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Fundamentals

What Is Penetration Testing? A Plain-English Guide

Everything a business owner, CTO or compliance lead needs to know about penetration testing — without the jargon.

Updated October 20263 min readBy the BestPentesting Security Research Team

Penetration testing (also called a pentest or ethical hacking) is an authorised, simulated attack on your systems by security professionals, carried out to find and prove exploitable weaknesses before real attackers do. Unlike an automated scan, a penetration test shows what an attacker could actually achieve — such as reading other customers' data, taking over admin accounts or moving from a laptop to your domain controller.

Why organisations run penetration tests

  • Find real, exploitable risk — including logic flaws scanners can't detect.
  • Meet compliance requirements — PCI DSS, SOC 2, ISO 27001, HIPAA and many regulators expect regular testing. See compliance requirements.
  • Win enterprise deals — customers' security questionnaires routinely ask for a recent third-party pentest report or attestation.
  • Validate security investments — check that your WAF, EDR and monitoring actually detect and stop attacks.
  • Before major releases — test new products and significant changes before attackers do.

Black box, grey box and white box

ApproachWhat testers getBest for
Black boxNothing beyond a target (URL, IP range)Simulating an outside attacker; external perimeter
Grey boxUser accounts, some documentationMost web/API tests — best depth per budget
White boxSource code, architecture, admin accessHigh-assurance applications, crypto, critical logic

Main types of penetration testing

Web application

Authentication, access control, injection, business logic and client-side issues. Our service.

API

REST, GraphQL and gRPC endpoints — authorization (BOLA), mass assignment, rate limits.

Mobile

iOS/Android apps, local storage, certificate pinning, and the APIs behind them.

Network (external / internal)

Exposed services, patching, segmentation and Active Directory attack paths.

Cloud

IAM escalation, storage exposure, Kubernetes and serverless. Our service.

Wireless

Wi-Fi encryption, rogue access points, guest network isolation.

Social engineering

Phishing, vishing and physical intrusion to test people and process.

Red teaming

Objective-based, stealthy, multi-week adversary simulation testing detection and response.

The phases of a penetration test

  1. Scoping & rules of engagementAgree targets, exclusions, test windows, contacts and legal authorisation.
  2. ReconnaissanceMap the attack surface: subdomains, endpoints, technologies, users and exposed services.
  3. Vulnerability discoveryCombine automated tools with manual analysis to identify weaknesses.
  4. ExploitationSafely prove impact — access data, escalate privileges, chain issues together.
  5. Post-exploitationAssess lateral movement, persistence and business impact within agreed limits.
  6. Reporting & debriefExecutive summary, risk-rated findings, reproducible evidence and remediation guidance.
  7. RetestVerify fixes and issue an updated report or attestation.

Standards and methodologies

Reputable penetration testing companies align their work with recognised frameworks:

  • OWASP Web Security Testing Guide (WSTG) and OWASP Top 10 / API Security Top 10 for applications
  • OWASP MASVS / MASTG for mobile applications
  • PTES (Penetration Testing Execution Standard) for overall engagement structure
  • NIST SP 800-115, the technical guide to information security testing and assessment
  • OSSTMM for operational security testing
  • MITRE ATT&CK for mapping red team techniques to real adversary behaviour

How often should you pentest?

At minimum annually and after significant changes — a new product, major feature, infrastructure migration or acquisition. Fast-moving SaaS teams increasingly add lighter, continuous testing between annual deep-dives.

What you receive at the end

A professional engagement delivers a written report with an executive summary, technical findings rated by risk, proof-of-concept evidence, remediation advice, a debrief call and, after retesting, an attestation letter you can share with customers or auditors.

Next: learn how to choose a pentest company or see what a pentest costs.

BestPentesting Security Research Team
Written and technically reviewed by practising penetration testers and SOC analysts. Last reviewed October 2026. See our methodology.

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