Pen Test Definition

What is penetration testing?

Penetration testing is an authorized, manual security assessment in which ethical hackers simulate real-world attacks against your systems, networks, or applications to identify and safely exploit vulnerabilities before criminals do. It shows you not just where you are vulnerable, but how an attacker could chain weaknesses together to access sensitive data or disrupt operations.

Why Pen TEst

Why penetration testing matters?

Penetration testing isn’t just a technical exercise – it is one of the most direct ways to understand how much real risk your organization is carrying at any moment. Instead of relying on scanner output or assumptions, it shows how an attacker could actually move through your environment, what they could reach, and how that would impact your business. That insight lets you move beyond “check the box” compliance and invest in the fixes and controls that genuinely lower your likelihood of a breach. At the same time, live attack simulations expose how well your people, processes, and tools stand up under pressure, revealing whether your incident response works when it really counts.

Go beyond compliance checklists

Many regulations require testing, but high-quality tests help you meaningfully reduce breach likelihood instead of just “passing an audit.”

Improve security investments

Findings highlight which fixes and controls most reduce risk so you can prioritize remediation and future budget.

Test incident response

Realistic attack simulations reveal how quickly your team detects, responds, and contains threats.

Validate real risk, not just theoretical issues

Pen tests show how vulnerabilities combine into actual attack paths that threaten data, uptime, and reputation.

Recent Computer Vulnerabilities

Typical Pen Test Methodology

What a penetration test typically includes

A well-executed penetration test follows a structured process designed to uncover and clearly demonstrate real security risk, not just catalog technical flaws. While every engagement is tailored to your environment and objectives, most high‑quality tests include several key phases that ensure coverage, safety, and useful outcomes.

Phase 1

Scoping & objectives

Define what’s in scope, what “success” looks like, and any boundaries for testing so the engagement focuses on the systems and risks that matter most to your organization.

Phase 2

Reconnaissance & mapping

Map your attack surface by identifying assets, technologies, and potential entry points an attacker could see from the outside or within your environment.

Phase 3

Vulnerability identification & exploitation

Use manual techniques and carefully controlled tools to uncover and safely exploit weaknesses, demonstrating how they can be chained into realistic attack paths.

Phase 4

Post‑exploitation & impact

Analyze what an attacker could do with gained access—such as reaching sensitive data, escalating privileges, or moving laterally—and quantify the potential business impact.

Phase 5

Reporting & remediation support

Deliver a prioritized report that translates technical findings into clear business risk, with concrete remediation guidance and optional retesting to verify fixes.

Typical Pen Test Types

Types of penetration tests

Different environments face different kinds of attacks, so there is no one-size-fits-all penetration test. Types of penetration tests are tailored to where your most important assets live -your networks, cloud platforms, applications, or people – so you can focus effort on the areas that, if compromised, would hurt your business the most. By choosing the right mix of test types, you get a clearer picture of how attackers could actually move through your organization.

Network Penetration Testing

Tests internal and external network infrastructure including:

  • Firewalls and network segmentation
  • Routers, switches, and wireless networks
  • Operating systems and services
  • Remote access systems

Web Application Testing

Evaluates custom applications for vulnerabilities like:

  • SQL injection and command injection
  • Cross-site scripting (XSS)
  • Authentication and session flaws
  • Business logic vulnerabilities

Mobile Application Testing

Assesses iOS and Android apps including:

  • Client-side security controls
  • Data storage and encryption
  • API communication security
  • Platform-specific vulnerabilities

Cloud Security Assessment

Tests cloud infrastructure and services across platforms like AWS, Azure, and Google Cloud:

  • Misconfigured storage buckets and databases
  • Identity and Access Management (IAM) weaknesses
  • Insecure APIs and serverless functions
  • Container and Kubernetes security
  • Cross-account access vulnerabilities
  • Compliance with cloud security frameworks

Social Engineering Testing

Evaluates human vulnerabilities through:

  • Phishing email campaigns
  • Phone-based pretexting
  • Physical social engineering
  • USB drop attacks

Physical Security Testing

Tests real-world security controls:

  • Badge cloning and access control bypass
  • Lock picking and physical barriers
  • Social engineering and tailgating
  • Sensitive area access

Pen Test vs Vuln Scan

Real Penetration Testing vs. Vulnerability Scanning

Here’s a critical distinction many don’t understand: most “penetration tests” sold today are actually just automated vulnerability scans with minimal human analysis.

Real Penetration Testing:

  • Human experts simulate actual attack techniques
  • Validates every finding through exploitation
  • Zero or minimal false positives
  • Discovers unknown vulnerabilities
  • Identifies complex attack paths
  • Takes 2-4 weeks
  • Costs $12,000-$100,000+

Vulnerability Scanning:

  • Automated tools check for known vulnerabilities
  • Produces reports with hundreds of findings
  • High false-positive rate
  • Cannot find business logic flaws
  • Misses complex attack chains
  • Takes 1-3 days
  • Costs $2,000-$10,000

Pen Test Snake Oil

How to Spot Scans Masquerading as Penetration Tests

Here’s a critical distinction many don’t understand: most “penetration tests” sold today are actually just automated vulnerability scans with minimal human analysis.

Pricing Red Flags:

  • Quote based only on number of IP addresses, number of web apps, number of pages
  • No in-depth discussion of scope or hands on assessment of workload
  • Prices that seem too good to be true for the work being requested
  • Same price per target regardless of complexity

Process Red Flags:

  • Promise results in less than a week
  • No pre-engagement planning phase
  • Methodology relies on automation for vulnerability discovery.
  • No discussion of rules of engagement, legacy systems, or blackout periods.

Deliverable Red Flags:

  • Reports contain canned output, false positives, or scan policy information
  • High volume of low or informational risk findings (low value)
  • Little to no proof of exploitation
  • Generic remediation advice
  • Basic executive summary

The analogy we use: Testing your security with just automated scans is like testing a bulletproof vest with a squirt gun instead of live ammunition. It might check a box, but it doesn’t reflect real-world threats.

Regulations

Regulations That Require Penetration Testing

Knowing when to run penetration tests is just as important as choosing the right kind of test. Instead of treating them as a one-time project, leading organizations build testing into an ongoing security rhythm that reflects how fast their environments change and how much risk they can afford to carry at any moment. That usually means combining a regular cadence (such as at least annual testing) with event-driven tests after major changes – like new applications, cloud migrations, or acquisitions – so your last assessment is never too out of date to be trusted.

PCI DSS (Payment Card Industry Data Security Standard)

  • Who: Any organization that processes, stores, or transmits credit card data
  • Requirement: Annual penetration testing (11.3)
  • Quarterly ASV scanning also mandated
  • Must test after significant changes
  • Segmentation validation required

FFIEC (Federal Financial Institutions Examination Council)

  • Who: US banks, credit unions, and financial institutions
  • Requirement: Regular penetration testing based on risk assessment
  • Must test internet-facing systems
  • Social engineering testing recommended

SWIFT CSP (Customer Security Programme)

  • Who: Financial institutions using SWIFT network
  • Requirement: Annual penetration testing of SWIFT infrastructure
  • Must cover all SWIFT-connected components

23 NYCRR 500 (New York Cybersecurity Requirements)

  • Who: Financial services companies operating in New York
  • Requirement: Annual penetration testing and bi-annual vulnerability assessments
  • Must be based on risk assessment

HIPAA/HITECH

  • Who: Healthcare providers, health plans, healthcare clearinghouses, and business associates
  • Current: Risk assessments required, penetration testing recommended
  • Proposed (Dec 2024): Annual penetration testing will be mandatory
  • Must test physical and technical controls

FISMA (Federal Information Security Management Act)

  • Who: US federal agencies and contractors
  • Requirement: Annual security testing including penetration testing
  • Must follow NIST SP 800-53 controls

ISO 27001

  • Who: Any organization seeking ISO certification
  • Requirement: Regular testing as part of risk assessment
  • Frequency based on risk analysis

SOC 2

  • Who: Service organizations storing customer data in the cloud
  • Requirement: Testing to validate security controls
  • Frequency determined by auditor based on risk
  • SOC 2

TISAX (Trusted Information Security Assessment Exchange)

  • Who: Automotive industry suppliers
  • Requirement: Penetration testing for high protection needs
  • Must follow VDA ISA guidelines

NIST Cybersecurity Framework

  • Who: Critical infrastructure sectors (voluntary but becoming mandatory)
  • Requirement: Penetration testing as part of “Detect” function
  • Being adopted by various sectors as mandatory

EU NIS2 Directive

  • Who: Essential and important entities in EU (energy, transport, banking, healthcare, digital infrastructure)
  • Requirement: Regular security testing including penetration testing
  • Enforcement begins October 2024

Nevada Gaming Control Board Regulation 5

  • Who: Gaming establishments and online gaming operators in Nevada
  • Requirement: Annual penetration testing of critical systems

Malta Gaming Authority

  • Who: Online gaming operators licensed in Malta
  • Requirement: Penetration testing before launch and periodically

NY DFS Cybersecurity Regulation

  • Who: Insurance companies operating in New York
  • Requirement: Annual penetration testing and bi-annual vulnerability assessments

FERPA (Family Educational Rights and Privacy Act)

  • Who: Educational institutions receiving federal funding
  • Requirement: Security testing recommended for systems containing student records
  • Many institutions require annual testing as best practice

GLBA (Gramm-Leach-Bliley Act)

  • Who: Financial institutions offering consumer financial products/services
  • Requirement: Regular testing as part of information security program

Massachusetts 201 CMR 17.00

  • Who: Any organization storing Massachusetts residents’ personal information
  • Requirement: Regular monitoring and testing of security systems

California IoT Security Law

  • Who: Manufacturers of IoT devices sold in California
  • Requirement: Security testing before product release

Why Choose Netragard for Penetration Testing?

Beyond helping you meet regulatory requirements (PCI, SOC2, FINRA, etc.), our mission is to meaningfully improve your security and prevent breaches. We do that by using the same tools and methods that real threats would use to help you find vulnerabilities before they do. 

Threat Emulation Expertise

Our team consists of experienced security professionals with deep technical knowledge, industry-recognized certifications (OSCP, OSWE, GPEN, CISSP, CRTO, etc.), and real-world hacking experience. Unlike firms that rely on automated scans, we manually assess your environment to uncover vulnerabilities others miss.

Actionable Insights, Not Just Reports

Our penetration testing reports go beyond simply listing vulnerabilities to clearly outline how an attacker could compromise your environment. We provide a step-by-step attack path, so you can visualize how we gained access, and include practical remediation strategies that align with your business operations.

Direct Access to Our Pen Testers

You’ll have direct access to your penetration tester to walk you through their findings, answer your questions, and ensure you understand how to mitigate risks effectively. However, we aim to go beyond that to bridge the gap between red and blue teams, building deeper familiarity with attackers’ mentality and approach.

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