How to Plan and Prepare for Penetration Testing
As security technology and threat awareness among organizations improves so do the adversaries who are adopting and relying on new techniques to maximize speed and impact while evading detection.
Ransomware and malware continue to be the method of choice by big game hunting (BGH) cyber criminals, and the increased use of hands-on or "interactive intrusion" techniques is especially alarming. Unlike malware attacks that rely on automated malicious tools and scripts, human-driven intrusions use the creativity and problem-solving abilities of attackers. These individuals can imitate normal user or administrative behaviors, making it challenging to distinguish between legitimate activities and cyber-attacks.
The goal of most security practitioners today is to manage risk at scale. Gaining visibility, reducing the noise, and securing the attack surface across the enterprise requires the right people, processes, and security solutions.
With the use of penetration testing services, organizations can proactively combat these new and evolving threats helping security practitioners identify and validate what is normal and what is potential malicious activity. Penetration testing consists of varied technologies, both human-led and automated, and the use of certified pentesting experts, or ethical hackers, to emulate a cyber-attack against a network and its asset(s). Pentesters will use real-world tactics and techniques like those of attackers with the goal of discovering and exploiting a known or unknown vulnerability before a breach occurs.
This type of proactive offensive security approach requires planning and preparation by security leaders to maximize the effectiveness of penetration testing, including choosing the right security provider to meet your security and business objectives.
The Steps to Successful Penetration Testing
The following steps are necessary to properly prepare and plan for penetration testing, all of which will be outlined in further detail:
Establish team: Determine the security leaders that will be involved in the penetration testing initiative, including establishing a main POC or central organizer. Outline roles and responsibilities and provide clear objectives.
Stakeholders: Identify the key stakeholders and decision-makers. What are their roles and when will their approvals be needed and at what stage of the penetration testing.
Create a project plan: Ensure that a clear project plan is created that outlines the scope of the testing, specific systems and assets to be tested, timeline, objectives, and expected outcomes.
Choose a testing methodology: Select the right testing methodology to fit the scope. Common methodologies include Black Box, White Box, and Gray Box testing. Also consider the specific techniques your organization would like to deploy whether it is social engineering, API Fuzzing, external-facing web app testing, etc.
Support for the security team: Consider what support the security team will need and whether the organization has the right expertise, resources, and budget. Determine whether the project will be handled internally or if an external pentesting service provider is needed. If selecting an external service provider, ask about the type of support and expertise that they offer.
Debrief of Report: Preparing a comprehensive report of the pentesting findings and recommendations for remediation will be important. Debrief with your team, and pentesting service provider if using one, to analyze the findings and potential risk associated with them. Collaborate closely with stakeholders to ensure the results are properly understood and a timeline is agreed upon for timely remediation.
Remediation action steps: Prepare a report of detailed findings and provide clear guidance on the prioritization of vulnerabilities based on severity, identifying action steps to mitigate these risks. Maintain effective communication, accountability, and quick resolution.
Retest and validate: Additional retesting may be needed to validate the effectiveness of the remediation efforts, and they have been successfully addressed. Ensure that no new issues have arisen during the pentesting process.
Preparing for Penetration Testing Services
Understand Your Attack Surface
To understand your attack surface, it is important to have complete visibility of your cyber assets.
There are three main considerations to understanding your attack surface:
1. Visibility of Your Attack Surface: Identify hidden and unmanaged cyber assets
Attackers are increasingly taking advantage of the attack surface as an organization's digital footprint grows. This expanded attack surface makes it easier for bad actors to find weaknesses while making it harder for security practitioners to protect their IT ecosystem. Identifying all cyber assets and potential vulnerabilities can be a tough challenge. Without full visibility into every possible attack vector, assessing and communicating an organization's exposure to risk becomes nearly impossible.
2. Prioritizing Risk: Making decisions based on risk
Keeping track of and evaluating risk without continuous assessments, leave organizations vulnerable. Security leaders need clear visibility into the key factors influencing risk to guide strategic decisions and keep stakeholders informed. By assessing risks regularly, DevSecOps teams gain actionable insights that help strengthen defenses, fix vulnerabilities, and prevent security breaches.
3. Mitigating Risk: Reducing attack surface risk
Security practitioners often find themselves reacting to threats, hindered by limited time and visibility, and without the guidance needed to anticipate risks. A large attack surface requires more than just optimizing threat defense – it demands proactive measure to discover, assess, and address cyber risk before an attacker strikes.
Determine the Scope
When determining the scope of a penetration test, consider the following before testing begins:
1. Identify What to Test: What areas and assets the organizations would like to test? This involves identifying critical systems, applications, networks, or data that could be vulnerable to attacks.
2. Establish Goals: Security teams will also want to consider the business goals for penetration testing, whether it's to focus in on human security levels through phishing techniques, or to test endpoints that can be bypassed, it is important to know where there may be potential weak spots in specific areas or to test the entire infrastructure.
3. Compliance Requirements: Some industries have specific regulations that may dictate what needs to be included in your penetration testing. Having knowledge about which regulations the organizations need to comply with along with testing requirements can help narrow the testing scope.
Security practitioners should be armed with this information as well as essential details such as organizational infrastructure, domains, servers, devices with IP addresses, or authorized user credentials (depending upon the pentesting method), and any exclusions.
What are Some of the Common Assets to Test?
External Assets
Web Applications: The most common external asset(s) that benefits from penetration testing services is web applications. External web app pentesting identifies potential attack paths and mitigates specific vulnerabilities depending on the applications' architecture and technology used. These are often called internet- or public-facing applications that are accessible over the internet. The most common vulnerabilities found are SQL injections, XSS, authentication and/or business logic flaws, credential stuffing, and more.
In addition, penetration testing services for external assets can include, but are not limited to, mobile applications, APIs, Cloud, external networks, IoT, and secure code review.
Internal Assets
Network Infrastructure: The most common penetration testing for internal assets is internal networks and systems. Most security practitioners and organizations assume that internal networks are more secure than external-facing systems, but this is no longer true. The goal of attackers who do gain access to an internal network is to move laterally across systems, escalating privileges, and comprising confidential and sensitive data. The most common vulnerabilities found are misconfigured active directories (ADs), weak passwords or poor authentication, and outdated or unpatched software and systems.
Penetration testing services for internal assets can include but are not limited to, internal applications, APIs and API endpoints, workstations and laptops, Thick Client applications, and testing across all phases of the software development life cycle (SDLC).
In Conclusion
Complying with regulatory mandates has become more and more stringent and new regulations continue to be implemented around the world affecting various industries, including prime targets like the financial, healthcare, and critical infrastructure sectors.
Preparing and planning for penetration testing services is no small feat and there are many questions that will need to be answered and preparation and planning to be done before the testing begins. But there is no doubt that the benefits of penetration testing services are worth the effort to maintain a strong security posture now, tomorrow, and in the future.
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