Runbook 03 — Penetration Testing Methodology
Penetration testing should not depend on random tools or ad hoc techniques.
A professional engagement follows a structured methodology that can be applied across:
NETWORKS
WINDOWS
LINUX
ACTIVE DIRECTORY
WEB APPLICATIONS
APIs
CLOUD
CONTAINERS
ENTERPRISE INFRASTRUCTUREThe purpose of this runbook is to provide a technology-independent penetration testing methodology that can be reused across different types of authorized security assessments.
The core workflow is:
PRE-ENGAGEMENT ↓SCOPE ↓RULES OF ENGAGEMENT ↓RECONNAISSANCE ↓DISCOVERY ↓ENUMERATION ↓VULNERABILITY ANALYSIS ↓ATTACK-PATH DEVELOPMENT ↓CONTROLLED VALIDATION ↓EVIDENCE COLLECTION ↓RISK ANALYSIS ↓REPORTING ↓REMEDIATION ↓RETESTING ↓CLOSUREUse this runbook only in the GoHackersCloud lab, systems you own, intentionally vulnerable training environments, or environments where you have explicit authorization.
Runbook Information
Section titled “Runbook Information”Runbook: 03 — Penetration Testing Methodology
Track: OffSec
Category: Core Penetration Testing Runbook
Difficulty: Beginner → Advanced
Primary Role: Penetration Tester / Security Consultant
Environment: Technology Independent
Primary Goal: Conduct repeatable, evidence-driven penetration tests
Primary Deliverable: Professional Penetration Testing Report
When to Use This Runbook
Section titled “When to Use This Runbook”Use this runbook for:
Network Penetration Testing
Internal Penetration Testing
External Penetration Testing
Web Application Testing
Active Directory Testing
Windows Assessment
Linux Assessment
Cloud Security Testing
API Security Testing
Enterprise Penetration Testing
Purple Team ExercisesThe Pentesting Mental Model
Section titled “The Pentesting Mental Model”Avoid this:
TOOL ↓SCAN ↓EXPLOIT ↓REPORTUse this instead:
UNDERSTAND ↓HYPOTHESIZE ↓VALIDATE ↓CORRELATE ↓MEASURE IMPACT ↓DOCUMENT ↓REMEDIATE01 — Pre-Engagement Planning
Section titled “01 — Pre-Engagement Planning”Before technical activity, understand:
Why Is the Test Being Performed?
What Business ProblemAre We Trying to Evaluate?
Which Assets Matter Most?
What Type of AssessmentHas Been Requested?
What Are the Customer'sRisk Concerns?Pre-Engagement Questions
Section titled “Pre-Engagement Questions”Document:
Assessment Type:
Business Objective:
Primary Security Concerns:
Critical Systems:
Critical Data:
Stakeholders:
Testing Dates:
Reporting Audience:
Compliance Requirements:
Communication Channel:02 — Define the Assessment Type
Section titled “02 — Define the Assessment Type”Clarify whether the engagement is:
External
Internal
Assumed Breach
Web Application
API
Cloud
Active Directory
Wireless
Enterprise
Red Team
Purple TeamEach assessment may use the same overall methodology but different technical depth.
03 — Define the Scope
Section titled “03 — Define the Scope”The scope should answer:
WHAT CAN BE TESTED?and:
WHAT CANNOT BE TESTED?Document:
IP Addresses
Networks
Domains
Applications
APIs
Cloud Accounts
Systems
Accounts
Locations
Third PartiesScope Template
Section titled “Scope Template”Engagement:
Organization:
Assessment Type:
In-Scope Networks:
In-Scope Hosts:
In-Scope Domains:
In-Scope Applications:
In-Scope APIs:
In-Scope Accounts:
Excluded Systems:
Third-Party Systems:
Testing Window:
Emergency Contact:04 — Validate Ownership
Section titled “04 — Validate Ownership”Before testing:
Confirm Customer Ownership
Confirm Third-Party Authorization
Confirm Cloud Account Ownership
Confirm Domain Ownership
Confirm Application OwnershipNever assume that a publicly reachable asset belongs to the customer.
05 — Establish Rules of Engagement
Section titled “05 — Establish Rules of Engagement”Rules of engagement define:
HOW TESTING MAY BE PERFORMEDDocument:
Allowed Techniques
Restricted Techniques
Prohibited Techniques
Testing Hours
Notification Requirements
Escalation Process
Stop Conditions06 — Establish Stop Conditions
Section titled “06 — Establish Stop Conditions”Testing should stop when:
Service Instability Occurs
Unexpected Sensitive Data Appears
A Third-Party Asset Is Reached
Customer Requests a Stop
Production Operations Are Impacted
An Out-of-Scope Environment Is Found
Unexpected Account Lockouts Occur07 — Establish Communication
Section titled “07 — Establish Communication”Define:
Primary Contact
Technical Contact
Emergency Contact
Daily Update Requirements
Critical Finding Notification
Secure Evidence Transfer08 — Prepare the Workspace
Section titled “08 — Prepare the Workspace”Create:
Pentest/|+-- 01-Scope/|+-- 02-Recon/|+-- 03-Discovery/|+-- 04-Enumeration/|+-- 05-Vulnerability-Analysis/|+-- 06-Attack-Paths/|+-- 07-Evidence/|+-- 08-Findings/|+-- 09-Report/|+-- 10-Cleanup/|+-- 11-Retest/09 — Establish Evidence Standards
Section titled “09 — Establish Evidence Standards”For every important activity capture:
Timestamp
Tester
Source
Target
Current Identity
Command / Method
Expected Result
Observed Result
Security Significance
Evidence Reference
Finding Reference10 — Maintain an Activity Log
Section titled “10 — Maintain an Activity Log”Create:
TIME ↓ACTION ↓TARGET ↓RESULT ↓NEXT STEPThis is extremely useful when reconstructing the assessment later.
11 — Reconnaissance
Section titled “11 — Reconnaissance”Reconnaissance means gathering enough context to understand the environment before deeper testing.
Depending on assessment type, investigate authorized:
Domains
IP Ranges
Applications
Technologies
Business Services
Infrastructure
Known Assets12 — Passive vs Active Reconnaissance
Section titled “12 — Passive vs Active Reconnaissance”Passive reconnaissance:
Uses Existing InformationWithout Directly InteractingWith the TargetActive reconnaissance:
Directly InteractsWith In-Scope SystemsUse only methods permitted by the engagement.
13 — Build the Initial Asset List
Section titled “13 — Build the Initial Asset List”Record:
| Asset | Type | Purpose | Owner | Criticality |
|---|---|---|---|---|
| portal.example.lab | Web | Customer Portal | App Team | High |
| 10.10.10.10 | Server | Identity | Infra | Critical |
| API01 | API | Business API | App Team | High |
14 — Discovery
Section titled “14 — Discovery”Discovery answers:
WHAT EXISTS?For an authorized network, examples may include:
nmap -sn <AUTHORIZED_SUBNET>The objective is to identify:
Hosts
Network Devices
Servers
Applications
Security Appliances15 — Build the Discovery Inventory
Section titled “15 — Build the Discovery Inventory”Document:
IP
Hostname
MAC if Available
OS Guess
Role
Network Zone
Criticality16 — Prioritize Assets
Section titled “16 — Prioritize Assets”Use:
Critical
High
Medium
LowPrioritize systems that control:
Identity
Administration
Sensitive Data
Applications
Security Controls
Backups
Management17 — Service Enumeration
Section titled “17 — Service Enumeration”Once assets are identified, determine:
WHAT IS RUNNING?For authorized systems:
nmap -sV -sC -p <PORTS> <TARGET>Document:
Port
Protocol
Service
Version
Purpose
Authentication
Exposure18 — Avoid Tool-Driven Testing
Section titled “18 — Avoid Tool-Driven Testing”Do not think:
PORT 445=TRY EVERYTHING SMBInstead:
PORT 445 ↓SMB SERVICE ↓WHAT ROLE DOES IT SERVE? ↓WHO CAN ACCESS IT? ↓WHAT DATA / TRUST DOES IT EXPOSE?19 — Enumerate by Technology
Section titled “19 — Enumerate by Technology”Your next questions depend on the technology.
For Windows:
Users
Groups
Services
Shares
Tasks
Domain ContextFor Linux:
Users
Groups
sudo
Services
Cron
PermissionsFor web:
Pages
Roles
APIs
Objects
WorkflowsFor cloud:
Identities
Roles
Resources
Policies
Network Exposure
Logging20 — Build Enumeration Hypotheses
Section titled “20 — Build Enumeration Hypotheses”Instead of collecting unlimited information, ask targeted questions.
Example:
HYPOTHESIS:
This application server may usea service account with accessto additional internal resources.Then collect evidence specifically related to that hypothesis.
21 — Vulnerability Analysis
Section titled “21 — Vulnerability Analysis”Vulnerability analysis asks:
WHAT SECURITY WEAKNESSES EXIST?These may include:
Missing Patches
Weak Configuration
Excessive Privilege
Broken Authorization
Weak Segmentation
Insecure Services
Exposed Sensitive Information
Legacy Technology
Weak Identity Governance22 — Separate Observation from Vulnerability
Section titled “22 — Separate Observation from Vulnerability”Example observation:
RDP Port 3389 Is OpenThis is not automatically a vulnerability.
A vulnerability might be:
RDP Management ServiceIs Exposed to an UnauthorizedUser NetworkContext matters.
23 — Validate Scanner Results
Section titled “23 — Validate Scanner Results”Never copy scanner output directly into a report without verification.
For each important result:
Does It Exist?
Is the Version Correct?
Is the Configuration Relevant?
Is the Asset Actually Vulnerable?
What Conditions Are Required?
What Is the Business Impact?24 — Prioritize Manual Validation
Section titled “24 — Prioritize Manual Validation”High-priority areas often include:
Authentication
Authorization
Administrative Interfaces
Identity Privileges
Service Accounts
File Permissions
Network Segmentation
Sensitive Data
Business Logic25 — Build the Finding Register
Section titled “25 — Build the Finding Register”Create:
| ID | Observation | Asset | Status | Priority |
|---|---|---|---|---|
| PT-001 | Excessive local admin | APP01 | Validate | High |
| PT-002 | Weak segmentation | Network | Validate | High |
| PT-003 | Missing API authorization | Portal | Validate | Critical |
26 — Develop Attack Paths
Section titled “26 — Develop Attack Paths”A vulnerability rarely exists in isolation.
Think:
STARTING POSITION ↓WEAKNESS ↓PERMISSION ↓TRUST ↓INTERMEDIATE SYSTEM ↓HIGHER PRIVILEGE ↓TARGET27 — Map Relationships
Section titled “27 — Map Relationships”Relevant relationship types include:
CanAccess
MemberOf
AdminTo
CanModify
CanAuthenticate
CanReach
CanRead
CanWrite
Trusts
Owns28 — Create an Attack Graph
Section titled “28 — Create an Attack Graph”Example:
user01 | | MemberOf vSupport | | AdminTo vAPP01 | | Uses vService Identity | | AccessTo vDB0129 — Prioritize Attack Paths
Section titled “29 — Prioritize Attack Paths”Evaluate:
Starting Access
Number of Steps
Required Privilege
Target Criticality
Reliability
Existing Controls
Detection
Business Impact30 — Validate the Hypothesis
Section titled “30 — Validate the Hypothesis”Before validation:
HYPOTHESIS ↓SCOPE CHECK ↓RISK CHECK ↓MINIMUM TEST ↓OBSERVE ↓DOCUMENT31 — Use Controlled Validation
Section titled “31 — Use Controlled Validation”The objective is:
PROVE THE RISKnot:
CAUSE MAXIMUM IMPACTUse the minimum action necessary to demonstrate the issue.
32 — Establish Proof Requirements
Section titled “32 — Establish Proof Requirements”Before testing, decide what constitutes sufficient proof.
Example:
Finding:Unauthorized administrative function
Sufficient Proof:A standard test user receives asuccessful response from the restrictedfunction against synthetic lab data.You do not need to perform unrelated administrative actions.
33 — Stop After Sufficient Proof
Section titled “33 — Stop After Sufficient Proof”Once you have demonstrated:
The Weakness Exists
The Starting Position Can Reach It
The Security Boundary Fails
The Impact Is Understandablestop expanding the activity unnecessarily.
34 — Handle Sensitive Data Carefully
Section titled “34 — Handle Sensitive Data Carefully”If testing exposes:
Credentials
Personal Data
Business Records
Secrets
Tokens
Configurationuse:
Minimum Collection
Redaction
Secure Storage
Access Control
Documented Handling35 — Evidence Collection
Section titled “35 — Evidence Collection”Good evidence should prove the finding independently.
Include:
Relevant Request
Relevant Response
Command Output
Screenshot
Permission Listing
Configuration Snippet
Timestamp
Asset36 — Avoid Weak Evidence
Section titled “36 — Avoid Weak Evidence”Avoid:
Unexplained Screenshots
Massive Tool Output
Unredacted Secrets
Evidence Without Target Information
Evidence Without Context37 — Build the Evidence Index
Section titled “37 — Build the Evidence Index”| Evidence ID | Finding | Asset | Type | Description |
|---|---|---|---|---|
| EV-001 | PT-001 | APP01 | Output | Local admin membership |
| EV-002 | PT-002 | Network | Test | Segmentation validation |
| EV-003 | PT-003 | Portal | HTTP | Unauthorized API response |
38 — Write the Finding
Section titled “38 — Write the Finding”A strong finding answers:
WHAT IS WRONG?
WHERE IS IT?
WHY DOES IT MATTER?
HOW WAS IT VALIDATED?
WHAT SHOULD BE DONE?Finding Template
Section titled “Finding Template”Finding ID:
Title:
Affected Asset:
Severity:
Description:
Starting Position:
Required Conditions:
Evidence:
Attack Path:
Technical Impact:
Business Impact:
Root Cause:
Recommendation:
Detection Opportunity:
Retest Procedure:39 — Separate Technical and Business Impact
Section titled “39 — Separate Technical and Business Impact”Technical:
A standard user can accessan administrative endpoint.Business:
A compromised employee accountcould modify application-wideadministrative settings.Both matter.
40 — Identify Root Cause
Section titled “40 — Identify Root Cause”Ask:
Why Does This Weakness Exist?
Was It a Design Problem?
Configuration Problem?
Governance Problem?
Legacy Requirement?
Privilege Creep?
Missing Review?
Missing Ownership?41 — Common Root Causes
Section titled “41 — Common Root Causes”Examples:
Weak Access Control
Poor Segmentation
Excessive Privilege
Configuration Drift
Legacy Systems
Missing Patch Governance
Weak Identity Governance
Lack of Ownership
Incomplete Security Testing42 — Risk Analysis
Section titled “42 — Risk Analysis”Risk should consider more than technical severity.
Use:
LIKELIHOOD ×IMPACT +BUSINESS CONTEXT43 — Risk Factors
Section titled “43 — Risk Factors”Consider:
Starting Access Required
Authentication Required
Ease of Abuse
Exploit Reliability
Target Criticality
Data Sensitivity
Privilege Gained
Blast Radius
Detection
Existing Controls44 — Risk Rating Example
Section titled “44 — Risk Rating Example”| Severity | Typical Meaning |
|---|---|
| Critical | Direct or near-direct compromise of a critical security boundary |
| High | Significant privilege or sensitive-system exposure |
| Medium | Meaningful weakness requiring additional conditions |
| Low | Limited impact or difficult conditions |
| Informational | Hardening or architecture observation |
45 — Correlate Findings
Section titled “45 — Correlate Findings”Suppose you identified:
Finding A:Weak Segmentation
Finding B:Broad Local Administrator
Finding C:Service Account Excessive PrivilegeIndividually:
A + B + CTogether:
USER NETWORK ↓SERVER ↓LOCAL ADMIN ↓SERVICE IDENTITY ↓CRITICAL SYSTEMThis may represent a much larger risk.
46 — Build Attack Path AP-01
Section titled “46 — Build Attack Path AP-01”Attack Path ID:PT-AP-01
Starting Position:Standard enterprise user
Step 01:User can reach APP01 management service.
Step 02:Support group has unnecessary localadministrative access.
Step 03:APP01 uses an overprivilegedservice identity.
Target:Critical application environment.
Impact:Compromise of a standard support identitycould lead to significantly broaderenterprise access.47 — Identify Path-Breaking Controls
Section titled “47 — Identify Path-Breaking Controls”For every path ask:
WHERE CAN WE BREAK IT?Example:
USER ↓SERVER ↓SERVICE IDENTITY ↓DATABASEPotential path breaks:
Network Segmentation
Remove Local Admin
Reduce Service Privilege
Restrict Database Access
MFA
Monitoring48 — Prioritize Path-Breaking Remediation
Section titled “48 — Prioritize Path-Breaking Remediation”Sometimes fixing one control can break multiple findings.
Example:
REMOVE BROAD ADMIN GROUPmay break:
AP-01
AP-03
AP-05This is often more valuable than addressing findings individually.
49 — Create the Remediation Roadmap
Section titled “49 — Create the Remediation Roadmap”Use:
IMMEDIATE
SHORT TERM
MEDIUM TERM
STRATEGICExample:
Immediate:Remove unnecessary administrative rights.
Short Term:Restrict network management access.
Medium Term:Implement managed service accounts.
Strategic:Deploy PAM and administrative tiering.50 — Reporting
Section titled “50 — Reporting”Your report should be useful to:
Executives
Security Leadership
Infrastructure Teams
Application Teams
Developers
Identity Teams
SOC Teams51 — Executive Summary
Section titled “51 — Executive Summary”The executive summary should answer:
What Was Tested?
What Was the Overall Risk?
What Were the Major Attack Paths?
Which Business Assets Were Exposed?
What Should Be Fixed First?Executive Summary Example
Section titled “Executive Summary Example”The penetration test identified multiplesecurity weaknesses across identity,network, operating-system, andapplication layers.
The most significant risk resulted fromseveral weaknesses combining into attackpaths toward high-value enterprisesystems.
Priority remediation should focus onrestricting administrative access,strengthening network segmentation,reducing excessive identity privilege,and enforcing server-side authorization.52 — Technical Findings
Section titled “52 — Technical Findings”Each technical finding should contain:
Title
Severity
Affected Assets
Description
Evidence
Impact
Root Cause
Recommendation
Retest53 — Avoid Reporting Tool Names as Findings
Section titled “53 — Avoid Reporting Tool Names as Findings”Bad:
Nmap Found Port 22Better:
SSH Administrative Service IsReachable From an UnauthorizedNetwork SegmentReport the security problem, not the tool output.
54 — Avoid Generic Recommendations
Section titled “54 — Avoid Generic Recommendations”Bad:
Improve Security.Better:
Restrict TCP/22 to the dedicatedadministrative network and approvedmanagement hosts.Recommendations should be:
Specific
Actionable
Prioritized
Relevant55 — Build the Remediation Table
Section titled “55 — Build the Remediation Table”| Priority | Finding | Action | Owner |
|---|---|---|---|
| Immediate | Broad local admin | Remove group | Windows Team |
| Short Term | Weak segmentation | Restrict management | Network Team |
| Medium | Service privilege | Redesign identity | IAM Team |
56 — Detection Opportunities
Section titled “56 — Detection Opportunities”Every offensive finding should create a defensive question:
HOW COULD THISHAVE BEEN DETECTED?57 — Map Attack Paths to Telemetry
Section titled “57 — Map Attack Paths to Telemetry”Example:
AUTHENTICATION ↓PRIVILEGE USE ↓SERVER ACCESS ↓APPLICATION ACCESSPossible telemetry:
Identity Logs
Endpoint Logs
Network Logs
Application Logs
Cloud Logs
SIEM Alerts58 — Include Detection Guidance
Section titled “58 — Include Detection Guidance”For important findings document:
Log Source
Relevant Event
Detection Logic
Expected Baseline
Alert ConditionThis improves remediation beyond configuration alone.
59 — Cleanup
Section titled “59 — Cleanup”At engagement completion:
Remove Test Accounts
Remove Test Files
Restore Modified Configuration
Remove Temporary Memberships
Terminate Sessions
Delete Synthetic Objects
Verify Service Health
Secure EvidenceCleanup Record
Section titled “Cleanup Record”Asset:
Change:
Original State:
Final State:
Verification:
Tester:
Timestamp:60 — Retesting
Section titled “60 — Retesting”Retesting asks:
DID THE FIXACTUALLY REMOVE THE RISK?Do not only verify:
Configuration ChangedVerify:
Original Security PathNo Longer Works61 — Retest Workflow
Section titled “61 — Retest Workflow”ORIGINAL FINDING ↓REPRODUCE BASELINE ↓VERIFY REMEDIATION ↓REPEAT SECURITY TEST ↓CHECK RELATED PATHS ↓CLOSE / REOPEN62 — Retest Status
Section titled “62 — Retest Status”Use:
Resolved
Partially Resolved
Not Resolved
Risk Accepted
Not Retested63 — Engagement Closure
Section titled “63 — Engagement Closure”Before closing:
Evidence Finalized
Cleanup Verified
Critical Findings Communicated
Final Report Delivered
Retest Plan Agreed
Sensitive Data Disposed Properly
Lessons Learned Recorded64 — Lessons Learned
Section titled “64 — Lessons Learned”Ask:
What Worked Well?
What Slowed Testing?
Which Assets Were Unknown?
Which Controls Were Effective?
Which Control Failures Repeated?
What Should the Next AssessmentFocus On?65 — Methodology by Assessment Type
Section titled “65 — Methodology by Assessment Type”Network
Section titled “Network”SCOPE ↓DISCOVERY ↓PORTS ↓SERVICES ↓CONFIGURATION ↓SEGMENTATION ↓ATTACK PATHWindows
Section titled “Windows”IDENTITY ↓GROUPS ↓SERVICES ↓TASKS ↓FILES ↓REGISTRY ↓PRIVILEGE PATHIDENTITY ↓GROUPS ↓SUDO ↓FILES ↓SUID ↓CAPABILITIES ↓SERVICES ↓PRIVILEGE PATHActive Directory
Section titled “Active Directory”DOMAIN ↓USERS ↓GROUPS ↓PERMISSIONS ↓GPO ↓DELEGATION ↓TRUST ↓ATTACK PATHWeb Application
Section titled “Web Application”AUTHENTICATION ↓ROLES ↓OBJECTS ↓AUTHORIZATION ↓WORKFLOWS ↓APIs ↓BUSINESS IMPACTIDENTITY ↓RESOURCE ↓POLICY ↓NETWORK ↓DATA ↓LOGGING ↓TRUST ↓ATTACK PATH66 — Daily Pentest Workflow
Section titled “66 — Daily Pentest Workflow”At the beginning of each testing day:
REVIEW SCOPE
REVIEW NOTES
REVIEW OPEN HYPOTHESES
CHECK CUSTOMER UPDATES
VERIFY TESTING POSITIONDuring testing:
ENUMERATE
FORM HYPOTHESIS
VALIDATE
CAPTURE EVIDENCE
UPDATE FINDINGSAt the end:
UPDATE ACTIVITY LOG
BACK UP EVIDENCE
UPDATE ATTACK PATHS
REVIEW CRITICAL FINDINGS
PLAN NEXT ACTIONS67 — Hypothesis Worksheet
Section titled “67 — Hypothesis Worksheet”Use:
Hypothesis ID:
Observation:
Hypothesis:
Required Conditions:
Validation Method:
Expected Result:
Actual Result:
Evidence:
Finding:
Next Step:68 — Finding Review Checklist
Section titled “68 — Finding Review Checklist”Before reporting a finding verify:
Is It Reproducible?
Is It In Scope?
Is the Evidence Clear?
Is the Impact Realistic?
Is the Severity Justified?
Is the Root Cause Identified?
Is the Recommendation Actionable?
Is the Retest Procedure Defined?69 — Attack Path Review Checklist
Section titled “69 — Attack Path Review Checklist”For each path:
Is the Starting Position Realistic?
Does Every Relationship Exist?
Are Any Assumptions Unverified?
What Security Controls Exist?
What Is the Final Target?
What Is the Business Impact?
Where Can the Path Be Broken?70 — Penetration Testing Checklist
Section titled “70 — Penetration Testing Checklist”Pre-Engagement
Section titled “Pre-Engagement”- Business objective understood
- Assessment type confirmed
- Stakeholders identified
- Communication established
- Assets documented
- Networks documented
- Applications documented
- Accounts documented
- Exclusions documented
- Ownership confirmed
Rules of Engagement
Section titled “Rules of Engagement”- Allowed techniques documented
- Restricted techniques documented
- Stop conditions documented
- Emergency contact documented
- Testing window confirmed
Workspace
Section titled “Workspace”- Evidence directories created
- Activity log started
- Evidence standard established
- Secure storage confirmed
Reconnaissance
Section titled “Reconnaissance”- Known assets reviewed
- Domains reviewed
- Infrastructure context reviewed
- Initial inventory created
Discovery
Section titled “Discovery”- Hosts discovered
- Systems classified
- Unknown assets documented
- Critical systems prioritized
Enumeration
Section titled “Enumeration”- Ports reviewed
- Services reviewed
- Technologies identified
- Authentication points identified
- Administrative interfaces identified
Vulnerability Analysis
Section titled “Vulnerability Analysis”- Scanner results validated
- Configuration weaknesses reviewed
- Privilege relationships reviewed
- Authorization reviewed
- Segmentation reviewed
- Sensitive data exposure reviewed
Attack Paths
Section titled “Attack Paths”- Findings correlated
- Starting positions identified
- Relationships mapped
- High-value targets identified
- Path-breaking controls identified
Validation
Section titled “Validation”- Scope rechecked
- Minimum proof defined
- Controlled validation performed
- Testing stopped after sufficient proof
Evidence
Section titled “Evidence”- Timestamps captured
- Targets identified
- Sensitive data redacted
- Evidence indexed
- Evidence linked to findings
Reporting
Section titled “Reporting”- Findings reproducible
- Business impact documented
- Root causes documented
- Recommendations actionable
- Remediation priorities defined
Cleanup
Section titled “Cleanup”- Temporary changes removed
- Test accounts removed
- Sessions terminated
- Services verified
- Cleanup documented
Retest
Section titled “Retest”- Original findings reproduced
- Fixes verified
- Attack paths retested
- Status documented
40 Penetration Testing Methodology Review Questions
Section titled “40 Penetration Testing Methodology Review Questions”- What is the purpose of penetration testing?
- Why is pre-engagement planning important?
- What is scope?
- What are rules of engagement?
- What is a stop condition?
- Why must asset ownership be verified?
- What is reconnaissance?
- What is the difference between passive and active reconnaissance?
- What is host discovery?
- What is service enumeration?
- Why is an open port not automatically a vulnerability?
- What is vulnerability analysis?
- Why should scanner results be manually validated?
- What is a testing hypothesis?
- What is an attack path?
- What is a trust relationship?
- Why should findings be correlated?
- What is controlled validation?
- Why should a tester stop after sufficient proof?
- What is the minimum proof principle?
- Why is evidence collection important?
- What makes good penetration-testing evidence?
- Why should sensitive information be redacted?
- What is a finding register?
- What is root-cause analysis?
- Why is business impact different from technical impact?
- What factors should influence severity?
- What is a path-breaking control?
- Why can one remediation break multiple attack paths?
- What belongs in an executive summary?
- Why should findings avoid tool-centric titles?
- What makes a good remediation recommendation?
- Why should penetration tests identify detection opportunities?
- Why is cleanup mandatory?
- What is retesting?
- What is the difference between remediation verification and attack-path retesting?
- What statuses can be used during retesting?
- Why are lessons learned useful?
- How does methodology differ from tools?
- What makes a penetration testing process repeatable?
Final Penetration Testing Mental Model
Section titled “Final Penetration Testing Mental Model”Remember:
BUSINESS OBJECTIVE ↓AUTHORIZED SCOPE ↓ENVIRONMENT ↓ASSETS ↓SERVICES ↓IDENTITIES ↓PERMISSIONS ↓TRUST ↓WEAKNESSES ↓ATTACK PATHS ↓BUSINESS IMPACT ↓REMEDIATION ↓RETESTDo not think:
Which Tool Should I Run Next?Think:
WHAT DO I KNOW?
WHAT DO I NEED TO KNOW?
WHAT HYPOTHESISAM I TESTING?
WHAT IS THE SAFESTWAY TO VALIDATE IT?
WHAT DOES THE RESULTMEAN FOR THE BUSINESS?A strong penetration tester moves through:
OBSERVATION ↓HYPOTHESIS ↓VALIDATION ↓EVIDENCE ↓FINDING ↓ATTACK PATH ↓BUSINESS RISK ↓REMEDIATIONThe tools used to perform these steps will change.
The methodology should remain consistent.
What’s Next?
Section titled “What’s Next?”➡️ Runbook 04 — Web Application Pentest
The next runbook applies this methodology specifically to modern web applications.
You will work through:
SCOPE ↓APPLICATION MAPPING ↓AUTHENTICATION ↓SESSION MANAGEMENT ↓AUTHORIZATION ↓INPUT HANDLING ↓BUSINESS LOGIC ↓APIs ↓FILE HANDLING ↓SECURITY CONFIGURATION ↓CONTROLLED VALIDATION ↓EVIDENCE ↓REPORTING ↓RETESTThe goal will be to create a repeatable web application penetration testing workflow that focuses on application behavior, security boundaries, business impact, and professional reporting rather than random payload testing.