What's the big deal about penetration testing?

Penetration testing, colloquially referred to as a “pen test,” is an authorized attempt to gain access to a company’s resources without the knowledge of usernames, passwords and other usual mean of access. [1] Essentially, it’s paying someone to hack—or break into—your network. It allows you to understand how effective your privacy and security controls really are, before someone/something malicious breaks into your network and causes irreparable damage.

Penetration testing is designed to test your business’ prevention, detection and response capabilities.

Whether your organization is deploying a new service, meeting compliance mandates or assessing its network weaknesses, penetration testers use the latest tactics, techniques and procedures to emulate what attackers are doing in the real world.

First things first: you need to understand the benefits of penetration testing. Here are a few of the big ones:

• Risk Identification
• Prioritization of remediation efforts
• Validation of internal and/or external security controls
• Satisfies compliance needs, including HIPAA, SEC, NYCRR, PCI 3.x.

Additionally, regulators or cybersecurity experts within your organization will want to understand certain things about your cybersecurity practices. Here are some of the questions pen testing can answer:

• What are my most critical security gaps that could be exploited?
• How would my prevention and detection capabilities stand up to the latest threat tactics?
• What methods would an attacker use to bypass my security controls?
• Are my IT Admins and security personnel making good choices?
• If a user or system is compromised, how will the rest of the network withstand the attacker?

So how does pen testing work?

At eSentire, our pen-testers typically follow a five-step process. Here, we’ll give you a high-level outline of the methodology used to help you understand how penetration testing works.

1. Establish rules of engagement: This is where you work with your pen-testers to help them understand your goals and objectives, including which questions you’re trying to answer (see above). You can also discuss your timeline expectations and reporting requirements.
2. Remote testing appliance configured and deployed: This step is only done if needed.
3. Execution: This is where the action happens, which is why we’ve broken it down into three sub-steps:
   1. Open Network Services Enumeration: Here, your pen-testers will interrogate available network services to determine if there is any additional information that could lead to a compromised network. This could include DNS, SNMP, Net-BIOS and many others.
   2. Open Network Services Exploitation: The pen-testers use the information from step a) to attempt to compromise your network services. Some methods they may try are brute force, authentication bypass and public exploit.
   3. Post Exploitation and Movement: In the last step of execution, the pen-testers identify any vectors that could compromise your wider network of domain infrastructure. The techniques they used demonstrate the potential of an initial compromise.
4. Manual Verification and Prioritization
5. Reporting: Here’s the other big one. In this final step, the pen-testers provide you with an executive summary, a summary file, and of course, their detailed findings.

Because the reporting piece is so critical, we’re going to dive into it a bit more. In your post-pen test report, you can expect an executive summary and a detailed technical report.

The executive summary is created for a high-level perspective. It is targeted towards a non-technical audience, so the language used is not overly complex. The summary consists primarily of a brief description of the results, as well as the findings and recommendations. It lists the scope, approach, findings, high-risk and systemic issues, and what is needed to remedy these issues and reduce the risk of a compromised network.

Like the name suggests, the technical report is targeted towards technical staff and provides detailed findings and recommendations. It details the methodology employed, the positive security aspects identified, the technical findings, a risk rating for each vulnerability exploited, remediation steps and more.

“If you’re performing Penetration Testing infrequently or have commissioned a large scope of work, keep in mind the requirements of the “post-test” phase. Often, the report will describe remediation measures that could take considerable time and money to implement. Avoid the temptation to just file away the reports that specify challenging or time-consuming remediation.” - Gartner

Is it time for a pen test?

Like we mentioned earlier, penetration testing allows you to find the vulnerabilities in your network before someone else does. It’s an important part in understanding where you stand with your cybersecurity practices and how well-equipped you are to withstand future (inevitable) cyber threats and attacks.

eSentire Penetration Tests

eSentire certified security testers perform a myriad of penetration tests on a yearly basis across a variety of industries and organizations of all sizes. Whether an organization is deploying a new service, meeting compliance mandates or assessing network weaknesses, our testers use the latest tactics, techniques and procedures to emulate what attackers are doing in the real world.

Leveraging intelligence from our Managed Detection and Response (MDR) platform which identifies attacks that bypass traditional security controls, we are uniquely equipped to conduct testing that other vendors cannot. Once we achieve the goal, vulnerabilities are prioritized by risk and the eSentire Advisory Services team provides remediation consultation to reduce the potential window of exploitation and avoid regulatory fines.