What is Penetration Testing? | What is pen testing?

What is Penetration Testing ( or pen testing)?

Penetration testing (or pen testing) is a proactive security measure in which cybersecurity professionals simulate cyberattacks on an application, computer system, or network. The purpose of this simulation is to uncover vulnerabilities that malicious hackers could exploit. This process involves actively examining the system's defenses, mimicking the tactics of real-world attackers, to identify and rectify weaknesses.

In essence, it serves as a comprehensive security stress test to ensure maximal system protection.

Who performs Penetration Tests or pen tests?

Trained cybersecurity experts or teams, called penetration testers or pen testers or ethical hackers, perform pen testing. They actively search for and exploit security weaknesses in computer systems and networks to help organizations identify and fix vulnerabilities before real hackers can exploit them.

Now, let’s explore penetration testing methods further. You'll learn how to identify potential security gaps in systems and networks.

Types of Penetration Testing

1. Targeted Testing: In targeted testing, a pentester focuses on specific parts of the system that attackers are likely to attack. Doing so helps the pentester check how secure important things like sensitive data or key parts of the system are.  For example, imagine your computer is like a castle. You know attackers often try to break into the treasure room, so instead of checking every corner of the castle, you focus on making sure the treasure room is really secure.

2. External Testing: External testing is like pretending to be a hacker outside your organization. Ethical hackers try to break into your system just like real attackers, using tricks like phishing emails or scanning your network for weaknesses. Doing so helps ethical hackers see if your defenses, like walls and alarms, are strong enough to keep bad guys out. Think of it as checking if the locks on your house's doors and windows are working well against burglars.

3. Internal Testing: Internal testing involves pretending to be a sneaky employee already inside your organization. Pentester acts like an employee who wants to do bad things, like accessing files they shouldn't. Doing so helps the pentester find out if there are weak spots in your security that could let insiders cause harm.

4. Black Box Testing: Black box testing is like solving a puzzle without knowing what it looks like. You try to break into a system without knowing how it works or its composition. It's similar to trying to open a locked box without knowing what's inside or how the lock works. You just use your skills and what you can find out there, like a thief would.

5. White Box Testing: White box testing is when a pentester has all the information about a system. Pentester knows how it's built, what's inside it, and how it's supposed to work. It's like having the blueprint of a building before trying to find its weak points. With this knowledge, the pentester can look deep inside and find problems that might not be obvious

Let’s now learn through a step-by-step guide of penetration testing, which includes planning, scanning, gaining and maintaining access, and analyzing to identify and exploit vulnerabilities in a system.

Penetration Testing Steps and pen testing tools

These Steps and tools are a complete toolkit for a pentester.

Step 1: Plan and Conduct Reconnaissance

This stage of pen testing involves thorough planning and information gathering about the target system or network. You should collect as much data as possible to understand the organization's infrastructure, including IP addresses, domain names, network topology, and potential entry points.

You can use techniques such as DNS reconnaissance, WHOIS lookups, and searching for publicly available information on social media platforms, company websites, and online forums.

Let’s learn through examples below.

Recon tools:

1. Open Source Intelligence (OSINT) Tools:

1. Shodan: Known as the "search engine for internet-connected devices," Shodan allows you to discover specific types of computers connected to the internet using various filters.

2. theHarvester: Use this tool for gathering information, like email addresses, subdomains, hosts, employee names, open ports, and banners. Where does it get this info? It searches through various public sources such as search engines, PGP key servers, and even a computer database called SHODAN.

3. Recon-ng: A full-featured Web Reconnaissance framework written in Python. Use this for a powerful environment to conduct open source web-based reconnaissance quickly and thoroughly.

4. Maltego: An open-source intelligence (OSINT) and graphical link analysis tool for gathering and connecting information for investigative tasks.

B. Domain and IP Analysis Tools:

1. nslookup, dig

   For DNS reconnaissance to identify domain names and IP addresses. The tools 'nslookup' and 'dig' are used for something called DNS reconnaissance.

   DNS stands for Domain Name System. It's like the address book of the internet. When you type in a URL, like www.google.com, the DNS translates that into an IP address, which is a numerical label assigned to each device connected to a computer network.

   'Nslookup' and 'dig' are tools that help us to look up this information. We use them to identify domain names and IP addresses.

nslookup [example.com](<http://example.com/>)
dig example.com

2. whois

   The "whois" tool is like an online directory for websites. When you use "whois" with a domain name, it tells you who owns that domain. Use whois to get information such as the domain's registration and expiry dates, and who registered it. To use it, you type "whois" followed by the domain, like this:

   whois [example.com](<http://example.com/>)

3. DNSdumpster: A domain research tool that can discover hosts related to a domain. It's useful for mapping out a target's DNS information.

4. Robtex: Used to find various DNS and Network information including MX records, DNS records, and host information among others.

5. Wireshark: A network protocol analyzer that lets you capture and interactively browse the traffic running on a computer network.

C. Social Media Analysis:

1. Creepy: A geolocation OSINT tool. Generates maps based on geolocation data tracking during a set period of time. It can be used to identify the movements of a target.

2. Followerwonk: Focuses on Twitter analytics which can be used to gather detailed information about a target's Twitter account including information on followers, their location, and activity.

3. Snusbase: A database for searching public records and publicly leaked data breaches. Useful for finding sensitive personal information.

This information gathering step is crucial because the more we know about a target, the better we can plan our test. Think of it like doing your homework before a big test - the better prepared you are, the better you'll do!

5 questions to ask yourself: Here are 5 questions to ask yourself during the planning and reconnaissance step of penetration testing:

1. What is the ultimate goal of your penetration test?
   My goal is to identify and exploit system vulnerabilities to assess security.

2. Who is the target, or what system(s) are you planning to test?
   My target is the organization’s application or network that needs security assessment.

3. What specific information do you need to gather about the target to accomplish your goal?
   I need to gather information about system specifications, IP addresses, accessible ports, and software versions.

4. What methods or tools will you utilize to gather this information?
   I will use tools like DNS reconnaissance, WHOIS lookups, and social media platforms to gather this information.

5. Are there any potential risks or challenges that could arise during this step, and how can you mitigate them?
   Risks could include potential system damage or legal issues, which I plan to mitigate by obtaining proper permissions and following ethical guidelines.

Step 2: Active Reconnaissance

During this stage, scan your target system or network actively to identify potential vulnerabilities and entry points for exploitation. Probe network ports, services, and applications to discover open ports, running services, and potential weaknesses.

Use techniques such as port scanning, vulnerability scanning, and service enumeration to identify vulnerable systems and services.

Example commands:

Nmap: Use Nmap to actively discover open ports and services running on your target systems. Check out the Nmap cheat sheet here.

nmap -sS -T4 [example.com](<http://example.com/>)

2. Amass: Use Amass to performs TCP port scanning based on the banner grabbing technique.

   amass enum -d clicktheclapbutton50timesplz.com

3. Nuclei:** Use nuclei to scans web applications and identifies security vulnerabilities. Using it you can find and fix potential weak points in a system before malicious hackers can exploit them.
   Sharing with you this helpful cheatsheet to get started.

   nuclei -t <https://example.com> -t ~/nuclei-templates/my-template.yaml

4. ReconFTW: You can use ReconFTW to perform reconnaissance on web targets. It automates the process of gathering information and scanning for vulnerabilities, making it an efficient and essential tool in a penetration tester's arsenal.

You can use this tool to performs tasks such as subdomain enumeration, checking for potential subdomain takeovers, checking for exposed databases or git repositories, scanning for open ports and services, and much more

Use the command ./reconftw.sh -d target.com -r to run ReconFTW against a specific target. The -d flag is used to specify the target domain, and the -r flag is used to run the tool in recon mode, focusing on information gathering.

5. Masscan: Known as the fastest Internet port scanner, it is similar to Nmap but designed for scanning vast areas of the internet or large networks at high speed. It's used to identify open ports and services.

6. Hping: A command-line oriented TCP/IP packet assembler/analyzer. While traditionally used for crafting packets, it can be used to conduct ping sweeps, port scans, and even OS fingerprinting.

7. Nessus: Primarily a vulnerability scanner, Nessus can be used for active reconnaissance by scanning systems to identify vulnerabilities, misconfigurations, and other potential points of entry.

8. Wireshark: Though typically used for packet analysis, Wireshark can be utilized actively to capture and analyze packets flowing from and to a target system during an active scan.

9. Nikto: A web server scanner which performs comprehensive tests against web servers for multiple items, including potentially dangerous files and programs.

10. Fiddler: A web debugging tool that captures HTTP traffic between chosen computers and the internet. It is used to inspect traffic and to conduct active manipulation to test how web applications respond to various inputs.

11. Aircrack-ng: A network software suite consisting of a detector, packet sniffer, WEP and WPA/WPA2-PSK cracker, and analysis tool for wireless LANs. Use this one for active reconnaissance in wireless networks.

Step 3: Exploitation or Gaining Access

In Step 3, you should attempt to exploit identified vulnerabilities to gain unauthorized access to the target system or network. You can exploit software vulnerabilities, misconfigurations, weak passwords, or insecure network protocols, conduct password attacks, and leverage social engineering techniques.

Example commands:

Metasploit: Metasploit is a tool you can use to conduct through penetration testing. Think of it as a comprehensive kit that helps you identify and exploit vulnerabilities within a system. It's like a toolbox filled with various methods (known as exploits) and tools (referred to as payloads) that you can use to test different types of vulnerabilities. So, when you're conducting a security test, Metasploit helps you simulate attacks on a system, just like a real hacker would do.

Hydra: You can use password-cracking tool to guess or 'crack' passwords. This is especially used in brute-force attacks against remote authentication services.

A brute-force attack involves trying every possible combination of passwords until the correct one is found. Imagine trying to open a combination lock by trying every possible set of numbers; that's essentially what a brute-force attack is. It's not subtle, but if you have enough time and computing power, it can be effective. Remember, these tools should only be used ethically and legally, such as when testing the strength of your own passwords or systems.

hydra -l [username] -P [password list] [target] [protocol]

SQLMap: You can use this tool for detecting and exploiting SQL injection vulnerabilities in web applications.

Burp Suite: You can use BurpSuite to test for web application security testing. It is essentially a proxy server that sits between the client (browser) and the server (web server). It intercepts and logs traffic passing through it, which allows you to modify the traffic before it reaches the server. This makes it an invaluable tool for testing the security of web applications..

Example usage:

Start Burp Suite and configure your browser to use it as a proxy. Navigate to the target web application and use the site map to understand its structure. Use the intercept feature to alter HTTP requests and responses. Use the repeater feature to modify and resend individual requests.

Start Burp Suite -> Proxy -> Options -> Set Proxy Listeners

Akto: You can use Akto to test for API vulnerabilities and the OWASP API Top 10. Simply import your API inventory, and with one click, you can find all vulnerabilities in APIs including broken access control, broken authentication, SSRF, open redirect and misconfigurations.

ZAP (Zed Attack Proxy): An open-source web application security scanner. You can use it to find vulnerabilities in web applications while actively interacting with them.

Step 4: Maintaining Access

After gaining initial access, your goal now is to maintain persistence within the target environment to simulate a real-world attacker. Establish backdoors, create user accounts, or install malicious software to ensure continued access.

Use techniques such as deploying remote access tools, creating hidden user accounts, and establishing covert communication channels.

Example commands:

• Netcat or nc: Often referred to as the "Swiss army knife" of networking, Netcat can be used to maintain access by setting up reverse shells or bind shells on a compromised host.

nc [options] [hostname/IP] [port]
nc -l -p 1234

This command will listen on port 1234 for incoming TCP connections.

• Meterpreter: You can use this tool to perform different actions on the target system once inside, it gives you a wide range of capabilities. Imagine having a magic toolbox that lets you do all sorts of things once you've entered a computer system. You can manipulate files, elevate privileges to gain more access, and even communicate over the network. It's like having a Swiss Army knife for digital systems once you've managed to find a way in.

• Mimikatz: A post-exploitation tool you can use to extract plaintexts passwords, hash, PIN code, and kerberos tickets from memory.

• PowerShell Empire: A post-exploitation framework that will allow you to manage and maintain access to compromised Windows environments.

• Cobalt Strike: A threat emulation tool you can use for post-exploitation activities. It has features such as beaconing payloads (which can communicate back to the attacker-controlled server) and the ability to spawn covert channels for communication.:

• psexec: A light-weight telnet-replacement that lets you execute processes on other systems, complete with full interactivity for console applications. It's part of the Sysinternals suite of tools and can be used for maintaining access by executing processes remotely.

• SilentTrinity: A post-exploitation agent powered by Python, IronPython, C#, and .NET's DLR, useful for situations where a high degree of stealth and flexibility is required to maintain access.

• Shellter: A dynamic shellcode injection tool that can be used to inject malicious code into native Windows applications. This can be used to maintain access by creating trojanized versions of legitimate software.

• Evil-WinRM: A tool specifically designed for penetration testing of Windows Remote Management (WinRM) services; it can be used to maintain persistent access through WinRM, which is enabled by default on Windows servers.

• BloodHound: While primarily used for mapping out relationships within Active Directory environments, BloodHound can help in maintaining access by identifying high-value targets and understanding the network layout.

Pro Tip: Always obtain proper permissions and follow ethical guidelines when conducting penetration testing.

Step 5: Analysis and Reporting

In the final stage, analyze the findings from the testing process and prepare a detailed report. Document successful exploits, compromised systems, and recommendations for remediation.

1. Start with an introduction: Begin by summarizing what was found and why it matters.

2. Explain how the test was done: Talk about the tools and methods used and explain how vulnerabilities were found and what was looked at.

3. List the findings: Make a list of all the issues found, saying what they are and how serious they are. Show proof, like pictures or logs, to back up each problem.

4. Look at the risks: Think about how likely it is that each problem could be used by bad actors. Consider what could happen if the problems were not fixed.

5. Give advice on fixing things: Offer clear advice on how to fix each problem. Suggest what should be fixed first and why.

6. Finish with a summary: Recap the main findings and why they're important. Talk about any big patterns or trends seen during the test.

7. Include extra details if needed: Add any extra information that might help, like raw data or more technical notes. Attach any other documents that could be useful.

8. List where information came from: Say where any outside information, tools, or guidelines came from. Show where to find more information if needed.

5 questions to ask yourself

1. What critical problems did I find, and why are they dangerous?

2. Did I list and sort all the problems by how bad they are?

3. What should be done to fix the problems and make things safer?

4. Does the report contain references to the vulnerabilities found?

5. Is the report easy to understand for everyone, explaining what's wrong and what to do about it?

Finally, Did you enjoy Pentesting using the above guide?

Did you enjoy finding those vulnerabilities? It's like solving a big puzzle and making applications and APIs secure. Even if you faced some challenges, that's okay! Every problem you solve helps you learn more. If you enjoyed your first pentest, you're on a fun journey of learning and making a difference. Keep it up!

1. Web Application Penetration Testing

Web Application Penetration Testing means you are actively assessing web applications to find security weaknesses.

You can follow the above guide to scrutinize input fields for injection vulnerabilities like SQL injection and cross-site scripting (XSS), test authentication and authorization mechanisms, and examine session management practices. You should also search for misconfigurations in web servers and applications that could cause data breaches or unauthorized access.

Here is a list of vulnerabilities you should look for in a Web Application Penetration Testing

Example: Penetration Testing of an e-commerce application like amazon.com

1. Application Discovery:

   Identify the web application endpoints associated with Amazon.com, including the main website, subdomains, and any additional services or applications. Use tools like web crawlers (such as Burp Suite Spider or Akto) to discover hidden pages, directories, and API endpoints.

2. Reconnaissance and Information Gathering:
   Gather information about the Amazon.com web application, including its technologies, frameworks, third-party libraries, and potential vulnerabilities. Use tools like Wappalyzer, BuiltWith, or manual inspection of HTTP headers to identify the technologies used in the application stack.

3. Vulnerability Assessment:
   Conduct vulnerability scans and assessments to identify common security vulnerabilities and weaknesses in the Amazon.com web application.
   Use automated vulnerability scanning tools like Akto to identify vulnerabilities such as SQL injection, cross-site scripting (XSS), and insecure server configurations.

4. Authentication and Authorization Testing:
   Test the authentication and authorization mechanisms implemented in the Amazon.com web application. Attempt to bypass authentication controls, such as login screens or session management, using techniques like brute force attacks, credential stuffing, or session fixation. Verify proper enforcement of user roles and permissions to ensure that users can only access authorized functionality and data.
   Check out this checklist to test for different vulnerabilities.

5. Input Validation and Output Encoding:
   Test the input validation and output encoding mechanisms implemented in the Amazon.com web application to prevent common security vulnerabilities. Validate the handling of user-supplied data, such as form inputs, URL parameters, and HTTP headers, to prevent injection attacks (e.g., SSTI, SQL injection, XSS).
   Verify that output data is properly encoded to prevent XSS attacks and other injection vulnerabilities.

6. Session Management and Secure Communications:
   Evaluate the session management and secure communications mechanisms implemented in the Amazon.com web application.
   Verify that session tokens are securely generated, transmitted, and invalidated upon logout or session timeout. Ensure the use of secure communication protocols (e.g., HTTPS) and proper certificate validation to protect sensitive data in transit.

7. Security Headers and Configuration Review:
   Review the security headers and server configurations implemented in the Amazon.com web application to prevent common security vulnerabilities and misconfigurations.
   Verify the presence of security headers such as Content Security Policy (CSP), Strict-Transport-Security (HSTS), and X-Frame-Options to mitigate various attack vectors.
   Assess server configurations for security best practices, such as secure SSL/TLS configurations, secure cookie settings, and proper error handling.

8. Reporting and Remediation:
   Document findings from the web application penetration test, including identified vulnerabilities, their severity, and recommendations for remediation.
   Provide actionable remediation guidance to the Amazon.com development team, including code fixes, configuration changes, and security best practices.

2. Mobile Application Penetration Testing

In Mobile application penetration testing, you should analyze both the client-side (mobile app binaries) and server-side components of mobile apps to discover vulnerabilities.

You must examine the app's user authentication, sensitive data storage, and backend server communication. You should assess the app's encryption mechanisms, identify insecure API endpoints, and evaluate the app's resistance to reverse engineering and tampering. You must also consider platform-specific vulnerabilities and security best practices for iOS and Android applications.

Web application penetration testing involves scrutinizing input fields for vulnerabilities. On the other hand, mobile application penetration testing involves analyzing both the client-side (mobile app binaries) and server-side components.

Here is a list of vulnerabilities you should look for in a Mobile Application Penetration Testing

Example: Penetration Testing of a food delivery mobile app - Doordash.com

1. Application Installation and Setup:
   Install the DoorDash mobile app on a testing device or emulator.
   Set up any necessary testing accounts or profiles within the app.

2. Reconnaissance and Information Gathering:
   Conduct reconnaissance to gather information about the DoorDash mobile app, such as its version, supported platforms (iOS/Android), and relevant APIs. Use tools like APKTool (for Android) or class-dump-z (for iOS) to extract information from the app binary.

3. Static Analysis:
   Perform static analysis of the DoorDash mobile app to identify potential security vulnerabilities in the codebase.

   Review the source code for insecure coding practices, hardcoded credentials, sensitive data storage, and other common issues.
   Use static analysis tools like MobSF, QARK, or jadx for Android, and Hopper, IDA Pro, or class-dump for iOS.

4. Dynamic Analysis:
   Execute the DoorDash mobile app on a testing device or emulator.
   Monitor the app's network traffic, file system activity, and runtime behavior using tools like Burp Suite, Wireshark, Akto.
   Identify potential security vulnerabilities, such as insecure data transmission, sensitive data leakage, or runtime manipulation.

5. Authentication and Authorization Testing:
   Test the authentication and authorization mechanisms implemented in the DoorDash mobile app.
   Attempt to bypass authentication controls, such as login screens or session management, using techniques like brute force attacks, credential stuffing, or token manipulation.
   Verify proper enforcement of user roles and permissions to ensure that users can only access authorized functionality and data.

6. Input Validation and Data Sanitization:
   Test the input validation and data sanitization mechanisms implemented in the DoorDash mobile app.
   Attempt to exploit input validation flaws, such as SQL injection, XSS (Cross-Site Scripting), or command injection, to manipulate the app's behavior or access unauthorized data.
   Validate the handling of user-supplied data, such as form inputs, HTTP headers, and URL parameters, to prevent common security vulnerabilities.

7. Session Management and Secure Communications:
   Evaluate the session management and secure communications mechanisms implemented in the DoorDash mobile app.
   Verify that session tokens are securely generated, transmitted, and invalidated upon logout or session timeout.
   Ensure the use of secure communication protocols (e.g., HTTPS) and proper certificate validation to protect sensitive data in transit.

8. Reporting and Remediation:
   Document findings from the mobile penetration test, including identified vulnerabilities, their severity, and recommendations for remediation.
   Provide actionable remediation guidance to the development team, including code fixes, configuration changes, and security best practices.

Resources:

• https://mas.owasp.org/MASTG/General/0x04b-Mobile-App-Security-Testing/

• https://www.hackthebox.com/blog/intro-to-mobile-pentesting

• https://pentester.land/tags/mobile-app-hacking/

3. Network Penetration Testing

This involves focusing on finding security vulnerabilities in network infrastructure, including routers, switches, firewalls, and network services.

As a pentester, you should conduct port scanning to discover open ports and services, perform vulnerability scanning to identify network device weaknesses, and assess network segmentation and access control measures' effectiveness. You should also evaluate the security of wireless networks, including Wi-Fi encryption protocols and access point configurations. Check out the tools mentioned in above sections.

Here is a list of vulnerabilities you should look for in a Network Penetration Testing

Example of Network Penetration Testing

1. Understanding Network Infrastructure:

Familiarize yourself with the organization's network architecture, including routers, switches, servers, firewalls, and wireless access points.

Example: Understand the layout of the network, such as internal subnets, DMZ (Demilitarized Zone), and external facing systems. Tools: Network diagrams, documentation, and network scanning tools like Nmap.

2. Identify Attack Surface:

Identify potential entry points and attack vectors into the network, such as exposed services, misconfigured devices, or weak authentication mechanisms.

Example: Identify publicly accessible servers, VPN endpoints, or wireless networks that could be targeted by attackers.

Tools: Port scanners like Nmap, reconnaissance tools like Shodan or Recon-ng.

3. Enumeration and Discovery:

Enumerate network hosts, services, and protocols to gather information about the network topology and available resources.

Example: Use Nmap to scan for live hosts, open ports, and running services on target systems.

Tools: Nmap, Masscan, Netcat, Wireshark for packet capture and analysis.

4. Vulnerability Scanning:

Conduct vulnerability scans to identify known security vulnerabilities in network devices, operating systems, and software applications.’

Example: Use Nessus or OpenVAS to scan for common vulnerabilities like missing patches, default credentials, or insecure configurations.

Tools: Nessus, OpenVAS, Nikto, Metasploit.

5. Exploitation:

Exploit discovered vulnerabilities to gain unauthorized access to network assets or compromise target systems.

Example: Exploit a known vulnerability in an outdated web server to gain remote code execution and access sensitive data.

Tools: Metasploit Framework, ExploitDB, PowerShell Empire.

6. Privilege Escalation:

Escalate privileges on compromised systems to gain administrative access and expand control over the network.

Example: Exploit misconfigured permissions or vulnerabilities in operating systems to gain elevated privileges.

Tools: Windows Credential Editor (WCE), PowerSploit, Linux Privilege Escalation Checkers.

7. Data Exfiltration:

Attempt to exfiltrate sensitive data from the network using covert channels, encrypted communication, or file transfer protocols.

Example: Use tools like Netcat or FTP to transfer stolen data to an external server without detection.

Tools: Netcat, FTP, TFTP, Steghide for steganography.

8. Reporting and Remediation:

Document findings from the penetration test, including identified vulnerabilities, exploited systems, and recommendations for remediation.

Example: Provide a detailed report outlining discovered vulnerabilities, their impact, and actionable recommendations for mitigating security risks.

Tools: Penetration testing report templates, documentation tools like Markdown or Microsoft Word.

Resources:

• https://book.hacktricks.xyz/generic-methodologies-and-resources/pentesting-network

• https://pentestmonkey.net/

4. Cloud Penetration Testing

This involves assessing the security of cloud platforms such as Amazon Web Services (AWS), Microsoft Azure, and Google Cloud Platform (GCP).

You must evaluate the configuration of cloud resources, including virtual machines, storage buckets, databases, and networking components. You assess the security of identity and access management (IAM) policies, analyze the effectiveness of encryption mechanisms for data at rest and in transit, and identify potential security misconfigurations that could expose sensitive data or lead to unauthorized access.

Here is a list of vulnerabilities you should look for in a Cloud Penetration Testing

Example of Cloud Penetration Testing

1. Scope Definition:

• Clearly define the scope of the cloud penetration test, including the cloud service provider (e.g., AWS, Azure, GCP), specific services to be tested, and any compliance requirements.

2. Enumeration and Discovery:

• Enumerate cloud assets, including virtual machines, storage buckets, databases, and network configurations.

• Use cloud-specific enumeration tools like AWS CLI, Azure CLI, or GCP Cloud SDK to identify resources and services.

3. Configuration Review:

• Review the configuration of cloud services and resources to identify misconfigurations, insecure defaults, and unnecessary exposures.

• Use tools like CloudSploit, Scout Suite, or Prowler to assess cloud configuration security.

4. Vulnerability Assessment:

• Conduct vulnerability scans and assessments to identify known vulnerabilities and weaknesses in cloud infrastructure and applications.

• Utilize cloud-native vulnerability scanning tools like AWS Inspector, Azure Security Center, or Google Cloud Security Command Center.

5. Exploitation:

• Exploit identified vulnerabilities to gain unauthorized access to cloud resources, compromise cloud infrastructure, or escalate privileges.

• Use techniques like server-side request forgery (SSRF), misconfigured IAM roles, or insecure APIs to exploit cloud services.

6. Data Exposure and Exfiltration:

• Identify sensitive data stored in cloud storage buckets, databases, or other cloud services.

• Attempt to exploit misconfigured access controls or weak encryption to access and exfiltrate sensitive data from the cloud environment.

7. Network Security:

• Assess the network security of cloud environments, including virtual networks, subnets, security groups, and access control lists (ACLs).

• Use tools like VPC Flow Logs, Azure Network Watcher, or GCP VPC Flow Logs to monitor network traffic and detect anomalies.

8. Reporting and Remediation:

• Document findings from the cloud penetration test, including identified vulnerabilities, exploited resources, and recommendations for remediation.

• Collaborate with cloud administrators and DevOps teams to prioritize and implement security controls based on the test results, ensuring continuous improvement of cloud security posture.

Resources:

• https://cloud.hacktricks.xyz/pentesting-cloud/pentesting-cloud-methodology

• https://owasp.org/www-project-cloud-native-application-security-top-10/

5. Container Penetration Testing

As container technology adoption increases, you must assess the security of containerized environments like Docker and Kubernetes.

As a pentester, you should search for vulnerabilities in container images, assess security of container orchestration platforms, and evaluate effectiveness of container runtime security measures. You must examine container networking configurations, container isolation mechanisms, and container security policies to identify potential attack vectors and security gaps.

Example of Container Penetration Testing

1. Understanding Container Technology:

• Familiarize yourself with container technology, including Docker, Kubernetes, and container orchestration platforms.

• Understand the architecture, components, and security considerations of containerized environments.

2. Scope Definition:

• Define the scope of the container penetration test, including the container orchestration platform, container images, and deployed applications.

• Identify specific targets, such as Docker hosts, Kubernetes clusters, container registries, and microservices.

3. Container Enumeration and Discovery:

• Enumerate containerized environments to identify running containers, images, and deployed applications.

• Use container-specific enumeration tools like Docker CLI, Kubernetes API, or container orchestration scanners to gather information about the environment.

4. Container Image Analysis:

• Analyze container images for security vulnerabilities, misconfigurations, and insecure dependencies.

• Use container scanning tools like Clair, Trivy, or Anchore to perform vulnerability assessments and identify known security issues in container images.

5. Container Exploitation:

• Exploit identified vulnerabilities in container images or runtime environments to gain unauthorized access or compromise containerized applications.

• Use techniques like container escape, privilege escalation, or container breakout to exploit weaknesses in container isolation.

6. Container Orchestration Security:

• Assess the security of container orchestration platforms like Kubernetes, Docker Swarm, or Amazon ECS.

• Review Kubernetes configuration files, Docker Compose files, and container deployment manifests for security best practices and potential misconfigurations.

7. Network Security:

• Evaluate network security controls within containerized environments, including network segmentation, firewall rules, and network policies.

• Use tools like kube-hunter, kube-bench, or Docker Bench for Security to assess the security posture of container networks and identify weaknesses.

8. Data Exfiltration and Post-Exploitation:

• Attempt to exfiltrate sensitive data from containerized environments using covert channels, container-to-container communication, or exposed APIs.

• Conduct post-exploitation activities to maintain persistence, escalate privileges, and move laterally within containerized environments.

9. Reporting and Remediation:

• Document findings from the container penetration test, including identified vulnerabilities, exploited containers, and recommendations for remediation.

• Provide actionable remediation guidance to improve the security posture of containerized environments, including patch management, configuration changes, and security best practices.

• Collaborate with DevOps teams, container administrators, and security engineers to prioritize and implement security controls based on the test results, ensuring continuous improvement of container security postur

Resources:

• https://book.hacktricks.xyz/network-services-pentesting/2375-pentesting-docker

• https://www.cobalt.io/blog/pentesting-containers-overview-security-best-practices

• https://hackersploit.org/docker-for-penetration-testing/

6. Embedded Devices (IoT) Penetration Testing

In penetration testing for embedded devices, also known as IoT penetration testing, pentesters focus on assessing the security of connected devices such as smart appliances, medical devices, industrial control systems, and automotive systems.

As a pentester, you must evaluate the security of device firmware, communication protocols, and network interfaces. You should look for vulnerabilities that could be exploited to gain unauthorized access to the device, manipulate its behavior, or extract sensitive information. You should also consider the unique challenges posed by IoT devices, such as limited processing power, resource constraints, and the need for secure remote management.

Example of IoT Penetration Testing

1. Preparation and Reconnaissance:

• Gather information about the target system, including IP addresses, domain names, network architecture, and potential vulnerabilities.

• Perform reconnaissance using tools like Nmap, Shodan, or OSINT (Open-Source Intelligence) techniques to identify exposed services and attack surfaces.

2. Scanning and Enumeration:

• Scan for open ports, running services, and potential vulnerabilities on the target system using tools like Nmap, Masscan, or Nessus.

• Enumerate system resources, user accounts, and network shares to gather additional information that could aid in exploitation.

3. Vulnerability Assessment:

• Conduct vulnerability scans and assessments to identify known security vulnerabilities and misconfigurations in the target system.

• Use automated vulnerability scanning tools like Nessus, OpenVAS, or Qualys to identify common vulnerabilities and weaknesses.

4. Exploitation:

• Exploit identified vulnerabilities to gain unauthorized access to the target system or compromise its security.

• Utilize penetration testing frameworks like Metasploit, ExploitDB, or custom scripts to exploit known vulnerabilities and weaknesses.

5. Privilege Escalation:

• Escalate privileges on compromised systems to gain administrative access and expand control over the target environment.

• Use techniques like kernel exploits, misconfigured permissions, or weak authentication mechanisms to escalate privileges.

6. Post-Exploitation:

• Conduct post-exploitation activities to maintain access, gather sensitive information, and pivot to other systems within the target network.

• Use post-exploitation frameworks like Empire, Cobalt Strike, or PowerShell scripts to establish persistence and move laterally within the network.

7. Data Exfiltration:

• Attempt to exfiltrate sensitive data from the target system or network using covert channels, encrypted communication, or file transfer protocols.

• Use tools like Netcat, FTP, or custom scripts to transfer stolen data to an external server without detection.

8. Reporting and Remediation:

• Document findings from the penetration test, including identified vulnerabilities, exploited systems, and recommendations for remediation.

• Collaborate with stakeholders to prioritize and implement security patches, configuration changes, and other remediation measures based on the test results.

Resources:

• https://www.exploit-db.com/docs/english/18094-hacking-embedded-devices-for-fun-&-profit.pdf

• https://www.iotpentestingguide.com/

7. API Penetration Testing

This involves assessing the security of APIs used to exchange data between different applications and services.

As a pentester, you must evaluate the authentication and authorization mechanisms used to access APIs, assess the effectiveness of input validation and output encoding mechanisms, and identify potential security vulnerabilities such as injection attacks, broken authentication, and insecure direct object references (IDORs).

You must analyze the impact of API rate limiting and throttling mechanisms on API security, assess the effectiveness of API logging and monitoring solutions, evaluate the security of API documentation, and ensure complete API inventory.

Example of API Penetration Testing

1. Information Gathering:

• Identify all APIs associated with the application, including endpoints, methods, and parameters.

• Collect documentation, such as API specifications, Swagger/OpenAPI definitions, or any other relevant documentation.

2. Threat Modeling:

• Evaluate potential threats to the APIs based on their functionalities and the sensitivity of the data they handle.

• Prioritize identified threats according to their potential impact on the system and likelihood of exploitation.

3. Authentication and Authorization Testing:

• Test authentication mechanisms such as OAuth, JWT, or API keys to ensure they are implemented securely.

• Verify that proper authorization controls are in place to restrict access to sensitive resources based on user roles and permissions.

4. Input Validation Testing:

• Validate input fields for vulnerabilities such as SQL injection, Cross-Site Scripting (XSS), and command injection.

• Ensure that input data is properly sanitized to prevent these vulnerabilities from being exploited.

5. Session Management Testing:

• Test the management of user sessions to prevent issues such as session fixation, session hijacking, and insufficient session expiration.

• Ensure that session tokens are securely generated, transmitted, and stored.

6. Error Handling Testing:

• Assess how the API handles error conditions and exceptions.

• Check for potential information leakage through error messages that could reveal sensitive information about the system.

7. Data Integrity Testing:

• Verify that data transmitted between the client and server is protected against tampering.

• Test the API's resistance to data manipulation attacks and ensure that integrity checks are in place.

8. Rate Limiting and DoS Testing:

• Assess the API's ability to handle a high volume of requests and prevent abuse.

• Test for rate-limiting mechanisms to mitigate the risk of DoS attacks and ensure the availability of the API.

9. Security Headers and Encryption Testing:

• Check for the presence of security headers such as Content Security Policy (CSP), Cross-Origin Resource Sharing (CORS), and HTTP Strict Transport Security (HSTS).

• Verify that sensitive data is transmitted securely over HTTPS and encrypted using strong cryptographic protocols and algorithms.

10. Documentation, Remediation, and Retesting:

• Document all findings from the penetration testing, including identified vulnerabilities, their severity, and recommendations for remediation.

Resources:

• Check out the best api security practices.

• Learn about the OWASP API Top 10 vulnerabilities.

8. CI/CD Pipeline Penetration testing

This involves assessing the security of the continuous integration and continuous deployment (CI/CD) pipeline infrastructure, including the build servers, version control systems, artifact repositories, and deployment environments.

As a pentester, you must evaluate the security of the CI/CD toolchain, assess the effectiveness of access controls and authentication mechanisms, and identify potential security vulnerabilities such as insecure configurations, inadequate logging and monitoring, and unauthorized access to sensitive data.

You must analyze the impact of vulnerabilities in third-party dependencies and libraries used within the CI/CD pipeline, assess the security of pipeline automation scripts and configurations, and evaluate the effectiveness of security controls and mitigations implemented throughout the CI/CD process.

Example of CI/CD Pipeline Penetration testing

1. Understanding CI/CD Pipeline:

• Familiarize yourself with Continuous Integration (CI) and Continuous Deployment (CD) principles.

• Understand the workflow, components, and technologies involved in a CI/CD pipeline.

2. Identify Pipeline Components:

• Identify key components such as version control systems, build servers, artifact repositories, and deployment tools.

• Understand how these components interact and the potential security implications of each.

3. Threat Modeling:

• Conduct a threat modeling exercise to identify potential security threats and attack vectors in the CI/CD pipeline.

• Prioritize threats based on their impact and likelihood of exploitation.

4. Security Assessment:

• Conduct security assessments of each pipeline component, including:

  • Version control: Ensure proper access controls, review for sensitive information exposure.

  • Build servers: Check for misconfigurations, unauthorized access, and insecure build scripts.

  • Artifact repositories: Validate access controls, scan for vulnerabilities in stored artifacts.

  • Deployment tools: Review configuration settings, check for insecure deployment practices.

5. Automation Security Testing:

• Integrate security testing tools into the pipeline to automate security assessments:

  • Static Application Security Testing (SAST) tools like SonarQube or Checkmarx to scan code repositories for vulnerabilities.

  • Dependency scanning tools like OWASP Dependency-Check to identify vulnerabilities in third-party dependencies.

  • Dynamic Application Security Testing (DAST) tools like Akto to scan deployed applications for vulnerabilities.

6. Configuration and Secret Management:

• Review configuration settings and ensure secure handling of secrets (e.g., API keys, passwords) within the pipeline.

• Avoid hardcoding sensitive information and utilize secure vaults or secrets management solutions.

7. Data Protection and Privacy:

• Ensure proper handling of sensitive data throughout the pipeline.

• Encrypt data in transit and at rest, implement access controls, and adhere to privacy regulations (e.g., GDPR).

8. Reporting and Remediation:

• Document findings from the penetration testing, including identified vulnerabilities, their severity, and recommendations for remediation.

• Provide actionable remediation guidance to the development and operations teams.

• Conduct follow-up assessments to verify that vulnerabilities have been addressed effectively.

9. Continuous Monitoring:

• Implement continuous monitoring solutions to detect and respond to security incidents in real-time.

• Monitor pipeline activities, access logs, and deployment events for suspicious behavior.

10. Education and Training:

• Provide training to developers and operations teams on secure coding practices, secure configuration, and best practices for CI/CD security.

• Foster a culture of security awareness and collaboration within the organization.

Resources:

• https://cloud.hacktricks.xyz/pentesting-ci-cd/pentesting-ci-cd-methodology

• https://about.gitlab.com/topics/ci-cd/

Legal and Ethical Considerations for Penetration Testing

Ethical Considerations:

1. Authorization: You need explicit permission from the organization or person who owns the system or network you're testing. This ensures ethical and legal testing. Keep clear documentation of what you're allowed to test to avoid misunderstandings.

2. Transparency: Be open with your clients about your methods, tools, and techniques. This builds trust and helps them understand the testing process and its implications. It also allows them to give feedback.

3. Confidentiality: Keep any data you collect during testing private and don't share it with unauthorized people. Only disclose vulnerabilities to authorized personnel to protect your clients from potential attacks.

4. Responsibility: Make sure you conduct testing responsibly and professionally, without causing harm to anyone involved. Put measures in place to prevent damage and address any vulnerabilities you find promptly.

Legal Considerations:

1. Compliance: You must follow all relevant laws and regulations, like data protection and privacy laws. This includes laws such as the Computer Fraud and Abuse Act (CFAA) and the General Data Protection Regulation (GDPR).

2. Liability: Consider the potential for legal consequences that could arise from your testing, such as damage to systems. To reduce your liability, make sure you work with qualified testers and have appropriate insurance coverage.

3. Documentation: Keep detailed records of your testing, including what you tested, how you did it, and what you found. This helps demonstrate that you conducted testing responsibly and can prove your diligence in the event of a security breach.

Final Thoughts

You are now equipped with the knowledge and understanding to carry out penetration testing.

An adept penetration tester not only identifies critical vulnerabilities but also fully understands their potential implications. Through this process, you are contributing significantly to your organization's cybersecurity, ensuring robust defenses against potential threats.

Remember, the effectiveness of penetration testing lies in its meticulous implementation. So, apply what you've learned diligently, stay updated with the latest cybersecurity trends, and continue enhancing your skills in pentesting.