Penetration Testing vs. Configuration Assessment

When it comes to assessing your company's security posture, the options can seem overwhelming.

Many organizations have heard of penetration testing and assume it's the only way to find weaknesses. While a pen test is a valuable service, it's not always the right first step for organizations looking to security their digital home. Sometimes, a configuration assessment offers a more direct and valuable path to securing your environment. 

So, when should you use one over the other? 

Penetration Testing: The "Black Box" Approach 

A pen test is like a simulated attack. An ethical hacker, with varying levels of information about your network, attempts to exploit vulnerabilities to gain access to your systems. The goal is to see if a determined attacker can get in and, if so, how far they can get. Pen testing is often driven by compliance requirements for insurance, legal, or contractual reasons. 

When a Pen Test is the Right Choice: 

• You have publicly exposed services: If your business has web applications, APIs, or other services exposed to the internet, a pen test can help discover vulnerabilities an attacker could exploit from the outside. 

• You don't know what you don't know: For large, complex, or rapidly changing environments, a pen test can be a useful tool to discover rogue services or forgotten systems that might be vulnerable. 

• You have a specific, high-value target: If you're a large company with a unique, custom-built application, a targeted pen test can ensure it's robust and secure. 

Configuration Assessment: The "Inside-Out" Approach 

A configuration assessment is like an internal audit. Instead of trying to break in, the security professional gets an inside look at your systems and their settings. The goal is to identify misconfigurations, unpatched systems, or overly open security settings that have been improperly configured, disabled or just drift over time from what you had initially setup. This is often where you find the "accidental" vulnerabilities, like a firewall rule that was temporarily opened for a vendor and then forgotten, or a patch that inadvertently undid a critical security setting (I can no longer count how many times I have run into this one). 

When a Configuration Assessment is the Right Choice: 

• You have key cloud tenants: Cloud environments like Office 365, Azure, or Google Workspace have an almost infinite number of configuration options. An assessment can ensure your security settings are properly configured and aligned with best practices. 

• Your team is overwhelmed: When IT and security teams are focused on day-to-day firefighting, they may not have the time to stop and evaluate how their environment is configured. A configuration assessment provides a fresh, expert perspective. 

• You've had staff turnover: If there have been a lot of changes in your IT or security team, a configuration assessment can help you understand exactly how your systems are set up and if there are any settings that need to be revisited. 

Making the Right Choice 

While a pen test can provide a "shiny" report on what an attacker could do, a configuration assessment delivers a more practical and prescriptive list of actions to improve your security posture. It's often easier and more cost-effective to fix an internal misconfiguration than to hire a team to find a novel external exploit. 

For many organizations, the best approach is to start with a configuration assessment to get your "house in order." This ensures your foundational security controls are working as they should be. From there, you can layer on a targeted pen test to confirm that your external defenses are just as solid.  

Ultimately, both penetration tests and configuration assessments play a vital role in a comprehensive security strategy. Understanding their distinct purposes is key to making a smart investment for your company.