How to Use Pen Tests to Protect Your Company From Digital Threats

Data breaches, system failures, bugs, and website defacement can seriously harm a company's reputation and profits. Typically, companies realize the importance of auditing their infrastructure, evaluating established interaction patterns, and assessing the business logic of their services only after developing security processes or facing urgent challenges. This maturity often stems from the necessity to ensure product or service security and to meet regulatory requirements.

One effective method for conducting an information security audit is through penetration testing (pen test). Companies can either develop this expertise internally or choose a skilled and trustworthy contractor to perform the tests. The contractor would conduct thorough testing and provide detailed penetration reports, complete with recommendations for safeguarding corporate data.

The latter option, hiring a skilled contractor for penetration testing, is more frequently chosen, particularly by small and medium-sized businesses (SMBs), as it offers considerable savings in both time and money. The service provider outlines all stages of the process, develops a pen testing strategy, and suggests ways to eliminate threats. This approach ensures transparency, with a defined scope for testing, clear results, and compliance with both regulatory and business requirements.

What Is Penetration Testing?

Penetration testing broadly involves evaluating the security of information systems by mimicking the tactics of an actual attacker. However, it is not just about finding vulnerabilities and security gaps. It also includes a thorough examination of the business logic behind services. This means manually analyzing financial transactions and the flow of goods, scrutinizing mobile applications, web forms, etc. Sometimes, it is not the security perimeter that poses the risk but rather the business logic itself. This can inadvertently provide opportunities for an attacker or fraudster with legitimate access to the company's systems to siphon off funds or cause harm in various other ways.

Penetration Testing Methodologies

Let's now explore the diverse methodologies of penetration testing:

Black Box Method

In a black box testing method, the tester has little to no prior knowledge about the target system. They may only have basic information like URLs, IP addresses, or a list of systems and services. This method is primarily used for auditing perimeter security and externally accessible web services, where the tester simulates an external attack with limited initial data.

Gray Box Method

Here, the tester has some knowledge about the system they are testing but lacks admin rights or detailed operational patterns. This methodology is often applied to audit open banking services, mobile applications, and internal infrastructure. The penetration tester operates with a regular user's credentials, requiring them to independently analyze the business logic, conduct reverse engineering, attempt to escalate their privileges, and potentially breach more secure segments like processing centers, databases, or payment services.

White Box Method

In the white box approach, the tester has complete knowledge of the system, including source code, architecture diagrams, and administrative privileges. This method goes beyond just demonstrating hacking skills; it is more about identifying existing defects in software products or business services, understanding the implications of improper product use, exploring potential action vectors that could lead to malfunctions, and pinpointing process shortcomings, such as inadequate controls or regulatory non-compliance.

A unique aspect of pen tests involves social engineering, where testers try to trick company employees into revealing critical data, assessing their awareness of information security. This may include making QR codes as part of social engineering tactics to evaluate employee susceptibility to phishing. Alongside, advanced AI language tools and specialized essay writing services are employed to create convincing phishing messages, making them challenging for even security professionals to detect.

Additionally, the contractor might provide services like controlled DDoS attacks (stress testing) or simulated spam attacks.

How To Implement Penetration Tests

Implementing penetration tests begins with defining specific objectives and the scope of the test, which includes determining the systems, networks, or apps to be examined. Depending on these objectives, a suitable testing methodology is chosen. The next step is selecting the testing team, which can either be an internal group or external experts. Once the testing starts, the team simulates various attacks to identify system vulnerabilities, covering potential weaknesses in software, hardware, and human factors. After the test, analyzing the results is critical to understanding the vulnerabilities and their potential impacts. 

A Non-Disclosure Agreement

A non-disclosure agreement (NDA) is signed with the contractor during a penetration test to ensure confidentiality. In some cases, a contrasting agreement, known as a "disclosure agreement," is also executed. This agreement permits the legitimate disclosure of discovered bugs or zero-day vulnerabilities, allowing for transparent communication of critical security findings under specific conditions.

Pen Test Frequency and Duration

In terms of frequency, it is recommended to run penetration testing after every noticeable change in the infrastructure. How often these changes occur depends on your business processes. Usually, full-fledged pen tests are done every six months or once a year - but agile businesses should consider running continuous pen testing if they are deploying at a faster pace. The rest of the time, after each minor configuration change, you can use scanners. Scans are cheaper and reveal basic problems. On average, the pen test lasts a month, sometimes longer. If they last for several months, it is already red teaming.

Bug Bounty 

One of the methods for carrying out a penetration test is through a bug bounty program. This approach offers extensive coverage as numerous specialists attempt to uncover vulnerabilities in the company's services and products. A key benefit of this method is that it is cost-free until a threat is identified. However, there are drawbacks. A specialist might only report a vulnerability to the extent needed to claim a reward without delving deeper into the analysis. Additionally, there is a risk of vulnerabilities being disclosed before the company can address them, or even specialists may sell the discovered vulnerabilities on the black market if the offered reward is deemed insufficient.

Red Teaming 

For a large or rapidly expanding operation, you may wish to consider a Red Team Assessment. This approach stands out for its complexity, thoroughness, and element of surprise. In such assessments, your information security specialists are kept in the dark about when, where, and on which systems the test attacks will occur. They will not know which logs to monitor or what precisely to look out for, as the testing team will endeavor to conceal their activities, just as an actual attacker would.

Why a Pen Test May Fail

Potential downsides of a pen test can include too much interference from the client, restrictions on specific testing actions (as if to prevent damage), and limiting the scope to a very narrow range of systems for evaluation.

It is crucial to understand that even the most diligent contractor might not uncover critical or high-level vulnerabilities. However, this does not necessarily mean they have underperformed. Often, it may be the customer who has set conditions for the pen test that make it extremely challenging, if not impossible, to identify any vulnerabilities. 

Penetration testing is, by nature, a creative process. When a customer restricts the scope of work or the tools available to the contractor, they may inadvertently hinder the effectiveness of the test. This can lead to receiving a report that does not accurately reflect the actual state of their security, wasting both time and money on the service.

How Not To Run Pen Tests

BAS, an automated system for testing and modeling attacks, along with vulnerability scanners, are tools some might consider sufficient for pen testing. However, this is not entirely accurate. Not all business services can be translated into a machine-readable format, and the verification of business logic has its limitations. Artificial intelligence, while helpful, still falls short of the intelligence and creativity of a human specialist. Therefore, while BAS and scanners are valuable for automating routine checks, they should be integrated as part of a comprehensive penetration testing process rather than being relied upon exclusively.

Pen Testing Stages

From the perspective of the attacking team, penetration testing typically involves these stages:

1. Planning and reconnaissance: Define test scope and goals and gather intelligence on the target system or network to identify vulnerabilities.
2. Scanning: Use static (code analysis) and dynamic (running code analysis) methods to understand the target reactions to intrusion attempts.
3. Gaining access: Exploit vulnerabilities using attacks like SQL injection or cross-site scripting (XSS) to understand the potential damage.
4. Maintaining access: Test if the vulnerability allows for prolonged system access, mimicking persistent threats that aim to steal sensitive data.
5. Analysis: Compile findings into a report detailing exploited vulnerabilities, accessed data, undetected duration in the system, and security recommendations.

How To Choose a Reliable Penetration Testing Provider

When selecting a provider for penetration testing services, it is important to establish a level of trust with the contractor. Key factors to consider include:

• The contractor's overall experience and history in providing these services
• Achievements and awards received by specific individuals, teams, or projects within the contractor's organization; recent involvement in CREST is also a notable indicator
• Certifications held by the contractor's team members, as well as licenses for conducting such activities
• Customer testimonials and recommendations, which may also include anonymous feedback
• The contractor's expertise in particular audit areas, with examples of involvement in complex projects, such as those with high-tech companies or process control systems
• Considering the arrangement of small-scale test tasks, mainly if the contractor is relatively unknown in the market

The availability of qualified penetration testing specialists is limited, so it is crucial to prioritize companies for whom pen testing is a primary service. These companies should have a dedicated team of qualified specialists and a separate project manager to oversee pen tests. Opting for a non-specialized company often leads to outsourcing, resulting in unpredictable outcomes.

If you consistently use the same pen test provider over the years, especially if your infrastructure remains static or undergoes minimal changes, there is a risk that the contractor's specialists might become complacent or overlook certain aspects. To maintain a high level of scrutiny and fresh perspectives, it is advisable to periodically rotate between different contractors.

Best Penetration Testing Services

1. BreachLock

BreachLock's pen testing service offers human-verified results, DevOps fix guidance, robust client support, and a secure portal for retests. It also provides third-party security certification and thorough, compliance-ready reports.

Benefits

• Human-verified results with in-depth fix guidance
• Retest-capable client portal, adding service value
• Delivers third-party security certification and detailed reports for compliance
• Strong client support during and post-testing

Drawbacks

• Somewhat unclear documentation that requires expertise in the field

Clients may prefer BreachLock for its blend of human and tech solutions and focus on detailed, compliance-ready reports.

2. SecureWorks

SecureWorks' penetration testing service is recognized for its comprehensive offerings and high-quality services, which have earned it a strong reputation in the field. They offer personalized solutions and tailor their services to industry-specific standards. While the cost is on the higher side, it is justified by their in-depth expertise and the overall value provided. 

Benefits

• Comprehensive service offerings with strong expertise
• Services are well-tailored for large enterprises
• Focus on long-term regulatory compliance and personalized solutions
• Recognized for high-quality services and strong industry reputation

Drawbacks

• More expensive compared to some lower-cost options

Clients seeking depth in security expertise and comprehensive, enterprise-level service might find SecureWorks a preferable option, especially for long-term, strategic IT security planning for evolving infrastructure.

3. CrowdStrike

CrowdStrike's penetration testing service offers testing of various IT environment components using real-world threat actor tools, derived from CrowdStrike Threat Intelligence. This approach aims to exploit vulnerabilities to assess the risk and impact on an organization.

Benefits

• Utilizes real-world threat actor tools for effective vulnerability assessment
• Focuses on testing different IT environment components comprehensively

Drawbacks

• Focus on larger enterprises

Clients might prefer CrowdStrike for its use of advanced threat intelligence tools and comprehensive testing of diverse IT components, suitable for organizations seeking detailed risk and impact analysis.

Conclusion

Security analysts predict a rise in the demand for penetration testing services, driven by the rapid digitalization of business operations, and growth in telecommunications, online banking, social and government services. As new information technologies are adopted, businesses and institutions increasingly focus on identifying security vulnerabilities to prevent hacks and comply with regulatory requirements.