PowerShell Automation for Entra PIM: Introducing Mark Orr's Tool 'Intrepid'

Welcome back to the blog! If you have been following our podcast series, you know we frequently dive deep into modern cloud security, identity architecture, and ways to make life easier for IT administrators without lowering your security guardrails. In a recent episode, we sat down with Microsoft MVP Mark Orr for a masterclass on identity-driven security, privilege management, and the core philosophies of Zero Trust. If you haven't had a chance to listen yet, make sure you check out the full discussion over at the ENTRA PIM EXPLAINED: Securing Privileged Access with Mark Orr [MVP] episode page.

One of the most compelling topics we touched on during that conversation was the friction inherent in modern Privileged Identity Management (PIM). While Just-In-Time (JIT) access is an absolute must-have for any enterprise security posture, the repetitive daily ritual of navigating web portals to activate multiple roles can drive administrators crazy. To solve this exact problem, Mark built a custom PowerShell utility called Intrepid. In this post, we are going to expand on the topics covered in that episode, breaking down the security risks of standing privileges, how Intrepid streamlines bulk PIM activations, and how you can maintain rigorous security policies while removing unnecessary administrative friction.

Introduction to Privileged Access Friction in Microsoft Entra PIM

Microsoft Entra Privileged Identity Management has fundamentally transformed how organizations handle administrative permissions. Gone are the days when an IT professional held a permanent Global Administrator or Exchange Administrator account for eight to ten hours a day. Instead, PIM enforces the principle of least privilege by allowing users to hold eligible role assignments rather than active ones. When an administrative task needs to be performed, the user requests activation, provides a justification, and—if configured—passes multi-factor authentication or approval workflows.

However, this massive security improvement comes with a noticeable downside: administrative friction. In a complex enterprise environment, a single engineer might need to activate three or four different roles just to troubleshoot a multi-layered deployment or execute a routine maintenance window. Opening the Entra admin center, searching for each role individually, clicking activate, typing a justification, and completing authentication prompts for every single role becomes tedious very quickly. When security controls introduce massive amounts of daily friction, human nature takes over, and administrators start looking for workarounds. That friction is precisely what leads to insecure behavior, such as leaving roles active far longer than necessary or lobbying management for permanent role assignments.

The Security Risk of Permanent Role Activation

To understand why tools like Intrepid are so important, we have to look back at why permanent role assignments are such a dangerous anti-pattern in modern cybersecurity. As Mark Orr emphasized during our podcast conversation, identity is the new security perimeter. Attackers no longer waste time trying to crack heavy perimeter firewalls when they can simply phish an employee or buy compromised credentials on the dark web.

If an administrator uses an account with permanent, active privileges—especially if that same account is used for daily productivity tasks like checking email and opening web links—a successful phishing attack immediately hands the keys to the kingdom over to an adversary. With a permanently active Global Administrator account, an attacker can silently create secondary backdoor accounts, alter Conditional Access policies, harvest sensitive data, and deploy ransomware across the entire tenant.

Privileged Identity Management mitigates this risk by ensuring that accounts remain unprivileged until an explicit, time-bound need arises. But simply having PIM enabled isn't enough if administrators leave their roles active all day out of convenience. Best practices dictate that elevated sessions should be strictly limited—ideally four hours or less—and deactivated the moment the task is complete. Bridging the gap between the security mandate of JIT administration and the operational need for efficiency requires smart automation.

Introducing Intrepid: The PowerShell Tool for Bulk PIM Activation

Recognizing the operational fatigue caused by repetitive PIM activations, Mark Orr developed 'Intrepid', an open-source PowerShell tool designed to simplify and automate the bulk activation of Microsoft Entra PIM roles. Instead of forcing administrators to click through multiple web graphical user interfaces every morning or whenever a maintenance window opens, Intrepid allows authorized engineers to script and streamline their elevation workflows.

Intrepid acts as a bridge between PowerShell scripting capabilities and the Microsoft Graph API endpoints that govern PIM role management. By defining a target set of roles within a configuration or script execution, an administrator can trigger requests for multiple roles simultaneously. The tool handles the orchestration behind the scenes, submitting the required justifications, tracking activation status, and ensuring that the requests adhere to the boundaries established within your Entra tenant.

This approach transforms a painful, multi-step manual chore into a single, streamlined execution. An engineer can sit down at their secure workstation, run their customized Intrepid script, and efficiently request every role needed for their shift or project without losing focus or wasting valuable time navigating web menus.

How Intrepid Respects Conditional Access and Authentication Contexts

A common concern among security architects when they hear about automated privilege escalation tools is whether automation bypasses security controls. After all, if a script can silently request administrative roles, could it also bypass multi-factor authentication, trusted locations, or device compliance checks?

The beauty of Intrepid is that it is built with security-first principles. It does not bypass Microsoft Entra Conditional Access policies; rather, it fully respects them. When an Intrepid script initiates a PIM role activation, Microsoft Entra evaluates the request against all active Conditional Access policies targeting that user and role. If a specific role requires a phishing-resistant credential, a compliant device, or a specific Authentication Context, the automation framework enforces those requirements.

If an authentication challenge or interactive prompt is required to satisfy a Conditional Access policy during the activation sequence, the workflow pauses or prompts appropriately to ensure compliance. This ensures that organizations do not have to sacrifice governance, auditing, or policy enforcement in the pursuit of administrative efficiency. You get the speed of automation combined with the uncompromised integrity of your existing Zero Trust architecture.

Streamlining Just-In-Time Administration Without Compromising Security

When implementing automation in enterprise environments, striking the right balance between security and usability is always the ultimate challenge. Too much security leads to shadow IT and frustrated users finding workarounds. Too much convenience leads to security breaches and compromised infrastructures.

Tools like Intrepid demonstrate that administrative efficiency and strict security posture are not mutually exclusive. By removing the friction from Just-In-Time administration, Intrepid encourages administrators to actually use PIM the way it was designed to be used. When activating three or four roles takes two clicks via a script instead of five minutes of manual web navigation, administrators are far more willing to deactivate those roles immediately after finishing their tasks.

Furthermore, scripting role activation allows organizations to standardize their justification strings, improve auditing visibility, and enforce consistency across engineering teams. Instead of varying justifications entered manually by different administrators, automated scripts can log standardized ticket numbers, change request IDs, or maintenance windows directly into the PIM audit trail.

Best Practices for Privileged Role Management in the Enterprise

As you look to incorporate tools like Intrepid into your own enterprise environment, it is worth reviewing broader best practices for privileged identity management to ensure your architecture remains resilient against modern threats:

• Isolate Administrative Identities: Never use a daily productivity account for administrative tasks. Privileged accounts should be cloud-only identities with no Exchange mailboxes, Teams licenses, or standard user workloads attached to them.
• Enforce Phishing-Resistant Authentication: Require hardware security keys, Windows Hello for Business, or passkeys for all privileged accounts. Strong authentication remains your best defense against credential theft.
• Keep Elevation Windows Short: Encourage your engineering teams to limit role activation durations. Four hours is usually more than enough time for most operational tasks. If more time is needed, a fresh request should be submitted.
• Leverage Conditional Access and Intune Compliance: Ensure that administrative access is only granted when both the user identity and the device satisfy rigorous compliance and health policies managed through Microsoft Intune.
• Automate Wisely: Utilize community tools and custom PowerShell scripts like Mark Orr's Intrepid to reduce administrative fatigue, but always audit your scripts to ensure they respect organizational governance and policy frameworks.

Ultimately, securing an enterprise cloud environment is an ongoing journey rather than a destination checkbox. As threat actors become more sophisticated, our administrative processes must evolve to match them. By combining robust tools like Entra PIM, phishing-resistant credentials, endpoint compliance, and clever automation tools like Intrepid, security teams can protect their infrastructure while empowering their engineers to work faster and safer.

To hear more insights from Mark Orr on military-grade discipline in IT, passwordless authentication strategies, and the evolving landscape of Microsoft security, make sure you listen to the full conversation on the podcast episode titled ENTRA PIM EXPLAINED: Securing Privileged Access with Mark Orr [MVP]. Thank you for reading, and stay secure out there!