I like to call them security assessments. A test you can flunk; an assessment tells you where you’re at.

-Dave Chronister founder of Parameter Security

In today's rapidly evolving cybersecurity landscape, penetration testing (pentesting) is a crucial practice for organizations aiming to protect their systems and data. Pentesting involves simulating cyberattacks to identify vulnerabilities in a company’s infrastructure, allowing businesses to fix potential weaknesses before malicious actors can exploit them. But how do you approach getting a pentest, and what should your organization consider? Here’s a step-by-step guide to help you navigate the process.

Why Should Your Organization Get a Pentest?

Pentesting is essential for organizations of all sizes and industries. It provides a proactive approach to cybersecurity by identifying vulnerabilities and offering actionable solutions. Companies should consider scheduling a pentest if they are experiencing any of the following:

• Deployment of new systems or applications

• Significant organizational changes, such as mergers or expansions

• Meeting compliance requirements (e.g., PCI-DSS, HIPAA)

• Preparing for audits or certifications

• Regular cybersecurity maintenance to ensure ongoing protection

In short, a pentest is your best defense against unknown vulnerabilities that could put your business at risk of being compromised.

Common Misconceptions About Pentesting

Many businesses have misconceptions about pentesting when they first approach the process. Some think it's a one-time event or believe that only large enterprises need it. In reality, pentesting should be a continuous part of an organization’s cybersecurity efforts. Even small businesses and startups can be targets for cyberattacks, making it essential to stay vigilant.

Additionally, pentests do not guarantee total security; instead, they highlight risks and provide insights to improve overall security measures.

Preparing for a Pentest

Before reaching out to a pentesting service, companies should take several steps to prepare:

• Identify scope: Determine whether you want to test your entire network, specific applications, or particular security controls.

• Understand your risks: Have an internal discussion to identify the most important assets of the organization.

• Ensure cooperation: Make sure relevant teams are on board and ready to provide necessary information to the pentesters.

  • Relevant teams could include: Infrastructure, networking, application owner, development. and leadership.

• Plan for remediation: Have a plan in place to quickly address vulnerabilities that the pentesters may find.

• Avoid Q4 pentests: The fourth quarter of the year is notorious for being the busiest time of year for companies that do pentests because organizations have waited too long to get their annual assessment done. Try to get pentests scheduled earlier in the year and spread them out if multiple are needed.

Proper preparation will not only streamline the process but also ensure the pentest delivers valuable results.

What Information Should You Provide to Pentesters?

To get the most accurate and comprehensive results, your organization needs to share critical information with the pentesters, including:

• Network architecture details

• System configurations

• Known vulnerabilities or past security incidents

• Specific security policies and procedures This collaboration ensures that the pentesters have a clear understanding of your environment and can deliver actionable insights tailored to your organization's needs.

• A single point of contact for regular and emergency communication.

How to Choose the Right Pentesting Provider

Choosing a pentesting provider can be daunting, but there are several factors to consider to ensure you're making the right decision:

• Certifications and Experience: Look for certifications such as OSCP, CEH, or CREST, but also ask about the provider’s industry experience. This can also include profiles on the individuals that will be performing the assessment.

• Client References: Request client references or case studies to understand their track record.

• Methodology: Ensure they use recognized frameworks like PTES for pentesting in general, OWASP for web applications or NIST for broader networks.

• Communication: A strong pentesting provider should communicate clearly, explaining technical details in a way that stakeholders at all levels can understand. Avoid providers who overpromise or seem to offer too-good-to-be-true results—security is complex, and no single test can guarantee protection.

• Reporting: A sample report will allow organizations to see how the report overall is structured. If a pentest is unwilling to provide one that’s a red flag.

• Pricing: Pentests are expensive. If a company comes in significantly lower than other pentest companies then this is an indication that the company lacks the proper skillset or outsources to a company with cheap labor.

The Pentesting Process: What to Expect

Once you’ve chosen a provider and prepared your organization, the pentest begins. Here’s an overview of what you can expect during the process:

• Initial Scoping: The pentesting team will meet with you to define the scope of the test and identify what will be targeted.

• Rules of Engagement: This ensure that everyone is aligned on the goals, risks, and limitations of the engagement

• Testing Phase: The pentesters will simulate attacks based on the agreed-upon scope. This can include network testing, application testing, or social engineering.

• Reporting: After the test, the pentesters will compile a detailed report outlining the vulnerabilities they discovered, along with recommendations for remediation.

• Debrief: The pentesting team will explain the findings and answer any questions. They may also help prioritize which vulnerabilities to address first and any technical questions on the exploitability of a vulnerability.

Different Types of Pentests: Black-Box, Gray-Box, and White-Box

Not all pentests are the same. Depending on your needs, you might choose between different types:

• Black-Box Testing: The pentesters have no prior knowledge of the environment. This simulates how an outside attacker would approach your systems. This will often take the most time and be the most expensive.

• Gray-Box Testing: The pentesters have limited knowledge, like login credentials or partial access. This allows for a balance between simulating internal and external threats.

• White-Box Testing: The pentesters have full access to system information, source code, and infrastructure. This test is the most thorough but requires significant collaboration. This is the most comprehensive and the most efficient for both time and budget.

Each type offers different insights, and choosing the right one depends on your objectives and current security posture.

Understanding Pentesting Reports

A pentesting report is one of the most important deliverables of the process. It typically includes:

• Detailed vulnerability findings: With severity rankings for each issue.

• Recommendations for fixes: Practical steps your organization can take to address the vulnerabilities.

• Risk analysis: How each vulnerability impacts your overall security.

Your team should use the report as a roadmap to improve security, focusing first on high-severity issues.

What If No Vulnerabilities Are Found?

If a pentest finds no major vulnerabilities, that’s great news! However, it doesn’t mean your company is fully secure forever. Cybersecurity is a continuous process, and as new threats emerge, regular pentests are necessary to stay ahead of potential risks.

Innovative Trends in Pentesting

As cybersecurity threats evolve, so does the practice of pentesting. Organizations should stay aware of trends like:

• Bug Bounty Programs: More companies are adopting crowd-sourced pentesting through ethical hacker communities. These programs are for mature companies that have address findings from several previous pentests. Bug bounties often require some sort of compensation to get value out of the program. If the environment is not in a state of low findings then the organization will be buying out large sums of bounties.

• Automated Pentesting: This is not a pentest. While adding it can help improve security it will have lots of false positives and only catch low hanging fruit. At the time of this blog post, nothing can replace a humans critical thinking in regards to a pentest.

By staying on top of these trends, businesses can ensure their security practices remain effective and up to date.

Conclusion: Why Pentesting is a Must for Every Business

Pentesting provides critical insights into your organization’s security and helps protect against evolving cyber threats. By understanding the process, preparing adequately, and choosing the right provider, businesses can significantly reduce their security risks.

Investing in regular pentests is not just a one-time event; it’s part of a continuous effort to keep your organization secure in a world where cyber threats are always changing.