Technology Advisor Blog

Penetration testing (or pen testing for short) is a proactive way to protect your business from cyberattacks. It simulates real-world attacks to identify vulnerabilities before cybercriminals can exploit them. For small businesses, often working with limited security resources, pen testing is a critical tool to uncover hidden risks, meet compliance requirements, and strengthen defenses.

Your business data and customer information need strong protection to maintain trust and meet compliance standards. Modern automated tools make professional security testing both accessible and cost-effective for smaller companies. Through regular testing, you can build a clear roadmap to strengthen your defenses and stay ahead of emerging threats.

Understanding Penetration Testing Basics

Could someone break in? After you’ve put security measures in place, a pen test lets you verify their effectiveness by hiring an ethical hacker to try to get in - so you can fix the gaps before someone with bad intentions finds them.   After you've done the work to secure your network, the best way to find out if a hacker can get in is to pay an ethical hacker to try to get in.  

Pen Test Analogy

Imagine hiring somebody to see if they can break into your building to identify any weak spots in your security. A pen test is not just a scan or checklist, but a hands-on test by an ethical hacker. You can think of it like a home inspector for your home. You may follow best practices for construction and maintenance, but a home inspector will actually look at the pipes and everything to see if it's okay. A pen test is a deep dive into your security.

Best Practices vs. Pen Tests

You can follow best practices like the CIS (Center for Internet Security) Controls, NIST Cybersecurity Framework, security patching, and strong passwords. But when you boil it down, the only way to really know if somebody can get on your network is to ask somebody to try.  CIS Controls lists penetration LAST on the list of things to do to secure your network.  FIRST do the work to secure your network.  THEN test it.

How a Pen Test Works

A thorough pen test starts with scans of your network so security experts can dig in. When we conduct a pen test for a client, we partner with an outside team that doesn't have access to any passwords. We put a device inside the network and do an external and internal scan to see if somebody could get in.

You might assume penetration testing is only for large enterprises with million-dollar cybersecurity budgets. And while it’s true that Fortune 500 companies like John Deere have spent upwards of $1.5 million on full-scale tests, small businesses don’t need to break the bank to benefit from this critical security step. Thanks to advancements in automation and AI, more affordable, right-sized testing options are now available.

At its core, a pen test answers two key questions: Can someone get into your network? And if they do, what damage could they cause? Even a scaled-down version tailored to your environment can provide valuable insights- and could help you avoid a costly breach down the line.

Consider this scenario: A cybercriminal tricks just one employee into clicking a malicious link. If they gain access to that single computer, can they move laterally through your network and reach others? Internal penetration testing helps answer that question. It simulates what could happen after an attacker gets in - revealing hidden vulnerabilities and weak points before a real threat does.

Protecting Your Business Data

Ultimately, the data in your business is the core of your operations. 

Whether it’s sensitive customer information, intellectual property, or operational records, data loss or compromise can be devastating. Here are a few examples of why data protection matters:

• For a nonprofit, your donor list is more than just names and email addresses - it’s your lifeline. It represents years of relationship-building, trust, and financial support. Beyond that, nonprofits often hold sensitive information about the people they serve - data that must be protected to preserve dignity, maintain confidentiality, and comply with ethical and sometimes legal standards. A breach could harm the very communities you're trying to help and erode public trust.

• For a medical office, patient records aren’t just files- they’re protected health information (PHI) governed by HIPAA. A data breach here could result in severe legal consequences, regulatory fines, and loss of patient trust. In a field where confidentiality is paramount, strong data protection is not optional - it’s part of your duty of care.

Whatever the data is, it's at the center of your security plan, which needs to focus on keeping that data safe, intact, and available. That's why conducting a pen test matters. Even if you have strong passwords and follow cybersecurity frameworks, you may have weaknesses that you don't know about. A pen test is a great way to find out how secure you are.

There's no such thing as 100% security, but if you can identify your unknowns, address them, and fix those vulnerabilities, you're going to be in far better shape.

Pen Test Requirements

Sometimes insurance companies or banks require a penetration test because they want to reduce risk. They don’t want to approve coverage or issue a loan, only to have the business suffer a cyberattack right after- putting both the business and the lender’s money at risk.

Penetration testing is an important step for small businesses to understand their cybersecurity risks and protect their most valuable asset: their data.

Small Business Pen Testing Costs and Value

Are you wondering about the cost and value of a penetration test for your small business? Pen testing uses automated tools and human hackers to see if your network can be broken into, revealing weak spots so you can strengthen your security.

Pen Testing Prices for Small Businesses

While a major company like John Deere might spend $1.5 million on a comprehensive package, small businesses can get assessments for a lot less. Penetration testing for small businesses involves dealing with smaller, less complex networks and a smaller number of endpoints.

Why Your Business Might Need a Pen Test

A penetration test (pen test) helps uncover vulnerabilities before attackers do. Here’s why it might be essential for your business:

• Financial and regulatory requirements: Banks, insurance providers, or industry regulators may require a pen test to reduce risk and ensure compliance.

• Client trust and reputation: Demonstrating strong security practices can set you apart. Studies show people are more likely to do business with companies that protect their data.

• Proactive risk management: A pen test is like insurance for your digital assets. It helps you find and fix weaknesses before they become costly problems.

How Pen Testing Differs from Vulnerability Assessments

A pen test is different from a vulnerability assessment, which looks for known vulnerabilities and tests them. The goal of a penetration test is for ethical hackers to actually try to get on your network.

We typically put a device on your network to do the internal penetration test. Imagine if one user clicks on a phishing email. Will a hacker be able to access other systems on your network, or will the attack be contained to just one system?

We also run an external penetration test to see if somebody can get onto the network through your IP address that faces the outside world.

The Importance of Regular Pen Testing

Most cyber attacks are random, with hackers scanning thousands of IP addresses. It's similar to a car thief checking for unlocked cars in a parking lot. The vast majority of cybercrime hits small businesses, as shown in the Verizon Data Breach Incident Report.

We recommend doing pen testing at least annually, but quarterly is even better. For a small business, you have a smaller environment, which means a smaller scope and a more affordable test.

Getting Actionable Results on a Budget

You’ll get actionable results from a pen test - clear insights you can use to build a roadmap for strengthening your network. You don’t have to fix everything at once, but you do need to know what’s at risk. In cybersecurity, “out of sight, out of mind” doesn’t cut it. Just like an annual physical, a pen test helps you spot issues early - so you can address them before they become serious problems.

You can get actionable results on a budget that works for you, lay out a remediation roadmap to cover the highest risk items, and prioritize from there.

Local Business Security Vulnerabilities

As a small business owner, you need to be aware of the potential security vulnerabilities that could put your company at risk. Penetration testing, also known as a pen test, is an important tool for identifying these vulnerabilities before criminals can exploit them. By conducting a pen test, you can uncover weaknesses in your security posture and take steps to address them, reducing the risk of a costly data breach or ransomware attack.

The Threat of Double Extortion

One of the most significant risks facing small businesses today is the threat of double extortion. Imagine this scenario:

• Criminals encrypt your data and demand a ransom payment
• They also threaten to expose sensitive information to your clients or the media if you don't comply
• Even if you have a strong backup system in place, this can result in significant reputational damage and loss of customer trust

Implementing Best Practices

To mitigate these risks, it's essential to follow cybersecurity best practices and implement a comprehensive security framework. Here are some key areas to focus on:

• Ensuring that employees do NOT have full admin rights on their computers, which can allow hackers to install malware and cause significant damage if an employee accidentally clicks on a malicious link
• Restricting the use of personal devices on your network
• Providing regular cybersecurity awareness training to your staff
• Having a business-class firewall in place to protect your network from external threats
• Ensuring that your firewall is properly configured to prevent intruders from gaining access to your network
• Keeping all software up to date
• Using strong passwords and multi-factor authentication

The Consequences of Weak Security

As a small business owner, you may not make national news if you suffer a data breach or ransomware attack, but the consequences can be just as severe. At EKARU, we've seen firsthand the results of weak security practices. Companies that have learned the hard way often come to us for help in building a stronger security plan.

Viewing Security as an Ongoing Process

The key is to view security as an ongoing process, not just a box to check off. Are you facing regulatory requirements such as CMMC, HIPAA, or FTC Safeguards? Take them seriously and implement appropriate security measures. This may involve designating a point person for security within your organization and conducting regular pen tests to identify and address vulnerabilities.

Investing in Smart Security Measures

Ultimately, investing in smart and affordable security measures can provide peace of mind and help you build trust with your customers. Are you a medical office, accounting firm, or manufacturing company? Taking a proactive approach to security is essential in today's digital age. By conducting regular pen tests and implementing best practices, you can reduce the risk of a costly data breach and protect your business for the long term.

Small Business Pen Testing Timeline

When considering penetration testing for your small business, you may wonder what the process entails and how long it takes. As IT and cybersecurity providers for small businesses in the greater Boston area, we typically work with an external team to conduct pen tests.

Reviewing Your Network: The First Step in Planning a Pen Test

Before a penetration test begins, it’s important to understand the overall structure and scope of your environment. This helps define the boundaries of the test and ensures it aligns with your business needs. Key elements to review include:

• Number of users and devices – Helps determine the scale and complexity of the test.

• Network topology and infrastructure – Includes cloud services, on-premises servers, remote access, and internal systems.

• Critical assets and applications – Identify what needs the highest level of protection.

• Third-party integrations – Understand how vendors and partners connect to your network.

• Goals of the test – Are you meeting a compliance requirement? Assessing overall risk? Preparing for insurance or regulatory needs?

A clear understanding of your network is essential for defining test objectives, scope, and priorities.

Conducting the Pen Test

Next, we coordinate with the external team to place a device inside your network. This allows us to run two different scans:

1. An external pen test to determine if a hacker can breach your firewall
2. An internal scan to simulate what happens if someone gains access to your network

Keep in mind, the most common way a hacker infiltrates a network is through an employee accidentally clicking on a malicious link. The internal scan assesses if an attacker can move laterally throughout your network after gaining initial access.

You shouldn't experience any performance impact during the testing phase, which typically lasts a minimum of one to two weeks. The process involves a combination of automated tests and manual testing by human hackers. Once the scans are complete, the outside team analyzes the data to identify any vulnerabilities.

Reviewing the Results

At the end of the testing phase, you receive a detailed report itemizing any problems found. As IT and cybersecurity professionals, we can help you develop a roadmap to strengthen your security based on the report's findings. You may have an internal IT team that can handle the remediation, or you may need assistance with some items. Regardless, it's essential to take action on the report's recommendations and document your actions.

The pen testing report is yours to keep, and you can choose to address the identified issues on your own or engage with our team at Ekaru. We can help translate the technical information in the report into actionable next steps for your business.

Why Pen Testing Matters

Penetration testing is one of the few ways to see your defenses in action and identify areas for improvement. As the saying goes, you can't fix what you don't know is broken. By including pen testing as part of your overall security plan, you can assess the effectiveness of your security safeguards and take proactive steps to protect your business.

We recommend conducting a pen test at least annually, but quarterly testing is ideal. If you're curious about what a pen test might look like for your small business, we're happy to answer any questions and help you determine if it's the right choice for your environment. Feel free to reach out to discuss how penetration testing can enhance your cybersecurity posture.

Protect Your Business with Professional Pen Testing Support

Professional pen testing shows you where hackers might target your business network. Our team helps small businesses set up testing programs that align with their budgets and operational needs.

We guide you through the results and build practical security improvements that make sense for your company. Over the past 20 years, we've worked with local businesses including medical offices, law firms, accounting firms, manufacturers, nonprofits, and more.  We work to get to know you and your technology goals and requirements.  Schedule a free consultation with us to see how pen testing can strengthen your security program and protect your business assets.

Topics: small business, cybersecurity, Cyber Insurance