Which One Makes Sense for You?
If you’re responsible for cybersecurity decisions, you’ve probably wrestled with this question: which type of security testing actually tells you something useful?
With ransomware attacks continuing to rise and hackers getting more sophisticated, running annual vulnerability scans doesn’t feel adequate anymore. Boards are asking harder questions about security ROI. You need to know where you truly stand against real threats.
That’s where penetration testing, red teaming, and purple teaming come in. The security industry sometimes uses these terms interchangeably. And honestly, the marketing materials doesn’t help clarify things either. But they’re not the same. Each serves different purposes and picking the wrong one can waste budget or miss critical gaps.
Let me break down what each actually does and when you might choose one over another.
Penetration Testing: Catching the Obvious (and Not-So-Obvious) Weak Spots
Penetration testing is controlled, authorised security evaluation. Think of it as your baseline technical health check, but more thorough than automated scanning.
The focus is straightforward: teams find and exploit vulnerabilities in your systems, applications, and network. We’re talking about missing patches, misconfigurations, weak authentication, and SQL injection flaws. The technical weaknesses that keep appearing in breach reports.
The scope is typically defined and bounded. You might test a specific application, network segment, or set of systems. You get a list of what’s vulnerable, how it was exploited, and what to do about it. It’s structured and efficient.
What penetration testing doesn’t test is how well your team detects threats or responds to incidents. I think of it as mapping your technical risk rather than testing your operational readiness. Which is fine. That’s what it’s designed for.
Best for: Organisations building or validating foundational security controls, meeting compliance requirements, or running regular assurance checks.
Red Teaming: Testing More Than Just Your Tech
Red teaming takes a completely different approach. Instead of hunting for individual vulnerabilities, red teams try to achieve specific objectives by whatever means necessary.
This is where your organisation gets tested like it would be in a real attack. The red team acts like a determined adversary, using techniques like phishing emails, social engineering calls, lateral movement, even physical access (if allowed) to see how far they can go undetected.
A red team might spend weeks building their attack, just like real adversaries do. They’ll research your employees on LinkedIn, craft convincing phishing campaigns, establish footholds in your network, and try to access sensitive data. All while your security team operates normally, unaware they’re being tested.
This approach reveals things penetration testing misses. How quickly does your SOC spot unusual activity? Do your incident response procedures actually work when people are stressed? Are there blind spots in your monitoring that attackers could exploit?
Best for: Organisations with mature security programs that want to validate their detection and incident response capabilities under pressure.
Purple Teaming: Learning While Fighting
Purple teaming brings the red team and your defenders into the same room–sometimes literally.
Instead of waiting for a final report, your defensive team gets immediate feedback. When the red team finds a way past your controls, they explain their methods right away. Your blue team can adjust their detection rules and test them immediately.
This collaborative approach speeds up learning. Rather than playing “gotcha” games, both teams focus on improving your actual security posture. Your defenders learn new attack techniques. Your red team understands why certain defenses exist.
The downside? It requires more coordination and, frankly, maturity from both sides. Your teams need to check their egos and work together openly, which isn’t always easy.
Best for: Teams looking to build in-house skills, mature their security operations, or close detection and response gaps quickly.
Which One Should You Choose?
Here’s how I usually think about it:
Start with penetration testing if:
- You’re early in your security program
- You need to meet compliance requirements
- You want a cost-effective way to identify technical weaknesses
- You need to validate that recent fixes actually work
Move to red teaming when:
- Your basic security controls are reasonably mature
- You want to test your incident response capabilities
- You need to understand real-world attack paths
- Executive leadership wants insight into actual security resilience
Consider purple teaming if:
- You’re committed to continuous security improvement
- You have both offensive and defensive capabilities internally
- You want to accelerate learning for both teams
- You’re running ongoing security programs rather than one-off assessments
I think many organisations benefit from using different approaches at different times. You might start with penetration testing to address obvious gaps, then move to red teaming once your defenses mature, and incorporate purple teaming as part of your ongoing improvement process.
The key is matching the testing approach to your current security maturity and specific goals. A penetration test won’t tell you much about your incident response capabilities, but a red team engagement might be overkill if you haven’t addressed basic vulnerabilities yet.
Making the Right Choice for Your Organisation
What I find most helpful is asking yourself what you actually want to learn. Are you trying to find technical vulnerabilities? Test your team’s response skills? Build internal capabilities through collaborative learning?
Your answer should guide your choice. And remember, this doesn’t have to be a one-time decision. As your security program matures, your testing needs will change too.
Perhaps the most important thing is that you’re testing something beyond automated scans and checklists. Whether you choose penetration testing, red teaming, or purple teaming, you’re taking steps toward understanding how your organisation performs against real threats.
The organisations that get this right usually start with one approach and evolve their testing strategy as their security program matures. They can answer board questions about ROI because they understand what they’re actually testing and why.
Let’s match your goals with the right test.
Whether you’re building your first security program or stress-testing a mature environment, choosing the right assessment method matters. If you’re unsure where to begin or just want a second opinion, we’re here to help choose the right testing method.