The Basics of Penetration Testing

Cybersecurity is a critical investment for companies today. As the adage goes, threat actors only have to be right once – and cybersecurity teams have to be right every time. With zero-day exploits, ransomware-as-a-service, and advanced persistent threats, there are more ways than ever to breach networks, and security operations teams are slammed. Security analysts monitor the network to ensure events and incidents are investigated and stopped before expensive breaches impact the organization’s bottom line. Every minute in the SOC counts, and every security investment matters when it comes to mitigating critical security risks.

What can Technology leaders do to shore up defenses proactively for security operations?

Technology leaders can ensure they are minimizing security risks by integrating penetration testing in developer workflows, in the CI/CD pipeline, and in application testing environments. When this early testing doesn’t happen, companies are exposing their data and users to unknown risks in production environments. Managing security testing earlier in test environments is a win-win for everyone involved, but traditional penetration testing vendors cause delays and use out-of-date methods.

A proactive penetration testing strategy – preferably streamlined with one qualified penetration testing as a service (PTaaS) provider – is a strong risk reduction mechanism that can be measured in shorter Mean Times to Discovery (MTTD) and Mean Times to Remediate (MTTR).

But what does that mean? In this blog, we’ll cover the basics of pentesting, how pentests help validate security and establish compliance readiness, and how pentesting helps ensure applications do not cause preventative, unnecessary breach impacts for security operations.

What is Penetration Testing?

Penetration Testing is a type of security testing in which highly skilled human hackers are hired to identify and exploit vulnerabilities in a digital environment. The digital environment may include a Web Application, Network, or any other type of digital asset.

A penetration test is controlled way for security leaders to answer the question, “if we were to experience a cyber-attack, how would it happen?” Another question that a penetration testing exercise answers for security leaders is “how much damage could a hacker cause if they were able to successfully exploit a vulnerability in our system?” A penetration testing report will outline all the findings, including a list of security risks discovered, and remediation guidance to fix the most critical risks to the organization. A penetration testing report explains the hacker’s perspective for a security leader and provides precise steps to proactively mitigate security risks before an impactful security incident occurs.

Why do we use Penetration Testing?

Organizations rely on penetration testing to achieve different objectives that primarily fall within these two main categories:

• Security Validation
• Compliance Testing

Security Validation Pentesting

Security leaders depend on penetration testing services for several security validation purposes that include building customers’ trust, passing vendor assessments, fulfilling contractual obligations, and obtaining security certificates. The overall idea of any use-case for Penetration Testing that falls under the Security Validation umbrella is to confirm that security controls are effective to both internal leadership and outside stakeholders.

Compliance Pentesting

Businesses are also tasked with meeting rigorous compliance requirements by penetration testing systems. PCI DSS, ISO 27001, SOC 2, and GDRP are just a few examples of compliance mandates with pentesting requirements. Penetration testing is not the only security requirement for meeting these compliance mandates. When organizations meet these standards, they also reinforce their brand reputation, save on fines associated with non-compliance, and reduce the stress of compliance audits.

What are the 3 types of Penetration Testing?

Black Box, Gray Box, and White Box are the three types of Penetration Tests. Each pentest type can be differentiated by the level or amount of information that the recipient provides to a human hacker before their pentest.

To break it down, here are their classifications:

Black Box Penetration Test (Outsider’s view)

A black box penetration test is the closest that an organization can get to simulating a real-life cyber-attack. During a Black Box penetration test, the tester is given the bare minimum level of information when it comes to credentials. A black box penetration test aligns best with organizations that have matured security strategies and controls in place. Since less information is given to the penetration testing in the case of a black box test, these engagements can often take longer than the other two types of pentests due to the amount of time an ethical hacker will need to spend researching the organization. Since black box penetration tests are the most similar real-life cyber-attack, the final report will reveal areas of a digital environment that would be exploited by a hacker.

Gray Box Penetration Test

In a gray box penetration test, the penetration tester/human hacker is given slightly more information than they would be given for a black box penetration test; however, the information is still extremely limited. Gray box penetration testing engagements give insight into what a targeted cyber-attack would look like for an organization from an impact perspective without the tester spending too much time researching the organization on their own.

White Box Penetration Test (Insider’s view)

White box penetration tests are the type of penetration tests that give testers the most information to work with prior to conducting the tests. For example, penetration testers are often given internal documents, user & admin credentials, access to source code, etc. Since there is more information given in white box penetration tests, it is an effective way for ethical hackers to target specific concerns within a digital environment and serves as the most comprehensive assessment of your digital assets.

How is Penetration Testing done?

The process of any penetration test can be defined with four simple steps:

1. Scoping
2. Execution
3. Remediation
4. Retesting

Scoping

It is important to always begin with the end-goal in mind before determining the scope of a pen test. Think about it – no organization is going to invest time and money into a penetration test with no objective in place. Every step of the penetration testing process should stem from the desired outcome.
The reality is that every organization has varying motivations for getting a Pentest done, and the scope of penetration tests motivated by compliance will be drastically different than those motivated by security validation objectives. For example, organizations who are simply motivated by obtaining a specific compliance are more likely to have a narrower scope, such as an individual web application or network, and companies motivated by security validation are more likely to desire a broader overview of the security posture of their entire attack surface.

Execution

Penetration tests are executed with specific methodology by highly skilled penetration testers (AKA ethical hackers). Thanks to organizations that have laid out a roadmap for testing for known vulnerabilities like Open Web Application Security Project (OWASP) and National Institute for Standards and Technology (NIST), penetration testers have much of their methodology defined for them before they even begin.
The best Penetration Testing providers are careful to fully utilize the skill and creativity of human hackers by using automation and AI to identify older known vulnerabilities, freeing up the technical practitioners to instead focus on hidden vulnerabilities that technology alone would miss.
Human talent is the costliest resource in the cybersecurity industry, and penetration testing providers that invest in maximizing automation for their testers have an advantage over other options. Human hackers bring value when their time isn’t allocated to manual techniques that could be automated, and/or drafting and formatting reports.

Remediation

Remediation is the process of patching any vulnerabilities that could otherwise be exploited during a cyber-attack if left unpatched. Although remediation was once a time-consuming and tedious process, there are now ways to diminish remediation timelines. Modern and innovative Penetration Testing providers provide detailed, evidence-backed reports with proof-of-concept, screenshots, and specific recommendations to follow during remediation. The less time that a DevOps team or system administrator spends remediating vulnerabilities, the more time that can be spent on revenue-generating projects. Remediating the exploitable vulnerabilities that are discovered during a penetration test is the goal of a penetration testing engagement.

Retesting

Once remediation is complete and all exploitable vulnerabilities have been patched, a retest is initiated. The goal of a retest is to confirm with 100% confidence that the patches implemented during remediation are effective in eliminating the exploitability of any vulnerabilities that were detected. Retesting gives security leaders peace of mind that their customers’ data and their systems are secure and that the report is ready for compliance auditing. Make sure to ask your penetration testing provider if a retest is included in the cost of your penetration test. Retesting is often what causes ‘scope creep,’ as not all penetration testing vendors will retest after the initial finding’s remediation activities are completed. Typically, recommended remediations must be completed before the penetration testing report is ready for auditors, customers, or third-party vendor assessors.

Penetration Testing can be Simple

Organizing a penetration test can feel overwhelming at first, but penetration testing engagements have gotten easier to conduct over the past few years, thanks to new innovations in the security industry. Companies are increasingly replacing traditional penetration testing providers and switching to Penetration Testing as a Service (PTaaS), a hybrid methodology that uses an optimal combination of manual penetration testing with automation and AI. With PTaaS, your pen testing engagements are faster than ever, remediation is accelerated, and providers can cover more ground than ever before in less time.

Spend Less and Save Time with PTaaS from BreachLock

Penetration Testing as a Service from BreachLock offers an effective and efficient risk management solution to significantly minimize the impact of a cybersecurity breach with a lower total cost of ownership (TCO) compared to other penetration testing vendors and alternatives. With BreachLock’s world-class team of in-house ethical hackers and advanced penetration testing technology, you get consistent findings faster and have remediation integrated into the penetration testing lifecycle. This way, you can focus on your business goals without worrying about data breaches.
Start your PTaaS journey with BreachLock and gain efficiency right away:

• Start your next Pentest within 24 hours
• Receive Pentest Reports 50% Faster
• Save 50% on total costs, compared to traditional pentesting options
• Integrate with Slack, Trello, JIRA

Contact us today for a Penetration Testing as a Service discovery call with one of our security experts who can assess your specific needs. We’ll be happy to provide you with a proposal outlining our services. In 24 hours, your first penetration test can begin. Partner with BreachLock today!