In 2025, financial services and fintech firms face strict regulations and advanced cyber threats. Compliance-only pen testing isn’t enough—continuous, strategic testing that targets real-world risks (cloud, APIs, vendors) is essential. The article explains the new regulatory landscape, modern attack vectors, and offers a roadmap for building a business-aligned pen testing program that protects assets, satisfies auditors, and builds trust.
With the average cost of a data breach in the financial sector soaring to $6.08 million[1]—a figure 22% higher than the global average—proactive defense is no longer a discretionary expense; it is a core business necessity. Penetration testing, the practice of simulating real-world cyberattacks to find and fix weaknesses before adversaries can, has evolved from a technical compliance check into a strategic imperative for protecting data, ensuring operational resilience, and maintaining market credibility.
In 2025, this matters more than ever due to a convergence of powerful forces:
- Tighter Regulations: Frameworks like the EU’s Digital Operational Resilience Act (DORA) and the amended Gramm-Leach-Bliley Act (GLBA) now require advanced, “threat-led penetration testing,”[2] moving far beyond simple compliance checks and demanding proof of real-world resilience.
- Increasingly Sophisticated Threats: AI-powered attacks are scaling threat discovery and social engineering with unprecedented efficiency. Meanwhile, interconnected digital supply chains create systemic risk, with a recent report linking a staggering “41.8% of FinTech breaches directly to third-party vendors”[3].
- The Need for Continuous Assurance: The speed of modern threats and agile development cycles renders the traditional model of ad-hoc, annual testing obsolete. The new standard is a continuous, integrated approach to security validation.
This guide moves past basic compliance to provide a strategic roadmap for senior leadership. It demonstrates how to build a risk-aligned penetration testing program that not only satisfies auditors but also protects your most critical assets and enables sustainable business growth.
The regulatory landscape in 2025
For financial services and FinTech firms, the 2025 regulatory environment mandates specific, rigorous security testing to ensure true operational resilience. Understanding these frameworks is the first step toward building a risk-aligned, compliant program that satisfies multiple authorities simultaneously.
Major frameworks
Framework | Applies To | Key Pen Testing Requirement |
PCI-DSS 4.0 | Entities handling cardholder data | Annual internal/external pen tests; quarterly vulnerability scans[4]. |
GLBA | US Financial Institutions (broadly defined) | Annual pen tests and biannual vulnerability assessments[5]. |
DORA / TIBER-EU | EU Financial Entities | Threat-Led Penetration Testing (TLPT) at least every 3 years[2]. |
GDPR | Entities processing EU data subject information | “Regularly testing, assessing and evaluating” security effectiveness[6]. |
Beyond compliance
Meeting regulatory mandates is the baseline, not the objective. A compliance-only mindset creates a dangerous illusion of security. As CISA Director Jen Easterly states, the goal should be to “shift away from focusing on individual vulnerabilities and to instead consider the issue from a strategic lens”[7]. This requires thinking like an adversary, not just an auditor.
An auditor verifies that a control exists; an adversary-focused test validates if it can withstand a real-world attack. This distinction is critical, as breaches initiated by “exploiting vulnerabilities surged by 180%”[7] in the last year. This reality is why regulators are evolving, with frameworks like DORA now mandating advanced “threat-led penetration testing” to ensure defenses are tested against realistic threat scenarios, not just compliance checklists.
Threat Landscape in 2025
The financial sector’s threat landscape is rapidly evolving, driven by sophisticated attack automation and deeply interconnected digital supply chains. A strategic penetration testing program must look beyond traditional vulnerabilities to address these emerging, high-impact risks.
AI‑Powered Attacks & Open Banking
Adversaries now leverage Artificial Intelligence to automate and scale attacks with alarming efficiency. Generative AI helps them craft sophisticated phishing and pretexting campaigns that bypass traditional human skepticism, directly weaponizing the “human element that is already implicated in 68% of all breaches”[7].
Simultaneously, the interconnected APIs essential for open banking and modern FinTech create a vast, shared attack surface that has become a prime target. A stunning 88.7% of financial services firms experienced an API-related security incident in the last year.[9] The scope of penetration testing must therefore expand beyond traditional applications to include rigorous API assessments and simulated social engineering campaigns that reflect these AI-driven threats.
Cloud & Supply-Chain Risks
While essential for business, cloud environments remain a critical risk area, with misconfigurations leading to the costliest types of breaches. The greater risk, however, often lies in the digital supply chain. For leading fintech companies, a staggering “41.8% of breaches originated from third-party vendors”[3]. This trend is accelerating, as third-party-related breaches overall “grew by 68% last year”[7].
- Hypothetical: A FinTech’s internal security is flawless, but its cloud-based analytics vendor uses a misconfigured S3 bucket. An attacker discovers the public bucket and downloads thousands of the brand’s customer records. The FinTech company is now liable for its vendor’s mistake, facing regulatory fines, customer churn, and severe reputational damage.
Your attack surface extends to every vendor you use. A strategic penetration test must validate these critical third-party and API integrations to manage this inherited risk.
Strategic vs. Compliance‑only Testing
Meeting regulatory mandates is the starting point for security, not the destination. A compliance-driven penetration test confirms that required controls are in place, but it often fails to answer the most critical question for a CEO or board member: “Are we actually secure against a real-world attack?”
Limitations of Compliance‑Only Pen Testing
The most dangerous assumption in cybersecurity is that compliance equals security. A compliance-only test often devolves into a “check-the-box” exercise. This approach is fundamentally flawed because you must think like an adversary, not an auditor.
An auditor verifies if a door has a lock; an adversary checks if the window is open, if the key is under the mat, or if they can talk an employee into letting them in. This distinction is critical, as it takes an average of “258 days for an organization to even identify and contain a data breach,”[1] proving that compliant systems are compromised daily without anyone noticing. A strategic test validates whether your defenses can withstand a creative, determined attack, not just pass a compliance check.
Defining Asset‑Specific Objectives
Business-prioritised testing is objective-driven. Instead of asking “Are we compliant?,” it asks “Can an attacker compromise our core payment API?” This requires a simple, repeatable framework that aligns testing with business risk.
A strategic testing lifecycle should follow these steps:
- Objectives: Define the business goal (e.g., “Secure our new mobile banking app before launch”).
- Threat Modeling: Identify the most likely attackers and their methods.
- Testing: Execute a tailored test to simulate those specific threats.
- Reporting: Translate technical findings into business risk and provide a clear remediation roadmap.
- Remediation: Fix the identified vulnerabilities.
- Retest: Validate that the fixes are effective.
Examples of objective-driven tests include:
- A pre-release API test to ensure a new product doesn’t introduce critical vulnerabilities.
- A cloud environment test focused on finding common misconfigurations that lead to data exposure.
- An AI system red team to assess the resilience of machine learning models against data poisoning or evasion attacks.
Testing Types & Advanced Approaches
To counter sophisticated threats, organizations must move beyond basic vulnerability scanning and embrace a spectrum of advanced testing methodologies. Each serves a distinct strategic purpose.
Traditional Penetration Testing
This is the foundational layer of security validation, typically performed to meet compliance mandates like PCI DSS and GLBA. It involves a combination of automated and manual techniques to identify known vulnerabilities in networks, servers, and applications, following established frameworks like the OWASP Top 10. Methodologies include:
- Black-Box: Testers have no prior knowledge, simulating an external attacker.
- White-Box: Testers have full knowledge (e.g., source code), allowing for a deep, comprehensive review.
- Gray-Box: Testers have partial knowledge (e.g., user credentials), simulating an insider threat or an attacker who has already breached the perimeter. This is often the most efficient and relevant approach for fintechs.
Red Teaming & TIBER‑EU
Red teaming is a more advanced, objective-driven exercise. Instead of finding as many vulnerabilities as possible, a red team simulates a specific adversary to test an organization’s detection and response capabilities. The goal isn’t just to find flaws, but to see if the Security Operations Center (SOC) and incident response teams can detect and stop a sophisticated, multi-stage attack in progress.
TIBER-EU (Threat Intelligence-Based Ethical Red Teaming) is the methodology endorsed by EU banks and mandated by DORA. It takes red teaming a step further by using bespoke threat intelligence to simulate the specific actors most likely to target the financial institution.
Continuous / Automated Red Teaming & BAS
The speed of modern development requires continuous, not just annual, security validation.
CART (Continuous Automated Red Teaming) | BAS (Breach & Attack Simulation) | |
Purpose | Simulate persistent, evolving adversary behavior | Automate known attack techniques |
Scope | End-to-end attack chains over time | Specific control validation (firewalls, EDRs) |
Frequency | Continuous, real-time | Periodic or on-demand |
Outcome | Tests detection & response readiness | Verifies configuration and coverage gaps |
Industry Statistics
Data from across the industry reinforces the need for a robust, multi-layered testing strategy.
- Web application attacks remain a dominant threat vector, with the Verizon DBIR noting that web applications are a primary vector for both credential theft and vulnerability exploitation[7]
- The ROI of continuous testing models is clear. Organizations that extensively use security AI and automation—often validated by BAS platforms and pentesting—save an average of “$1.9 million on the cost of a breach”[1] compared to firms with no such deployment.
Furthermore, having a tested incident response plan, validated through exercises like red teaming, reduces breach costs by an average of “$248,000 annually”[1].
Choosing a Provider & Structuring Engagement
Vendor Selection Criteria
Selecting the right partner is critical for a successful engagement. Use this checklist to evaluate potential providers.
- Sector Experience: Have they worked with fintechs, banks, or investment firms of your size and complexity?
- Compliance Knowledge: Do they have deep expertise in PCI DSS, GLBA, and DORA?
- Certified Experts: Are their testers certified with respected, hands-on credentials like OSCP or CREST?[8]
- Transparent Methodology: Do they combine deep manual testing with automation? Can they explain their process clearly?
- Quality Reporting: Do their sample reports include a clear executive summary, risk-prioritized findings, and actionable remediation advice?
- Post-Engagement Support: Is retesting to verify fixes included? Will their experts be available to your team for questions?
Testing Engagement Lifecycle
A professional engagement follows a structured lifecycle to ensure clear communication and valuable outcomes.
- Scoping: Define the systems, applications, and assets to be tested.
- Rules of Engagement (RoE): Formalize the testing window, communication protocols, and what is off-limits.
- Testing: The provider executes the test according to the agreed-upon methodology.
- Report Delivery: A comprehensive report is delivered, detailing findings and recommendations.
- Remediation: Your team fixes the identified vulnerabilities.
- Retest: The provider validates that the fixes are effective and updates the report.
An ideal report includes an executive summary, CVSS-based risk ratings, proof-of-exploit evidence, and a prioritized remediation roadmap with a defined retest window.
Measuring ROI & Business Impact
The investment in strategic penetration testing delivers a clear and measurable return by reducing financial risk and enabling business growth.
- Cost Savings: The primary ROI comes from avoiding the “$6.08 million average cost of a breach in the financial sector.”[1] By identifying and fixing critical vulnerabilities, you directly reduce the likelihood of a catastrophic incident.
- Audit Readiness: A mature testing program streamlines compliance audits, reducing the internal time and resources spent gathering evidence and responding to auditor requests.
- Improved Controls: Continuous testing tools like BAS provide hard data to justify security investments and optimize existing controls, ensuring your budget is spent effectively.
Beyond cost avoidance, a mature testing program streamlines compliance audits, reducing the internal time and resources spent gathering evidence. Key Performance Indicators (KPIs) to track include the number of critical vulnerabilities found and remediated, the average time-to-remediation for high-risk findings, and audit pass rates.
Final Thoughts
In today’s financial services landscape, where AI-driven threats, third-party risks, and regulatory scrutiny are intensifying, compliance-only security is no longer enough. Organizations must adopt a continuous, adversary-aware approach to testing—one that validates not just whether controls exist, but whether they actually work under real-world attack conditions.
By shifting from checkbox assessments to strategic, objective-driven testing, financial firms can strengthen resilience, reduce breach risk, and accelerate enterprise trust. With the right partner, penetration testing becomes more than a security exercise—it becomes a business enabler.
Ready to build a testing program that aligns with your strategic goals? Contact Cybri to discuss a continuous, tailored approach to penetration testing for your financial services organization.
Referencs
- IBM. (2024). Cost of a Data Breach Report 2024
- European Central Bank. (2024). TIBER-EU Framework
- SecurityScorecard. (2025). Defending the Financial Supply Chain: Strengths and Vulnerabilities in Top Fintech Companies
- PCI Security Standards Council. PCI DSS v4.x
- Federal Trade Commission. FTC Safeguards Rule: What Your Business Needs to Know
- General Data Protection Regulation (GDPR). Art. 32 GDPR – Security of processing
- Verizon. (2024). 2024 Data Breach Investigations Report
- Infosec Institute. (2025). Top 10 Penetration Testing Certifications for 2025
- Akamai. (2024). 2024 API SECURITY IMPACT STUDY Financial Services Industry
Frequently Asked Questions
Yes. DORA mandates threat-led penetration testing (TLPT) at least every three years for critical EU financial entities. GLBA requires annual penetration tests and biannual vulnerability scans for U.S. financial institutions. These frameworks demand more than surface-level assessments—they require realistic, adversary-simulated exercises.
At minimum, annually. However, given the high velocity of threats and product releases, many fintech firms adopt continuous penetration testing or PTaaS models to maintain resilience and meet ongoing compliance requirements.
Reports should include a threat profile, test objectives, tactics used, detected vs. undetected stages, and business impact analysis. TIBER-EU also requires alignment with intelligence inputs and risk-based scoping.
Absolutely—and you should. With over 41% of breaches in fintech traced to vendors, testing third-party APIs, cloud tools, and integrated services is a critical component of modern pen testing strategies.
Not necessarily. While red teaming is more advanced, focused red team exercises—like targeting a high-value API or cloud identity flow—can offer valuable risk insights without a full-scope adversarial simulation.
Yes. Cybri supports tailored penetration testing and red teaming for FinTechs, banks, and cloud-native financial service providers—including those subject to DORA, GLBA, and PCI DSS.
