General

Penetration Testing

ResilientX

Penetration testing is a methodical simulated cyberattack against an organization's information systems, performed with the target's consent. The goal is to evaluate the security of IT infrastructures by identifying ways to circumvent defenses.

Penetration tests are designed to be methodical and compliant with agreed-upon rules of engagement. This differentiates ethical, authorized pen testing from malicious and illegal hacking attempts.

Skilled cybersecurity professionals called ethical hackers carry out penetration tests using tools and techniques that mimic the behaviors of real-world attackers. However, rather than causing damage, ethical hackers work to improve security.

Penetration testing involves hiring cybersecurity professionals to simulate real-world attacks against an organization's networks, applications, devices, and employees. By exploiting vulnerabilities, pen testers help uncover security weaknesses before actual cybercriminals and hackers can take advantage of them. Organizations can then fix the problems to strengthen their cyber defenses.

As cyberthreats become more frequent, sophisticated and costly, penetration testing provides an essential layer of proactive security. Read on to learn more about what pen testing entails, its benefits, and how to implement an effective pen testing program

Penetration tests target a wide range of IT assets, including:

  • Networks: Tests network perimeters, connections, firewalls and other defenses. Assesses risks related to remote attackers and insider threats.
  • Web applications: Targets customer-facing apps, backends, APIs and related components. Aims to prevent data loss.
  • Mobile applications: Assesses apps on devices like smartphones and tablets. Important for securing customer data.
  • Cloud environments: Validates security of assets hosted in public, private and hybrid cloud environments.
  • Operational technology: Tests programmable logic controllers (PLCs), supervisory control and data acquisition (SCADA) systems, and other tech underlying infrastructure.
  • Employees: Uses social engineering to assess human vulnerabilities, like susceptibility to phishing and pretexting.

Penetration testing focuses on finding security vulnerabilities that real attackers could exploit to breach systems, gain persistent access, move laterally across the network, escalate privileges, and exfiltrate sensitive data.

Beyond technical controls, penetration tests also assess policies, processes, and personnel preparedness related to cybersecurity, such as incident response plans.

Penetration tests follow a common sequence of steps:

  • Planning: Define scope and rules of engagement. Determine which systems, locations and personnel will be included.
  • Reconnaissance: Gather information on the target by fingerprinting systems, probing defenses, inspecting configurations, etc.
  • Exploitation: Actively exploit vulnerabilities using techniques drawn from MITRE ATT&CK and other frameworks that document real-world adversary behavior.
  • Post-exploitation: Simulate adversaries’ goals like installing backdoors, moving laterally, escalating privileges, stealing data, and cleaning up traces.
  • Reporting: Document all vulnerabilities found, exploits performed, and post-intrusion activities. Provide remediation recommendations.
  • Remediation: Fix security gaps based on risk levels. Retest to validate controls.

Companies can choose black-box testing, where no internal information is provided, or white-box testing, where pen testers get full transparency into systems, networks, etc.

Why Penetration Testing is Important ?

Cyberthreats grow more severe each year. The 2022 Verizon Data Breach Investigations Report analyzed 5,212 breaches and found that ransomware and cyberespionage are leading motives. Financial pretexting and phishing remain prevalent social engineering tactics.

Hackers are also adopting new techniques like triple extortion ransomware, supply chain hijacking, deepfakes for social engineering, and more. The MITRE ATT&CK framework documents over 350 distinct adversarial tactics as of 2022.

Meanwhile, digital transformation expands the enterprise attack surface. Remote work, bring your own device (BYOD) policies, cloud migrations, and increased connectivity through IoT and OT all introduce new vulnerabilities. Attacks on operational technology in particular are rising given its prevalent use in utilities, manufacturing, healthcare, and other critical infrastructure sectors.

This evolving threat landscape makes vulnerability assessments and simple penetration tests inadequate. Today, in-depth penetration testing that mimics advanced persistent threats (APTs) is essential for a proactive cyber defense.

Specific benefits of comprehensive penetration testing include:

  • Testing effectiveness of controls against dynamic cyberthreats, not just known vulnerabilities. Up to 60% of data breaches involve vulnerabilities for which patches were available but not applied. Pen testing helps ensure existing controls are properly configured, not just present.
  • Providing firsthand insight into real-world attacker behaviors that security teams can use to improve detection and response capabilities. Penetration testers leverage the same tools and techniques as threat actors.
  • Uncovering IT infrastructure blind spots and gaps that periodic vulnerability assessments miss. Pen testers look for combinations of subtle issues that attackers could leverage together.
  • Meeting regulatory compliance requirements related to cybersecurity assessments. Tests help demonstrate due diligence.
  • Producing evidence to justify cybersecurity investments to business leaders. Detailed reports can quantify exposure.

Overall, implementing regular penetration testing provides assurance that cyberdefenses are aligned to meet the level of risk an organization faces. Testing also builds organizational muscle memory to deal with real intrusions more smoothly.

Looking for a Continuous Penetration Testing solution ? Book a Demo

Types of Penetration Tests

There are several categories and variants of penetration tests, each designed to assess different IT assets and scenarios:

Network Penetration Testing

Network pen testing targets on-premises and cloud-based networks, servers, endpoints, network devices like routers and firewalls, wireless networks, and related infrastructure. Network tests focus on perimeter defenses as well as insider risks.

Tests are conducted from outside and inside the network perimeter. External testing simulates remote attackers with no internal access or credentials. Internal testing emulates threats from malicious insiders or attackers who have stolen legitimate credentials.

Network penetration testers use techniques like:

  • Port scanning to check for open ports that could enable unauthorized access
  • Packet sniffing to intercept unencrypted traffic that could contain login credentials or sensitive data
  • Vulnerability scanning to detect known software flaws like buffer overflows
  • Exploiting network service vulnerabilities to gain shell access on target systems
  • Crack password hashes via brute force, dictionary, or rainbow table attacks
  • Test firewall rules to see what content is allowed and blocked
  • Denial-of-service attacks to overwhelm bandwidth or resources
  • aMan-in-the-middle attacks to intercept or alter communications

The goal is to penetrate perimeter defenses, move laterally between systems, escalate privileges, and gain access to sensitive data. This simulates multi-stage cyberattacks like advanced persistent threats (APTs).

Web and Mobile Application Penetration Testing

Application pen testing evaluates the security of web-based applications, mobile apps, APIs, backend databases, and related components. Testing aims to uncover risks like:

  • Code vulnerabilities that enable exploits like SQL injections, cross-site scripting (XSS), arbitrary remote code execution, etc.
  • Broken authentication and improper session management that lead to account takeovers
  • Vertical and horizontal privilege escalation flaws
  • Privacy leaks of sensitive data
  • Lack of secure cryptocurrency management
  • Vulnerable components including third-party libraries and dependencies

To test applications, ethical hackers use techniques like:

  • Analyzing source code
  • Intercepting and manipulating traffic
  • Reverse engineering mobile apps
  • Fuzzing inputs by submitting random, unexpected, or malformed data
  • Stealing session cookies
  • Exploiting password reset features
  • Capturing API requests to find authentication flaws
  • Reverse engineering to decompress and decode apps

Ultimately, the goal is to identify application vulnerabilities that could enable loss of data integrity, breach of confidentiality, or denial of availability.

Cloud Penetration Testing

As adoption of infrastructure-, platform-, and software-as-a-service models grows, testing cloud security has become vital. Cloud environments require specialized penetration testing skills, tools, and approaches.

Cloud penetration testers focus on:

  • Misconfigured cloud storage that enables data leaks
  • Intercepting unencrypted data in transit between cloud servers
  • Testing IAM controls and privilege settings
  • Evaluating the security of VMs, containers, serverless and other cloud-native technologies
  • Assessing risks related to sharing cloud accounts across teams and business units
  • Abusing vulnerabilities in APIs and web interfaces used to manage cloud resources
  • Lateral movement between cloud-based systems and on-premises resources

Ultimately, testers aim to breach cloud accounts, infrastructure, and applications while avoiding detection by native security controls. This reveals risks and validates whether security architecture meets best practices.

Infrastructure Penetration Testing

Infrastructure pen testing targets operational technology (OT), Internet of Things (IoT) devices, and embedded systems like those found in:

  • Manufacturing and heavy industry
  • Energy, utilities, and oil and gas
  • Building automation and smart facilities
  • Transportation, aviation, and maritime
  • Government, military, and aerospace

Specialized OT/IoT pen testing evaluates risks related to:

  • Legacy systems with insecure protocols like FTP
  • Unencrypted network traffic exposing proprietary data
  • Devices with hard-coded or stolen credentials
  • Remote access systems like RDP left unsecured
  • SCADA and other control systems accessible from corporate IT networks
  • Safety instrumented systems not properly segregated
  • Lack of monitoring, logging, and security analytics

Infrastructure penetration testers require OT expertise and aim to avoid business disruption while testing. Their goal is to show how adversaries could manipulate physical processes by compromising cyber-physical systems.

Social Engineering as Penetration Testing

Despite technological controls, humans often remain the weakest link. Social engineering tests assess organizational susceptibility to manipulation via:

  • Phishing, vishing, and SMiShing attacks
  • Pretexting scams and baiting tactics
  • Quid pro quo scenarios that weaponize authority
  • Tailgating physical access control
  • Threats that trigger emotional responses
  • Impersonation and disguise to gain trust

The goal is to gain information, unauthorized access, or the cooperation of staff through deception. Results highlight vulnerabilities related to policies, training, and overall security awareness.

Organizations also pair social engineering pen tests with technical ones to model multi-stage cyberattacks – for example, using phishing to gain a foothold on the network before exploiting technical flaws.

Wireless Penetration Testing

Wireless networks and devices—including Wi-Fi, Bluetooth, mobile hotspots, RFID, ZigBee and more—are vulnerable to various attacks, including:

  • Traffic interception due to lack of encryption
  • Cracking weak passwords to access routers and devices
  • SSID spoofing
  • Rogue access points used as an entryway into wired networks
  • Jamming and denial of service (DoS)
  • Evil twin attacks to eavesdrop on connected clients

Wireless pen testing focuses on these types of risks. Testers target wireless clients, access points, routers, backend authentication systems and related infrastructure.

Penetration Testing Standards and Methodologies

Penetration testers follow established methodologies and standards to ensure their work is meticulous, controlled, and compliant. Some common pen testing standards include:

  • OSSTMM: Open Source Security Testing Methodology Manual: The Open Source Security Testing Methodology Manual, widely known as the OSSTMM, is a peer-reviewed manual for security testing and analysis. 
  • Penetration Testing Execution Standard (PTES): Industry guidelines for penetration testing, maintained by the Penetration Testing Framework community. Covers planning, reconnaissance, attack execution and reporting.
  • NIST SP 800-115: Technical guide to penetration testing published by the National Institute of Standards and Technology (NIST). Covers methodology, testing types, and regulations.
  • CREST: Accreditation for pen testers administered by the Council of Registered Ethical Security Testers. CREST certifies individuals and companies for specific penetration testing skills.
  • ISO 27001: Global information security standard published by the International Organization for Standardization (ISO). Provides best practices for penetration tests and ethical hacking.
  • OWASP Testing Guide: Manual for application security testing published by the Open Web Application Security Project (OWASP). Covers web apps, APIs, client-side software, and more.
  • WASAP: Methodology for testing applications created by the Web Application Security Consortium. Focuses on vulnerabilities like injection flaws and improper authentication.

Standards bodies like NIST also catalog common pen testing tools, tactics, and vulnerabilities. MITRE ATT&CK is the most comprehensive framework mapping real-world adversary techniques that pen testers emulate.

By adhering to recognized standards, penetration testers produce high-quality assessments while minimizing business risk. Familiarity with standards also helps IT staff better interpret and utilize test findings.

Rules of Engagement for Ethical Penetration Testing

Penetration testing involves authorized cyberattacks—essentially fakes. However, since testers use real hacking techniques, tests must be carefully scoped and executed to avoid causing damage. Clear rules of engagement help maintain ethical standards.

Typical rules of engagement for penetration tests cover:

  • The specific assets, locations and personnel to be tested. For example, testing may only cover the payments system, not the entire network.
  • The time frame for testing, like outside office hours.
  • Any attacks or objectives that are prohibited, like distributed denial of service (DDoS).
  • The level of network disruption that is permissible. Some downtime may be unavoidable.
  • Required reporting procedures in the event of an actual incident, like an outage, during testing.
  • How results should be documented and communicated. For example, results may need to be revealed gradually to avoid overwhelming clients.
  • Authorization to Social Security numbers, payment card data, protected health information (PHI), and other sensitive data records when required.
  • Responsibility for remediating vulnerabilities found during the test. In most cases, the target organization will handle fixes after the test concludes.
  • Compliance with applicable laws and regulations.
  • Limitations on the use of results. For example, prohibiting disclosure of findings for marketing purposes.
  • Who within each organization should be notified about testing and updated on progress.

Well defined rules of engagement help organizations balance testing effectiveness with overall business risk management. They help set expectations for what will happen during a penetration test.

Why Organizations Should Prioritize Penetration Testing Now

With cyber incidents surging annually, penetration testing provides a critical layer of defense-in-depth. Here are some top reasons to implement comprehensive pen testing:

  • Gain Confidence Security Controls Are Working: Penetration testing provides empirical evidence about organizations’ ability to prevent intrusions, detect anomalies, and respond to incidents. Repeated testing builds confidence security architectures and staff capabilities match the real-world threats. Testing also reveals whether existing tools and controls are properly configured and integrated. For example, tests may show that two-factor authentication stops remote logins but VPNs still permit access. This intelligence allows IT teams to optimize environments.
  • Uncover Gaps Scanners Alone Miss: Automated vulnerability scanning is important but insufficient. Scans only detect known bugs. Penetration testers ascertain whether those bugs are actually exploitable. Testers also uncover logical flaws scanners miss, like multi-stage attacks. This is crucial as hackers focus on chaining together subtle flaws more frequently today. Defenders need to understand compound risk scenarios the way attackers see them.
  • Get Ahead of Threat Actors: Penetration testers replicate tactics research shows actual hackers are adopting currently based on trends in the cybercrime underground. Tests model ransomware, supply chain hijacking, OT system intrusions, and more using TTPs from MITRE ATT&CK and similar knowledge bases. This intelligence allows defenders to get ahead of threats before targeted attacks occur. Tests also build muscle memory for security teams, creating familiarity with newest attack techniques.

Penetration Testing and Compliance Requirements

Many regulations and standards call for periodic penetration testing to help manage cyber risk. These include:

  • Payment Card Industry Data Security Standard (PCI DSS)
  • Health Insurance Portability and Accountability Act (HIPAA)
  • Sarbanes-Oxley Act (SOX)
  • Gramm–Leach–Bliley Act (GLBA)
  • Federal Information Security Management Act (FISMA)
  • North American Electric Reliability Corporation Critical Infrastructure Protection Standards (NERC CIP)

Well-documented penetration tests provide evidence of compliance during audits. Ongoing testing also ensures continued adherence as environments evolve.

Penetration Testing Process and Steps

While individual tests vary based on scope and objectives, penetration tests generally follow these steps:

Penetration Testing Planning

During planning, the penetration testing team coordinates with the client to:

  • Identify which networks, applications, devices, facilities, and personnel to test.
  • Determine type of test: white-box, gray-box, or black-box.
  • Establish rules of engagement covering authorized activities.
  • Define goals and success criteria. For example, breach customer data in under 12 hours without detection.
  • Select tools, techniques, and personnel.
  • Create schedule spanning preparation, execution, reporting and remediation phases.

Reconnaissance

Before attacking systems, the pen testing team gathers detailed intelligence about the target environment, including:

  • Preliminary network topology maps and inventories of assets
  • OS, hardware, and software versions running
  • Exposed services like file sharing, databases, web apps, etc.
  • Entry and exit points of networks along with defenses
  • Technologies used for authentication, encryption, monitoring, etc.
  • Business processes, data flows, and technical dependencies
  • Source code, credentials, or internal documentation depending on test type

Exploitation

With reconnaissance complete, pen testers begin actively exploiting vulnerabilities to achieve set objectives, including:

  • Breach networks via exploits for flaws found during scans
  • Crack password hashes through brute force and dictionary attacks
  • Intercept insecure communications like email, FTP, and other unencrypted traffic
  • Plant backdoors and rootkits on systems to enable persistent access
  • Abuse systems administration tools like PowerShell for privilege escalation
  • Exfiltrate data through covert channels
  • Combine social engineering with technical attacks for multi-stage compromises

Throughout exploitation, pen testers avoid disruption to business operations and preserve access for later activities.

Post-Exploitation

After gaining access, pen testers focus on modeling an attacker's goals like:

  • Moving laterally between systems to spread access
  • Capturing and cracking hashed passwords
  • Monitoring internal network traffic
  • Disabling logging and anti-virus to avoid detection
  • Defacing websites or modifying data to prove impact
  • Covering tracks by deleting bash history, log entries, etc.

Post-exploitation activities demonstrate weaknesses in segmentation, logging, monitoring, and incident response preparedness.

Documentation and Reporting

Penetration testers document all tools, techniques, commands, and outcomes. Evidence proves which vulnerabilities were exploited and repreoducibility. Thorough documentation also simplifies remediation.

Testing concludes with a final report containing:

  • Executive summary for leadership covering major findings, impact, and recommendations
  • Technical details on all vulnerabilities found, exploits performed, and post-intrusion activities
  • Prioritized remediation roadmap with specifics on how to address weaknesses
  • Raw technical evidence like packet captures and log excerpts
  • Appendices with supplementary data for IT staff

Clear, actionable reporting is key so organizations can efficiently remediate issues.

Remediation

Guided by the penetration test report, IT teams:

  • Patch vulnerabilities based on severity ratings
  • Improve processes like patch management where gaps were found
  • Tune intrusion detection rules to strengthen monitoring
  • Reset passwords and close backdoors left by testers
  • Retrain staff on policies and procedures related to findings

Quick remediation is essential for reducing risk. Organizations also schedule new tests to validate fixes.

Key Penetration Testing Tools

Penetration testers leverage a wide range of tools to efficiently find vulnerabilities and automate exploiting them. Here are some of the most important tools:

  • Nmap: Powerful port scanner finds open ports that lead to exploits. Also fingerprints OS versions.
  • Wireshark: Sniffs and analyzes network traffic to intercept credentials and sensitive data.
  • John the Ripper: Cracks password hashes quickly via brute force, dictionary, and other attacks.
  • sqlmap: Automates SQL injection attacks against web applications.
  • Metasploit: Exploit framework containing thousands of pre-written exploits and payloads.
  • Cobalt Strike: Post-exploitation tool for privilege escalation, lateral movement, covert channels, and other threat emulation.
  • Burp Suite: Intercepts and manipulates web traffic to uncover application flaws.
  • OWASP ZAP: Scans web applications for vulnerabilities like injection, XSS, and broken auth.
  • Hashcat: Password recovery tool for cracking complex hashes through brute force.
  • Aircrack-ng: Cracks wireless network keys.
  • Kali Linux: Pen testing-focused Linux distribution with hundreds of built-in tools.

These are just a small sample of the diverse toolset penetration testers apply. Commercial tools like Core Impact also exist alongside open source tools. Automation capabilities continue advancing too.

Penetration Test Report

The end report provides a roadmap for improving security:

Executive Summary

A 2-5 page overview for leadership covers:

  • Scope of testing performed
  • Major findings and vulnerabilities uncovered
  • Risks and potential business impact
  • Prioritized recommendations and next steps

The executive summary focuses on business risk, not technical details. It aims to justify remediation investments.

Technical Report

For IT and security teams, the full technical report presents:

  • Detailed explanations and evidence of all vulnerabilities found
  • All exploits, tools, commands, and methodologies utilized
  • Exact steps performed during network intrusion and post-exploitation
  • Packet captures, log excerpts, and other raw technical data
  • Step-by-step remediation guidance, like recommended patches and configuration changes

The technical report provides actionable insights teams can use to strengthen defenses.

Presentation

Interpreting a lengthy report can be challenging. Many pen testers hold interactive presentations to walk clients through:

  • Sample attacks performed during the test
  • Explanations of unfamiliar tools and techniques
  • Recommendations and next steps for remediation

Presentations provide opportunities for live Q&A with testers. They help contextualize findings for broader internal audiences.

Remediation Roadmap

The roadmap outlines a priority plan for addressing vulnerabilities, including:

  • Quick wins: Simple fixes like patching known flaws or changing passwords. These immediately raise security posture.
  • Short-term projects: Broader configuration and architecture changes that take weeks of planning.
  • Long-term initiatives: Major controls like new firewalls or IAM systems requiring months of implementation.
  • Personnel training: New education for IT, security teams, and end users based on social engineering findings.

A detailed roadmap gives direction for strengthening defenses against techniques used during the pen test. Tracking progress over time shows ROI.

Integrating Penetration Testing into Security Programs

To maximize effectiveness, organizations should integrate penetration tests into broader security programs spanning:

  • Asset Management: Maintain continuously updated inventories of networks, software, and devices so tests cover everything.
  • Vulnerability Management: Combine pen testing with vulnerability scanning for efficient risk assessment of known and unknown flaws.
  • Risk Assessments: Incorporate test findings into ongoing security risk quantification based on likelihood and impact.
  • Incident Response: Use tests to assess and refine intrusion detection, containment, eradication, and recovery capabilities.
  • Threat Modeling: Factor pen testing insights about real-world attacks into proactive threat models that identify top risks.
  • Security Training: Incorporate pen test tactics into awareness training so staff learn to recognize attacks.
  • Policy Review: Assess whether policies like password complexity and BYOD usage may require revision based on test findings.
  • Compliance: Schedule tests to support external and internal audits, gathering evidence to prove security due diligence.
  • With integrated testing, organizations gain multidimensional insights into defenses on an ongoing basis rather than through one-off annual assessments.

Start Building a Penetration Testing Program in 4 Steps

To initiate a new pen testing program, organizations can follow these steps:

  1. Assess Existing Assets and Risks: Catalog all assets, including on-premises and cloud networks, OT, applications, mobile apps, remote access systems, wireless networks, etc. Estimate the business impact and likelihood of compromise for each. This quantifies areas of highest risk to guide test priorities.
  2. Define Testing Scope and Objectives: Determine which assets need live pen testing versus more frequent automated scanning based on risk. Define specific objectives for pen tests like achieving lateral movement or data exfiltration without detection. Consider business constraints and rules of engagement.
  3. Internal and External Pen Testing Resources: Evaluate in-house penetration testing skills and tools versus leveraging an MSSP. Using both internal and external resources provides benefits and avoids overreliance on either. Build relationships with pen testing partners.
  4. Establish Remediation Processes: Implement streamlined processes for acting on pen test findings using change management workflows. Assign risk ratings like critical, high, moderate and low to better prioritize vulnerabilities for remediation.

Ongoing Penetration Testing Is Now Essential

Regular comprehensive penetration testing provides empirical confidence in cyber defenses. Tests identify specific security gaps, improve risk awareness, and enable data-driven prioritization of investments.

By proactively pen testing networks, endpoints, applications, clouds and employees, organizations can protect their most valuable assets and operations from compromise. Penetration testing has become an indispensable component of cyber resilience.

Related Blog Posts
No items found.
Related Blog Posts
No items found.