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What Should Small and Medium-Sized Businesses Choose: Red Team or Penetration Testing?

Imagine your business is growing rapidly. You’re constantly adopting new technologies and improving your services. But with this growth comes an increasing number of potential threats that could harm your reputation and finances. For large corporations, this is nothing new, but small and medium-sized businesses (SMBs) often underestimate the scale of risks associated with cyber threats. In fact, according to a study by Verizon, nearly 43% of all cyberattacks are aimed directly at small and medium businesses. What's even more alarming is that most of the companies that fall victim to these attacks are unable to fully recover.


So, why should SMBs pay special attention to cybersecurity? The answer is simple: cybercriminals know that these businesses often lack the resources for robust security measures, yet their data is just as valuable as that of large corporations. Moreover, any data breach or operational downtime could cost you not just money but also the trust of your customers.


One of the key questions business owners face is: which cybersecurity approach should they choose—Penetration Testing or Red Team? Both methodologies aim to improve security, but they differ significantly. Penetration Testing, or pentesting, identifies vulnerabilities in specific components of your system, whereas Red Team focuses on simulating a full-scale attack on the entire organization, mimicking the actions of real hackers.


In this article, we’ll take a closer look at which approach is better suited for your business: Penetration Testing or Red Team.


What is Penetration Testing?


Penetration Testing, or pentesting, is a controlled and authorized attempt to breach a system with the goal of identifying its weaknesses. In simple terms, it’s a simulation of a real-world hacking attack, conducted by certified cybersecurity experts to show where your system is vulnerable. This process helps assess how well your existing security measures perform and whether they’re prepared to fend off actual threats.

For small and medium-sized businesses, where resources for a comprehensive cybersecurity system may be limited, pentesting provides a clear understanding of the real state of your security without incurring excessive costs.


Types of Penetration Testing


Not all penetration tests are the same, and they can vary depending on the scope of the project and the testing goals. Let’s explore a few different techniques used in penetration testing.



Black Box Testing


"Black Box" testing, also known as external penetration testing, assumes that the ethical hacker has minimal or no prior knowledge of the company’s IT infrastructure or security systems. It's called "Black Box" because penetration testers conduct the test "in the dark," meaning they have no information about the company's IT systems or security measures. This simulates a real-world cyberattack where attackers also lack access to the system's internal data. "Black Box" tests are often used to mimic genuine cyberattacks.


The testing starts from outside the network, where the tester has no knowledge of existing security systems or the architecture of the local network. Because the attack is blind, these tests can take the longest to complete.


White Box Testing


"White Box" testing involves the tester having full knowledge of the network infrastructure and existing security systems. While this type of test doesn’t simulate a real external attack, it is one of the most detailed testing methods available.

Although "White Box" testing can be conducted faster due to the transparency of information, for large organizations with multiple applications, it might take several months to obtain comprehensive results.


Gray Box Testing


"Gray Box" testing simulates what might happen if a user with malicious or improper intent gains access to the system. It combines both "Black Box" and "White Box" approaches. In this case, the tester has partial information or limited access to the company’s internal network. Using this knowledge, the tester attempts to find vulnerabilities and gain unauthorized access to other parts of the system, mimicking the actions of an internal threat or a malicious insider.


The time frame for "Gray Box" testing is usually shorter than for "Black Box" but longer than for "White Box," due to the tester's limited knowledge of the network.



Conducting a penetration test is not just a technical measure; it’s a strategic tool that helps small and medium-sized businesses (SMBs) protect their infrastructure from threats that could have devastating consequences. Let’s explore how penetration testing can become a vital element of your company’s cybersecurity and stable growth.


If you're interested in the topic of penetration testing, we recommend reading our article “Penetration Testing as a Key Component of Cybersecurity and Security Standards” where we discuss the main stages of conducting a penetration test in detail. The article also explains how penetration testing helps ensure compliance with international standards such as ISO 27001, and why this is critical for building a robust information security system.


Benefits of Penetration Testing for Small and Medium-Sized Businesses


Cost-Effective Way to Assess Security


There’s a common misconception that cybersecurity is a significant expense only for large corporations, but penetration testing (pentesting) is an affordable and efficient way for small businesses to evaluate their security. Pentesting allows businesses to quickly identify critical vulnerabilities within their infrastructure that could lead to severe incidents. It covers key system components such as network configurations, applications, and authentication systems, enabling businesses to detect weaknesses and prevent them from being exploited by cybercriminals.


For businesses with limited resources, pentesting is a practical tool to enhance the basic level of security and make their infrastructure less susceptible to attacks. Using pentesting as a preventive measure helps reduce risks related to common cyber threats, particularly those arising from outdated systems or misconfigurations.


Ensuring Compliance with Standards


Small and medium-sized businesses that handle sensitive information, such as financial or personal data, often need to comply with international security standards like PCI DSS, GDPR, or ISO/IEC 27001. If you’re a service provider for fintech companies, adhering to these or similar security standards is essential.


  • PCI DSS (Payment Card Industry Data Security Standard) is designed to protect payment card information. It establishes security requirements for organizations that process, transmit, or store cardholder data to safeguard against fraud and cyberattacks.

  • GDPR (General Data Protection Regulation) is the European Union regulation focused on protecting personal data and privacy for EU citizens. It requires companies to ensure a high level of data protection and grants users control over how their data is handled.

  • ISO/IEC 27001 is an international standard for information security management, outlining the requirements for establishing, implementing, maintaining, and continuously improving an information security management system (ISMS) within an organization.


If you’re interested in ISO certification, we recommend reading our article titled "What You Need to Know About the New Changes in ISO 27001:2022." The article explores the latest updates to the ISO 27001 standard, how these changes affect organizations, and how they can help improve information security and meet today’s cybersecurity requirements.


At ESKA, we have extensive expertise in achieving certification under GDPR and ISO/IEC 27001 standards, and we assist other companies in preparing for compliance with these requirements. We support businesses at every step of the process, from analyzing existing security systems to implementing necessary measures and successfully passing audits.


Regular penetration testing is one of the key steps in ensuring compliance with these standards. It allows companies to evaluate the state of their security systems, reduce the risk of data breaches, and meet regulatory requirements. Not only does this help avoid fines, but it also increases customer trust by protecting their data in an ever-evolving cyber threat landscape.


Preventing Attacks


A proactive approach to cybersecurity involves identifying vulnerabilities before malicious actors can exploit them. Penetration testing (pentesting) allows businesses to simulate real attack scenarios on their systems, uncovering weak points that might be overlooked during routine security audits. This is particularly important for companies that rely on critical systems and applications, where even minor vulnerabilities could lead to significant consequences, such as data breaches, operational disruptions, or compromised information.


By conducting regular pentests, companies can also develop effective incident response plans, minimizing the damage from potential attacks. This is a crucial step in maintaining a high level of infrastructure resilience in an ever-evolving threat landscape.


Expert Advice


ESKA recommends incorporating pentesting as a key element of your cybersecurity strategy, with a focus on regular testing to identify emerging vulnerabilities and system flaws. Doing so will not only help maintain compliance with security standards but also protect your business from sophisticated attacks that could result in substantial financial losses and damage to your reputation.


Examples of Situations Where Pentesting is Essential

Let’s explore several real-world scenarios where penetration testing becomes critically important for small and medium-sized businesses (SMBs).


  1. Implementing New Software


    Rolling out new software modules or upgrading existing systems always introduces potential security risks. New features may create vulnerabilities, especially if security wasn’t prioritized during development. When introducing new services, such as online payment processing modules or API integrations, there’s always the possibility of security gaps, including cross-site scripting (XSS), SQL injections, or improper authorization handling.


    Tip: After each significant software update or the implementation of new features, conduct a pentest to identify both existing and newly introduced vulnerabilities.


  2. Preparing for a Security Compliance Audit


    For businesses that must adhere to standards such as PCI DSS, GDPR, or ISO 27001, conducting a pentest is not only a requirement but also a vital step to verify compliance with security measures. Pentesting helps identify weaknesses in time and allows companies to fix them before an audit, reducing the risk of fines and ensuring the security of sensitive data.


    Tip: Use pentesting as a preventive measure before an audit to identify vulnerabilities in advance and minimize the risk of non-compliance with security standards.


  3. Suspected Data Breach


    If there are suspicions of a data breach or unauthorized access, pentesting becomes a crucial tool for identifying points of entry and assessing the scope of the problem. It allows businesses to determine the vulnerabilities that may have been exploited during the attack and strengthen their defenses to prevent future incidents.


    Tip: If you suspect your system has been compromised, a pentest will help you quickly assess the situation, identify weak points, and recommend long-term security measures to prevent future breaches.


While pentesting is highly effective, it has its limitations, as it typically focuses on specific technical aspects of security. For a more comprehensive approach to assessing cybersecurity, especially considering human factors and organizational processes, it is worth considering Red Teaming.


Let’s now delve into the details of Red Teaming — an approach that simulates real cyberattacks and evaluates how well your organization can handle the most serious threats.


What is Red Team?


A Red Team is a specialized group of cybersecurity experts tasked with conducting comprehensive simulated attacks on an organization's IT infrastructure to identify its weaknesses and test the effectiveness of existing security measures. Red Teams operate like real-world attackers, using the same tactics, techniques, and procedures (TTPs) employed by cybercriminals. They simulate attacks at all levels, from network infiltration to the compromise of critical systems, to assess how well the company is protected against actual threats.


Red Teaming is especially important for small and medium-sized businesses (SMBs) because it allows for realistic attack simulations and readiness assessments. Here’s why Red Teaming matters for SMBs:


  • Assessment of Real Threats: The Red Team simulates multi-step attacks, incorporating both technical and social elements, to uncover hidden vulnerabilities.

  • Early Detection of Weaknesses: SMBs often lack the resources for comprehensive cybersecurity. Red Teams help identify vulnerabilities before they are exploited by attackers.

  • Cost Savings: Investing in Red Teaming is far more affordable than addressing the aftermath of a cyberattack.

  • Reputation Protection: By preventing data breaches, Red Teaming helps maintain customer trust.

  • Skill Development: Collaboration between the Red Team and the internal security team (Blue Team) improves the company’s overall defensive strategies and the skills of its personnel.


Red Teaming allows SMBs to enhance cybersecurity without significant investment while boosting customer and partner confidence.


Key Difference Between Red Team and Penetration Testing


While both penetration testing (pentesting) and Red Teaming aim to identify vulnerabilities, the key difference lies in the approach and scope. Pentesting focuses on specific parts of the infrastructure or system to find and exploit technical vulnerabilities. It is a short-term activity with a limited focus.


Red Teaming, on the other hand, is a more comprehensive process that covers the entire cybersecurity landscape of an organization. The goal of the Red Team is to simulate complex, multi-step attacks that combine both technical and social aspects, including targeting employees (e.g., social engineering), physical access, and data exfiltration. Red Teams operate without predefined restrictions, aiming to remain undetected for an extended period.


Stages of Red Team Operations


  1. Reconnaissance and Preparation: In the first stage, the Red Team gathers information about the company from open sources (OSINT) to identify potential entry points. This includes analyzing publicly available information, domains, employees, and potential system vulnerabilities.

  2. Simulating Complex Attacks: After reconnaissance, the team performs real-world attack simulations. This could include phishing campaigns to gather credentials, exploiting software vulnerabilities, or even physical access to facilities. The Red Team uses the same methods as attackers to test the effectiveness of both technical and administrative security measures.

  3. Integration with Blue Team: After the attacks, the Red Team collaborates with the Blue Team (the internal security team) to analyze the results. This phase, known as "Purple Teaming," involves both teams sharing knowledge to improve the overall security strategy. The goal is to help the Blue Team develop more effective defense strategies and improve their ability to detect and respond to real attacks.

  4. Reporting and Recommendations: At the end of the test, the Red Team produces a detailed report analyzing the vulnerabilities discovered and provides recommendations for remediation. This report is essential for the ongoing improvement of the company's cybersecurity posture.


Benefits of Red Teaming for Small and Medium-Sized Businesses (SMBs)


  1. Realistic Testing: Red Teaming gives SMBs the opportunity to test their readiness for real-world threats without putting the business at risk. This helps evaluate the effectiveness of security measures in conditions closely resembling actual attacks.

  2. Identifying Hidden Weaknesses: Red Teams help identify vulnerabilities that may go unnoticed in traditional pentesting or internal audits. This allows businesses to fix weaknesses before attackers can exploit them.

  3. Improving Blue Team Skills: Collaboration between the Red and Blue Teams helps improve the effectiveness of the internal defense team by teaching them how to better respond to sophisticated attacks.

  4. Reducing Security Costs: Investing in Red Teaming can help SMBs avoid significant financial losses resulting from cyberattacks. It’s more cost-effective to invest in preventive measures than to deal with the aftermath of an attack.


When Red Teaming is the Best Option for Your Business


  • Testing Resilience to Advanced Attacks: 

    If your company handles sensitive information or operates in a high-risk industry (finance, healthcare), Red Teaming is essential for testing resilience to complex multi-step attacks.

    • Example: If you provide services to a bank or other institution, attackers could breach their systems through vulnerabilities in your infrastructure. Red Team simulations can help uncover these weaknesses. For instance, the simulation may include simultaneous physical attacks on server rooms and phishing attacks on employees, testing your team’s ability to respond to such threats. Investing in these simulations helps avoid real attacks and significant losses.


  • Identifying Organizational Weaknesses: 

    Companies looking to test not only technical but also organizational aspects of security (e.g., employee readiness for phishing attacks) can benefit from Red Teaming.

    • Example: If you manage an IT company where many employees have access to sensitive information, the Red Team can test your staff’s ability to resist social engineering attacks. For instance, a simulation could involve sending phishing emails to project managers to assess how easily attackers could gain access to critical data through human error.


  • Evaluating Readiness for Real Threats: 

    For businesses seeking to understand how well their cybersecurity aligns with current threats, Red Teaming allows for realistic testing that mimics the tactics used by modern cybercriminals.

    • Example: A medical clinic that stores sensitive patient data could benefit from a Red Team simulation to test the security of its data against cyberattacks. Hackers might try to bypass external security systems through weak employee passwords. This test helps you understand how prepared your system is for real-world threats and how quickly vulnerabilities can be addressed.


Advantages of This Approach


  1. Deep Threat Understanding: Red Teaming allows businesses to assess their real-world security posture and identify threats that might be missed during standard pentests or internal reviews.

  2. Comprehensive Approach: By simulating not only technical but also social and organizational aspects of attacks, Red Teaming helps evaluate cybersecurity at all levels of the business.

  3. Predicting Real Consequences: Red Teaming demonstrates how an attack might unfold, the potential damage to the business, and offers ways to minimize risks.

Red Teaming helps businesses prepare for real-world threats by identifying weaknesses and providing recommendations for improvement. It is a crucial step for any organization aiming to minimize cyber incident risks and ensure long-term resilience to attacks.


Key Differences Between Penetration Testing and Red Teaming


Penetration Testing and Red Teaming are both widely used to assess cybersecurity, but they have significant differences in their approach, scope, and objectives. It is important to understand how these tools can help businesses protect their infrastructure.


1. Objective and Scope

  • Penetration Testing has a more specific goal—to find and exploit vulnerabilities in certain systems or applications. It focuses on identifying technical weaknesses, such as open ports, vulnerable web applications, or misconfigurations. This approach is aimed at discovering known vulnerabilities and helps businesses quickly address risks.

  • Red Teaming, on the other hand, has a broader scope. Its objective is to test the overall resilience of the company to complex, multi-step attacks that include both technical and social aspects. Red Teaming simulates real attacks from various angles (technical, organizational, and physical) to assess how well the company can defend itself against a wide range of threats.


2. Depth and Scale of Testing

  • Penetration Testing typically focuses on specific elements of the infrastructure or applications and has a limited scope. Pentesters may test individual components like websites, servers, or network devices. The depth of testing depends on the chosen area, but overall, pentesting has a clearly defined range.

  • Red Teaming covers the entire IT infrastructure, including the human factor. Red Teams may use advanced social engineering techniques, attempt to gain physical access to facilities, and test employees' responses to cyber threats. In other words, Red Teaming evaluates not only technical security but also organizational and even physical processes.


3. Time and Complexity

  • Penetration Testing is usually completed in a shorter timeframe because it focuses on specific systems or applications. The duration of a pentest can vary from a few days to a few weeks, depending on the complexity of the system and the number of checks. Pentesting is easier to plan and execute because it has defined goals and areas of focus.

  • Red Teaming is a long-term process that can last from several weeks to months. This is due to the comprehensive approach, where the team simulates real-world attacks and tries to remain undetected for an extended period. The complexity is also higher because of the use of more sophisticated and multifaceted attack methods.


4. Cost for the Business

  • Penetration Testing is usually a more affordable option since it involves less work and takes less time. The cost of a pentest depends on the size of the infrastructure being tested, but in general, pentesting is accessible for most businesses, including small and medium-sized ones.

  • Red Teaming is a more expensive option as it requires more time, resources, and experts. However, the cost is justified by the fact that Red Teaming provides a deeper and broader evaluation of a business’s resilience to real-world threats. It is an investment in the long-term security of the company, especially if the business handles sensitive data or operates in high-risk industries.


5. Results and Reporting:

  • Penetration Testing provides a detailed report on the technical vulnerabilities found during the test. The report will specify which vulnerabilities were identified, their severity, and how they can be fixed. This is a specific action plan for technical teams on what needs attention.

  • Red Teaming provides a more comprehensive report that covers not only technical vulnerabilities but also organizational weaknesses. The company will receive information on how employees responded to attacks, which organizational processes need improvement, and where physical or social vulnerabilities exist. The Red Team report helps businesses see the full picture of their cybersecurity and offers recommendations to improve both technical and organizational processes.


Factors to Consider When Choosing Between Red Team and Penetration Testing


The choice between Red Teaming and Penetration Testing depends on several key factors that determine which approach will provide the greatest benefit in terms of assessing cybersecurity. These factors can significantly impact the effectiveness of the selected approach in protecting the business.


1. Company Size and Resources

The size of the company determines the available resources and its maturity level in terms of cybersecurity. Small and medium-sized businesses often have limited budgets and a smaller number of security specialists, making penetration testing a more cost-effective option for identifying targeted vulnerabilities in critical systems.

In contrast, large enterprises with developed infrastructures and numerous critical assets require deeper analysis. Red Teaming allows for a comprehensive assessment, not just of technical security aspects, but also of the organization’s readiness to face complex, multi-layered attacks, including tests involving social engineering and physical access.


2. Regulatory Requirements and Standards (e.g., PCI DSS, GDPR)

Companies operating in regulated industries (financial, healthcare, or government institutions) must consider compliance requirements imposed by standards like PCI DSS, GDPR, or ISO/IEC 27001. To comply with such standards, regular penetration tests are the minimum requirement to quickly detect technical vulnerabilities and ensure regulatory adherence.


However, Red Teaming can provide a broader view of threats and risks that may not always be covered in regulatory assessments. For instance, Red Teaming can assess the effectiveness of incident response processes, overall resilience to social engineering attacks, and identify gaps that may go unnoticed during regular penetration testing.


3. Current Security Maturity Level

Companies with a lower level of security maturity may benefit more from Penetration Testing. This approach allows for the quick identification of obvious technical vulnerabilities that can be addressed with minimal effort. Penetration testing offers a focused assessment of specific systems or applications and requires less time and fewer resources.


On the other hand, Red Teaming is more relevant for companies with a higher level of cybersecurity that want to go beyond identifying technical vulnerabilities and assess their readiness for real-world attacks. Organizations with mature security systems can use Red Teaming to test overall resilience and coordination between different departments (security, IT, operations, etc.).


4. Timeframes and Budget

Penetration Testing is usually completed more quickly and requires fewer resources. It provides a targeted analysis with minimal impact on the organization, allowing testing to be conducted within a few weeks. If a company has a limited budget and needs a quick security assessment, penetration testing is the optimal choice.


Red Teaming, on the other hand, requires more time and resources, as it involves simulating multi-step attacks that can last from several weeks to several months. However, the depth of testing and the ability to obtain a realistic picture of the company’s cyber resilience justify the investment for organizations with higher security requirements.


5. Business Strategic Security Goals

The choice between Penetration Testing and Red Teaming also depends on the company’s strategic goals in the field of cybersecurity. If the primary goal is to identify and fix specific technical vulnerabilities in critical systems, penetration testing will be the most rational choice, providing quick testing and concrete recommendations for addressing issues.


However, if the company aims to build a long-term cybersecurity strategy and assess its readiness for complex, real-world attacks, Red Teaming will provide comprehensive testing of systems, processes, and personnel. This approach is ideal for organizations looking to enhance their resilience not only at the technical level but also at the organizational level, identifying weaknesses in response processes, incident management, and security strategies.


ESKA Case Studies


We have prepared several real-life case studies from ESKA to demonstrate the practical importance of Penetration Testing (pentesting) and Red Team operations. These examples show how timely identification of vulnerabilities and proactive cybersecurity measures can protect businesses from potential threats and minimize risks associated with data breaches and malicious attacks.


1. Penetration Test for an Insurance Company

  • Industry: Insurance

  • Service: Penetration Testing

  • Problem: A large insurance company faced risks of leaking confidential customer data due to potential vulnerabilities in its digital infrastructure. The main concern was the need to ensure the security of their online platforms for customers and employees, particularly in protecting personal and payment information.

  • What was done: A comprehensive penetration test of their system was conducted, including web application testing, API security assessments, and network configuration reviews. Identified vulnerabilities were promptly addressed, significantly enhancing the security level of the system. The testing allowed the company to reduce the risk of data breaches and ensure compliance with industry standards.

  • Case Link: Penetration Test for Insurance Company


2. Penetration Test for a SaaS Platform

  • Industry: SaaS (Software as a Service)

  • Service: Penetration Testing

  • Problem: The SaaS platform encountered potential vulnerabilities within its application that processes sensitive customer data. The company needed to ensure a high level of security, as the platform was integrated with multiple third-party services through APIs, increasing the risk of cyberattacks.

  • What was done: ESKA's team conducted a thorough penetration test, covering the web application and API integrations. Several critical vulnerabilities that could have led to data leaks were discovered. All vulnerabilities were resolved, and recommendations were provided for further security improvements to ensure data protection and reduce the risks of API-related attacks.

  • Case Link: Penetration Test for SaaS Platform


3. Penetration Test for a Startup

  • Industry: Startup

  • Service: Penetration Testing

  • Problem: A tech startup faced challenges in ensuring the security of its new product during the early development stages. The startup team had limited experience in cybersecurity and needed assistance in identifying weak points before launching the product to the market.

  • What was done: A penetration test was conducted to assess the security of the system and the web application. Identified weaknesses included potential threats from vulnerabilities in authentication and misconfigurations. After the test, recommendations for security improvements were provided, helping the startup secure its product and build user trust in the platform.

  • Case Link: Penetration Test for a Startup


FAQ


How do I determine which type of penetration testing is suitable for my organization in 2024?

The choice of penetration testing type depends on several factors, including the size of your organization, the complexity of your IT infrastructure, compliance requirements, and the nature of your business operations. Engaging a cybersecurity expert to assess your specific needs and risks will help determine the most appropriate type of penetration testing for your organization.


What is Red Teaming, and how does it differ from a standard penetration test?

Red Teaming is a comprehensive approach to assessing an organization’s cybersecurity, simulating real-world cyberattacks from various angles (technical, physical, and social). The goal of Red Teaming is to evaluate the organization’s ability to detect and respond to complex, multi-layered attacks. Unlike a standard penetration test, which focuses primarily on technical aspects of a system, Red Teaming covers a wider scope, including physical security and social engineering, providing a deeper analysis.


When should penetration testing be conducted?

The most critical time to conduct penetration testing is before a security breach occurs. In the event of a security incident, testing becomes necessary afterward to verify the effectiveness of implemented measures. Best practices recommend conducting penetration tests during the development phase or before a system is launched into production.


When is the right time to conduct Red Teaming?

Red Teaming is most suitable for organizations with advanced security systems that want to test their readiness for complex and targeted attacks. Ideal times to conduct Red Teaming include after completing major security projects, before compliance audits with international standards, or to assess resilience to targeted attacks during critical business periods.


How often should penetration tests be conducted?

Organizations should plan to conduct security testing at least once a year, along with additional assessments following significant infrastructure changes, before launching new products, or during mergers and acquisitions. Large companies that handle substantial amounts of personal or financial data, or those with strict compliance requirements, should consider conducting more frequent penetration tests to ensure ongoing security.

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