Thinking Like an Attacker
Cybersecurity is often described as a chess game, but that analogy is flawed. In chess, both players see the board. In cybersecurity, the defender must protect every piece, while the attacker only needs to find one weak square.
Penetration Testing (Pentesting) is the art of simulating an attack to find those weak squares before the real adversaries do. It is not just about running tools like Metasploit or Nmap; it is a rigorous methodology of thinking, probing, and documenting.
Vulnerability Assessment vs. Penetration Testing
- Vulnerability Assessment: A broad scan. “You have 50 unlocked doors.” It identifies potential issues but doesn’t check if they can actually be exploited.
- Penetration Testing: The deep dive. “I found an unlocked door, walked in, bypassed the security camera, and successfully opened the safe.” It proves the impact of a vulnerability.
The Penetration Testing Lifecycle (PTES)
Professional hacking isn’t chaos; it’s structured. We follow the Penetration Testing Execution Standard (PTES).
1. Pre-engagement Interactions
Before typing a single command, we define the rules: Scope, legal boundaries, and “Rules of Engagement” (RoE).
- What are we testing? (IPs, Domains)
- When are we testing? (To specific hours?)
- What is off-limits? (Do not touch the production DB!)
2. Intelligence Gathering (Reconnaissance)
This is 80% of the job. We learn everything about the target.
- Passive Recon: Gathering info without touching the target (Google Dorks, LinkedIn, Shodan). The target doesn’t know you are watching.
- Active Recon: Engaging the target (Port scanning, DNS transfers). The target might see you in their logs.
3. Threat Modeling
We analyze the data. “Given they use an old Apache server on Port 80, and their developers post Python code on GitHub, where is the most likely entry point?” We map out attack vectors.
4. Vulnerability Analysis
We scan for known weaknesses (CVEs). Is that Apache version vulnerable to Log4Shell? Are there specific misconfigurations?
5. Exploitation
The “Hacking” part. We use the vulnerability to gain access. This could be launching a buffer overflow payload or guessing a weak password.
6. Post-Exploitation
We are in. Now what?
- Privilege Escalation: Can we go from a web user to Root/Admin?
- Pivot: Can we use this machine to jump to other secure servers in the internal network?
- Persistence: Ensuring we can get back in later.
7. Reporting
The most important part. If you can’t explain it to the business, you haven’t provided value. A report details what was found, how it was exploited, the business impact, and how to fix it.
The Legal Importance
Permission is the difference between a job and a jail sentence.
Never scan, poke, or probe a network without explicit, written authorization. In this series, we will be building our own Home Labs (using Virtual Machines) to practice these skills safely.
Our Toolkit
Over this series, we will master industry-standard tools:
- Kali Linux: The OS of choice.
- Nmap: The network mapper.
- Burp Suite: The web proxy for app testing.
- Metasploit: The exploitation framework.
But remember: Tools don’t hack; people do. The tool is just an extension of your knowledge.
Next Part: We will set up our virtualization lab and execute our first Passive Reconnaissance mission using OSINT tools like theHarvester, Shodan, and Google Dorks.
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