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Running AppLocker Policy Testing Across VMs with Hyper-V

#1
09-15-2021, 09:27 PM
Running AppLocker Policy Testing Across VMs with Hyper-V

When you're tasked with deploying an AppLocker policy in an organization, the last thing you want is for the policy to disrupt the functionality of existing applications. Setting up a test environment using Hyper-V is crucial because it lets you isolate changes and observe how the policy impacts various applications without risking a production environment. Hyper-V is a powerful virtualization tool that allows multiple operating systems to run concurrently on a single physical host. This is particularly useful for IT professionals who need to spin up virtual machines quickly for testing purposes.

The first step in this process involves preparing your Hyper-V setup. I usually ensure that the Hyper-V feature is enabled on the Windows Server or Windows 10 machine. You can do this through the 'Turn Windows features on or off' menu. Once Hyper-V is active, launching Hyper-V Manager helps create and manage your virtual machines.

Creating a new VM is straightforward. You simply choose ‘New’ and then ‘Virtual Machine.’ A wizard will guide you through the process, where I often allocate resources like CPU, RAM, and disk space according to the requirements of the policy you are testing. For most testing scenarios, I generally assign at least four GB of RAM and a couple of virtual processors, but it ultimately depends on the applications you want to test with AppLocker policies.

Once the VM is set up, the importance of isolating testing environments becomes evident. Suppose I plan to test an AppLocker policy that restricts script execution. In that case, I will set up a VM running Windows 10 and configure it to have just the necessary applications installed. For instance, I might install Microsoft Office, some web browsers, and a script execution application like PowerShell. This optimized setup ensures that I can focus solely on how AppLocker affects these applications without unnecessary noise from other programs.

Next, configuring the AppLocker policy itself is where things get interesting. Windows provides tools like the Local Security Policy Editor or Group Policy Management Console. I prefer working via Group Policy because it allows centralized management if you ever expand this beyond mere testing. Within the Group Policy, you will navigate to the AppLocker node under Security Settings. You can create rules for executable files, scripts, Windows Installer files, and packaged apps.

For example, say you want to block the execution of PowerShell scripts. You'd create a rule specifically prohibiting scripts based on publisher or path. Utilizing the ‘path’ condition lets you specifically target items, whereas the ‘publisher’ condition allows granular controls based on trusted code signatures.

It’s crucial to deploy these policies in an audit-only mode initially. This is a feature that I often leverage. You can set Polices to either audit the actions that would be taken or enforce them directly. In audit mode, you can evaluate what applications would have been blocked without causing disruptions. To switch between modes, simple modifications can be made to the existing policy configuration.

After setting the AppLocker policy in audit mode, I often run test scenarios on the applications installed in your VM. For instance, simply trying to execute a script that should theoretically be blocked generates logs that you can review. You can find these logs in the Event Viewer under the Applications and Services Logs > Microsoft > Windows > AppLocker > EXE and DLL.

Examining these logs gives precise details about the scripts or programs that were blocked, including the exact path and the reason for the block. I usually take notes on these logs to adjust my policy rules as necessary. As I gather more data, I can refine my AppLocker policy rules for optimal security without hindering productivity.

Another effective method I employ for testing includes running various applications in different user context scenarios. If you set up AD accounts with distinct security permissions, you can test how the AppLocker policy behaves for different user roles. This adds another layer of detail to your testing. With Hyper-V, I can easily duplicate the same VM image and modify user roles or permissions as needed without reconfiguring everything from scratch.

If I've set the policy to audit and wanted to tighten security based on observations from the Event Viewer, I would create more specific rules. Maybe a web application allowed by the policy is causing problems, so I would create a rule to allow its execution specifically while blocking everything else that could pose risks in the same category.

An example of how complex this can get arises when working with scripts. You might start with a fairly permissive policy, but overtime realize specific PowerShell scripts are misused, and the need to block specific scripts becomes a priority. When running the tests, particularly with automation scripts, configuring permissions for specific paths vs. others often leads to better application performance with enhanced policy security.

Once you’ve adjusted the policy to your satisfaction through testing, transferring the finalized policy to a production environment is the next logical step. You could choose to export the Group Policy Object (GPO) settings and import them on a domain controller. This process is one I’ve often repeated, allowing policies to be shared across various organizational units, ensuring consistent application protection across workforce machines.

In production, constant monitoring of AppLocker logs is essential. A setup should be in place to regularly review if any unauthorized applications attempt to execute and whether the policies are yielding the desired effect without hindrance. Continuous evaluation is significant as applications -- as we know -- are always evolving, and governments and regulations around app security are frequently updated.

One not-so-fun discovery comes in the form of compatibility issues. Some applications will genuinely need to run with elevated privileges or inherit certain permissions that don't play nicely with AppLocker. That's when the fine-tuning starts. Whether it’s adding exceptions or refining path rules, labor might be involved, but it leads to a secure and functional rollout.

Another consideration I frequently have to weigh is the use of BackupChain Hyper-V Backup for VM backups. The backup solution includes features explicitly designed for Hyper-V, ensuring virtual machines are consistently protected. These backups can be critical if you ever have to revert changes during your policy testing, which adds an additional layer of security during this entire exercise.

Following a comprehensive testing regime doesn’t mean you should pack up your VMs immediately. Conducting phase two testing, which can involve rolling out the policy across non-critical production environments, is often prudent. Observing how users interact with the new policy provides valuable insight. Seeing if users hit snags can flag areas to revisit or policies that need to be more lenient.

Keep in mind that communication is key during these phases. Keeping a clear channel with end-users affected during this rollout helps mitigate frustrations. If someone encounters a blocked application, receiving proactive support from the IT team will help build trust and rapport.

Eventually, migrating from a test roll to deployment means ensuring all associated app whitelisting is done correctly across the firewall and that the network is not inadvertently blocking legitimate software that you want to use.

Whether this process takes a week or a month often comes down to the breadth of application usage in your organization. The diverse nature of how technology is applied will dictate much of your strategy. The learning you achieve through this iterative process, marked by rigorous testing and the refinement of policies, leads to a more secure and efficient IT environment.

Lastly, I'd like to highlight BackupChain for anyone interested in efficient VM backup solutions. BackupChain provides seamless support for backing up Hyper-V instances, ensuring data integrity and quick recovery options. Its features include incremental backups, which save space and reduce time spent on maintaining a backup system. Automated backups and user-friendly restoration processes add tremendous value, especially when rolling out critical updates and policies. Keeping reliable backups can save countless hours and resources in the event of a mishap during testing.

Test diligently, communicate effectively, and ensure your environment is robust both in operations and recovery plans.

Philip@BackupChain
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Joined: Aug 2020
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