Pen Test for Compliance: What NYDFS, SOC 2, and HIPAA Auditors Want to See

What makes a pen test report worth handing over to your auditor is the depth of the test underneath it. NopSec Adversarial Simulation was built to deliver that depth — the same five-phase methodology our team has run for eighteen years, executed on a different model and at a different cadence. Here is what that looks like in practice.

What an Adversarial Simulation test actually contains

Every Adversarial Simulation engagement follows the same five-phase methodology our pen testing team has refined over eighteen years of manual engagements: reconnaissance, vulnerability enumeration, exploitation, privilege escalation, and report generation.

Each phase feeds the next. Reconnaissance maps your external surface and prioritizes targets. Enumeration confirms what is actually present and exploitable. Exploitation is the real thing — agents attempt to compromise confirmed vulnerabilities, not just catalog them. When an off-the-shelf exploit does not exist, the system writes a proof-of-concept on the fly and tests it. If a path fails, it pivots and tries another route. Privilege escalation chains findings the way an attacker would chain them, looking for the systemic weaknesses that no single CVE captures.

The deliverable is a formal pen test report. Documented scope, methodology, findings with severity ratings, exploitation paths showing what a real attacker would actually do in your environment, remediation guidance per finding, and a complete attack log an auditor can trace end to end. Not a scanner export. Not an aggregated dashboard. The same kind of report a senior tester would produce after a manual engagement, generated faster and on the cadence your environment actually changes.

Human in the loop oversight runs through every engagement. Scope confirmation, exploitation approval, finding validation, and report sign-off all flow through a human reviewer before anything reaches you. When the auditor asks who decided that a finding was a false positive, or who approved the scope, the answer is a person, not a model.

Translate our offensive security expertise and craftsmanship into AI agents

NopSec has been doing penetration testing for eighteen years. CTO Michelangelo Sidagni and Head of Security Research Shawn Evans have spent careers performing pen tests and red team engagements. The methodology embedded in Adversarial Simulation is not a category we entered. It is the category we have been operating in since the company was founded, with a methodology refined across manual engagements against live environments, against real adversaries, against the same kinds of attack surface our customers are defending today.

That same offensive DNA is now engineered into purpose-built agents that follow the methodology our team taught them, under the oversight of the same humans who taught it.

Why we built Adversarial Simulation

The traditional pen testing model has not meaningfully changed in twenty years. Senior testers are scarce. Engagements are scoped, scheduled months out, run for a week or two, and delivered as a polished report. That model produces excellent annual results. It does not match how environments change.

Our team kept seeing the same pattern in customer conversations. The annual engagement was good work. The eleven months that followed were unvalidated. New deployments, new integrations, new acquisitions, new exposure — none of it captured in the report on file. Most teams could not afford a second engagement, and out-of-cycle validation after a major change was almost never budgeted at all.

Adversarial Simulation is what we built to fill those eleven months. Same methodology, same human oversight, different delivery model. Pen-test-grade results, on the cadence your environment actually demands.

What the regulations expect

You already know the frameworks. NYDFS Part 500 requires annual internal and external penetration testing, vulnerability assessments tied to your risk assessment, and as of November 2025, certified asset inventory and universal multifactor authentication.¹² SOC 2 expects the testing function to operate consistently across the audit window, with findings triaged on a defined cadence and remediation owners assigned and tracked. HIPAA Section 164.308(a)(8) ties the evaluation requirement to environmental and operational changes, not to a calendar.³

The frameworks reach the same destination by different paths: it is not enough to run a test. You need to run a program. The output of an Adversarial Simulation engagement is structured to slot directly into the evidence packages auditors are asking for under any of these frameworks.⁴

Early access

Adversarial Simulation is available at $2,999 per test through the Pentest Starter tier. Early access begins May 19 for the first 100 customers for 30 days.

That price reflects what audit-grade external validation costs when eighteen years of pen testing methodology is engineered into automation and human oversight is built into the workflow rather than billed by the hour. It does not reflect a compromise on what the test contains. We held the line on rigor and engineered the economics around it.

What to do next

Your next NYDFS, SOC 2, or HIPAA exam is going to ask for evidence that your testing program is operating, not just that a test was run. NopSec Adversarial Simulation produces that evidence at $2,999 per test. Early access list coming soon!

Sources

1. New York Codes, Rules and Regulations, Title 23, Part 500, Sections 500.5 (Vulnerability Management) and 500.9 (Risk Assessment). ↩
2. NopSec, “Ideal Customer Profile v2.0.” Documents the November 2025 NYDFS amendments adding universal multifactor authentication and certified asset inventory requirements. ↩
3. United States Department of Health and Human Services, HIPAA Security Rule, 45 CFR § 164.308(a)(8) (Administrative Safeguards — Evaluation). ↩
4. NopSec, “Adversarial Simulation Marketing Plan v3,” Message Pillar D: Compliance-friendly evidence. ↩