How often should you run a penetration test?

Cyber threats are evolving fast — and penetration testing remains one of the most effective ways to identify security gaps before attackers do. But how often should you run a pen test? 

Some businesses assume an annual test checks the box. Others believe their firewall or antivirus will handle the heavy lifting. The truth? There’s no one-size-fits-all answer. Pen testing frequency depends on your industry’s regulatory environment, your risk exposure, and how often your systems and infrastructure change. 

For example, companies in finance, healthcare, and critical infrastructure often require quarterly or even continuous testing to stay compliant and secure. Meanwhile, a small local business might get by with annual testing unless there’s a major change, like a merger or system upgrade, in which case testing should happen immediately. 

Annual penetration testing is the security bare minimum often mandated by compliance frameworks and widely considered a best practice. While it may meet baseline regulatory requirements, it’s often not enough for businesses with high-risk exposure or evolving systems. 

Why is annual testing still important? 

Annual testing helps maintain compliance with frameworks like: 

• ISO 27001: Pen testing supports an organization’s Information Security Management System (ISMS). 

• PCI DSS: Requires annual penetration tests for businesses handling credit card data. 

• HIPAA: Encourages regular testing to protect electronic protected health information (ePHI). 

• SOC 2: Annual testing is standard for demonstrating security controls for service organizations. 

Who does annual testing work for? 

• Small businesses in non-regulated industries: Think local shops or service providers not handling sensitive data. 

• Professional services: Firms with simple infrastructures and secure cloud providers. 

• Organizations with stable IT:  Businesses with little change to systems or architecture. 

Limitations of annual testing 

Cyber threats don’t operate on an annual schedule so if you’re only testing once a year, vulnerabilities could go undetected for months. For businesses that handle sensitive data, consider more frequent testing or layering pen tests with continuous vulnerability scanning - something we include with all Target Defense pen test packages. 

Businesses in finance, healthcare, or retail - industries that process sensitive information or large volumes of transactions, should consider testing every 3 to 6 months. These environments often undergo constant change, increasing the chances of new vulnerabilities emerging. 

Industries that need more frequent testing: 

Finance & FinTech (quarterly or monthly) 

Why:

Financial institutions are a prime target for cybercriminals - and it’s easy to see why. They deal with valuable data, real-time transactions, and strict regulations that are always shifting. In some cases banks and FinTech companies may be liable for fraudulent transactions if customers are able to demonstrate weaknesses or errors in the app or website. So whether it’s a bank, fintech app, or payment processor, staying ahead of threats with regular testing isn’t just smart - it’s essential. 

Risks: 

• Payment fraud 

• Account takeovers 

• Insider threats 

• Social engineering 

Healthcare & pharma (quarterly or semi-annually) 

Why:

The healthcare sector holds incredibly sensitive information - from patient records to medical research, so any disruption can impact not just privacy, but patient care itself. With ransomware and IoT risks on the rise, regular testing ensures identifiable and exploitable weaknesses are caught early on. It’s worth noting that many ransomware attacks dont rely on traditional network vulnerabilities and often start with malicious files being opened or users connecting infected devices. This is why pen testing should be paired with configuration reviews, strict endpoint protocols, and robust user awareness training to ensure a strong defense.

Risks: 

• Ransomware targeting electronic health records (EHRs) 

• IoT device vulnerabilities 

• Unauthorized software execution 

E-Commerce & retail (quarterly) 

Why:

Online retailers and e-commerce platforms handle thousands of transactions a day, often spiking during holidays or sales. That high volume makes them a magnet for cyberattacks aimed at checkout pages and payment systems. Frequent testing helps close those gaps before attackers get in. 

Risks: 

• Checkout vulnerabilities 

• Injection attacks 

• Card skimming (e.g. Magecart) 

Why it matters 

Frequent testing identifies new risks introduced by software releases, vendor changes, and new integrations. It also helps meet stricter compliance timelines and builds trust by showing a proactive security posture. 

Let’s face it, for some companies, annual or quarterly testing just isn’t enough. If things are changing constantly, or if you’re working with sensitive info, waiting months between tests can leave you wide open. That’s where more frequent pen testing comes in. Monthly or ongoing assessments help catch issues early, before they cause real damage. 

Who’s this for? 

Critical infrastructure & big organizations 

Why:

These companies are huge targets. Lots of systems, lots of data, and usually a lot at stake. Think utilities or national infrastructure. If something goes wrong, it’s not just an IT issue - it’s a public one. Testing regularly helps stay ahead of the risks. 

Examples:

Energy networks, telecom providers, cloud platforms, defense contractors 

FinTech & payment apps 

Why:

In fast-moving spaces like crypto or mobile banking, updates happen all the time. And so do attacks. It doesn’t take much - one missed bug in a payment system can blow up fast. Frequent testing helps you catch those changes before someone else does. 

Examples:

Crypto wallets, neobanks, online payment tools 

Businesses under strict compliance 

Why:

Some companies don’t have much of a choice. Rules like SOC 2 expect you to prove you’re keeping up with your security. Regular pen testing isn’t just a nice-to-have, it’s required. 

Examples:

SaaS platforms, healthcare tech, finance companies 

Security isn’t static and neither should your testing be. Some events call for immediate or “as-needed” penetration testing, including: 

• Infrastructure changes – New networks, tools, or cloud migrations 

• After a breach – Confirm that vulnerabilities are closed 

• New locations – Test VPNs and physical access 

• New payment systems – Meet PCI DSS guidelines 

• Mergers or acquisitions – Inherited risks from legacy systems 

Red teaming goes beyond typical penetration testing. Instead of just spotting weaknesses in your systems, it looks at how well your team can actually respond to a real-world attack. It's about simulating the entire experience - from breach to response - to see how your defenses hold up under pressure. 

It’s a good fit for: 

• Companies with mature security setups looking to push their defenses further 

• Highly regulated industries where risk is high and downtime isn’t an option 

• Teams that want to test more than just their tech, including how well people and processes respond when things go sideways