Penetration Testing and Red Teaming

Penetration testing and red teaming are both methods of testing an organization’s defensive posture. Each has the end goal of evaluating a company’s weaknesses, but they use varying means to achieve that goal. Penetration testing is often more targeted and less concerned with avoiding defensive measures. Red teaming can be more flexible in its scope and is often used to test detections and defensive measures.

penetration testing vs red teaming

Penetration Testing

Penetration testing simulates an attacker targeting resources from various perspectives. There can be many different types of tests targeting both physical and digital infrastructure. Commonly, tests will be done with a limited scope to test the security controls of specific devices. The scope can often adapt as certain sensitive areas are discovered, and the penetration tester works with the client. Client coordination is vital during penetration testing to ensure proper controls are being tested and the client’s needs are met.

Typically, penetration tests are done with less regard for security controls. This means that the tester is often less concerned with being detected and instead wants to see how security controls perform under attack. Tests can also be done with gradually increasing intensity levels to see how well detections function during a test. This can help the defensive team understand how well their defensive infrastructure works.

Many penetration tests are commonly performed, including external, internal, web application, and physical tests. Each of these will simulate an attacker targeting an organization from a different perspective and targeting different devices. Penetration tests will represent a snapshot of an organization’s security posture, as they are typically reasonably limited on time. Because of this, penetration testing should be done regularly when any significant changes are made to the infrastructure.

Penetration testing is an extremely important phase in security implementation. Organizations should implement it before the release of new products, annually, or when any major infrastructure changes have occurred. Unlike red teaming, penetration testing can be done at lower security maturity levels. Comprehensive penetration testing can also be an effective way to develop and refine a security program in its development.

Red Teaming

Red teaming works similarly to penetration testing and employs many of the same tactics but considerably emphasizes stealth and evasion. A red team operation will involve testers using various techniques to see how much access to an organization they can gain without setting off any detections by the defending team. Seeing how well the defense or blue team detects a persistent threat adds great value.

The scope is often broader during red teaming engagements than during a penetration test. Depending on what the client wants, this can include social engineering, attacking a wide variety of devices, attacks on physical infrastructure, and more. Red team engagements simulate an advanced threat establishing and maintaining a presence in the network, and the techniques are meant to be similar to what an attacker would do without causing any damage or disruptions.

Red team engagements often will last for much longer than a penetration test. The scope and goals can also evolve as weak points are patched up, and coordination with the blue team evolves the target landscape. Both teams will work closely throughout the engagement to find potential problems and remediate them as they are identified. Due to how long red team operations often take, the scope can evolve as changes are made to the network.

Red team operations are better suited for organizations with well-established and mature security teams. A large advantage that these tests have over penetration tests is the ability to test how well the blue team functions, but this benefit may be lost on less mature organizations. Red teaming engagements will also return more value in a more established network than a recently deployed environment, as these are far more likely to have massive, glaring vulnerabilities that are more suited to penetration testing.

Meet Your Security Goals With Blue Goat Cyber

Whatever your organization’s needs may be, Blue Goat can help you get there. Our team is highly experienced in many different types of tests and is comfortable working with teams of varying maturity levels. We can work with you to test anything from pre-release products to mature internal networks. Contact us to schedule a consultation.

Red Teaming and Penetration Testing FAQs

Please schedule a 30-minute Discovery Session with us so we can best understand your objectives.

Yes, penetration testers and red teams can be comprised of the same individuals, albeit employing distinct approaches and techniques for various assessments. While both roles involve evaluating the security of an organization's systems and networks, their primary emphasis and methodologies may differ. Penetration testers typically focus on identifying vulnerabilities and exploiting them to gain unauthorized access, providing a valuable perspective on potential weaknesses. On the other hand, red teams adopt a more comprehensive approach, simulating real-world attacks to test the overall resilience of a system or organization. By assuming the mindset of skilled adversaries, red teams not only attempt to breach security controls, but also assess the organization's incident response and detection capabilities. Consequently, although there is overlap between these roles, the primary distinction lies in the scope, objectives, and overall strategies employed during the testing and assessment process.

Penetration testing and red teaming are both crucial methods for evaluating an organization's defensive posture. While they share the common goal of identifying weaknesses, they employ different approaches to achieve it. In penetration testing, the focus is often on targeted attacks, with less concern for evading defensive measures. This allows testers to assess how security controls perform under attack, and can also involve gradually increasing the intensity to evaluate the efficacy of detection mechanisms.

On the other hand, red teaming takes a more comprehensive and stealthy approach. Similar to penetration testing, it employs various tactics, but the emphasis lies on evading detection. The objective of a red team operation is to simulate the actions of an advanced threat, attempting to gain access to an organization's network without triggering any alarms or raising suspicions. It aims to mimic the techniques employed by real attackers, without causing any damage or disruption.

One significant advantage of red team assessments is their ability to test the effectiveness of the blue team, or the defending security team. This aspect is particularly valuable for organizations with well-established and mature security teams. However, for less mature organizations, this benefit may not be as pronounced.

At Blue Goat, we understand the importance of tailoring our testing services to suit the unique needs of each organization. Our highly experienced team is well-versed in a variety of testing methods and can adapt to work with teams at different stages of maturity. Whether you need to assess pre-release products or evaluate the security of mature internal networks, we have the expertise to assist you in achieving your goals.

A Red Team Assessment, also known as red teaming, functions similarly to penetration testing, employing similar tactics to evaluate an organization's security defenses. However, red teaming places a heightened emphasis on stealth, evasion, and emulating the tactics of real-world malicious actors. The primary objective of a red team assessment is to assess the organization's detection and response capabilities rather than solely focusing on identifying vulnerabilities.

During a red team operation, testers utilize a wide array of techniques to gauge the extent of access they can gain within the organization without triggering any alarms or detections by the defending team. By adopting the mindset of an Advanced Persistent Threat (APT), the red team strives to infiltrate and access sensitive information as quietly as possible, simulating the actions of a real-world attacker seeking to evade detection.

This approach provides invaluable insights into how well the defending or blue team can identify and respond to a persistent threat. By meticulously evaluating the organization's detection and response capabilities, a red team assessment offers a comprehensive assessment of the effectiveness of the existing security measures, enabling the organization to strengthen its defenses and enhance its overall security posture.

Red teaming works similarly to penetration testing and employs many of the same tactics but considerably emphasizes stealth and evasion. A red team operation will involve testers using a wide variety of techniques to see how much access to an organization they can gain without setting off any detections by the defending team. This has the great added value of seeing how well the defense or blue team detects a persistent threat. The scope is often broader during red teaming engagements than during a penetration test. Depending on what the client wants, this can include social engineering, attacking a wide variety of devices, attacks on physical infrastructure, and more. Red team engagements simulate an advanced threat establishing and maintaining a presence in the network, and the techniques are meant to be similar to what an actual attacker would do without causing any damage or disruptions. Red team operations often will last for much longer than a penetration test. The scope and goals can also evolve as weak points are patched up, and coordination with the blue team evolves the target landscape. Both teams will work closely throughout the engagement to find potential problems and remediate them as they are identified. Due to the nature of how long red team operations often take, the scope can evolve as changes are made to the network.

Furthermore, a red team assessment utilizes various methods to achieve its objectives. In addition to the aforementioned social engineering, attacking devices, and targeting physical infrastructure, other techniques may also be employed. These can include wireless attacks, external assessments, and more. The aim is to identify vulnerabilities that align with the goals of the assessment, rather than simply focusing on multiple vulnerabilities. It is important to note that a red team assessment is not suitable for every organization and is best performed by those with mature security programs.

By utilizing these comprehensive methods during a red team assessment, organizations can gain valuable insights into their defense capabilities and identify potential weaknesses that may go unnoticed through traditional penetration testing.

Penetration testing and red teaming are both methods of evaluating an organization's defensive posture, but they differ in their approaches and objectives. While both aim to identify weaknesses, they employ varying means to achieve this goal. Penetration testing often focuses on targeted assessments and is less concerned with evading defensive measures. On the other hand, red teaming allows for greater flexibility in scope and aims to test the effectiveness of an organization's detection and defensive capabilities.

During a penetration test, the simulated attacks simulate an attacker's perspective, targeting various resources from both physical and digital perspectives. These tests typically have a defined scope, focusing on specific devices to assess their security controls. However, as the penetration tester works closely with the client, the scope may adapt to address newly discovered sensitive areas. Client coordination is crucial to ensure that the proper controls are being tested and the client's specific needs are met.

Similarly, red teaming engagements employ many of the tactics used in penetration testing but place a greater emphasis on stealth and evasion. Red team operations involve testers employing various techniques to assess how much access they can gain within an organization without triggering any defensive measures. The primary objective of a red team assessment is to test an organization's defense or blue team's ability to detect and respond to a persistent threat.

Unlike penetration testing, red teaming engagements often have a broader scope. Depending on the client's objectives, these engagements may include social engineering, attacks on various devices, and exploiting physical infrastructure. The goal is to simulate the actions of an advanced threat, mirroring the techniques that an attacker would employ without causing any damage or disruptions.

It's important to note that red team operations are better suited for organizations with well-established and mature security teams. The significant advantage of red teaming lies in its ability to evaluate the effectiveness of the blue team. However, this benefit may be less impactful for less mature organizations. Additionally, red team assessments provide more value in established networks than newly deployed environments, as the latter are more likely to have obvious vulnerabilities better suited for penetration testing.

Penetration testing, as a crucial security measure, aims to simulate an attacker's perspective when targeting resources. This comprehensive process encompasses various tests that assess physical and digital infrastructure. Typically, tests are conducted with a limited scope, specifically focusing on evaluating the security controls of specific devices or areas. However, the scope can be adjusted throughout the testing process as sensitive areas are discovered, ensuring that all necessary controls are thoroughly examined.

During penetration testing, an essential aspect is maintaining effective client coordination. This collaboration between the penetration tester and the client is vital to ensure that the testing meets the client's requirements and expectations. By closely working together, the penetration tester can understand the client's specific needs and tailor the testing accordingly, ensuring that all potential vulnerabilities are adequately evaluated.

Unlike other security assessments, penetration tests prioritize examining the performance of security controls rather than avoiding detection. This approach allows the tester to assess how well the security infrastructure withstands an attack and whether the defensive measures effectively detect and respond to intrusions. Gradually increasing the intensity levels during the test provides valuable insights into the functionality of detection systems, aiding the defensive team in understanding the effectiveness of their overall security posture.

Penetration testing, also known as security testing, should be conducted on a regular basis to ensure the protection of organizations' digital assets. It is generally recommended that all organizations schedule security testing at least once a year. However, it is essential to conduct additional assessments in the event of significant infrastructure changes, prior to important events such as product launches, mergers, or acquisitions.

For organizations with large IT estates, high volumes of personal and financial data processing, or strict compliance requirements, more frequent pen tests are strongly encouraged. Such organizations should consider conducting penetration testing with a higher frequency to continually assess and strengthen their security measures.

To further enhance security practices, organizations can adopt agile pen testing or continuous pen testing. Unlike traditional pen testing, which occurs at specific intervals, agile pen testing integrates regular testing into the software development lifecycle (SDLC). This approach ensures that security assessments are conducted consistently throughout the development process, aligning with the release schedule of new features. By doing so, organizations can proactively address any vulnerabilities and mitigate risks to customers, without significantly impacting product release cycles.

Cloud penetration testing is a specialized and crucial process involving comprehensive security assessments on cloud and hybrid environments. It is crucial to address organizations' shared responsibility challenges while using cloud services. Identifying and addressing vulnerabilities ensures that critical assets are protected and not left exposed to potential threats.

Cloud penetration testing involves simulating real-world attacks to identify and exploit vulnerabilities within the cloud infrastructure, applications, or configurations. It goes beyond traditional security measures by specifically targeting cloud-specific risks and assessing the effectiveness of an organization's security controls in a cloud environment.

The importance of cloud penetration testing lies in its ability to uncover security weaknesses that might be overlooked during regular security audits. As organizations increasingly adopt cloud services, they share the responsibility of ensuring the security of their data and assets with the cloud service provider. This shared responsibility model often poses challenges regarding who is accountable for various security aspects.

Cloud penetration testing not only helps in understanding the level of security provided by the cloud service provider but also provides insights into potential weaknesses within an organization's configurations or applications. By proactively identifying these vulnerabilities, organizations can take necessary steps to mitigate risks and strengthen their security posture.

When choosing a pen test provider, you'll want to consider several important factors to ensure your organization's highest level of cybersecurity.

Selecting the right pen test provider is crucial for your organization's security. It's about identifying vulnerabilities and having a partner who can help you remediate them effectively. To make an informed decision, here's what you should look for:

Expertise and Certifications: One of the key factors to consider is the expertise of the pen testers. Look for providers with a team of experts holding certifications such as CISSP (Certified Information Systems Security Professional), CSSLP (Certified Secure Software Life Cycle Professional), OSWE (Offensive Security Web Expert), OSCP (Offensive Security Certified Professional), CRTE (Certified Red Team Expert), CBBH (Certified Bug Bounty Hunter), CRTL (Certified Red Team Lead), and CARTP (Certified Azure Red Team Professional). These certifications demonstrate a high level of knowledge and competence in the field.

Comprehensive Testing Services: The cybersecurity landscape constantly evolves, and threats are becoming more sophisticated. To stay ahead, you need a provider with expertise and resources to test your systems comprehensively. Look for a pen test provider like Blue Goat Cyber that offers testing across various areas, including internal and external infrastructure, wireless networks, web applications, mobile applications, network builds, and configurations. This ensures a holistic evaluation of your organization's security posture.

Post-Test Care and Guidance: Identifying vulnerabilities is not enough; you need a partner who can help you address them effectively. Consider what happens after the testing phase. A reputable pen test provider should offer comprehensive post-test care, including actionable outputs, prioritized remediation guidance, and strategic security advice. This support is crucial for making long-term improvements to your cybersecurity posture.

Tangible Benefits: By choosing a pen test provider like Blue Goat Cyber, you ensure that you receive a comprehensive evaluation of your security posture. This extends to various areas, including internal and external infrastructure, wireless networks, web and mobile applications, network configurations, and more. The expertise and certifications of their team guarantee a thorough assessment.

We follow a seven phase methodology designed to maximize our efficiency, minimize risk, and provide complete and accurate results. The overarching seven phases of the methodology are:

  1. Planning and Preparation
  2. Reconnaissance / Discovery
  3. Vulnerability Enumeration / Analysis
  4. Initial Exploitation
  5. Expanding Foothold / Post-Exploitation
  6. Cleanup
  7. Report Generation

Blue Goat Cyber employs a comprehensive approach to gather intelligence for a penetration test. We begin by actively seeking out relevant information about the targets. This includes identifying the devices, services, and applications the targets utilize. In addition, Blue Goat Cyber meticulously explores potential valid user accounts and executes various actions to uncover valuable data. By conducting this meticulous information-gathering process, Blue Goat Cyber ensures we comprehensively understand the target's infrastructure and potential vulnerabilities for a successful penetration test.

Agile penetration testing is a proactive and continuous approach to security assessments that focuses on collaborating with developers to identify and resolve potential vulnerabilities throughout the entire software development cycle. Unlike traditional methods, which often involve testing at isolated points in time, agile penetration testing involves integrating regular testing into the software development lifecycle (SDLC).

By integrating security assessments throughout the development process, agile penetration testing helps ensure that every release, whether it involves minor bug fixes or major feature updates, undergoes thorough vetting from a security perspective. This ongoing assessment goes hand-in-hand with the release schedule, allowing for real-time identification and mitigation of vulnerabilities.

The key distinction of agile penetration testing lies in its developer-centric approach. With traditional testing methods, developers may only receive feedback from security assessments infrequently, potentially leaving room for vulnerabilities to go undetected or unresolved. Agile penetration testing, on the other hand, emphasizes close collaboration between security professionals and developers, ensuring that security vulnerabilities are proactively identified and addressed in a timely manner.

Through this collaborative approach, agile penetration testing helps foster a more secure development process by integrating security considerations as an integral part of the overall development cycle. It aligns with agile development principles, promoting iterative and continuous improvement while ensuring that security risks are minimized. By doing so, agile penetration testing aims to deliver products that are more resilient to potential threats and provide customers with a higher level of confidence.

Agile penetration testing, also known as continuous pen testing or agile pen testing, offers numerous advantages for organizations. Organizations can enhance security measures and mitigate risks by integrating regular testing into the software development lifecycle (SDLC) rather than conducting infrequent testing.

One key benefit of agile penetration testing is its alignment with the release schedule. Unlike traditional pen testing, which can disrupt product release cycles, agile pen testing ensures that new software features are thoroughly tested for vulnerabilities without causing delays. This approach enables organizations to balance security and efficiency, as it addresses potential risks in a timely manner and ensures that the final product is secure before it reaches customers.

Furthermore, agile penetration testing reduces the reliance on a potentially time-consuming reconnaissance phase. Instead, adversaries are simulated by conducting testing that mimics their actions. This gives organizations insights into the vulnerabilities that a persistent attacker might exploit, similar to the knowledge an insider might possess. By conducting such grey box testing, organizations can authentically assess their security stance while saving time and resources.

Another advantage of agile pen testing is its ability to identify and address vulnerabilities throughout the entire SDLC. Integrating testing into the development process can identify potential weaknesses early on, preventing them from becoming critical security gaps later. This proactive approach ensures that security measures are not an afterthought but an integral part of the software development process.

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