9 Common Cyber Security Challenges in Achieving PCI DSS Compliance

Complying with PCI DSS can be challenging, especially given the technical complexity and ongoing effort required. Different organizations face different hurdles – a small business might worry about cost, while a large enterprise might struggle with a sprawling IT environment. Below are some of the most common challenges and pain points encountered on the road to PCI compliance:

1. Defining the Scope of Compliance: One of the first and biggest challenges is understanding what systems and data fall under PCI DSS scope. Many organizations struggle to identify all places where cardholder data resides or flows ⁹, including backup systems or logs. If you overlook a system (say, a forgotten database storing old card numbers), you could end up with security gaps and non-compliance. Thoroughly mapping out your cardholder data environment (CDE) is crucial ⁶.
2. Technical Complexity of Security Controls: Implementing and managing all the required security measures can be technically complex. For example, setting up network segmentation, maintaining encryption keys, managing log servers, and configuring firewalls all require expertise. PCI mandates robust measures like firewalls, encryption, and granular access controls, which can be challenging to configure correctly and maintain over time ⁶. IT professionals often find that legacy systems add extra difficulty – older systems or software might not easily support modern encryption or logging standards ¹. Upgrading or patching legacy tech is costly and slow, but ignoring it leaves compliance gaps.
3. Resource Constraints (Time, Money, People): Achieving compliance isn’t just an IT project; it demands time and effort across the organization. Small and medium-sized businesses often have limited budgets and IT staff, making it hard to allocate sufficient resources to PCI compliance⁷. The initial push to become compliant can require investments in new tools (e.g., logging systems, upgraded firewalls) and possibly external consulting. Maintaining compliance year-round also consumes resources – running scans, reviewing logs, training staff, etc. For businesses focused on day-to-day operations, PCI tasks can feel burdensome ⁶. However, the cost of non-compliance (breaches, fines) is usually far higher in the long run.
4. Maintaining Continuous Compliance: PCI compliance is not a one-time checklist, but an ongoing process ¹. This is a mindset challenge: some organizations put in effort to pass an annual assessment, then lapse on security the rest of the year. Falling out of compliance between assessments is common if there isn’t continuous monitoring. Regular tasks like patch management, user access reviews, anti-virus updates, and quarterly scanning must be sustained indefinitely ¹. Ensuring you don’t “set and forget” controls takes organizational discipline and often a dedicated compliance team or point-person. As one compliance expert noted, staying aware of changes year-to-year and adjusting your security infrastructure accordingly can be demanding ¹.
5. Keeping Up with Evolving Standards and Threats: The security landscape doesn’t stand still – new cyber threats emerge, and the PCI DSS itself gets updated (as we saw with v4.0). Many businesses find it challenging to keep up-to-date with changes in the standard and adapt their policies and systems accordingly ⁶. For instance, the introduction of new requirements (like the expanded MFA rule) might require significant changes to IT environments. Likewise, the rise of cloud services, APIs, and fintech innovations means IT professionals must continuously interpret how PCI requirements apply in new scenarios. This learning curve and need for agility can be tough, especially without expert guidance.
6. Third-Party and Supply Chain Risks: Outsourcing doesn’t eliminate responsibility. If you use third-party service providers (for payment processing, cloud hosting, IT support, etc.), their security controls can impact your compliance. A big challenge is ensuring all third-party vendors who touch card data are themselves PCI compliant ⁶. PCI DSS requires you to manage vendor risk (Requirement 12.8 deals with service provider oversight). However, many breaches have occurred through third-party weaknesses. It’s challenging to thoroughly vet and monitor partners’ security. If a vendor is breached, you could be the one fined if card data is compromised under your watch.Businesses must include vendors in the scope of their compliance program, but doing so adds coordination complexity.
7. Lack of Security Awareness or Training: Even with great tech controls, human error can undermine compliance. Organizations often overlook staff training, but untrained employees might mishandle card data (e.g., writing it down, emailing it) or fall for phishing scams ⁹. IT professionals sometimes face an internal culture challenge: getting non-IT staff to follow security procedures. For example, if employees find the rules cumbersome (like not storing certain data or using MFA tokens), they might skirt them unless they understand why it’s crucial. Creating a security-conscious culture is a challenge, but without it, social engineering and mistakes can lead to compliance failures and breaches ⁹.
8. Managing and Documenting Compliance Efforts: PCI DSS requires a lot of documentation – policies, network diagrams, access control lists, incident response plans, etc. For large organizations, producing evidence for an assessor (or even a Self-Assessment Questionnaire for smaller entities) can be daunting. Many companies struggle with organizing documentation and records of all the controls in place. During an audit or self-assessment, insufficient or poorly organized documentation is a common pitfall that can slow down or jeopardize the certification process.It’s a challenge to keep all these artifacts up-to-date, especially in fast-changing IT environments.
9. Incident Response and Breach Preparedness: Ironically, planning for failure is part of compliance. PCI DSS requires having an incident response plan. However, preparing for a potential data breach – and integrating those plans with compliance – is challenging. Many businesses don’t test their incident response regularly. If a breach happens and the response is chaotic, it can result in not only damage to data but also violations of PCI rules (e.g., not informing the right parties in time, not containing the issue). Handling a security incident smoothly under pressure requires practice and clear procedures ¹, which is something firms often only realize after experiencing a scare.

These challenges can seem overwhelming, but the good news is that none of them are insurmountable. In the next sections, we will discuss best practices and strategies to address these issues and make achieving (and maintaining) PCI DSS compliance much easier. Understanding where the pain points are is the first step – now we’ll focus on how to overcome them.