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The Ultimate Penetration Testing Methodology (2025 Edition)

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0. Physical Access Attacks: The First Gate

If you’re fortunate (or allowed) to touch the physical environment, you’ve already bypassed many security walls. Techniques range from booting into live Linux distros to extracting data from unattended systems. USB-based payloads, BIOS password resets, and GUI session hijacks are your arsenal. Don’t forget the power of rubber duckies and HID attacks.

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1. Discovery Phase: Locating Digital Assets

Internal Test: Start by identifying live hosts within the network using tools like netdiscover, arp-scan, or even ping sweeps. Use Nmap for an in-depth scan of detected IPs.

External Test: Conduct OSINT. Use tools like Amass, theHarvester, and Shodan to enumerate the digital footprint of your target. Domain enumeration and subdomain brute-forcing (via Sublist3r or Assetfinder) are essential.

🔁 Once internal access is gained during an external assessment, re-initiate this entire methodology within the new scope.

LogoWaybackurls: The Ultimate Tool for Recon in Bug Bounty HuntingMediumchevron-right

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2. Network Reconnaissance (Internal Only)

Before interacting directly with any machine, gather intelligence by monitoring network traffic to uncover valuable information.

Passive Reconnaissance: Use tools like Wireshark or tcpdump to silently capture network packets. This can reveal sensitive data such as plaintext credentials, session tokens, or unencrypted communications — all without alerting users or security systems.

Active Reconnaissance: Take a more aggressive approach by launching Man-in-the-Middle (MITM) attacks. Tools such as Ettercap, Bettercap, or ARP poisoning techniques let you intercept and manipulate network traffic between devices, enabling you to capture credentials, inject payloads, or redirect traffic.

Additional Targets to Explore:

  • SMB Shares: Discover accessible shared folders that might contain sensitive files.

  • NetBIOS Name Resolution: Identify hosts and services using legacy naming protocols.

  • Rogue LLMNR/NBT-NS Responses: Exploit these local name resolution protocols to perform spoofing attacks and capture authentication hashes.

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3. Port Scanning & Service Discovery

Classic and mandatory.

Focus on open ports and running services. Tools: Nmap, Rustscan, Masscan for speed.

Identify OS fingerprinting (-O) and version detection (-sV) for better exploit mapping.

LogoNmap Cheat Sheet: Essential Commands and Advanced Techniques for ScanningMediumchevron-right

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4. Search for Known Vulnerabilities

Now that you know the services and their versions:

  • Search ExploitDB, NVD, and Rapid7.

  • Use searchsploit locally for quick matches.

  • Use Vulners or Nuclei for automated CVE hunting.

Sometimes you’ll find a pre-auth RCE and can skip many steps!

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5. Manual Service Exploitation

Start poking at known misconfigurations:

  • FTP: Anonymous login, directory traversal

  • SMB: Null sessions, EternalBlue

  • RDP/SSH: Weak credentials, misconfigs

Don’t miss the web application layer. Use Burp Suite, ffuf, and Nikto to probe HTTP surfaces. SQLi, XSS, SSRF, and IDOR are low-hanging fruit.

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5.1 Automated Scanning Tools

Use Legion, Nessus, or OpenVAS for wide sweeps. Always verify manually.

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5.2 Brute Forcing Services

Hydra, Medusa, and Patator are your allies. Pair with rockyou.txt, SecLists, or custom wordlists.

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6. Phishing: The Social Vector

If technical vectors fail, go social. Clone login portals, craft payloads using Gophish, and harvest credentials. Link tracking + sandbox detection = higher success.

Include macro-based Office payloads, HTA files, and rogue Wi-Fi portals.

LogoTop 20 phishing tools to use in 2024 | VeryLazyTechwww.verylazytech.comchevron-right

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7. Shell Acquisition: Your Beachhead

Once code execution is yours:

  • Use nc, bash -i, or PowerShell to spawn reverse shells

  • Obfuscate payloads to bypass AVs (e.g., msfvenom, Donut, Veil)

  • Drop payloads through lateral movement tools

For AV evasion in Windows, research Defender exclusion abuses, and Living Off The Land Binaries (LOLBins).

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8. Post-Exploitation Footing

You’re in. Now:

  • Linux: whoami, uname -a, sudo -l, check cron jobs

  • Windows: whoami, systeminfo, net user, PowerView for AD enumeration

Check PowerShell history and browser autofill.

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9. Exfiltration & Infiltration

To move data out:

  • Use scp, ftp, or covert channels (e.g., DNS tunneling)

  • Drop in privesc scripts like LinPEAS, WinPEAS

  • Use HTTPS to evade perimeter detection

LogoFile Transfer Cheatsheet: Windows and Linux | VeryLazyTechwww.verylazytech.comchevron-right

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10. Privilege Escalation: From Foot Soldier to King

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10.1 Local Escalation

Check for misconfigured services, scheduled tasks, writable binaries. Use LinEnum, Linux Exploit Suggester, WinPEAS, Seatbelt.

Review:

  • UAC bypasses

  • Token impersonation (Windows)

  • SUID/SGID binaries (Linux)

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10.2 Domain Escalation (AD)

Use BloodHound and SharpHound to map relationships.

  • Exploit misconfigured ACLs

  • Abuse Kerberoasting

  • Dump secrets with mimikatz

Don’t overlook:

  • LAPS extraction

  • DCSync attacks

  • GPP Passwords in SYSVOL

LogoActive Directory Methodology | VeryLazyTechwww.verylazytech.comchevron-right

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11. Post-Exploitation: Loot & Persistence

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11.1 Looting Credentials

Search for:

  • Saved credentials in browsers

  • Passwords in scripts and config files

  • SAM & SYSTEM hive extraction

Use tools like LaZagne, mimikatz, and Credential Roaming abuse.

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11.2 Persistence Mechanisms

  • Scheduled tasks

  • Registry run keys

  • DLL hijacking

  • Golden/Silver tickets (AD-specific)

Use at least two persistence vectors for resiliency.

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12. Pivoting: The Red Web Expands

Time to branch into new networks:

  • Use proxychains, Chisel, or SSH tunnels

  • Reinitiate asset discovery in new subnet

  • Map routes and establish new footholds

Check:

  • AD trust relationships

  • NTLM relaying techniques

  • Pass-the-Hash and Pass-the-Ticket options

🧠 Bonus: Combine BloodHound maps with credentials for max lateral movement efficiency.

Penetration testing isn’t about scripts — it’s about strategy, improvisation, and understanding your terrain. Adapt this methodology to your environment. Always obtain written permission. Log everything. Learn from each engagement.

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