps to safely pilot a Conditional Access policy without disrupting admin access

Before you start, make sure the basics are in place so testing and monitoring run smoothly.

📌 General prerequisites:

• Microsoft Entra ID P1 or P2 license (for Conditional Access)
• At least one privileged group defined in Entra ID (e.g., Global Admins, Tier-0 IT Ops)
• Access to Microsoft Entra sign-in logs and Conditional Access Insights
• PowerShell or Azure Portal access for audit log queries

💡Optional but helpful: NinjaOne deployed for endpoint monitoring.

Step 1: Configure Conditional Access in report-only mode

Begin at the safest starting point by configuring CA in report-only mode. This simulates policy behavior without enforcing it, so you can observe its impact and make adjustments without disrupting workflows.

1. Sign in to the Microsoft Entra Admin Center.
2. Navigate to Protection > Conditional Access > New policy.
3. Target a specific group (e.g., “Tier-0 Admins” or “Privileged Access”).
4. Configure conditions such as:

• • Sign-in risk
  • Device platform
  • Application targeting

5. Under Enable policy, select Report-only (not “On”).
6. Save and name the policy a descriptive name (e.g., “CA Pilot – Tier 0 – Audit Only”).

Once saved, the policy logs its simulated results in sign-in logs. This lets you observe what would have happened if the policy were enforced without impacting users.

Step 2: Choose a contained pilot group

A contained pilot group acts as your controlled lab for CA testing. Limit the scope to a small set of high-risk users (ideally 5-10) to catch issues early without affecting critical operations. This group serves as your proving ground, where a handful of users experience the policy’s real-world impact before full enforcement.

1. Select 5 to 10 high-risk users to participate. Ideal selections include:

• • Accounts with Global Administrator or Security Administrator roles.
  • Users with elevated access to Microsoft 365 or Intune access.
  • Users recently flagged with Identity Protection risk signals.

2. Create a dedicated Entra ID (Azure AD) group for this pilot.
3. Apply the Conditional Access policy (in report-only mode) to this group only.

Step 3: Define pilot objectives clearly

Set measurable success criteria that align with both business and security needs. Know exactly what you’re solving for because clear goals will guide your policy design, shape evaluation, and help determine when the pilot is ready to scale.

1. Establish criteria for success, such as:

• • CA logs show expected prompts, denials, or exceptions.
  • No legitimate workflows are blocked during report-only mode.
  • Risk conditions trigger only when appropriate.
  • Alerts and exclusions (e.g., break-glass accounts) behave as designed.

2. Document these criteria so they can be measured consistently throughout the pilot.

Step 4: Communicate the test plan

Security policies work best when people understand not just the what, but also the why. This step is about preparing users by communicating the test plan. Doing so reduces resistance, sets expectations, and ensures support is available when needed.

Notify participating users with a short overview that covers:

• The policy is in audit (report-only) mode. No real enforcement yet.
• No action is required unless feedback is requested.
• The purpose is to simulate enforcement and gather insights.
• The timeline for rollout and review.

This avoids confusion, reassures users that their workflows won’t be disrupted, and builds trust in the process.

Step 5: Monitor logs for impact and Edge cases

To understand the actual impact of your policy, monitor logs to see whether CA is behaving as intended or blocking legitimate access. This step helps you catch misconfigurations, spot anomalies, and refine your approach before enforcement.

1. In the Microsoft Entra Admin Center, navigate to Monitoring > Sign-in logs.
2. Filter results by:

• • Conditional Access Status = “Report-only”
  • Result = “Would have failed” or “Would have prompted MFA”

3. Review whether blocked or challenged events were expected, or if they are false positives.

Alternatively, use PowerShell:

This provides a structured list of impacted users and applications.

💡 Also read Analyze Conditional Access Policy Impact.

Step 6: Tune policy conditions based on insights

Once you’ve reviewed the data, it’s time to refine and adapt your policies. In this method, you adjust conditions based on pilot results to resolve false positives and access issues, improving user experience without compromising security.

1. If false positives appear in the logs, adjust conditions such as:

• • Lowering sign-in risk thresholds to reduce overly aggressive blocking
  • Adding exclusions for specific apps or device platforms that are known to be safe
  • Including named locations or trusted IPs to reduce friction
  • Confirming break-glass accounts are excluded from all CA policies

2. Re-run the policy in report-only mode or within the pilot group to validate changes.
3. Repeat this cycle until the logs show high confidence and minimal disruption.

Step 7: Move to phased enforcement

Now it’s time to roll out. Use a gradual, step-by-step expansion, from the pilot group to more admins, and finally to all privileged roles.

1. Once confident in pilot results:

• • Update the policy from Report-only to On.

2. Initially, enforce the policy only for the pilot group.
3. Monitor sign-in logs and user feedback closely for issues.
4. Gradually expand the group scope:

• • Add more departments, roles, or access levels in stages.

5. After each expansion stage, review metrics and user feedback. Tune if needed, then proceed.
6. When stable, apply to all targeted roles and finalize related controls (e.g., block legacy auth).

This phased approach reduces risk, validates readiness at each stage, and builds confidence in full deployment.

Step 8: Document results and lessons learned

Even after full enforcement, the work isn’t done. This method captures insights for future rollouts and audits by documenting what worked, what failed, and how issues were resolved. This creates evidence for compliance and supports continuous improvement.

1. Use a matrix to track each rollout phase:

2. Record observations from each phase.
3. Note any adjustments made to policy conditions.
4. Decide whether to proceed, pause, or roll back.
5. Store these results in a central, accessible location for audit readiness and future rollouts.

How to verify your CA policy rollout

Before calling the rollout complete, verify that your CA policy is working as intended. Here’s a checklist for verification:

• Confirm CA policy status in the Entra admin portal
• Review audit logs for accurate policy targeting
• Test break-glass account bypass
• Ensure alerts and sign-in anomalies appear as expected
• Validate that only intended users were affected

Additional considerations

Remember these practices to strengthen your Conditional Access strategy and ensure long-term stability, security, and audit readiness.

Break-glass accounts

Always test break-glass (emergency access) accounts before enforcement. These accounts are excluded from CA policies to guarantee you can regain access if something goes wrong. Testing them confirms they work as intended before enforcement begins.

💡 Tip: Monitor their usage to detect and prevent abuse.

Legacy authentication

Disable legacy authentication or exclude it from CA to prevent bypass. Legacy protocols don’t support modern authentication and can undermine your CA policies. To avoid exploitation, disable legacy auth in your tenant or enforce CA blocks specifically for these protocols.

“What If” tool

Use Entra’s “What If” tool to simulate sign-ins before deployment. This helps validate policy logic in advance, catch misconfigurations early, and reduce surprises during rollout.

Scoped groups

Avoid enforcing CA across all users without first trialing scoped groups. Misconfigured policies applied globally can cause widespread access issues or lockouts. As covered earlier, start with small, targeted groups, then scale gradually for smoother deployment.

NinjaOne integration

NinjaOne can assist in strengthening your CA strategy by:

• Monitoring endpoints for compliance states or update failures related to Conditional Access.
• Sending alerts when endpoints fall out of CA compliance (e.g., encryption, patching).
• Automating remediation scripts on devices impacted by Conditional Access failures.
• Enhancing visibility into user behavior or compliance readiness before enforcement.

Safely pilot Conditional Access policy for privileged users to prevent lockouts

Starting Conditional Access with a small, high-risk group in report-only mode is the safest way to roll it out. It lets you test the policy, catch issues early, and adjust without risking lockouts. MSPs can build confidence in the rollout, confirm what works, and scale enforcement safely.

Related topics:

• How to Configure Conditional Access Policies in Entra ID (Azure AD)
• What is MEM (Microsoft Endpoint Manager)?
• Streamline Microsoft Entra (Azure AD) Connection Checks with PowerShell
• How to Educate Clients on the Differences Between MFA, SSO, and Conditional Access
• How to Enforce Conditional Access Policies Based on Risk and Location