How Automated Pentesting Changes the Game

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In our last post, we explored why pentesting still matters, tracing its history from human-led pentesting to the challenges of cost, consistency, and limited frequency.

Now it's time to look at the next chapter — automated pentesting — and why it’s becoming the go-to approach for MSPs looking to scale their security offerings and ensure the clients they take on are not introducing risk to themselves.

From Vulnerability Scanners to Automated Pentests

Before we dive into automated pentesting, let’s clear up a common misconception: Pentesting is not the same as vulnerability scanning.

Vulnerability scanners (like Nessus, OpenVAS, Tenable, or Qualys) are designed to find known weaknesses—misconfigurations, outdated software, missing patches.

They are fast and useful, but they stop short of proving exploitability.

Automated pentesting tools, on the other hand, take things a step further:

• They simulate real-world attacks

• Attempt to exploit vulnerabilities in a safe, controlled manner

• Chain multiple weaknesses together to mimic how attackers pivot inside a network

• Deliver prioritized findings that reflect actual business risk

  
  

In short: scanning tells you what might be wrong; automated pentesting shows you what an attacker could actually do and the resulting impact.

Why Automated Pentesting Works for MSPs

MSPs face a tricky balance—clients expect robust security, but margins and staffing realities mean you can’t have a human pentester on every account. Automated pentesting changes the equation.

Key advantages:

1. Frequency Without Fatigue Run tests quarterly, monthly, or even weekly without burning out your security team.

2. Consistency Across Clients The same methodology, every time, ensures comparable results and eliminates the “human variability” factor.

3. Scalable Service Delivery Whether you have 10 clients or 200, automated pentesting scales with your customer base.

4. Actionable Prioritization Many pentesting platforms including ThreatMate integrate EPSS (Exploit Prediction Scoring System) and CVSS to sort findings by actual exploit likelihood, helping you focus on the most dangerous issues first.

   
   

How Automated Pentesting Works (Under the Hood)

While features vary by platform, the core workflow generally includes:

1. Reconnaissance Mapping assets, services, and potential entry points.

2. Vulnerability Discovery Identifying misconfigurations, outdated software, and exposed services.

3. Exploitation Simulation Safely testing whether vulnerabilities can be exploited—and how far an attacker could go.

4. Lateral Movement & Privilege Escalation Attempting to move deeper into the network, chaining multiple vulnerabilities together.

5. Reporting & Remediation Guidance Delivering clear, prioritized reports your team can act on immediately.

   
   

Operationalizing Automated Pentesting for MSPs

Here’s how forward-thinking MSPs are integrating automated pentesting into their offerings:

• Prospecting Run a pentest on prospects to build out a cybersecurity risk assessment. This is a strong way to differentiate yourself, while also learning earyl what you are getting in to.

• Quarterly or Monthly Security Reviews Provide clients with fresh, data-backed proof of their current security posture.

• Incident Response Readiness Simulate attacks to validate defenses after a breach or major system change.

• Compliance Support Use results to satisfy PCI-DSS, HIPAA, SOC 2, and other framework requirements.

  
  

The Business Case

Automated pentesting isn’t just a technical upgrade—it’s a business growth engine.

MSPs offering it can:

• Justify premium security packages

• Increase client retention by proving ongoing value

• Create upsell opportunities with remediation and consulting services

  
  

Next Up: The Pentesting Toolbox

In our next post, we’ll break down the essential tools—open-source and commercial—that security teams use during pentests, from reconnaissance to reporting. You’ll see how these tools fit into both manual and automated workflows.

Pentesting isn’t going away—it’s becoming faster, smarter, and more scalable. MSPs that embrace automation now will be the ones leading the market tomorrow.