Advance Penetration Testing Methodology for the year 2023
INTRODUCTION
Author:- Pratik Chhetri (My All Social Link Available in this)
In today's digital age, cyber threats are an ever-present danger, and organizations must take proactive steps to safeguard their systems and networks against potential attacks. Pentesting, a widely adopted security testing methodology, plays a crucial role in identifying and mitigating security vulnerabilities, ensuring that organizations can stay one step ahead of cybercriminals.
PHASES OF PENETRATION TESTING
Penetration testing, also known as pen testing, is a simulated attack on a computer system, network or web application, designed to identify and exploit vulnerabilities. It is a critical part of any security assessment process and is used to evaluate the security posture of an organization. In this blog post, we will discuss the phases of penetration testing.Planning and Reconnaissance
The first phase of penetration testing involves planning and reconnaissance. This includes identifying the scope of the assessment, defining the objectives of the test, and gathering information about the target environment. This phase is crucial, as it lays the foundation for the rest of the testing process. It includes gathering information about the target's network infrastructure, applications, and systems, as well as identifying potential vulnerabilities and attack vectors.Scanning and Enumeration
The second phase of penetration testing involves scanning and enumeration. During this phase, the tester uses various tools to scan the target environment for vulnerabilities, such as open ports, services, and other network assets. The tester also enumerates the target environment to identify potential attack vectors and gather additional information about the target environment.Gaining Access
The third phase of penetration testing involves attempting to gain access to the target system or application. The tester will use various techniques, such as password cracking, social engineering, and exploitation of vulnerabilities, to gain access to the target system or application. Once access is obtained, the tester will attempt to escalate privileges to gain further access to the target environment.Maintaining Access
The fourth phase of penetration testing involves maintaining access to the target environment. This phase is critical for testing the target's ability to detect and respond to an ongoing attack. The tester will attempt to remain undetected while maintaining access to the target environment, and will also attempt to cover their tracks to avoid detection.Covering Tracks
The fifth and final phase of penetration testing involves covering tracks. During this phase, the tester will attempt to remove any evidence of their presence from the target environment. This includes deleting log files, modifying system files, and other activities to make it difficult for the target to detect the attack.WHAT I DO IN MY PLANNING AND RECONNAISSANCE PHASE
The Planning and Reconnaissance phase is the first and most crucial phase in the penetration testing process. During this phase, the penetration tester gathers information about the target system, identifies potential vulnerabilities and attack vectors, and defines the scope of the assessment. Here are the steps involved in the Planning and Reconnaissance phase:
Step 1: Define the Scope of the Assessment
The first step in the Planning and Reconnaissance phase is to define the scope of the assessment. The scope defines what systems, networks, or applications will be tested and what testing methods will be used. This step involves working with the client to determine the testing goals and objectives, identifying the target environment, and defining the rules of engagement.
Step 2: Gather Information about the Target System
The next step in the Planning and Reconnaissance phase is to gather information about the target system. This step includes researching the target organization, identifying their network infrastructure, and identifying their public-facing assets. The penetration tester can use open-source intelligence (OSINT) tools to gather information from publicly available sources such as social media, search engines, and public records.
Step 3: Identify Potential Vulnerabilities and Attack Vectors
The third step in the Planning and Reconnaissance phase is to identify potential vulnerabilities and attack vectors. This step involves using vulnerability scanners, port scanners, and other reconnaissance tools to identify potential vulnerabilities in the target environment. The penetration tester should also identify potential attack vectors, such as web applications, mobile devices, and social engineering.
Step 4: Define the Testing Methodology
The fourth step in the Planning and Reconnaissance phase is to define the testing methodology. This step involves selecting the appropriate testing tools and techniques based on the identified vulnerabilities and attack vectors. The penetration tester should also define the testing approach, such as black-box, gray-box, or white-box testing.
Step 5: Obtain Authorization and Consent
The final step in the Planning and Reconnaissance phase is to obtain authorization and consent. This step involves working with the client to obtain authorization to conduct the testing and defining the rules of engagement. The penetration tester should also obtain written consent from the client before beginning the testing process.
In conclusion, the Planning and Reconnaissance phase is critical to the success of a penetration testing engagement. By defining the scope of the assessment, gathering information about the target system, identifying potential vulnerabilities and attack vectors, defining the testing methodology, and obtaining authorization and consent, the penetration tester can lay the foundation for the rest of the testing process. This phase sets the stage for a successful engagement by ensuring that the testing goals and objectives are aligned with the client's business objectives and that the testing approach is appropriate for the target environment.
Tools that I use in this phase
There are several tools and websites that can be used during the Planning and Reconnaissance phase of a penetration testing engagement. Here are some of the most common ones along with a short description:
- Nmap - A network mapping tool that can be used to discover hosts and services on a network, as well as identify open ports and running services.
- Shodan - A search engine for internet-connected devices that allows you to find vulnerable devices and systems that are publicly accessible.
- Whois - A command-line tool that allows you to obtain information about domain name registration, including contact information for the domain owner and administrative contact.
- Recon-ng - A reconnaissance tool that automates the process of gathering information about a target system, including social media profiles, email addresses, and network infrastructure.
- The Harvester - A tool that can be used to collect email addresses, subdomains, and other information about a target system from public sources.
- Maltego - A graphical tool that can be used to visualize relationships between information about a target system, including domain names, IP addresses, and social media profiles.
- Google Dorks - A collection of advanced search operators that can be used to identify sensitive information and vulnerabilities in a target system.
- OSINT Framework - A collection of tools and resources for open-source intelligence gathering, including search engines, social media platforms, and data visualization tools.
- Sublist3r - A tool that can be used to enumerate subdomains for a target domain, which can be useful for identifying potential attack vectors.
- Spiderfoot - A tool that can be used to gather information about a target system from a variety of sources, including DNS records, web pages, and social media profiles.
WHAT I DO IN MY SCANNING AND ENUMERATION PHASE
The Scanning and Enumeration phase is the second phase of a
penetration testing engagement. During this phase, the penetration tester uses
various scanning and enumeration tools to identify vulnerabilities and gather
information about the target system. Here are the steps involved in the
Scanning and Enumeration phase:
Step 1: Identify Active Hosts and Services
The first step in the Scanning and Enumeration phase is to
identify active hosts and services on the target network. This step involves
using port scanning tools such as Nmap or Masscan to scan the target network
and identify open ports and running services. The goal is to identify potential
attack vectors and vulnerable services that can be exploited in later phases.
Step 2: Enumerate Services and Gather Information
The next step in the Scanning and Enumeration phase is to
enumerate the identified services and gather additional information about the
target system. This step involves using enumeration tools such as Enum4linux,
SMBMap, or Metasploit's auxiliary modules to identify user accounts, shares,
open file handles, and other system information. The goal is to identify
potential vulnerabilities and misconfigurations that can be exploited in later
phases.
Step 3: Identify Vulnerabilities and Exploits
The third step in the Scanning and Enumeration phase is to identify vulnerabilities and exploits for the identified services and applications. This step involves using vulnerability scanning tools such as Nessus, OpenVAS, or Qualys to identify known vulnerabilities and missing patches. The penetration tester can also use exploit databases such as Exploit-DB, Metasploit, or Packetstorm to identify available exploits for the identified vulnerabilities.
Step 4: Prioritize Vulnerabilities and Plan Exploitation
The fourth step in the Scanning and Enumeration phase is to
prioritize the identified vulnerabilities based on their severity and potential
impact on the target system. This step involves working with the client to
determine the level of risk associated with each vulnerability and developing a
plan for exploitation. The penetration tester should also consider the
potential impact of each exploit on the target system and the likelihood of
success.
Step 5: Document Findings and Report to Client
The final step in the Scanning and Enumeration phase is to
document the findings and report them to the client. This step involves
creating a comprehensive report that details the vulnerabilities and potential
attack vectors identified in the Scanning and Enumeration phase, along with
recommendations for remediation. The penetration tester should also work with
the client to develop a plan for addressing the identified vulnerabilities and
mitigating the associated risks.
In conclusion, the Scanning and Enumeration phase is a
critical phase in a penetration testing engagement. By identifying active hosts
and services, enumerating services and gathering information, identifying
vulnerabilities and exploits, prioritizing vulnerabilities and planning
exploitation, and documenting findings and reporting to the client, the
penetration tester can identify potential vulnerabilities and attack vectors
that can be exploited in later phases. This phase provides valuable information
that can be used to develop a comprehensive plan for addressing the identified
vulnerabilities and mitigating the associated risks.
Tools that I use in this phase
There are several tools and websites that can be used during the Scanning and Enumeration phase of a penetration testing engagement. Here are some of the most common ones along with a short description:
- Nmap - A network mapping tool that can be used to discover hosts and services on a network, as well as identify open ports and running services.
- Masscan - A high-speed port scanner that can scan the entire internet in under 6 minutes.
- Enum4linux - A tool that can be used to enumerate user accounts, shares, and other system information on Windows and Samba systems.
- SMBMap - A tool that can be used to enumerate SMB shares on Windows and Samba systems.
- Metasploit - A framework for developing and executing exploits against a variety of targets, including web applications, databases, and network infrastructure.
- Nessus - A vulnerability scanning tool that can be used to identify known vulnerabilities and missing patches.
- OpenVAS - A vulnerability scanning tool that can be used to identify known vulnerabilities and missing patches, as well as perform network discovery and host identification.
- Qualys - A cloud-based vulnerability scanning tool that can be used to identify known vulnerabilities and missing patches, as well as perform web application scanning and compliance testing.
- Exploit-DB - A database of exploits for a wide range of targets, including web applications, databases, and network infrastructure.
- Packetstorm - A website that provides a wide range of security tools, including vulnerability scanners, penetration testing tools, and exploit databases.
In conclusion, the tools and websites listed above are just
a few of the many resources that can be used during the Scanning and
Enumeration phase of a penetration testing engagement. The specific tools and
techniques used will depend on the scope of the assessment and the target
system, but using a combination of these tools can help the penetration tester
identify potential vulnerabilities and attack vectors that can be exploited in
later phases.
WHAT I DO IN MY GAINING ACCESS PHASE
The Gaining Access phase is the third phase of a penetration
testing engagement. During this phase, the penetration tester attempts to
exploit identified vulnerabilities and gain access to the target system. Here
are the steps involved in the Gaining Access phase:
Step 1: Select Exploits
The first step in the Gaining Access phase is to select the
exploits that will be used to attempt to gain access to the target system. This
step involves reviewing the results of the vulnerability assessment and
determining which exploits are likely to be successful. The penetration tester
may also develop custom exploits or modify existing ones to increase their
effectiveness.
Step 2: Launch Exploits
The next step in the Gaining Access phase is to launch the
selected exploits against the target system. This step involves using a variety
of tools and techniques, including Metasploit, social engineering, and custom
exploits, to attempt to gain access to the target system. The penetration
tester may use a combination of exploits to bypass security controls and gain
access to sensitive data or systems.
Step 3: Escalate Privileges
The third step in the Gaining Access phase is to escalate
privileges on the target system. This step involves using techniques such as
password cracking, privilege escalation exploits, or social engineering to gain
administrative access to the target system. The penetration tester may also
attempt to gain access to other systems on the network or move laterally within
the target environment.
Step 4: Maintain Access
The fourth step in the Gaining Access phase is to maintain
access to the target system. This step involves using various techniques to
ensure continued access to the system, even if security controls are put in
place or the system is rebooted. The penetration tester may install backdoors,
create new user accounts, or modify system settings to ensure continued access
to the target system.
Step 5: Document Findings and Report to Client
The final step in the Gaining Access phase is to document
the findings and report them to the client. This step involves creating a
comprehensive report that details the successful exploits and access gained in
the Gaining Access phase, along with recommendations for remediation. The
penetration tester should also work with the client to develop a plan for
addressing the identified vulnerabilities and mitigating the associated risks.
In conclusion, the Gaining Access phase is a critical phase
in a penetration testing engagement. By selecting and launching exploits,
escalating privileges, maintaining access, and documenting findings and
reporting to the client, the penetration tester can demonstrate the potential
impact of identified vulnerabilities and provide valuable information that can
be used to develop a comprehensive plan for addressing the identified
vulnerabilities and mitigating the associated risks.
Tools that I use in this phase
The Gaining Access phase of a penetration testing engagement
requires the use of a variety of tools and techniques. Here are some of the
most commonly used tools and websites:
- Metasploit Framework - An open-source framework used for developing, testing, and executing exploits against a wide range of targets. It can be used to gain access to systems, escalate privileges, and maintain access.
- Mimikatz - A post-exploitation tool that can be used to extract passwords and other sensitive information from Windows systems. It can be used to escalate privileges and maintain access.
- Cobalt Strike - A commercial penetration testing tool that includes a range of features for gaining and maintaining access to target systems, including a variety of exploits, a command-and-control server, and post-exploitation modules.
- Empire - An open-source post-exploitation tool that can be used to establish a foothold on target systems, escalate privileges, and maintain access. It includes a range of modules for executing various types of attacks.
- Netcat - A tool for reading and writing data across network connections using TCP or UDP. It can be used to create backdoors, transfer files, and execute commands on target systems.
- PowerSploit - An open-source PowerShell module that includes a range of post-exploitation tools for gaining and maintaining access to Windows systems. It includes modules for executing code, stealing credentials, and pivoting through the network.
- Hashcat - A password cracking tool that can be used to crack passwords on target systems. It supports a wide range of hash types and can be used to crack passwords for Windows systems, Unix systems, and web applications.
- John the Ripper - Another password cracking tool that can be used to crack passwords on target systems. It supports a wide range of hash types and can be used to crack passwords for Windows systems, Unix systems, and web applications.
- Exploit-DB - A database of exploits for a wide range of targets, including web applications, databases, and network infrastructure.
- GitHub - A code repository that can be used to find custom exploits and post-exploitation tools developed by the security community.
- In conclusion, the tools and websites listed above are just a few of the many resources that can be used during the Gaining Access phase of a penetration testing engagement. The specific tools and techniques used will depend on the scope of the assessment and the target system, but using a combination of these tools can help the penetration tester successfully gain access to the target system and demonstrate the potential impact of identified vulnerabilities.
WHAT TO DO AFTER GAINING ACCESS OR IN MAINTAINING ACCESS PHASE
Once a penetration tester has successfully gained access to
a target system during the Gaining Access phase, the next step is to maintain
that access for as long as possible. The Maintaining Access phase is critical
because it allows the tester to gather additional information, escalate
privileges, and potentially move laterally through the target network to access
additional systems.
Here are some of the steps that a penetration tester might
take during the Maintaining Access phase:
- Establish persistence: The first step in maintaining access is to establish persistence on the target system. This involves creating a backdoor or other mechanism that allows the tester to regain access to the system even if the original exploit is discovered and patched. There are a variety of techniques for establishing persistence, including creating a new user account, modifying system files, or installing a rootkit.
- Conduct reconnaissance: With persistence established, the penetration tester can begin conducting reconnaissance to gather additional information about the target system and network. This might involve looking for additional vulnerabilities or weaknesses that can be exploited, identifying other systems on the network that can be accessed, or gathering information about user accounts and credentials.
- Escalate privileges: Once the tester has gathered enough information, they may attempt to escalate their privileges on the target system. This can involve exploiting additional vulnerabilities, using stolen credentials to access other systems, or using techniques like pass-the-hash to impersonate other users with higher privileges.
- Move laterally: With higher privileges, the tester may attempt to move laterally through the target network to access other systems. This can involve using techniques like port scanning and service enumeration to identify other systems on the network, exploiting vulnerabilities on those systems to gain access, and repeating the process of establishing persistence and escalating privileges on each new system.
- Cover tracks: Throughout the Maintaining Access phase, it's important for the tester to cover their tracks to avoid detection. This might involve deleting logs, modifying timestamps on files, or using anti-forensic techniques to hide their presence on the system.
Tools that I use in this phase
Here are some of the tools and websites that may be used
during the Maintaining Access phase of a penetration test:
- Metasploit Framework: A popular open-source tool that provides a range of functionality for exploiting vulnerabilities, establishing persistence, and maintaining access on target systems.
- PowerShell Empire: A post-exploitation framework that can be used to establish persistence, escalate privileges, and move laterally through a target network using a variety of techniques.
- Cobalt Strike: A commercial tool that provides similar functionality to PowerShell Empire, including the ability to establish a persistent foothold on a target system and move laterally through a network.
- Mimikatz: A tool that can be used to extract credentials and other sensitive information from Windows systems, which can be useful for escalating privileges or accessing additional systems on the network.
- BloodHound: A tool that can be used to map out the relationships between user accounts, computers, and other objects in an Active Directory environment, which can help a penetration tester identify potential avenues for lateral movement.
- Responder: A tool that can be used to intercept and capture network traffic, including authentication requests, which can be used to steal credentials or perform other attacks.
- CrackMapExec: A tool that can be used to perform various post-exploitation tasks, including privilege escalation, credential theft, and lateral movement, in both Windows and Linux environments.
- Nmap: A popular tool for network exploration and reconnaissance, which can be used to identify additional systems on a target network that can be accessed and potentially exploited.
- Wireshark: A network protocol analyzer that can be used to capture and analyze network traffic, which can be useful for understanding the target network topology and identifying potential attack vectors.
- Github: A website that hosts a large number of publicly available tools and scripts that can be used for a variety of post-exploitation tasks, such as privilege escalation, lateral movement, and credential theft.
WHAT I DO IN MY COVERING TRACKS PHASE
The Covering Tracks phase is the final phase of a
penetration test, and it involves removing all traces of the penetration
tester's activities from the target system and network. The goal of this phase
is to ensure that the organization being tested is not able to detect that a
penetration test has been conducted, and to avoid any unnecessary disruption or
damage to the target systems.
Here are some of the steps that a penetration tester might
take during the Covering Tracks phase:
- Remove backdoors: The first step in covering tracks is to remove any backdoors or other mechanisms that were used to gain and maintain access to the target system. This might involve deleting files or registry entries, restoring modified files to their original state, or uninstalling any software that was installed.
- Delete logs: Many operating systems and applications maintain logs of user activity, including login attempts, file access, and system changes. These logs can be used to detect unauthorized access and identify the source of the attack. As part of the Covering Tracks phase, the penetration tester may attempt to delete or modify these logs to cover their tracks.
- Modify timestamps: In addition to deleting logs, the tester may also modify timestamps on files and other system objects to hide their activities. For example, they might change the creation or modification date of a file to make it appear that it was created at a different time, or modify the timestamp on a log file to make it appear that it was deleted earlier than it actually was.
- Uninstall software: If the tester installed any software as part of the penetration test, they should uninstall it during the Covering Tracks phase to ensure that it does not remain on the target system.
- Remove evidence of other activities: In addition to covering their own tracks, the penetration tester may also attempt to remove evidence of other activities that may have occurred on the target system. For example, if they discover evidence of malware or other security incidents, they may attempt to remove that evidence to avoid alerting the organization to other potential security issues.
- Document findings: Finally, as part of the Covering Tracks phase, the penetration tester should document their findings and provide a report to the organization being tested. This report should include a detailed description of the testing methodology, the vulnerabilities that were identified, and any recommendations for remediation.
In summary, the Covering Tracks phase is all about removing
any evidence of the penetration tester's activities from the target system and
network, to avoid detection and minimize the impact on the organization being
tested. By removing backdoors, deleting logs, modifying timestamps, and uninstalling
software, the penetration tester can ensure that the organization being tested
is not able to detect that a penetration test has been conducted.
Tools that I use in this phase
Here are some tools and websites that may be used during the
Covering Tracks phase of a penetration test:
- CCleaner: CCleaner is a utility program used to clean potentially unwanted files and invalid Windows Registry entries from a computer. It can be used to remove temporary files, cookies, and other traces of a penetration tester's activities.
- Eraser: Eraser is a free and open source data destruction tool that can be used to securely delete files and folders from a hard drive. It can be used to remove any files that were created or modified during the penetration test.
- BleachBit: BleachBit is a cross-platform utility that can be used to free up disk space and protect privacy. It can be used to remove temporary files, logs, and other traces of a penetration tester's activities.
- Shred: Shred is a command-line utility that can be used to securely delete files and directories from a Linux or Unix file system. It can be used to remove any files that were created or modified during the penetration test.
- Windows Event Viewer: The Windows Event Viewer is a tool used to view and manage event logs on a Windows computer. Penetration testers may use this tool to remove or modify logs to cover their tracks.
- Syslog-ng: Syslog-ng is an open source logging tool used to collect and store log messages from various sources. Penetration testers may use this tool to modify or delete log messages to cover their tracks.
- Metasploit Framework: The Metasploit Framework is a popular penetration testing tool that includes a number of modules for gaining access to and controlling remote systems. It can also be used to cover tracks by deleting or modifying logs and other system files.
- Nessus: Nessus is a vulnerability scanner that can be used to identify security issues on a network. During the Covering Tracks phase, penetration testers may use Nessus to identify any security issues that were introduced during the penetration test and ensure that they are properly remediated.
In addition to these tools, penetration testers may also
consult various online resources and forums to learn about additional
techniques and tools for covering their tracks. It's important to note that the
use of some of these tools and techniques may be illegal or unethical if used
outside the context of a legitimate penetration testing engagement, so it's
important to use them responsibly and within the bounds of ethical and legal
guidelines.
SHORT ENDING NOTE
In conclusion, a successful penetration testing engagement
requires careful planning, thorough reconnaissance, precise scanning and
enumeration, creative exploitation, stealthy maintenance of access, and
effective covering of tracks. The tools and websites listed in this blog are
only a starting point, and there are many additional resources and techniques
available to penetration testers. It's important to keep up to date with the
latest trends and tools in the industry to ensure that your penetration testing
skills remain relevant and effective.
For those interested in learning more about penetration testing, there are a number of excellent books available on Amazon. Here are some highly rated books on the subject which you should keep in your setup table:
- "Penetration Testing: A Hands-On Introduction to Hacking" by Georgia Weidman Buy now
- "Metasploit: The Penetration Tester's Guide" by David Kennedy, Jim O'Gorman, Devon Kearns, and Mati Aharoni Buy Now
- "Black Hat Python: Python Programming for Hackers and Pentesters" by Justin Seitz Buy Now
- "Advanced Penetration Testing: Hacking the World's Most Secure Networks" by Wil Allsopp Buy Now
These books provide a comprehensive introduction to the
world of penetration testing and offer practical guidance on the various phases
of a penetration testing engagement. Whether you're a beginner or an
experienced penetration tester, these books are sure to expand your knowledge
and skills.
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