▣ PENTEST / FIELD GUIDE
Methodology / Technical guide

One house.
One safe.
Five testing phases.

Learn penetration testing through an authorized burglary simulation: inspect the house, test an entry, map the rooms, cross permission boundaries, and explain the route toward the safe.

Start with Recon →

5 PHASES   /   COMMAND EXAMPLES   /   TOOL REFERENCES

Interactive briefing / 5 steps

Watch the engagement unfold.

USE ← → KEYS WHEN THE WALKTHROUGH IS FOCUSED
Phase 01 / 05

Recon

Inspect the house from outside

Check doors, windows, and vents, then identify the services they represent. An open entry point is not automatically an exploitable weakness.

Explore Recon →
Assessor checking doors, windows and vents of the houseASSESSORINNER ROOMSRESTRICTED AREASAFEENTRYINTERNAL NETWORKDoors / windows / vents = service entry points

Inspect doors, windows and vents

Discover exposed services
01 / 05

THE FLOW CAN LOOP: INTERNAL DISCOVERY MAY REVEAL NEW EXPLOITATION AND ESCALATION OPPORTUNITIES.

The common story / Metaphor key

The safe is the objective. The house is the system.

The assessor simulates a burglar with the homeowner’s authorization. The goal is to explain which security boundaries fail and what access those failures actually enable.

Explore the house metaphor →
01 / Workflow

A connected process, not a rigid checklist.

Recon informs validation. Initial access changes what you can observe. Internal discovery and privilege escalation often repeat as new paths emerge. Collect evidence and draft findings throughout the engagement.

01
PHASE / 01

Recon

Identify in-scope assets, reachable services, and application entry points before selecting a test.

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02
PHASE / 02

Exploit

Validate a specific weakness with a controlled test and show the minimum impact needed to demonstrate the finding.

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03
PHASE / 03

Internal Recon

After initial access—or from an agreed internal starting point—map reachable hosts, identities, and trust relationships.

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04
PHASE / 04

Privilege Escalation

Determine whether the current identity can obtain higher privileges through misconfiguration or a validated vulnerability.

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05
PHASE / 05

Reporting

Translate the observed attack path into clear technical evidence, business impact, and practical remediation.

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02 / Before you begin

Define the engagement.

Agree on authorization, target boundaries, credentials, testing windows, stop conditions, and how evidence will be handled. Internal tests may begin with an existing foothold; not every engagement requires exploitation.

One question per phase

  1. What is exposed?
  2. Can a weakness be demonstrated?
  3. What becomes reachable from here?
  4. Can this identity cross a privilege boundary?
  5. What should the organization fix, and why?
03 / Reading the examples

Commands with context.

All output is illustrative, not captured from a real assessment. The 192.0.2.0/24 network and example.test names are placeholders. Use an authorized lab and substitute approved targets. Tools and operating systems can produce different output.

Evidence follows the entire path

Preserve timestamps, target, test identity, request or command, observed response, and a concise explanation. Redact credentials and retain only the data needed to substantiate the finding.

Close the loop

Remove test artifacts, document changes, communicate urgent findings, and retest the original boundary after remediation. Reporting should connect technical weaknesses to demonstrated outcomes.

Methodology / Compare

Penetration Testing vs. Red Teaming

Both use authorized adversarial techniques. The key distinction is what the engagement is designed to learn—not simply which tools it uses.

DimensionPenetration TestingRed Teaming
Primary questionWhich weaknesses are exploitable, and what impact do they enable?Can an adversary achieve an agreed objective, and can defenders detect and respond?
ScopeUsually defined systems, applications, networks, or configurations.Often an objective-driven scenario across multiple approved attack surfaces.
ApproachPrioritizes identifying and validating weaknesses within the agreed scope.Emulates selected adversary behaviors and chains techniques toward the objective.
Defender awarenessCommonly coordinated with system owners; stealth is optional.May limit defender awareness to assess detection and response. Some exercises are collaborative.
Success measuresEvidence quality, demonstrated impact, coverage, and useful remediation.Objective outcomes, prevention and detection gaps, and response effectiveness.
DeliverablesValidated findings, reproduction steps, fixes, and retest results.Attack narrative, objective results, defensive observations, and improvement priorities.

Penetration test example

Assess an internal network and validate whether an exposed service and weak permissions allow unauthorized access to a business system.

Red team example

Emulate an agreed threat scenario to reach a designated test dataset, then evaluate where defenders prevented, detected, or responded to the activity.

These are common engagement patterns, not universal definitions. A penetration test can include detection checks, and red teaming can uncover vulnerabilities. The rules of engagement determine the actual scope and methods.

Reference: CISA red team assessment and defensive lessons ↗

Coverage / Beyond a single target type

Web. Mobile. Platform. IoT. OT.

Explore how the workflow changes across applications, infrastructure, connected devices, and industrial environments.

New / Practical depth

Follow the evidence, not just the tools.

ObservationControlled validationActionable finding
Every phase contributes to a reproducible security conclusion.

Each phase now includes four detailed method topics, diagrams, additional command examples, interpretation, and source references. Explore scope reconciliation, authorization comparisons, segmentation, identity paths, permission boundaries, and retesting.

Explore the expanded guide →