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Offensive Security and the Misconceptions Surrounding Enterprise Penetration Testing

The concept of Offensive Security is often misunderstood by clients who often confuse it with penetration testing, but these two solutions, while both vital, are in fact quite different.

Offensive Security is a popular industry umbrella term for all things pertaining to an organization's strategy surrounding cybersecurity, whereas penetration testing is more singular involving security teams attempting to break into a client’s systems.

At its core Offensive Security is a proactive and adversarial strategy aimed at securing computer systems, networks, and individuals from cyberattacks. Unlike more conventional security which primarily emphasizes reactive measures like software patching and identifying and resolving system vulnerabilities. Offensive security, on the other hand, concentrates on actively searching for attackers and attempting to disable or disrupt their operations before they impact an organization.

Trustwave’s approach to Offensive Security is of use all the tools at its disposal to determine if the client has the tools, techniques and procedures in place to help prevent threat actors from stealing data or gaining entry to its systems. Trustwave is a major provider or enterprise penetration testing,

The size of the client's organization is irrelevant, and a massive cybersecurity budget can be unnecessary because an Offensive Security program is designed to fit your needs and requirements in almost all cases.

Delivering an Offensive Security program for Trustwave is a relatively straight forward procedure. A client can be spun up and start having their security tested in a matter of weeks; current Trustwave clients can go into their Fusion Platform portal and directly schedule a test or scan without having to jump through multiple levels of approvals. Then, once the testing is complete, the client can view the results directly in Fusion.

Let's take a look at what is available through a typical Offensive Security program with Trustwave.

Vulnerability Scanning

Vulnerability scanning is an automated process utilized to detect vulnerabilities in an organization's assets. It involves using specialized software that scans target systems to identify running applications and services and determine if they contain vulnerabilities. This is accomplished by searching for known vulnerabilities specific to a software version and/or sending malicious, but benign, input to the assets.

Organizations can proactively detect and address vulnerabilities by conducting regular vulnerability scans, helping to prevent their exploitation.

Trustwave's Managed Vulnerability Scanning delivers data-driven security insights into IT assets and where they are vulnerable to attack and/or compromise. The release of hundreds of new threats into the wild each month can be a challenge to even the most mature internal cybersecurity teams. MVS is a pragmatic, human-led service where the SpiderLabs MVS team of experts runs vulnerability scans on your behalf. We offer clients a flexible, convenient way to let the experts do the heavy lifting.

Penetration Testing

Penetration testing is a form of Offensive Security where a human-led team assesses an organization's cyber defenses. The primary objective is to firstly identify vulnerabilities and then use those vulnerabilities to gain further access into the environment under test. Human-led penetration tests allow for chaining together of vulnerabilities to create more sophisticated attacks. a. Regular penetration tests aid organizations in mitigating vulnerabilities that are highly susceptible to exploitation by human attackers.

Trustwave is a CREST-certified organization for penetration testing and Simulated Target Attack & Response (STAR) penetration testing. Our global CREST membership demonstrates our investment in training and ensuring that our staff is up-to-date with the latest tools, tactics, and procedures.

Trustwave SpiderLabs handles all penetration testing and is capable of conducting a variety of tests, including internal and external network, application, mobile, Azure, and Amazon Web Services penetration testing.

Red/Blue/Purple Teaming

Red team exercises are similar to penetration tests in that they involve human testers rather than full automation. However, the main distinction is the focus on defensive efficacy penetration. Red team exercises are carried out covertly, exploiting attack chains to gain access and move laterally while trying to evade detection and bypass defensive controls.

Blue and purple team exercises refer to the different levels of collaboration and involvement among participants. For instance, purple team exercises involve direct collaboration between the offensive red and defensive blue teams to determine the state of an organization's security. These exercises aim to simulate real-world attacks, through defined scenarios such as data breaches or ransomware delivery, with specific objectives in mind.

Trustwave's Red Team is comprised of members from more than 16 countries globally. Trustwave conducts over 50 red team engagements each year and over 4,000 manual penetration tests.

Social Engineering 

While numerous tests mentioned earlier concentrate on targeting an organization's IT systems and circumventing digital defenses, it is crucial to acknowledge that cyber threat actors frequently direct their attacks towards the human element rather than exploiting software vulnerabilities.

Social engineering is the practice of manipulating people into breaking company security policy and divulging sensitive information. Malicious actors often employ social engineering tactics to gain access to a business's confidential data. Trustwave SpiderLabs offers a wide range of social engineering services that utilize these tactics to understand where vulnerabilities lie within a company's user base, offering a view into the organization's security posture and helping to prevent an actual compromise.

These cover phishing, spear phishing, vishing (or voice phishing using a telephone instead of email), SMiShing (Text, or SMS phishing), and onsite physical social engineering when testers take advantage of vulnerabilities in an organization's physical environment to walk directly into a facility to compromise sensitive information or technological systems.

Trustwave's bespoke and tailored approach Offensive Security programs allows for organizations to utilize the right services based upon their current and future security maturity goals and investment. Offensive Security is an extremely important part of any security program – Trustwave is here to help design and align your current program to fit risk appetite.