Why Pentesting Still Matters (and Now More Than Ever)
- Anup Ghosh
- Aug 7
- 3 min read
Cybersecurity is no longer a nice-to-have for MSPs, it’s mission-critical for yourself and your clients. As threat actors grow more sophisticated and SMB clients face increasing pressure to meet compliance and cyber insurance requirements, one security discipline has stood the test of time: penetration testing.
But not all pentests are created equal, and the way MSPs deliver this service is rapidly evolving. Let’s take a step back and understand the origins of pentesting, why it still matters today, and how it’s changing to meet the modern threat landscape.
The Origins of Pentesting: A Human-Driven Craft
Penetration testing has its roots in the 1960s and 70s, when early security professionals, many from military or government backgrounds, attempted to simulate how real-world attackers might compromise a system. These early efforts were manual, time-consuming, and the quality depended on the skill of the particular team doing the testing.
Over the years, human-led pentesting evolved into a specialized discipline. Skilled practitioners used a combination of tools, scripting, and intuition to:
Identify weaknesses in networks, applications, and endpoints
Attempt to exploit those weaknesses to prove their impact
Deliver detailed reports with recommendations for remediation
This process remains valuable today. But for MSPs, traditional pentesting often presents a series of challenges.
The Problem with Traditional Pentesting
While manual pentesting provides deep insight, it comes with trade-offs:
High Cost: A single manual pentest can cost thousands (or tens of thousands) of dollars.
Inconsistent Quality: The outcome depends on the skill, methodology, and diligence of the human tester.
Limited Scope: Human time is finite—tests are often narrow in scope and only represent a snapshot in time. Usually it is a capture-the-flag exercise vs a comprehensive assessment.
Low Frequency: Most organizations only conduct tests annually or for compliance, leaving long windows of exposure.
For MSPs, this model is difficult to scale across multiple clients and often leads to missed revenue opportunities or weak security coverage.
Why Pentesting Is More Relevant Than Ever
Despite its limitations, the concept of pentesting—simulating real attacks to validate defenses—is more vital now than ever before. Here’s why:
Attackers Don’t Wait: Real-world threats evolve daily; defenses must be tested continuously.
Compliance Requirements: Frameworks like SOC 2, PCI-DSS, HIPAA, and others increasingly mandate regular testing.
Client Expectations: SMBs now demand proof that their IT provider is taking proactive steps to secure their environment.
Insurance and Legal Exposure: A failure to validate security posture can lead to denial of cyber insurance claims or legal liability.
Pentesting is not just a checkbox exercise—it’s a core validation layer in a defense-in-depth strategy.
The Shift Toward Continuous, Automated Pentesting
The answer for MSPs isn’t to abandon pentesting—it’s to modernize how it’s delivered. By adopting automated pentesting solutions, MSPs can:
Perform assessments more frequently without breaking the bank
Deliver standardized and repeatable results across clients
Discover and validate vulnerabilities in real time
Differentiate themselves from competitors still offering one-and-done scans
This doesn’t replace human-led pentests, but it allows MSPs to offer ongoing offensive testing as part of a managed service.
Coming Up Next: How Automated Pentesting Changes the Game
In our next post, we’ll explore how automated pentesting tools work, how they compare to traditional vulnerability scanners, and how MSPs can operationalize them to better serve their clients.
Pentesting isn’t going away—it’s evolving. And MSPs that embrace this shift will be better positioned to protect their clients, prove their value, and grow their business.
To learn how you can adopt automated pentesting in your business, contact ThreatMate below.