Cybersecurity Risk Self-Assessment: 6 Gaps Fintech Companies Notice Last

A cybersecurity risk self-assessment is a quick internal review of a company's security based on a structured list of questions. For fintech companies, it shows which areas of protection rely on assumptions rather than verified facts, and where a more detailed assessment should begin. It is not an audit and not a replacement for a penetration test.

Over nine years of conducting penetration testing for fintech companies and banks, we have seen the same gaps repeated from one project to another. Here are the ones we encounter most often.

Below, we take a closer look at each of these situations: why it happens, how it typically ends, and how to check whether it exists in your company. If you want to assess your cybersecurity posture right away, a free cybersecurity risk self-assessment with 20 questions takes just five minutes.

Why should fintech companies conduct a cybersecurity risk self-assessment?

Fintech companies should conduct a cybersecurity risk self-assessment to quickly identify potential security gaps, verify their readiness for current regulatory requirements, and determine which areas require a more comprehensive professional audit.

The need arises because weak points in fintech are rarely visible from the inside. A company is rarely built around a single system: a payment gateway, a KYC provider, a partner bank, fraud detection tools, and analytics all work together. Every integration adds another channel through which money and personal data move. The attack surface expands gradually, and no individual connection appears particularly risky on its own.

At the same time, regulatory requirements continue to evolve. DORA, NIS2, PSD2, PCI DSS, and GDPR are updated at different rates, and even experienced teams do not always have time to verify what has changed specifically for them.

The most dangerous situation is not "we know about our problems," but "everything seems fine." In a SIEM implementation project for a financial company serving more than 200,000 customers, 12 previously undetected security incidents were identified during the pilot deployment alone. In other words, the absence of recorded incidents simply meant that there was no one monitoring and recording them.

Completing the cyber security self assessment questionnaire gives a company an initial understanding of its current cybersecurity posture and highlights the areas that require a more detailed assessment. It is not an audit or a comprehensive security evaluation, but a tool for rapid self-assessment without a budget, a procurement process, or the involvement of an external team. It examines security from six different perspectives rather than relying on a single metric, and the most valuable part of the results is the list of specific "No" answers. These answers reveal:

• specific gaps: no penetration test has been conducted for more than a year, APIs have never been tested separately, the cloud infrastructure has not been assessed, or an incident response plan exists but has never been exercised;
• areas where security is based on assumptions rather than verified facts;
• topics for the very first conversation with cybersecurity specialists, already framed as specific questions instead of the general request, "Please assess our security."

For this reason, a cyber security self assessment questionnaire is most useful in three situations: before onboarding a new partner that will conduct due diligence, before planning the cybersecurity budget to determine where investments should be prioritized, and simply every few months to see what has changed within your own environment.

What areas of cybersecurity does the assessment cover?

The cyber security self assessment questionnaire is based on Datami's nine years of experience conducting penetration testing for fintech companies and banks across the EU, the Baltic states, the United Kingdom, the DACH region, and Northern Europe. It takes into account the requirements of NIS2 (EU 2022/2555), GDPR (EU 2016/679), PCI DSS v4.0.1, PSD2 (EU 2015/2366), and DORA (EU 2022/2554), as well as the specifics of payment processes, transaction business logic, KYC procedures, and third-party vendor management.

1. Compliance and regulatory readiness. Regulatory gaps usually surface at the worst possible moment - during due diligence before onboarding a new partner. The issue is rarely the absence of documentation. During a security policy audit for an international BaaS company, seven key policies were in place, but most processes were assessed at the Defined / Repeatable maturity level - they were documented but not actively managed. That is why the first section focuses not on whether documents exist, but on whether they are actually embedded in day-to-day operations.
2. Penetration testing and security assessment. A penetration test conducted a year and a half ago describes a system that no longer exists: releases have changed, new endpoints have been added, and integrations have evolved. Even more often, the payment logic was never included in the scope, and no retesting was performed after vulnerabilities were fixed. The questions in this section focus on how recently the assessment was performed, what it covered, and whether remediation has been verified.
3. API and transaction security. Most costly incidents in fintech are caused not by a "server hack," but by flaws in business logic: insufficient authorization checks for specific objects, the ability to replay transaction confirmations, or ways to bypass business rules. A good example comes from a security audit of a P2P platform, where all three critical vulnerabilities out of ten identified were found in transaction processing mechanisms and smart contracts. The potential financial impact was estimated at approximately $300,000. That is why the questionnaire includes dedicated questions about endpoint access control, rate limiting, and transaction consistency.
4. Monitoring and incident response. DORA and GDPR impose strict deadlines for reporting incidents, but an incident response plan that has never been exercised is unlikely to work during a real attack. The difference is measurable. In the previously mentioned SIEM project, incident detection time was reduced from several days to 1–2 hours, while response time decreased from 2–3 days to 6–8 hours. The questions assess whether there is a documented response plan, who makes decisions outside business hours, and whether security events are actually monitored around the clock.
5. Third-party and supply chain risks. An incident affecting a payment provider or a KYC service can disrupt your operations regardless of how well your own infrastructure is protected. Yet vendor contracts rarely answer a simple question: how many hours does the provider have to notify you about a security compromise? In the BaaS project, one of the key outcomes was strengthening contractual security requirements for vendors and introducing regular third-party security reviews.
6. People, processes, and architecture. Access permissions tend to accumulate over time. Employees change roles, but their previous privileges remain in place. Without proper segmentation, a single compromised component can provide access to the payment environment. The questions in this section focus on regular access reviews, security awareness training, and the isolation of critical systems.

Which problems most often go unnoticed?

Several misconceptions are common even among mature teams, and these are exactly why security gaps can remain unnoticed for years.

Scanning is mistaken for penetration testing. An automated scanner detects common technical issues, but it does not test business logic or build attack chains from several minor weaknesses. During the audit of a P2P platform, automated tools were used alongside manual testing, and it was the manual assessment of transaction processing mechanisms that uncovered the critical findings.

Compliance is equated with security. A successful compliance assessment confirms that processes are in place. Whether the technical controls can withstand a real attack is a different question, and only practical testing can answer it. During a GCP cloud infrastructure audit conducted before PCI DSS certification, 12 vulnerabilities were identified, most of them in basic access configuration rather than in sophisticated attack scenarios.

Availability monitoring is confused with security monitoring. An uptime dashboard shows that the service is running. It does not show that an unauthorized account has been operating inside the system for weeks.

Responsibility is spread across multiple teams. When security formally belongs to development, infrastructure, and compliance at the same time, it effectively belongs to no one. The tasks are not deliberately ignored - they simply remain unassigned.

How does the assessment work?

The assessment is simple to complete: 20 questions, "Yes" or "No" answers, and five minutes of your time. Answering honestly is much more difficult.

The temptation to give a better answer than reality almost always exists. "We've had a penetration test", but it was conducted two years ago and did not include payment logic testing. "We have an incident response plan", but no one has opened it since it was written. Formally, the answer is "Yes" in both cases. In reality, the protection is not there.

So follow one simple rule: if you find yourself thinking, "Well, generally yes," or "Almost," the correct answer is "No."

A result that reveals more problems than you expected is better than one that simply confirms your assumptions. The first gives you a to-do list. The second gives you peace of mind that no one can guarantee.

The results do not constitute an audit, certification, or confirmation of compliance with regulatory requirements.

What does your result mean?

• 0–3 "No" answers – Low risk. The fundamental security processes are in place and require regular review.
• 4–7 – Medium risk. There are individual gaps that may affect security or regulatory compliance.
• 8–12 – High risk. Several important areas require assessment and prioritization.
• 13–20 – Critical risk. A comprehensive security assessment and a prioritized remediation plan are required.

This scale shows the overall scope of work. It does not determine the order of priorities.

What should you do after completing the assessment?

The priority is determined not by the score, but by the distribution of the answers. Three "No" responses scattered across organizational questions and three consecutive "No" responses in the payment logic and incident response section produce the same score but indicate completely different levels of risk. Based on our experience, the second scenario involves the area where the most costly vulnerabilities are usually found, and it should be addressed more urgently than the overall score alone might suggest.

The next steps are straightforward:

• identify which assets and data are truly critical;
• assess the technical risks in the areas with the highest number of "No" answers;
• conduct a penetration test or a security audit of your systems and payment logic;
• develop a vulnerability remediation plan with clear priorities;
• perform a retest after the improvements have been implemented.

A self-assessment does not replace a security audit, penetration testing, or a compliance assessment. It shows where your security relies on assumptions. The only way to determine whether those assumptions can withstand a real attack is through independent testing. For fintech companies, where regulators impose heightened security requirements for payment systems and APIs, that distinction has very practical implications.

Conclusion

The worst word in a security report is not "critical." A critical finding can be fixed. On one P2P platform, the client remediated three critical vulnerabilities within 48 hours. The worst phrase is "not assessed." That was the status of the vulnerabilities in a fintech company before the GCP audit, until the assessment turned that uncertainty into twelve specific findings with a structured remediation plan.

A self-assessment does not make a system more secure. No questionnaire can do that. What it does is transform part of "we don't know" into "we know." And a company that is aware of ten weaknesses is in a far better position than one that genuinely believes it has none.

Repeat the cybersecurity quiz after every significant change, whether it is a new integration, expansion into a new market, or a change of payment provider. If the assessment reveals gaps in critical areas, the next step is to validate them in practice. The Datami team conducts penetration testing tailored to payment logic, APIs, and the requirements of NIS2, PCI DSS, and DORA. It delivers a vulnerability remediation plan with clearly defined priorities based on the results.