Penetration testing, or Pen testing, is like hiring a security expert to check if your digital locks and doors are strong enough to keep hackers out. It involves simulating cyberattacks on your business systems to find weaknesses before real criminals do. These security tests help identify vulnerabilities that cybercriminals could exploit, allowing businesses to fix them before they become major issues.
For small and medium-sized businesses (SMBs), pen testing is an essential way to stay safe online. Cybercriminals don’t just target big companies, SMBs are often seen as easier targets because they might not have the same level of cybersecurity resources. Regular pen testing helps businesses find and fix security gaps before they lead to costly breaches, data leaks, or downtime that can impact business operations and customer trust.
Types of Pen Testing for SMBs
There are different types of pen testing, but the most useful ones for SMBs include:
Network Security Testing | Checks if hackers can break into your company’s internet network by finding weak passwords, misconfigurations, or other security flaws. If your business uses cloud services, network pen testing can also identify risks related to improperly configured access controls and exposed sensitive Data.
Server and Endpoint Security Testing | Assesses vulnerabilities in company servers, desktops, and laptops to identify misconfigurations, outdated software, and potential security loopholes that hackers could exploit. Since servers often store sensitive business and customer data, securing them is crucial for maintaining business continuity and preventing unauthorised access.
Website and App Security Testing | Looks at your business website and apps for weaknesses that hackers could use to steal data, install malware, or disrupt services. With more SMBs relying on web-based applications for sales, customer service, and internal operations, ensuring these platforms are secure is critical.
Employee Security Awareness Testing | Sends fake phishing emails and other social tricks to see how employees react and whether they need more security training. Since human error is a major cause of data breaches, testing employee awareness and providing cybersecurity education can significantly reduce risks.
Wi-Fi Security Testing | Ensures your wireless networks are protected from intruders who might try to break in through weak encryption, outdated security protocols, or unauthorised access points. This is particularly important for businesses with remote workers or multiple office locations.
Pen Testing can also be done in different ways depending on how much information the tester has:
Black Box Testing | The tester acts like a real hacker, with no inside knowledge of the system. This method is useful for simulating external attacks and testing how well an organisation’s perimeter defences hold up against unknown threats.
Grey Box Testing | The tester has some insider information, such as user credentials, to better simulate an attack from someone with partial access. This method is valuable for assessing risks posed by disgruntled employees, contractors, or attackers who have obtained stolen credentials.
White Box Testing | The tester has full knowledge of the system, including access to source code, architecture details, and credentials. This method is often used for in-depth security assessments to identify vulnerabilities at a granular level and ensure the system meets security best practices.
Which Pentest is Best for My Business?
Choosing the right pen test depends on your business size, industry, and security concerns. Here’s a simple guide to help you decide:
- If you are a small business with an online presence | Website and app security testing is a must to protect customer data and transactions.
- If your business handles sensitive customer information (eg. finance or healthcare) | A combination of network security testing and server/endpoint security testing will help ensure that sensitive data is not exposed.
- If your employees use emails and online systems regularly | Employee security awareness testing will help prevent phishing and social engineering attacks.
- If you want an overall assessment of your security posture | A combination of black, grey, or white box testing based on your needs will provide insights into vulnerabilities from different perspectives.
For businesses with compliance requirements (such as Essential Eight, SMB1001 or cyber insurance mandates), regular pen testing is often necessary. If you are unsure, give us a call, and one of our cybersecurity experts can discuss your needs.
Pen Testing as a Service | One-Off vs. Ongoing Testing
Businesses can either do pen testing once in a while or set up a system for ongoing checks. Traditional pen tests provide a snapshot of vulnerabilities at a specific time, which is helpful but may not be enough as threats evolve. Cybercriminals are constantly developing new attack techniques, so a security test conducted six months ago may not reflect today’s risks.
Continuous pen testing, on the other hand, helps businesses stay protected as new threats emerge. This approach uses automation and AI to regularly scan for vulnerabilities and test security defences.
Companies like Vonahi Security and Pentera offer automated pen testing solutions that regularly scan and test your security. This makes it easier and more affordable for SMBs to keep their systems safe without hiring full-time security experts. Automated pen testing tools can provide real-time alerts and remediation recommendations, reducing the time and effort required to maintain strong security.
Financially, this allows for businesses to choose a model that suits their budget and security needs. An annual pen test typically involves a one-time larger payment but provides a single, in-depth assessment of security vulnerabilities. A monthly automated pen testing option, on the other hand, spreads the cost over the year and offers continuous monitoring, allowing businesses to detect and remediate vulnerabilities as they arise. While an annual test may be sufficient for compliance purposes, ongoing testing provides a more proactive security approach, reducing the risk of prolonged exposure to new threats.
Why Pen Testing Matters for Compliance and Insurance
Pen Testing isn’t just a smart security move, it’s also becoming a requirement for many businesses. Various security guidelines and insurance providers expect companies to conduct regular security tests, including:
- Essential Eight (Australia) | A government-recommended strategy to protect businesses from cyber threats, which includes regular pen testing. Organisations that follow the Essential Eight framework are better equipped to prevent, detect, and respond to cyber incidents.
- SMB1001:2025 | The SMB1001 certification encourages small businesses to check for security gaps using pen testing. Additionally, SMB1001 provides a structured approach for SMBs to adopt cybersecurity best practices, making it easier for businesses to align their security efforts with industry standards in an affordable and scalable way.
- Cyber Insurance Requirements | Many insurance providers require businesses to conduct regular pen tests to qualify for coverage or get lower premiums. Insurers want to see that a company is taking proactive steps to reduce its cyber risk before providing coverage. If a business cannot demonstrate security due diligence, it may face higher premiums or even be denied coverage altogether.
In some cases, failing to perform regular pen tests could impact a company’s ability to file a cyber insurance claim. If a breach occurs and the insurer finds that the company did not follow recommended security practices, the claim may be rejected.
Additional Benefits of Pen Testing
Beyond compliance and insurance requirements, pen testing has other important benefits for SMBs:
- Prevents Financial Loss | A cyberattack can result in lost revenue, legal fees, regulatory fines, and reputational damage. Pen testing helps prevent these costs by identifying and fixing security issues early.
- Protects Customer Data | Customers trust businesses to keep their personal and financial information secure. A data breach can lead to loss of customer confidence and long-term damage to a brand’s reputation.
- Enhances Incident Response | Pen Testing provides businesses with valuable insights into how well they can detect and respond to security threats. If an attack happens, organisations that have been regularly testing their defences are more prepared to handle it effectively.
- Supports Business Growth | As SMBs expand, their digital infrastructure becomes more complex. Regular pen testing ensures that security scales with business growth, keeping new systems and applications secure from day one.
Final Thoughts
Pen Testing is a valuable tool to protect your business from cyber threats. Whether you opt for a one-off test or continuous monitoring, it helps identify vulnerabilities before criminals do. By following cybersecurity best practices and compliance standards, SMBs can reduce risks, improve security, and even save money on insurance. Investing in pen testing today can save businesses from major security incidents in the future. As cyber threats continue to evolve, regularly assessing and strengthening security defences is one of the best ways SMBs can stay protected.
Reach out to our team at IQPC to discuss how we can help with Pen Testing to keep your business data safe.
