A Practical Guide to Planning Your Next Penetration Test in 2025

Jan 16, 2025 • 3 min read

Planning a penetration test can feel like a massive headache, especially if you're not doing them regularly. After years of running pentests for organizations of all sizes, we've learned that half the battle is just figuring out where to start. So let's cut through the complexity and talk about what really matters.

The Cost of Penetration Testing

If you're new to pentesting, you might be surprised by the wide array of prices out there. If you're paying just a few hundred dollars, you're likely getting an automated scan with minimal human interaction – which isn't really a pentest at all.

Here's the truth about pentest costs – you're basically paying for two things: how good your testers are and how long they spend poking at your systems. While unlimited red-teaming would be nice (and hey, if you've got the budget, go for it), most teams need to be more strategic with their resources.

Get the Easy Stuff Out of the Way

Before you bring in the heavy hitters, run some basic scans. Use an External Attack Surface Management (EASM) tool to map out what you're actually working with. Use vulnerability scanning software to identify the issues that automation can easily find. You don't want to pay a skilled pentester hundreds of dollars an hour to find issues that an automated scanner could have caught.

Focus on What Matters Most

When planning your scope, prioritize what's most important to your business. Start with sensitive data. Focus first on systems storing or processing critical information. If you're testing for compliance (like PCI DSS), this naturally centers on regulated data. You'll also want to address business logic risks. Walk testers through your applications to explain unique workflows and potential risks. Understanding how your business operates helps identify vulnerabilities that matter most.

We've seen too many organizations waste time testing low-risk systems while leaving their crown jewels exposed. If you're handling credit card data, start there. Got intellectual property that keeps your CEO up at night? Prioritize those systems. Sometimes compliance requirements make this decision for you, but either way, protect the important stuff first.

Nearly every organization has that one bizarre legacy system or custom application that nobody quite understands anymore. These are gold mines for security issues because they're often built with business logic that automated tools can't understand. Walk us through how they work – weird edge cases and all.

Talk to Your Testers

Share what you already know about your environment. Found some weird stuff in your initial scans? Tell us about it. It helps focus the testing where it matters, and makes your budget go further.

Here's something most people don't realize: good pentesters aren't trying to make you look bad. We're on your side, trying to help you improve security before the adversaries can find the holes. The best results come when you:

Tell us about your environment (even the embarrassing parts)
Share what keeps you up at night security-wise
Point us toward the risky stuff first
Ask questions when our reports don't make sense to you

Don't Be Intimidated

At Halo Security, we believe penetration testing should be a collaborative experience, not a stressful one. Our friendly team of security experts guides you through every step of the process, from planning to final recommendations. We speak in plain English (not security jargon), answer all your questions, and focus on finding real security issues that matter to your business.