Stop doing penetration testing the old way

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Penetration testing used to be a once-a-year checkbox. Teams would bring in external consultants, run point-in-time assessments, and hope the final report demonstrated enough security maturity for their auditors. But this legacy approach is no longer enough. Frameworks like PCI DSS, FedRAMP, and NIST SP 800-53 demand clearer testing methodologies, more consistent remediation, and proof that your defenses work—year-round.

Why it matters: Penetration testing isn’t just a technical exercise. It’s a critical part of maintaining trust, reducing risk, and staying compliant. To meet evolving expectations and minimize business disruption, you need a better approach.

How penetration testing has traditionally worked

For years, penetration testing followed a predictable lifecycle: scope and plan, conduct the test, produce a report, and move on. Every step was manual, segmented, and often disconnected from real compliance timelines.

Penetration testers typically mimicked real-world attacks to identify how someone could exploit weaknesses in your environment. According to NIST SP 800-115, these tests involve reconnaissance, threat modeling, exploitation attempts, and analysis of your detection and response capabilities. Done correctly, they yield valuable insight into exploitable risks—but they’re labor-intensive and high-stakes.

Scheduling challenges. Coordinating downtime or isolating test environments required extensive back-and-forth. Getting safe windows approved by operations often delayed the test itself.

Evidence gaps. Even though most compliance frameworks don’t spell out how a penetration test must be documented, auditors expected clear scoping, rule-of-engagement definitions, and evidence of both testing methodology and retesting efforts.

Lack of integration. Traditional penetration testing usually lives outside your compliance platform. That makes it difficult to connect test findings to your risk register, remediation tickets, or framework-specific control mappings, prolonging evidence prep for audits.

The growing complexity of modern frameworks

Today’s compliance environment demands more than an annual report. Frameworks have grown stricter about cadence, tester qualifications, and what counts as completed testing.

PCI DSS v4.0 raises the bar. Starting March 31, 2025, organizations must show annual (or more frequent) penetration testing per updated testing procedures. This includes segmented environments for service providers and mandatory retests to prove remediation (Requirement 11.4.4). Any deviation or delay increases risk—not just to your systems, but potentially to your certification.

FedRAMP mandates independent third-party testing. Only accredited 3PAOs (Third Party Assessment Organizations) may perform accepted penetration tests. They must meet formal standards for team qualifications, such as having designated roles (guru-level testers, senior assessors, junior assessors) and documented experience.

NIST wants repeatable, risk-based testing. NIST SP 800-53, Control CA-8, calls for regular penetration testing as part of a broader assurance strategy, with optional red-team enhancements. While this applies mostly to federal systems, private-sector organizations leveraging NIST-CSF often follow suit.

SOC 2 may not require it—but your auditor likely does. Although SOC 2 doesn’t prescribe penetration testing, it’s often expected as supplemental evidence under the Security Trust Service Criteria. Failing to conduct one can result in a qualified opinion.

Common challenges in penetration testing

Done improperly, penetration testing wastes time, introduces unnecessary risk, or worse—creates a false sense of security. Common issues are avoidable but widespread.

Poor scoping undermines effectiveness. Incomplete asset lists or ambiguous rules of engagement mean critical systems can be missed or improperly tested. Unsafe parameters might even bring down your production systems.

Overuse of automation. Scans are not tests. Running vulnerability scanners without human interpretation leads to noisy reports filled with false positives. Worse, it ignores your detection and response capabilities—key evidence in serious frameworks like FedRAMP.

Unqualified testers create audit friction. Frameworks like FedRAMP and PCI DSS require documented independence and competency. Using in-house teams without proof of appropriate certifications or independence can delay compliance or force a retest.

Skipping the retest breaks compliance. It’s not enough to fix a finding. PCI DSS requires proof that exploitable vulnerabilities have been remediated and retested. Delivering only the initial report is no longer sufficient.

What penetration testing looks like in 2026

Penetration testing is shifting from static annual exercises to integrated, agile, and compliance-aligned workflows. Organizations are adopting platforms and methodologies that reflect new realities—continuous change, distributed systems, and multi-framework compliance.

Tests are integrated into platform workflows. In 2026, the idea that testing happens outside your compliance tool is obsolete. Instead, organizations expect penetration testing outputs to feed directly into compliance platforms, risk management dashboards, and auditor workspaces.

Qualified testing with traceable credentials. Testers will need to meet organization-specific and framework-mandated credentials. Expect automatic validation of certifications like CREST CRT, OffSec’s OSCP, or GIAC’s GPEN, including proof of independence and role mapping.

Clear linkage to evidence and follow-up. Every test needs to be mapped not just to a security finding—but to a control, a piece of auditor-visible evidence, and a remediation plan. Tests without follow-through will no longer satisfy compliance.

Always-on readiness. Regulators and auditors expect rapid evidence access, updated risk postures, and connections between test findings, incident response, and control status. That means tests must be timely, traceable, and tied to real business units.

How Thoropass simplifies and improves penetration testing

At Thoropass, we believe penetration testing should improve your security outcomes and simplify your compliance program—not add friction.

Integrated testing from a CREST-accredited team. Thoropass provides CREST-validated penetration testing through a documented six-step methodology. Our team handles scoping, safe testing, exploitation attempts, evidence production, remediation support, and formal retesting—all inside the same platform used to manage your audit readiness.

Built-in compliance alignment. Test results don’t sit in PDFs. We map findings directly to your control framework, including PCI DSS v4.0, FedRAMP, and SOC 2 Security criteria. That makes remediation clear and ensures you can demonstrate compliance with requirements like PCI DSS 11.4.4 or FedRAMP CA-8.

Retesting and evidence updates in one place. Once you resolve a vulnerability, we schedule and execute the retest, collecting traceable evidence and updating auditors in the same environment. No separate platform, no lost documents, and no missed deadlines.

Backed by platform automation and audit-grade workflows. Thoropass connects with over 100 systems to automate evidence collection, monitor controls across frameworks, and track your compliance status in real time. Your test activities feed directly into this loop—giving you a real-world view of both risk and readiness.

Team and tester qualifications you can trust. Our penetration testers not only hold certifications such as OSCP and GPEN, but also work in a structure that ensures organizational independence when frameworks demand it. And because we’re also a PCI QSAC and peer-reviewed CPA firm, we align our testing and attestation work to avoid conflicts of interest.

The future is integrated, agile, and audit-aligned

Legacy penetration testing no longer meets the needs of modern security and compliance teams. Between rising regulatory standards, tighter frameworks, and more complex environments, outdated methods just don’t deliver reliable outcomes—or acceptable audit evidence.

Thoropass transforms penetration testing by embedding it within your compliance platform, aligning it with your frameworks, and delivering it through trusted, accredited professionals. You’ll spend less time coordinating across tools and more time improving your security posture.

Schedule a discovery session today to see how integrated, audit-aligned penetration testing can simplify your security compliance journey.