Enterprise PEN Testing using Kali Linux
CyberWhale Security
Course Overview
Kickstart your cybersecurity career with this 16-hour, beginner-level course delivered through live, interactive online sessions. Designed specifically for graduates and working professionals looking to enter the industry with zero prior experience, this program combines expert instructor-led training with hands-on practical labs to teach you how modern cyber attacks work and how to defend against them.
Key Features
- 100% Beginner-Friendly: No technical background required.
- Live Trainer-Led: Interactive online classes with real-time Q&A.
- Hands-on Labs: Gain practical skills by simulating real-world threats.
What You'll Learn
- Current cybersecurity trends and real-world attack methods.
- How to identify malware, phishing, and social engineering.
- Foundational defense strategies to secure digital networks.
Who Is This For
- Graduates wanting to build a strong foundation for their first security role.
- Professionals looking to transition smoothly into the cybersecurity field.
Module-by-Module Syllabus
Introduction to Network Communication & Protocols
Build a solid networking foundation so every later attack technique makes sense at the packet level.
Topics Covered
- • OSI Model vs TCP/IP model — layer-by-layer walkthrough
- • IPv4 and IPv6 addressing, subnetting, and CIDR notation
- • Switching fundamentals: MAC tables, VLANs, ARP
- • Routing fundamentals: static vs dynamic routing, default gateways
- • DNS resolution process and record types (A, MX, NS, TXT, CNAME)
- • HTTP vs HTTPS, TLS handshake basics
- • Firewall types and packet filtering concepts
Lab Tools & Technologies
- › Wireshark — packet capture and protocol analysis
- › tcpdump — command-line packet sniffing
- › ping, traceroute / tracert — connectivity and path diagnostics
- › netstat / ss — socket and connection inspection
- › ipconfig / ifconfig / ip a — interface configuration
- › dig / nslookup — DNS query and record inspection
Hands-on Lab Deliverable
Capture and analyze live traffic in Wireshark to identify each OSI layer in a real HTTP session.
Operating Systems & Linux Basics
Get comfortable navigating both the Windows enterprise environment and the Linux attacker toolkit.
Topics Covered
- • Windows Workstation vs Windows Server roles
- • Active Directory (AD) structure: domains, OUs, GPOs, trust relationships
- • Windows Registry structure and security-relevant keys
- • Windows processes, services, and task scheduling
- • Linux filesystem hierarchy standard (FHS) and permissions model
- • Kali Linux installation, setup, and essential command-line operations
Lab Tools & Technologies
- › Kali Linux (VirtualBox / VMware image)
- › Windows Server 2019/2022 evaluation ISO — AD lab build
- › Windows 10/11 workstation VM (domain-joined)
- › PowerShell & Windows Command Prompt
- › systemctl, journalctl, ps, top, chmod/chown — Linux administration
- › RegEdit / reg.exe — Windows Registry inspection
Principles of Ethical Hacking
Understand the professional and legal framework that separates ethical hacking from criminal intrusion.
Topics Covered
- • The Scope–Assess–Document–Defend lifecycle
- • Rules of Engagement (RoE) and Statement of Work (SoW)
- • Legal and compliance considerations (authorization, NDA, data handling)
- • Industry methodologies: PTES, OSSTMM, NIST SP 800-115, OWASP Testing Guide
- • White-box vs Grey-box vs Black-box testing
- • CVSS scoring for prioritizing findings
Lab Tools & Technologies
- › RoE / SoW document templates
- › CVSS v3.1 calculator (FIRST.org)
- › Dradis Framework — collaborative engagement documentation
- › Faraday — vulnerability management & reporting platform
Hands-on Lab Deliverable
Draft a sample Rules of Engagement document and score a mock finding using the CVSS calculator.
Hacker Essentials
Learn the core offensive vocabulary and techniques used across every stage of an attack chain.
Topics Covered
- • Enumeration techniques for services, users, and shares
- • Vulnerability identification and CVE / CWE referencing
- • Exploit selection, payload construction, and shell types (bind/reverse)
- • Privilege escalation on Windows and Linux
- • Social engineering fundamentals: phishing, pretexting, vishing
- • Lateral movement and persistence mechanisms
- • AI-powered attack techniques and AI-assisted reconnaissance/exploitation
Lab Tools & Technologies
- › Nmap & enum4linux — service and SMB enumeration
- › Metasploit Framework & msfvenom — exploitation and payload generation
- › Searchsploit / Exploit-DB — exploit research
- › LinPEAS / WinPEAS — automated privilege-escalation enumeration
- › Netcat (nc) — bind/reverse shell handling
- › Social-Engineer Toolkit (SET) — phishing simulation
- › CrackMapExec / NetExec — lateral movement across Windows networks
- › AI copilots (e.g., PentestGPT-style prompting) for recon triage and reporting
Hands-on Lab Deliverable
Gain an initial foothold on a vulnerable VM, escalate privileges using LinPEAS/WinPEAS, and establish a persistence mechanism.
Penetration Testing Phases
Apply a repeatable, phase-driven methodology that mirrors real-world engagements end to end.
Topics Covered
- • Phase 1: Reconnaissance — passive & active information gathering
- • Phase 2: Scanning & Enumeration — mapping the attack surface
- • Phase 3: Exploitation — gaining initial access
- • Phase 4: Post-Exploitation — escalation, pivoting, data validation
- • Phase 5: Reporting — translating technical findings into business risk
Lab Tools & Technologies
- › theHarvester & Recon-ng — OSINT gathering
- › Maltego — entity relationship mapping
- › Nmap & Masscan — network and port scanning
- › Metasploit Framework — exploitation workflow
- › Burp Suite (Community/Pro) — web traffic interception
- › PowerShell Empire / Covenant — post-exploitation C2
- › Dradis / Faraday — evidence consolidation and report generation
Hands-on Lab Deliverable
Run a full recon-to-report cycle against a lab target, capturing evidence at every phase.
Enterprise Penetration Testing
Apply attack techniques at enterprise scale across networks, Active Directory, and web applications.
Topics Covered
- • Network exploitation: SMB, RDP, and service-level attacks
- • Active Directory attacks: Kerberoasting, AS-REP roasting, pass-the-hash
- • Password attacks: brute force, dictionary, credential stuffing, spraying
- • Privilege escalation paths in enterprise domains
- • Web application security fundamentals (OWASP Top 10)
- • Common web attacks: SQL injection, XSS, IDOR, file upload abuse, SSRF
Lab Tools & Technologies
- › Responder — LLMNR/NBT-NS poisoning and credential capture
- › Impacket suite (secretsdump, psexec, GetUserSPNs) — AD exploitation
- › BloodHound & SharpHound — AD attack-path mapping
- › Hashcat & John the Ripper — offline password cracking
- › Hydra — online brute-force / password spraying
- › Burp Suite Pro & OWASP ZAP — web application testing
- › SQLmap — automated SQL injection testing
- › Gobuster / Feroxbuster — directory & content discovery
Hands-on Lab Deliverable
Compromise a mock enterprise domain end-to-end: initial foothold → Kerberoasting → Domain Admin, plus one full web-app assessment.
Case Study — Real-World Pentest Simulation
Consolidate every skill from Modules 1–6 into one complete, professional engagement simulation.
Topics Covered
- • Building the Pentest Plan and scoping the engagement
- • Producing the Reconnaissance Report
- • Conducting and documenting the Vulnerability Assessment
- • Capturing Exploitation Evidence (screenshots, logs, command output)
- • Writing Post-Exploitation Notes (impact, lateral movement, data access)
- • Compiling the Full Pentest Report (executive summary + technical findings + remediation)
Lab Tools & Technologies
- › Dradis Framework / Faraday — end-to-end engagement workspace
- › Kali Linux full toolset (Nmap, Metasploit, Burp Suite, Impacket, BloodHound, Hashcat)
- › CVSS calculator — risk scoring for the final report
- › Report templates (executive & technical) provided by CyberWhale
Hands-on Lab Deliverable
Independently execute a simulated enterprise pentest and submit a polished, client-ready final report for instructor review.
Ready to Get Started?
Secure your spot in CW-PEN-100 and begin your journey into professional penetration testing.
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