How to Manage Software Licensing Audits (Adobe, Microsoft) Proactively

A software license audit is only daunting if you’re unprepared. Issues like undocumented usage, triggering unexpected fees, or resulting in penalties if compliance isn’t provable may arise if you’re not able to proactively manage software licensing audits. That’s why it’s crucial to understand the process to prevent license audit problems before they exist. In this guide, we will walk you through the best practices and strategies in managing software licensing audits.

At a glance

Prerequisites for managing software licensing audits

Before proceeding with software licensing audit management, make sure your environment meets the following requirements:

• Microsoft 365 Admin Center access and any Volume Licensing portals for managing Microsoft subscriptions and licenses.
• Adobe Admin Console centrally manages Creative Cloud and Acrobat DC licensing.
• PowerShell 5.1 or later, with administrative privileges at your management stations. (Check your PowerShell Version)
• Endpoint coverage via RMM tools or GPOs to reach all devices.
• Mechanisms to detect endpoints, such as registry checks, installed-software inventories, or file-system scans.

Task 1: Maintain a centralized license inventory

📌 Use Case:

Maintaining a centralized license inventory enforces a strong compliance posture. This task tracks every software title, licensing type, and activation model.

Below are recommended steps for maintaining a centralized license inventory.

1. Track the following:
   • Per-user licenses: These include licensing tied to an individual user account. Examples include software like Microsoft 365, Adobe CC, and more.
   • Per-device licenses: This covers licenses assigned to specific hardware, including volume licensing, OEM licenses, and other license types.
   • Subscription vs. perpetual: This task identifies subscription licenses (paid on a recurring basis) from perpetual licenses (paid once for perpetual use).
   • Cloud-assigned vs locally installed: Tracking of licenses to determine which software is provisioned through a cloud service, and which ones are physically stored on device storage.
2. Store the inventory using the following:
   • Cloud storage platforms: Store inventory data in cloud storage platforms like OneDrive or SharePoint.
   • IT documentation services: A purpose-built IT documentation platform for MSPs is also ideal for this task. Some comprehensive endpoint management platforms, like NinjaOne, also have integrated IT asset management, which can also be used to store and manage your license inventory.
   • Custom PowerShell-generated reports: Specific scripts also automatically pull licensing and installation data from endpoints, format it into readable reports (CSV, HTML, etc.), and save it in a central repository for ongoing audit readiness.

Task 2: Use PowerShell to discover installed licenses and software

📌 Use Case:

This task retrieves a filtered list of applications and licences through manual querying using PowerShell.

Automated discovery is critical for keeping your license inventory accurate. One way to do this is by using PowerShell to query installed software, check activation details of Microsoft 365 subscription apps, and retrieve activation status of Microsoft Office. Here are some example steps:

1. Open PowerShell as an administrator. Press the Windows key, type PowerShell, then right-click Windows PowerShell and select Run as administrator.
2. Run the following command:

• To list all Adobe and Microsoft Office installations on a device:

Get-CimInstance -ClassName Win32_Product |Where-Object
{ $_.Name -like “*Adobe*” -or $_.Name -like “*Office*” } | Select-Object Name, Version, InstallDate

This command retrieves Adobe and Microsoft Office applications installed on the local computer via MSI-based installers, showing their name, version, and install date.

💡 Note: The scope of this command is the device where it’s executed. If you have hundreds of computers, you would need to run this individually on each one. For scalability, organizations often use RMM tools like NinjaOne to automate this discovery by pushing mass scripts across all managed endpoints.

• To check activation details of Microsoft 365 subscription apps via the registry:

Get-ItemProperty HKLM:\SOFTWARE\Microsoft

\Office\ClickToRun\Configuration |

Select-Object ProductReleaseIds

• To retrieve activation status, you can:

cscript “C:\Program Files\Microsoft Office\Office16\ospp.vbs” /dstatus

Task 3: Detect Adobe licensing via registry and admin console

📌 Use Case:

This task verifies Adobe product licensing by checking registry keys and the Adobe Admin Console to identify unauthorized installations or expired licenses.

1. Open PowerShell as an administrator. Press the Windows key, type PowerShell, then right-click Windows PowerShell and select Run as administrator.
2. Run the following command:

Get-CimInstance -ClassName Win32_Product |Where-Object

{ $_.Name -like “*Adobe*” -or $_.Name -like “*Office*” }

|Select-Object Name, Version, InstallDate

This command gives administrators a filtered inventory of installed Adobe and Microsoft Office products across an endpoint, useful for quickly verifying whether licensed software is installed and when.

Task 4: Use GPO to enforce licensing compliance and application control

📌 Use Case:

This task prevents unauthorized or unlicensed software usage by applying Group Policy restrictions and controlling which applications can run within the network.

Group Policy provides a powerful control mechanism to enforce licensing and application control. Here’s a breakdown:

• Under User Configuration > Administrative Templates > System:
  • Enable Run only specified Windows applications to lock down software installs.
  • Or use Don’t run specified Windows applications to block known unlicensed or pirated apps.
• For more advanced control, use Software Restriction Policies or AppLocker to prevent unauthorized Adobe or Office versions.
  • Navigate to:
    • Computer Configuration > Windows Settings > Security Settings > Software Restriction Policies
    • Computer Configuration > Windows Settings > Security Settings > Application Control Policies > AppLocker
  • Or for instance, create path rules to block installers like setup.exe used by pirated software, or hash rules for known cracked versions.

Task 5: Validate via CMD and Windows license tools

📌 Use Case:

This task aims to confirm Windows and Microsoft Office activation status to avoid service disruptions and ensure devices meet licensing requirements.

1. Open the Command Prompt as an administrator. Press the Windows key, type cmd, right-click Command Prompt from the search results, and select Run as administrator.
2. To view Windows licensing and activation details, run:

slmgr.vbs /dli or slmgr.vbs /xpr

These commands display Windows activation status, license type, and whether the system is permanently activated.

3. To view Microsoft Office activation information, you need to run the ospp.vbs script. Microsoft installs this built-in script with every volume-licensed Office installation to report on your license and activation information. You don’t need to download it; it’s already on your system.

To run it, locate it first. The ospp.vbs script is typically located in the Office installation folder:

• C:\Program Files\Microsoft Office\Office16 (for 64-bit Office on 64-bit Windows)
• C:\Program Files (x86)\Microsoft Office\Office16 (for 32-bit Office on 64-bit Windows)

You have to navigate to the directory where the ospp.vbs script is stored. Use one of the following commands, depending on your Office version and system architecture:

• For 64-bit Office on a 64-bit OS, run:

cd “C:\Program Files\Microsoft Office\Office16”

• For 32-bit Office on a 64-bit OS:

cd “C:\Program Files (x86)\Microsoft Office\Office16”

💡 NOTE: The “Office16” folder is for Office 2016 and 2019. This number changes depending on the version (e.g., “Office15” for Office 2013, “Office14” for Office 2010).

Open Command Prompt (opened as administrator). Run the following script with the cscript command:

cscript ospp.vbs /dstatus

Running this script will display activation status, license type, and remaining grace period if applicable.

4. To ensure Adobe’s Creative Cloud process is running:

Get-Process “Creative Cloud”

5. To get a full list of installed products for additional cross-checking:

Get-ItemProperty HKLM:\Software\Microsoft

\Windows\CurrentVersion\Uninstall\* | Select-Object

DisplayName, DisplayVersion, Publisher, InstallDate

Task 6: Automate non-compliance alerts and cleanup

📌 Use Case:

You can do this task to automatically detect, alert, and remove unlicensed or prohibited software. It can help maintain compliance without relying solely on manual reviews.

Automation helps with scaling compliance checks. Here are some recommendations:

• Schedule scripts to detect unauthorized software by comparing installed lists to your licensed inventory.
• Use scripting to automatically uninstall trial or deprecated versions. For example, if you want to find and automatically remove any MSI-installed Microsoft Office products on a device:
  • Open the Command Prompt as an administrator. Press the Windows key, type cmd, right-click Command Prompt from the search results, and select Run as administrator.
  • Run the following command:

Get-CimInstance -ClassName Win32_Product -Filter “Name LIKE

‘%Office%'” |ForEach-Object { $_.InvokeMethod(‘Uninstall’, $null) }

• Log all actions such as deletions, alerts, and integrations. This can ensure audits are backed by evidence.

⚠️ Things to look out for

Additional considerations for managing software license audits

• BYOD and remote devices: Track installs via sign-ins using Microsoft 365 or Adobe accounts.
• Inactive accounts: Deactivate or reassign licenses for users dormant for 30 days or more.
• Retention policies: Store procurement and license records for at least 3 years to satisfy audit traceability.
• Audit requests: Be ready to produce reports showing license counts, assignments, usage history, and purchase logs on demand.

NinjaOne services for detecting and quarantining malware via RMM

NinjaOne and its tools can help MSPs maintain continuous license hygiene and confidently generate audit-ready reports.

Managing software licensing audits proactively

Carrying out operations to manage software licenses may seem tedious. However, following these recommendations can save you from unexpected, and most of the time, disruptive issues due to software license misaudits. In summary, we covered:

• How to discover and track Microsoft and Adobe software installations
• PowerShell, CMD, registry, and GPO methods to enforce compliance
• Centralized documentation and automation strategies
• How NinjaOne ensures software audit preparedness across all clients

All these strategies can help you proactively and confidently prepare for a software license audit.

Related topics:

• Viewing Software Inventory
• Software Inventory Reports
• What is Compliance Management? Definition & Importance
• IT Compliance: Definition, Standards, and Risks