23 NYCRR 500 is one of the few US regulations that names penetration testing directly in its text: §500.05 requires covered entities to conduct penetration testing annually, or implement continuous monitoring as an alternative, plus biannual vulnerability assessments — requirements the 2023 amendments reinforced alongside stronger MFA and governance obligations.
We deliver testing scoped and timed to satisfy that requirement, and reported to support your CISO's annual certification to the Superintendent.
We test your information systems on the cadence §500.05 specifies — annual penetration testing, or a continuous monitoring alternative — paired with biannual vulnerability assessment evidence, and format the output to slot directly into your CISO's annual compliance certification.
Why it matters
NYDFS covers banks, insurers and other financial services entities licensed in New York, and non-compliance has led to real, public enforcement penalties. The annual certification requires your CISO to personally attest to compliance — not something you want resting on undocumented or out-of-date testing.
What we test
- Information systems penetration testing (§500.05 annual requirement)
- Biannual vulnerability assessment
- Multi-factor authentication implementation testing
- Access privilege & governance review
- Incident response plan validation
- CISO annual certification evidence package
Common vulnerabilities we uncover
- No documented annual penetration test satisfying §500.05
- Missing biannual vulnerability assessment evidence
- MFA gaps against the 2023 amendment requirements
- Excessive or unreviewed access privileges
- An untested incident response plan
- Insufficient evidence for the CISO's annual certification
Our methodology
- Scoping & rules of engagement. We agree objectives, targets and boundaries for your nydfs cybersecurity regulation penetration testing, so testing is safe, authorized and focused on what matters to your business.
- Reconnaissance & mapping. We enumerate the full attack surface in scope, building a complete picture before any exploitation begins.
- Manual exploitation. Our senior testers chain vulnerabilities by hand — going far beyond automated scanners — to prove real, demonstrable impact.
- Analysis & reporting. Every finding is triaged, risk-rated with CVSS and written up with a copy-paste reproduction and clear remediation.
- Remediation support & free retest. We support your team through the fixes and retest the remediated issues to confirm they are genuinely closed.
Tools & techniques
We scope penetration testing to your information systems under §500.05, delivered on the annual or continuous-monitoring cadence the regulation specifies, alongside biannual vulnerability assessment evidence and a review of MFA implementation and access governance following the 2023 amendments.
When you need this engagement
- You are a bank, insurer or financial services entity licensed by NYDFS
- Your annual §500.05 penetration testing is due or overdue
- You need vulnerability assessment evidence for your CISO's certification
- You are implementing continuous monitoring as an alternative to annual testing
- You have had a prior incident and need to demonstrate remediation
What you receive
- Penetration test report satisfying §500.05
- Biannual vulnerability assessment documentation
- MFA & access-governance findings
- Incident response readiness validation
- CISO certification evidence package
- Free retest after remediation
What’s included in your report
Every nydfs cybersecurity regulation penetration testing engagement concludes with a comprehensive, board-ready report and a working session to walk your team through it. Your report includes:
- An executive summary with overall risk posture for non-technical stakeholders
- Detailed technical findings, each with a step-by-step, copy-paste reproduction
- CVSS v3.1 severity ratings and business-impact context for every issue
- Prioritized, actionable remediation guidance your engineers can apply directly
- A complimentary retest to confirm fixes and update finding status
- A formal attestation letter for customers, auditors and compliance programs
Standards & frameworks
NYDFS Cybersecurity Regulation (23 NYCRR 500)
2023 Amendment
Outcomes you can expect
After your nydfs cybersecurity regulation penetration testing, you will have clear, evidence-based visibility into your real security risk — not a scanner’s guesswork. You will know exactly which weaknesses an attacker could exploit, what the business impact would be, and the precise steps to fix them in priority order. Teams use our findings to close critical gaps, satisfy customer and regulator security requirements, and demonstrate due diligence to their board. With a complimentary retest included, you also get documented proof that the issues are genuinely resolved.
Engagement details & logistics
Every nydfs cybersecurity regulation penetration testing starts with a short, no-obligation scoping call to understand your goals, environment and constraints, followed by a fixed-price proposal and a clear statement of work. Most engagements are delivered fully remotely, with on-site work arranged where it genuinely adds value. Throughout testing we maintain an agreed communication cadence and escalate any critical, high-impact finding to you immediately rather than waiting for the final report. All work is performed under a signed NDA with strict data-handling controls, using safe, non-disruptive techniques and carefully coordinated rules of engagement to protect your production systems. On completion you receive your report and a walkthrough session, followed by a complimentary retest once your fixes are in place. Typical engagements are booked one to three weeks in advance, and urgent or pre-deadline testing can often be accommodated — just ask at hi@agentoffense.com.
Why organizations choose AgentOffense
Our nydfs cybersecurity regulation penetration testing is delivered by senior offensive-security engineers who test the way real attackers do — manually, creatively and with a relentless focus on proving genuine, demonstrable impact. Here is what sets our engagements apart:
- Manual, exploit-driven testing that chains vulnerabilities the way a real attacker would, going far beyond what automated scanners can find.
- Reproducible proof for every finding, with copy-paste reproduction steps your engineers can follow and independently verify.
- Honest severity calibration so you invest in fixing what genuinely matters and avoid wasting effort on false positives and noise.
- Clear, business-focused reporting that speaks to engineers and executives alike, tying every issue to real-world impact.
- A complimentary retest included, so you get documented proof that your fixes actually close the attack path.
- Responsible, collaborative delivery with a named point of contact and secure handling of all data throughout the engagement.
Explore related services
NYDFS Cybersecurity Regulation Penetration Testing is frequently scoped alongside our other offensive-security services for broader coverage. Explore related engagements that complement it:
How much does NYDFS Cybersecurity Regulation Penetration Testing cost?
Every nydfs cybersecurity regulation penetration testing is scoped and priced individually, so you pay for exactly the coverage you need — with no hidden extras. After a short, no-obligation scoping call we send a fixed-price quote, usually within one business day, with clear deliverables, a firm timeline and a complimentary retest included. The price of your nydfs cybersecurity regulation penetration testing depends on the size and complexity of the target and the depth of testing required, so you always know the cost up front before any work begins.
Get a fixed-price quote
Frequently asked questions
Does NYDFS actually require penetration testing?
Yes — unlike many US frameworks, 23 NYCRR 500 explicitly names penetration testing in §500.05, requiring it annually, or continuous monitoring as an alternative, plus biannual vulnerability assessments.
Who is a "covered entity" under NYDFS?
Banks, insurance companies and other financial services institutions operating under a license, registration or charter from the New York Department of Financial Services.
What changed in the 2023 amendment?
The amendment strengthened MFA requirements, added governance obligations, and increased scrutiny on the annual certification your CISO must personally sign.
Can continuous monitoring replace annual testing?
Yes, the regulation allows continuous monitoring as an alternative to annual penetration testing — we can help you determine and evidence whichever approach fits your environment.