7 Penetration Testing Best Practices for Small Businesses

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Penetration Testing
by John Svazic/ on 15 Apr 2024

7 Penetration Testing Best Practices for Small Businesses

You’re a small business with limited resources. How much time do you have to devote to such a complex task? Not a lot.

Not to mention, for the sake of regulatory compliance, you might have no choice but to devote some of your budget to penetration testing. In fact, not only does a pen test solidify your security posture, but it’s also a powerful form of risk and reputation management. If you handle any amount of sensitive data, trust is part of the buying process, so it’s a good idea to show off your security credentials with a pen test.

This article from EliteSec will help you understand the penetration testing best practices for small businesses and explain in detail why penetration testing is critical to your operations.

What is Penetration Testing?

Penetration testing is a cyber security methodology that allows ethical hackers, otherwise known as pen testers, to “hack” into your core systems. The key is that you’re allowing the penetration tester to breach your systems so that you can find where your security vulnerabilities lie. Once they’re done, they’ll recommend improvements you can make to your cyber security infrastructure in the future.

Keep in mind, that not all small businesses require penetration testing. Here are the types of small businesses that usually need it the most:

  • Healthcare Providers
  • Financial Service Providers
  • Law Firms
  • Educational Institutions
  • Tech Startups
  • Hospitality Businesses
  • Real Estate Agencies

Penetration testers secure your company from a data breach

The 3 Types of Penetration Testing

You’ll often hear about black, grey, and white box testing while researching penetration testing. Let’s remove some of the confusion:

Black Box Testing

Black Box testing simulates an external hacking or cyber attack and is characterized by the tester having no prior knowledge of the internal workings of the target system. This approach mirrors an attacker’s perspective, who would likely have no insider information about the network. Black Box testing is useful for understanding how an attacker might gain unauthorized access to the system from the outside.

For small businesses, this type of testing can highlight vulnerabilities in publicly accessible systems and identify weaknesses in their perimeter defenses. It can also test the effectiveness of current security policies and incident response times. However, it’s worth noting that Black Box testing might not provide comprehensive insights into internal vulnerabilities or complex security flaws due to its external focus.

White Box Testing

White Box testing, in contrast, offers a complete overview of the internal workings of the application or system being tested. Testers are given full access to all source codes, documentation, and network information. This method is akin to performing a thorough internal audit of the system’s security health.

For small businesses, White Box testing can be invaluable for uncovering hidden vulnerabilities that could be exploited from the inside or through sophisticated external attacks. It’s particularly beneficial for testing complex applications and ensuring that internal processes and transactions are secure. That said, many small businesses find this form of testing to be too resource-intensive.

Gray Box Testing

Gray Box testing strikes a balance between Black Box and White Box testing, offering a partial knowledge perspective. Testers have some information about the internal structures, which enables a more focused assessment than Black Box testing but is less comprehensive than White Box testing. This approach can simulate an attack from a user with limited privileges or insider information.

For small businesses, Gray Box testing is an efficient way to assess both external and internal security postures without the need for full system transparency. It allows businesses to identify how an attacker with limited inside knowledge might exploit both external and internal vulnerabilities. Plus, it’s cost-effective, making it suitable for small businesses looking to get a more detailed assessment than Black Box testing without the extensive resource investment required for White Box testing.

How Penetration Testing Can Benefit Small Businesses

Small businesses need to be proactive if they want to survive. Simulating attacks with a penetration test is one of the best ways to uncover the vulnerabilities in your cyber infrastructure. By doing so, penetration testing not only helps in safeguarding sensitive data but also in maintaining customer trust and loyalty, which are crucial for your growth.

Here are the main benefits of penetration testing for your small business:

  1. Protect your sensitive data: By identifying vulnerabilities that could be exploited for data breaches, small businesses can protect sensitive information such as customer data, financial records, and intellectual property, thereby avoiding potential losses and reputational damage.
  2. Comply with regulatory requirements: Many industries require adherence to specific cybersecurity standards (such as GDPR, HIPAA, or PCI-DSS). Penetration testing helps ensure that small businesses meet these regulatory requirements, avoiding legal penalties and fines.
  3. Save money in the long run: Although penetration testing involves upfront costs, it can result in significant savings by preventing costly security breaches. Data breaches are costly. Expenses such as legal fees, fines, and loss of business, can be far greater than the cost of penetration tests.

Ethical hacking

7 Best Practices in Small Business Penetration Testing

Before you make any critical decisions, take a step back and see your pen test as part of the bigger picture for your business. That means you need to start planning for who will do the pen test, and which attack surfaces it should cover.

Start With A Risk Assessment

Every penetration test, no matter how big or small, starts with a risk assessment. By understanding where the greatest risks lie, you can tailor your penetration testing efforts to focus on the most critical areas first, ensuring that resources are allocated efficiently.

A thorough risk assessment will prioritize vulnerabilities based on their potential impact, allowing small businesses to address the most severe threats to their operations. This approach not only optimizes the penetration testing process but also contributes to a more strategic and informed cybersecurity posture, ensuring that efforts and investments are directed where they can provide the maximum benefit in terms of risk mitigation.

Consider The Scope Of The Test

Ensure that the penetration test is both effective and manageable. This step requires businesses to define what will be tested, which can range from external network services to internal applications and even physical security controls. It’s vital to consider regulations that might influence the scope; for example, industries such as healthcare or finance may have specific cybersecurity testing requirements mandated by laws like HIPAA or GLBA. Additionally, conducting an inventory of vulnerable surfaces is critical; this includes not just software applications and network infrastructure, but also endpoints like employee devices, IoT devices, and third-party services.

By clearly defining the scope, small businesses can ensure that the penetration test comprehensively covers all critical assets and complies with any relevant regulations, thereby maximizing the test’s effectiveness in identifying security vulnerabilities.

Choose What To Test Wisely

You won’t be able to test everything. That’s just a simple fact of managing a business with limited financial resources.

That’s why it’s essential to prioritize testing efforts that will yield the most significant impact on your cybersecurity posture. Learning to pick goals involves identifying the most critical assets and systems that, if compromised, would pose the greatest risk to business operations. You need to strike a balance between comprehensive coverage and the practical limitations of what the business can support in terms of penetration testing.

You don’t want to bite off more than you can chew. While it would be nice to test everything, overextending your testing efforts could lead to unfinished tests and overlooked vulnerabilities. This targeted approach allows for a more in-depth and meaningful analysis of vulnerabilities, leading to actionable insights and a more secure IT environment.

Here are the key areas that most teams should focus on:

  • Web Applications
  • Internal Networks with access to sensitive customer data
  • Mobile applications

Outsource Penetration Testing To A Trusted Provider

Outsourcing penetration testing to a trusted provider is a strategic approach that offers numerous advantages, especially for small businesses that may lack the in-house expertise and resources to conduct comprehensive testing. This practice not only ensures that the testing is performed by professionals with specialized knowledge and experience in identifying and exploiting vulnerabilities but also provides an unbiased external perspective on the business’s cybersecurity posture.

By choosing a reputable and experienced provider, businesses can also ensure that the penetration testing process is aligned with industry best practices and compliance requirements, reducing the risk of regulatory issues. Additionally, an external provider can help in creating a more resilient cybersecurity strategy by offering recommendations based on the latest threat intelligence and security trends. This strategic partnership allows small businesses to focus on their core operations while ensuring their digital assets are protected against evolving cyber threats.

We’ll provide you with some heuristics for choosing a penetration testing provider along with some questions a bit later.

Retest Frequently

Frequent retesting allows businesses to verify that previously identified vulnerabilities have been adequately addressed and to uncover any new weaknesses that may have arisen from changes in their IT environment or external threat landscape. It’s not enough to treat penetration testing as a one-time activity; rather, it should be integrated into the ongoing security strategy, with tests scheduled at regular intervals or in response to significant system updates, new application deployments, or after recovering from a security incident.

For small businesses, the frequency of testing can be balanced with resource availability, aiming for at least an annual test, with more frequent assessments for critical or high-risk components. This approach not only helps in maintaining a robust defense against cyber threats but also supports compliance with industry regulations, which often require evidence of regular testing. By making penetration testing a routine part of their cybersecurity practices, small businesses can significantly enhance their resilience and maintain trust with customers and partners.

Develop A Holistic Security Strategy

Your strategy should encompass not just technical defenses, but also policies, procedures, and training aimed at mitigating a wide range of cyber risks. By adopting a holistic perspective, businesses can ensure that their security measures are layered and multifaceted, covering all aspects of their operations from physical security to employee awareness and beyond.

Here’s how you develop a holistic security strategy, step by step.

  1. Technical Measures: Beyond penetration testing, implement advanced security technologies such as firewalls, encryption, intrusion detection systems, and secure configurations for all hardware and software.
  2. Policies and Procedures: Develop and enforce security policies that guide how data is handled, accessed, and protected. These should include incident response plans, data backup strategies, and access control policies.
  3. Employee Training and Awareness: Since human error is a significant vulnerability, train your team on cybersecurity best practices. This helps create a culture of security awareness throughout the organization.
  4. Physical Security: Ensure physical access to critical infrastructure is secured and monitored. This includes server rooms, network hardware, and employee devices.
  5. Vendor Risk Management: Assess the security practices of third-party vendors and partners, as their vulnerabilities can also affect your business.
  6. Compliance and Legal Considerations: Stay informed about relevant cybersecurity regulations and standards in your industry, ensuring your practices comply with legal requirements.

Document Everything

Documenting the entire penetration testing process is crucial for ensuring accountability, improving security measures over time, and complying with regulatory requirements. A comprehensive documentation strategy should cover every phase of the penetration test, from planning to post-test analysis. Here’s how small businesses can approach this:

1. Pre-Test Planning

Document the primary goals, the scope of the test (what systems, networks, and applications will be tested), and any specific areas of concern. Make sure you include the findings from the initial risk assessment that informed the scope of the test. Outline the testing methods and tools that will be used, including any industry standards or frameworks that will guide the testing process.

2. Testing Phase

Record the specific tests performed, including the date, time, and tester conducting each test. Document all vulnerabilities uncovered during the test, including their severity, the system or application affected, and any immediate observations on potential impacts or remediation strategies.

3. Post-Test Analysis

Analysis of Findings: Provide a detailed analysis of the vulnerabilities discovered, including the risk each poses and recommended actions for remediation.

Remediation Plan: Outline a prioritized plan for addressing identified vulnerabilities, including responsible parties and timelines.

4. Remediation and Follow-Up

Document the actions taken to remediate each vulnerability, including the completion date and any follow-up testing results.

If vulnerabilities were retested, include the outcomes to confirm whether the remediation was successful.

5. Review and Lessons Learned

Summarize the findings and remediation efforts in a review meeting with all relevant stakeholders. Document the discussions, including any decisions made or additional actions required.

Capture insights gained during the process that could improve future penetration testing cycles or broader security practices. Remember that many industries require continuous penetration testing to adhere to regulatory requirements.

6. Compliance and Reporting

For businesses subject to regulatory requirements, ensure documentation meets any specific standards for cybersecurity assessments. Compile all documentation into a final report. This report should be accessible to authorized stakeholders and securely stored for future reference.

How To Choose A Penetration Tester: A Checklist

Relevant Experience and Expertise

  • Has experience in your specific industry.
  • Understands the unique challenges and threats in your sector.


  • Holds industry-recognized certifications (e.g., OSCP, CEH).

Scope of Testing

  • Can perform the specific types of tests you need (internal, external, web application, etc.).

Testing Methodology

  • Follows established methodologies (e.g., OWASP for web apps).

Customized Approach

  • Tailors the penetration test to fit your business’s unique needs.

Communication Skills

  • Offers clear, ongoing communication throughout the testing process.

Detailed Reporting

  • Provides comprehensive reports that include actionable recommendations.

Confidentiality and Data Protection

  • Demonstrates a strong commitment to privacy and data security.

Post-Testing Support

  • Available for follow-up support, including help with remediation and re-testing.

References and Reputation

  • Has positive reviews and testimonials from previous clients.
  • Can provide references upon request.

Penetration Testing Cost Transparency

  • Offers clear pricing upfront with a detailed breakdown of services.

Work With EliteSec To Fulfill Your Penetration Testing Needs

If you need a penetration test, this isn’t the type of thing you can sit on and wait to do later. In fact, companies in certain industries are legally obligated to carry out penetration testing multiple times a year. Frequency is the key to uncovering novel cyber threats.

At EliteSec, we have first-hand experience helping businesses fulfill their cybersecurity obligations. No matter what kind of business operations you need to protect, we’ll be able to advise you on the best course of action. Sit down with us for a free consultation and find out your next steps.

We’re happy to offer you a free 30-minute consultation where we can discuss these and other cybersecurity topics in more depth with you or your company. Book an appointment today!

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