The most powerful phase of a pentest happens before touching the target. Passive OSINT with Maltego, Shodan, and theHarvester — the intelligence picture that guides every attack decision.
The most powerful phase of a pentest happens before touching the target. Passive OSINT with Maltego, Shodan, and theHarvester — the intelligence picture that guides every attack decision.
The Penetration Testing Execution Standard (PTES) defines seven phases: pre-engagement, intelligence gathering, threat modeling, vulnerability analysis, exploitation, post-exploitation, and reporting. OWASP's Testing Guide adds web-specific methodology. Following a standard ensures consistency across engagements and demonstrates professionalism to clients.
Kali Linux is the industry standard attack distribution — 600+ pre-installed security tools. Set it up in VirtualBox with a host-only adapter for isolation. Create snapshots before each exercise. Complement Kali with a Windows 10 victim VM and Metasploitable 2 for a complete lab. The VulnHub site offers hundreds of downloadable vulnerable VMs.
Before any testing, define: in-scope IP ranges and domains, out-of-scope systems, testing window (dates/times), escalation contacts, and what to do if you find critical issues mid-test. The Rules of Engagement (RoE) document is your legal protection. Without it, penetration testing is computer crime.
# Verify Kali tools are current
sudo apt update && sudo apt full-upgrade -y
# Check key tools are available
nmap --version
metasploit-framework --version || msfconsole --version
burpsuite &
# Create a project directory structure
mkdir -p ~/pentest/client-name/{recon,scans,exploits,loot,report}
cd ~/pentest/client-name
# Start logging everything
script -a ~/pentest/client-name/session.log
# Document your lab IP layout
ip addr show eth0
arp -n
Write a one-page mock Rules of Engagement document for a fictional client engagement. Include scope, exclusions, testing window, and escalation procedures.
The foundations from today carry directly into Day 2. In the next session the focus shifts to Scanning, Enumeration, and Vulnerability Analysis — building directly on everything covered here.
Before moving on, verify you can answer these without looking:
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