All You Need to Know about Penetration Testing: Definition, Types, Pros and Cons

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You may be aware of cybersecurity’s importance for your company but also uncertain about where to start. Penetration testing companies offer a range of services to assess your security posture, helping you choose the right fit for your budget and needs.

Definition

A penetration test (pen test) is a legally sanctioned simulated assault carried out on a computer system to appraise its defenses. Penetration testers utilize the same tools, techniques, and methods as adversaries to discover and showcase the commercial ramifications of vulnerabilities within a system.

Penetration tests typically replicate a variety of attacks that could jeopardize a business. They can assess whether a system is resilient enough to withstand attacks from both authorized and unauthorized users, as well as a spectrum of system roles. With the appropriate parameters, a pen test can delve into any facet of a system.

Benefits of Penetration Testing

In a perfect world, software and systems would be built from the ground up with the intention of eradicating critical security weaknesses. A pen test offers valuable revelations regarding how effectively that goal was met. Pen testing can bolster an organization by:

  • Uncovering vulnerabilities within systems
  • Assessing the steadfastness of controls
  • Aiding compliance with data privacy and security regulations (e.g., PCI DSS, HIPAA, GDPR)
  • Furnishing both qualitative and quantitative illustrations of the current security posture, facilitating budget prioritization for management

Pen Tester Access Levels

The extent of access granted to pen testers hinges on the objectives of the pen test. Testers may receive varying degrees of information about, or access to, the target system. The approach can be fixed from the outset, or it can adapt as the testers’ understanding of the system deepens throughout the process. Here’s a breakdown of the three common access levels:

Black Box Testing (Opaque Box)

The pen testing team operates with minimal knowledge regarding the target system’s internal architecture. They mimic real-world attackers by probing for exploitable weaknesses from an external perspective.

Gray Box Testing (Semi-opaque Box)

The team possesses some knowledge, such as credentials for specific accounts. Additionally, they may have information about the system’s internal data structures, codebase, and algorithms. Pen testers might leverage this knowledge to build test cases based on detailed design documents, like architectural diagrams.

White Box Testing (Transparent Box)

Pen testers have full access to systems and related artifacts, including source code, binaries, containers, and potentially even the servers running the system. This approach offers the most comprehensive assessment in the least amount of time.

Pen Testing Phases: Simulating an Attack

Pen testers meticulously mimic real-world attacker strategies by following a structured approach with distinct phases:

Reconnaissance

In this phase, the team gathers as much intel as possible regarding the target system. Public and private sources are fair game, including internet searches, domain registration details, social engineering tactics, non-intrusive network scans, and, in some rare instances, even dumpster diving. This intel helps them map the target’s attack surface and identify potential vulnerabilities. The scope and objectives of the pen test dictate the extent of reconnaissance; it can range from a simple phone call to understand system functionality to a deep dive using various techniques.

Scanning

Here, pen testers leverage specialized tools to meticulously examine the target system or website for weaknesses.

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These weaknesses can include open services, security vulnerabilities in applications, and those stemming from open-source components. The specific tools used depend on the findings from the reconnaissance phase and how the test unfolds.

Gaining Access

Attackers can have various motivations, such as data theft, manipulation, deletion, financial maneuvering, or simply damaging an organization’s reputation. To execute each test scenario, pen testers strategize the most effective tools and techniques to gain access to the system. This might involve exploiting weaknesses like SQL injection or employing methods like malware, social engineering, or others.

Maintaining Access

Once pen testers establish access to the target system, their simulated attack hinges on maintaining that connection long enough to achieve their goals. These goals could involve exfiltrating data, modifying it, or exploiting functionalities to demonstrate the potential impact of a real-world attack.

Pen Testing Types: Covering All Angles

For optimal risk management, a pen testing strategy should be comprehensive, encompassing all critical areas within your environment. Here’s a breakdown of the most common types of pen testing:

Web Application Testing

Pen testers meticulously assess the effectiveness of security controls in web applications. They uncover hidden vulnerabilities, attack patterns, and any potential security gaps that could be exploited to compromise the application.

Mobile Application Testing

This approach combines automated and manual testing techniques to unearth vulnerabilities within mobile application binaries running on the device and the corresponding server-side functionalities. Server-side vulnerabilities can encompass session management issues, cryptographic weaknesses, authentication/authorization problems, and other common web service vulnerabilities.

Network Oenetration Testing

This type of testing identifies security weaknesses ranging from common to critical within an external network and its systems. Experts leverage checklists encompassing test cases for encrypted transport protocols, SSL certificate scoping issues, use of administrative services, and more.

Cloud Penetration Testing

Given the significant differences between cloud and traditional on-premises environments (shared security responsibility between the organization and the cloud provider), cloud pen testing demands a specialized skillset. This testing meticulously examines various aspects of the cloud environment, such as configurations, APIs, databases, encryption, storage, and security controls.

Container Penetration Testing

Containers obtained from Docker often harbor vulnerabilities that can be exploited at scale. Misconfiguration is another common risk associated with containers and their surroundings. Expert pen testing can effectively uncover both of these risks.

Embedded Device (IoT) Penetration Testing

Embedded devices and Internet of Things (IoT) devices like medical equipment, automobiles, smart appliances, industrial control systems, and wearables have unique software testing requirements due to factors like extended lifespans, remote locations, power limitations, and regulatory considerations. Experts conduct thorough communication analysis alongside client/server analysis to pinpoint vulnerabilities most critical to the specific use case.

Mobile Device Penetration Testing

Similar to mobile application testing, this approach utilizes both automated and manual techniques to identify vulnerabilities within application binaries running on mobile devices and the corresponding server-side functionalities. Application binary vulnerabilities can include authentication/authorization issues, client-side trust weaknesses, misconfigured security controls, and problems stemming from cross-platform development frameworks. Server-side vulnerabilities can encompass session management issues, cryptographic weaknesses, authentication/authorization problems, and other common web service vulnerabilities.

API Penetration Testing

This type of testing leverages both automated and manual techniques to cover the OWASP API Security Top 10 list. Some of the vulnerabilities and security risks pen testers target include broken object-level authorization, user authentication flaws, excessive data exposure, lack of resources/rate limiting, and more.

CI/CD Pipeline Penetration Testing

Modern DevSecOps practices integrate automated and intelligent code scanning tools into the CI/CD pipeline. Beyond static tools that identify known vulnerabilities, automated pen testing tools can also be integrated into the pipeline to simulate attacker tactics that could compromise application security. Automated CI/CD pen testing can unearth hidden vulnerabilities and attack patterns that static code scanning might miss.

Pen Testing: Summarizing Pros and Cons

As cyberattacks rise in both frequency and severity, organizations increasingly seek ways to assess their security posture.

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Regulations like PCI DSS and HIPAA even mandate periodic pen testing for compliance. Here’s a balanced view of pen testing’s advantages and drawbacks:

Pros are the following:

Uncovers Weaknesses in Existing Security Measures

Pen testing goes beyond light-weight vulnerability assessments by exposing weaknesses in current security practices like automated tools, configuration standards, code reviews, and architectural analysis.

Identifies a Wide Range of Vulnerabilities

Pen testing can reveal both known and unknown software flaws and security weaknesses, including minor ones that might go unnoticed but could be exploited as part of a complex attack.

Simulates Real-world Attacks

Pen testers mimic real-world attacker behavior, providing a realistic assessment of how a system would fare against a determined adversary.

Cons include:

Resource-intensive and Costly

Pen testing requires significant time and effort from skilled professionals, making it a costly endeavor.

Limited Prevention of Bugs and Flaws

Pen testing doesn’t guarantee the complete eradication of bugs and flaws from reaching production environments.

Conclusion

In conclusion, pen testing offers a valuable method for organizations to assess their security posture by simulating real-world attacks and uncovering vulnerabilities across various systems. While it requires investment and may not prevent all flaws, pen testing provides crucial insights for prioritizing security improvements and achieving a more robust defense.