Corporate Ethical Hacking Planning and Execution
1. Planning and Preparation
1.1 Establishing Objectives
- In this initial phase of planning and preparation for ethical hacking, the primary focus is on setting clear and achievable objectives for the engagement.
- This involves defining the specific goals and desired outcomes that the ethical hacking team aims to accomplish during the assessment.
- By establishing well-defined objectives, the team can align their efforts with the client’s needs and priorities, *nsuring that the ethical hacking process remains focused and effective.
- Clear objectives also provide a framework for measuring the success of the engagement and guiding decision-making throughout the assessment.
- Additionally, establishing objectives helps to communicate expectations with stakeholders and ensures that everyone involved understands the purpose and scope of the ethical hacking exercise.
1.1.1 Establishing Objectives for “The Web Integrators”
- Evaluate the security posture of client networks and systems to identify vulnerabilities and potential entry points for unauthorized access.
- Assess the effectiveness of current security measures and controls in place within client infrastructure.
- Identify weaknesses in web applications and APIs used by clients, ensuring protection of sensitive data and prevention of potential breaches.
- Test client systems’ resilience against social engineering attacks, including phishing and manipulation techniques targeting employees.
- Assess susceptibility to various types of attacks such as denial-of-service (DoS) and distributed denial-of-service (DDoS) attacks.
- Provide actionable recommendations and mitigation strategies to enhance client infrastructure’s overall security posture and minimize the risk of future security incidents.. Prioritize security vulnerabilities based on potential impact and likelihood of exploitation for efficient allocation of resources.
- Foster collaboration and communication between “The Web Integrators” and client security teams to proactively address cybersecurity threats and vulnerabilities.
- Ensure compliance with relevant regulatory requirements and industry standards governing information security practices.
- Build trust and confidence with clients by demonstrating commitment to protecting their digital assets and safeguarding business operations against cyber threats.
1.2 Defining Scope
- Define the specific boundaries and objectives of the ethical hacking engagement.
- Identify the systems, networks, and assets to be included in the assessment.
- Determine the depth and breadth of testing activities, including limitations and exclusions.
- Establish clear criteria for success and completion of the engagement.
- Align the scope with client expectations, budget constraints, and project timelines.
- Document scope in a formal agreement or statement of work to ensure mutual understanding and agreement between “The Web Integrators” and the client.
- Regularly review and update the scope as necessary to adapt to evolving project requirements or changes in client priorities.
1.3 Identifying Stakeholders
- Identify key individuals and groups involved or impacted by the ethical hacking engagement.
- Determine the roles and responsibilities of each stakeholder in the project.
- Establish lines of communication and channels for collaboration among stakeholders.
- Ensure representation from relevant departments, such as IT, security, legal, and management.
- Solicit input and feedback from stakeholders to inform decision-making and prioritize objectives.
- Address any conflicts or competing interests among stakeholders to ensure alignment and consensus.
- Regularly engage with stakeholders throughout the project lifecycle to maintain transparency and accountability.
1.4 Setting Rules of Engagement
- Define the guidelines, boundaries, and limitations for conducting the ethical hacking engagement.
- Specify the authorized scope of activities, including targets, techniques, and permissible actions.
- Establish rules for handling sensitive information and data obtained during the assessment.
- Clarify expectations regarding the timing, duration, and frequency of testing activities.
- Outline procedures for obtaining explicit consent and authorization from the client before conducting any intrusive or potentially disruptive tests.
- Address legal and ethical considerations, such as compliance with relevant laws, regulations, and industry standards.
- Communicate rules of engagement clearly and comprehensively to all team members and stakeholders involved in the project.
- Continuously monitor and assess adherence to rules of engagement throughout the engagement to ensure compliance and mitigate risks.
1.5 Assessing Legal and Regulatory Considerations
- Evaluate legal and regulatory requirements applicable to the ethical hacking engagement, including data protection laws, privacy regulations, and industry standards.
- Identify potential legal risks and liabilities associated with conducting security assessments, such as unauthorized access to systems or data breaches.
- Ensure compliance with relevant statutes and regulations governing cybersecurity practices, such as the Computer Fraud and Abuse Act (CFAA) in the United States or the General Data Protection Regulation (GDPR) in the European Union.
- Obtain necessary permissions, authorizations, or agreements from regulatory authorities or governing bodies to conduct security testing within legal boundaries.
- Consult with legal experts or counsel to interpret and navigate complex legal issues related to ethical hacking activities.
- Implement safeguards and measures to protect the confidentiality, integrity, and availability of sensitive information and mitigate legal risks.
- Document legal considerations and compliance efforts to demonstrate due diligence and accountability in adherence to legal and regulatory requirements.
- Regularly review and update legal assessments to adapt to changes in laws, regulations, or industry best practices.
1.6 Assembling the Ethical Hacking Team
- Identify and recruit skilled professionals with expertise in ethical hacking, cybersecurity, and information technology.
- Define roles and responsibilities within the ethical hacking team, including team leads, analysts, and specialists.
- Ensure diversity and complementarity of skills and knowledge within the team to cover various aspects of security testing.
- Provide ongoing training and professional development opportunities to enhance team members’ technical proficiency and keep abreast of emerging threats and trends.
- Foster a collaborative and inclusive team culture that encourages knowledge sharing, creativity, and innovation.
- Establish communication channels and workflows to facilitate coordination and collaboration among team members.
- Assign tasks and allocate resources effectively to maximize productivity and efficiency in executing testing activities.
- Foster a culture of accountability and professionalism, emphasizing ethical conduct, integrity, and respect for client confidentiality.
- Encourage continuous improvement and feedback mechanisms to identify areas for enhancement and optimize team performance.
- Cultivate a supportive and empowering work environment that promotes job satisfaction, engagement, and retention among team members.
1.7 Procuring Necessary Tools and Resources
- Identify the specific tools, technologies, and resources required to conduct ethical hacking assessments effectively.
- Evaluate available options and select appropriate tools based on the objectives, scope, and technical requirements of the engagement.
- Consider factors such as functionality, compatibility, ease of use, and cost-effectiveness when choosing tools and resources.
- Ensure that selected tools are up-to-date and compatible with the target environment to maximize their effectiveness and accuracy.
- Acquire necessary licenses, subscriptions, or permissions for using commercial tools and software legally and ethically.
- Explore open-source alternatives and community-driven resources to supplement commercial tools and address specific testing needs.
- Invest in hardware infrastructure, such as dedicated testing environments or virtualization platforms, to support realistic and safe testing scenarios.
- Develop custom scripts, utilities, or methodologies tailored to the unique requirements of the engagement, if off-the-shelf solutions are insufficient.
- Establish procedures for managing and maintaining tools and resources securely, including version control, patch management, and access control.
- Provide training and support to team members to ensure proficiency in using selected tools and resources effectively during testing activities.
1.8 Creating a Project Plan
- Define the overall project objectives, deliverables, and milestones for the ethical hacking engagement.
- Develop a detailed project schedule outlining tasks, dependencies, and timelines for each phase of the assessment.
- Allocate resources, including personnel, tools, and budget, to support the successful execution of the project plan.
- Identify potential risks and uncertainties that may impact project outcomes and develop mitigation strategies to address them proactively.
- Establish communication and reporting protocols to keep stakeholders informed about project progress, challenges, and outcomes.
- Conduct regular reviews and checkpoints to assess project performance against established goals and make necessary adjustments.
- Ensure alignment between the project plan and client expectations, scope, and contractual agreements.
- Document project assumptions, constraints, and decisions to provide a clear reference for team members and stakeholders.
- Continuously monitor and track project metrics, such as budget utilization, schedule adherence, and quality of deliverables, to ensure project success.
- Foster a collaborative and accountable project team culture that promotes transparency, teamwork, and accountability for achieving project objectives.
- Review and update the project plan as needed to adapt to changes in scope, requirements, or external factors affecting project execution.
1.9 Conducting Risk Assessment
- Identify potential threats and vulnerabilities that may pose risks to the security of the client’s systems and data.
- Evaluate the likelihood and potential impact of identified risks on the confidentiality, integrity, and availability of critical assets.
- Prioritize risks based on their severity, likelihood of occurrence, and potential business impact to focus resources on mitigating the most significant threats.
- Consider both technical vulnerabilities and human factors, such as user behavior and organizational culture, in assessing risks comprehensively.
- Engage with key stakeholders, including IT personnel, security experts, and business leaders, to gather input and insights on potential risks.
- Document risk assessment findings, including identified risks, their likelihood and impact ratings, and proposed mitigation strategies.
- Develop a risk treatment plan outlining specific actions and controls to address identified risks effectively.
- Monitor and review the effectiveness of risk mitigation measures over time and adjust strategies as necessary to address evolving threats and vulnerabilities.
- Communicate risk assessment results and mitigation efforts to relevant stakeholders to promote transparency and accountability in managing cybersecurity risks.
- Integrate risk assessment activities into the broader risk management framework of the organization to align with strategic business objectives and regulatory requirements.
1.10 Developing Communication Protocols
- Establish clear channels and protocols for communication within the ethical hacking team and with external stakeholders.
- Define roles and responsibilities for communication, including designated points of contact and escalation procedures for addressing issues or concerns.
- Determine the frequency and format of communication, such as regular meetings, status updates, and written reports, to keep stakeholders informed about project progress.
- Specify the types of information to be communicated, including project milestones, risks, issues, and key findings from testing activities.
- Ensure that communication protocols accommodate the diverse needs and preferences of stakeholders, such as technical and non-technical audiences.
- Implement secure communication channels and encryption mechanisms to protect sensitive information shared during the engagement.
- Establish guidelines for documenting and archiving communication records to maintain a clear audit trail of project activities and decisions.
- Foster open and transparent communication practices that encourage collaboration, feedback, and knowledge sharing among team members and stakeholders.
- Provide training and support to team members on effective communication techniques and tools to facilitate productive interactions.
- Continuously evaluate and refine communication protocols based on feedback, lessons learned, and changing project requirements to enhance effectiveness and efficiency.
2. Reconnaissance
2.1 Passive Reconnaissance Techniques
- WHOIS Lookup: Typically performed using external tools or online services dedicated to WHOIS queries.
- Social Media Analysis: Involves manual investigation or specialized tools tailored for social media intelligence.
- Job Postings and Career Pages: Requires manual research into job listings and career pages on the target organization’s website or other job platforms.
- Publicly Available Information: Involves gathering information from various public sources, such as company websites, press releases, news articles, and industry reports, through manual research or specialized tools.
- Passive DNS Monitoring: Typically performed using external tools or online services that monitor and analyze historical DNS data.
- Email Header Analysis: Involves analyzing email headers to gather information about the sender, recipient, mail servers, and message routing, usually done using specialized email forensics tools.
These techniques rely on manual investigation, specialized tools, or online services external to Metasploit for gathering information about the target organization’s digital footprint.
2.2 Active Reconnaissance Techniques
2.2.1 Port Scanning
Identifying open ports and services running on target systems.
2.2.1.1 Stealthy TCP SYN Port Scanning:**
A SYN scan is a stealthy port scanning technique that sends SYN packets to target ports and analyzes responses to identify open ports without completing the TCP handshake.
2.2.1.2 TCP Connect Scan:
This command will initiate a TCP Connect port scan using Metasploit, where a full TCP connection is established with each target port to determine its status. Adjust the RHOSTS option to specify the target IP range.
2.2.1.3 TCP NULL Scan:
This command will initiate a TCP NULL port scan using Metasploit, where packets with no flags set (NULL packets) are sent to target ports to determine their status. Adjust the RHOSTS option to specify the target IP range.
2.2.1.4 TCP FIN Scan:
This command will initiate a TCP FIN port scan using Metasploit, where packets with only the FIN flag set are sent to target ports to determine their status. Adjust the RHOSTS option to specify the target IP range.
2.2.1.5 TCP XMAS Scan:
This command will initiate a TCP XMAS port scan using Metasploit, where packets with the FIN, URG, and PSH flags set are sent to target ports to determine their status. Adjust the RHOSTS option to specify the target IP range.
2.2.1.5 UDP Scan:
This command will initiate a UDP port scan using Metasploit, where UDP packets are sent to target ports to determine their status. Adjust the RHOSTS option to specify the target IP range.
2.2.2 Service Enumeration
Gathering detailed information about the services and applications running on open ports.
2.2.2.1 Port Identification:
- Review the results of the port scan to identify open ports on the target system.
- Focus on ports commonly associated with services such as HTTP (port 80), HTTPS (port 443), SSH (port 22), FTP (port 21), SMTP (port 25), DNS (port 53), etc.
2.2.2.2 Service Identification:
Once open ports are identified, use tools like Nmap or banner grabbing techniques to determine the specific services and applications running on those ports. This command will initiate service identification using Metasploit, where the tool will attempt to extract service banners from open ports on the target system to identify the associated services and versions. Adjust the RHOSTS option to specify the target IP range.
2.2.2.3 Banner Grabbing:
Banner grabbing is a reconnaissance technique used to extract information from service banners, which are metadata or identification strings sent by network services upon connection establishment. These banners often include details such as service name, version number, and sometimes even operating system information. Banner grabbing can provide valuable insights into the target system’s configuration and potentially reveal vulnerabilities that can be exploited. This command will initiate banner grabbing using Metasploit, where the tool will attempt to extract service banners from open ports on the target system to identify the associated services and versions. Adjust the RHOSTS option to specify the target IP range.
Here are some examples of what service banners might look like for different types of services:
HTTP Service:
Server: Apache/2.4.29 (Ubuntu)
FTP Service:
220 ProFTPD Server (Version X.X.X) [hostname]
SSH Service:
SSH-2.0-OpenSSH_7.9p1 Debian-10+deb10u2
SMTP Service:
220 mail.example.com ESMTP Postfix (Ubuntu)
DNS Service:
BIND 9.11.3-1ubuntu1.13-Ubuntu (Ubuntu)
Database Service (MySQL):
5.7.33-log
2.2.2.4 Automation:
To list all available exploitation modules:
msfconsole
show exploits
2.2.3 Operating System Fingerprinting
Determining the operating system of target systems based on responses to network probes. This command will initiate operating system fingerprinting using Metasploit, where the tool will attempt to identify the operating systems running on the target systems within the specified IP range.
For example, when conducting operating system fingerprinting, Metasploit might provide the following types of fingerprints:
These fingerprints help in identifying the underlying operating system and version running on the target systems, which can be valuable information for penetration testing and security assessments. Adjust the RHOSTS option to specify the target IP range.
Here are a few examples of operating system fingerprints that might be provided by tools like Metasploit:
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Linux Kernel Fingerprint:
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Example: Linux 4.15.0-54-generic
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Windows Version Fingerprint:
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Example: Microsoft Windows 10 Pro Version 10.0.18363 Build 18363
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macOS Version Fingerprint:
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Example: Mac OS X 10.15.7
2.2.4 Vulnerability Scanning
Identifying potential security vulnerabilities in target systems or applications. This command will initiate a vulnerability scan targeting Windows systems to check for the Microsoft IIS WebDAV ScStoragePathFromUrl Remote Code Execution vulnerability.
2.2.4.2 For Linux Systems:
This command will initiate a vulnerability scan targeting Linux systems to check for SSH service version information.
2.2.4.3 For macOS Systems:
This command will initiate a vulnerability scan targeting macOS systems to check for the Webmin Package Updates Remote Command Execution vulnerability.
2.2.5 Password Cracking
Attempting to crack passwords or gain unauthorized access to target systems.
2.2.6 Exploitation
Attempting to exploit identified vulnerabilities to gain access or escalate privileges on target systems.
2.2.6.1 For Windows Systems:
This command will initiate the EternalBlue exploit targeting Windows systems to achieve remote code execution on vulnerable SMB versions.
2.2.6.2 For Linux Systems:
This command will initiate the ElasticSearch Remote Code Execution exploit targeting Linux systems.
2.2.6.3 For MacOS Systems:
This command will initiate the WebKit Script Execution exploit targeting macOS systems.
2.2.6.4 For Oracle Database:
This command will initiate the Oracle WebLogic Deserialization exploit targeting Oracle Database servers.
2.2.6.5 For WordPress:
This command will initiate the WordPress Admin Shell Upload exploit targeting WordPress sites.
2.3 Open Source Intelligence (OSINT) Gathering
2.4 Social Engineering Reconnaissance
2.5 Tools and Methods for Reconnaissance
3. Footprinting
3.1 Domain Name System (DNS) Footprinting
This command will initiate DNS enumeration using Metasploit, where the tool will gather information about the target domain’s DNS records, such as hostnames, IP addresses, mail servers, and more.
3.2 Network Enumeration
This command will initiate ARP sweep enumeration using Metasploit, where the tool will send ARP requests to the specified IP range to discover live hosts on the network and their corresponding MAC addresses.
3.3 Web Footprinting
This command will initiate Google enumeration using Metasploit, where the tool will search Google for indexed web pages related to the specified domain. It gathers information such as web pages, subdomains, URLs, and more associated with the target domain.
Results:
Upon running the enumeration, the results might include: \
- URLs of indexed web pages related to the target domain.
- Subdomains discovered through Google indexing.
- Information about web servers, technologies, and frameworks used on the target domain.
- Other publicly available information related to the target domain, such as social media profiles, forums, and more.
- These results provide valuable insights into the online footprint of the target domain, aiding in further reconnaissance and potential attack surface identification.
3.4 Footprinting Tools and Techniques
- Footprinting involves gathering information about a target system or network to identify potential vulnerabilities and attack vectors.
- Various tools and techniques are used for footprinting, including passive reconnaissance, active reconnaissance, and open-source intelligence (OSINT) gathering.
- Passive reconnaissance techniques involve collecting information from publicly available sources without directly interacting with the target system or network. Examples include browsing websites, analyzing social media profiles, and reviewing public records.
- Active reconnaissance techniques involve actively probing the target system or network to gather information. Examples include port scanning, network enumeration, and DNS interrogation.
- Open-source intelligence (OSINT) gathering involves using publicly available information sources, such as search engines, social media platforms, and online forums, to gather information about the target.
- Common footprinting tools include Nmap for port scanning and service enumeration, Shodan for searching for internet-connected devices, theHarvester for email harvesting, and Maltego for visualizing and analyzing data from various sources.
- Footprinting tools and techniques should be used responsibly and within legal boundaries, ensuring that proper authorization is obtained before conducting any reconnaissance activities.
- Footprinting is an essential phase in the reconnaissance process, providing valuable insights into the target system or network and helping identify potential attack vectors for further exploitation.
3.5 Footprinting Countermeasures
- Footprinting countermeasures are strategies and practices implemented to mitigate the risks associated with reconnaissance activities and protect against information disclosure.
- Implement network segmentation and access controls to restrict access to sensitive information and resources, limiting the exposure of critical assets to unauthorized users.
- Regularly monitor and audit publicly available information sources, such as websites, social media platforms, and online forums, to identify and remove sensitive information that could be exploited by attackers.
- Use deception techniques, such as honeypots and honeynets, to lure and trap attackers attempting reconnaissance activities, providing valuable insights into their tactics and techniques.
- Employ intrusion detection and prevention systems (IDPS) to detect and block reconnaissance attempts in real-time, alerting security teams to potential threats and vulnerabilities.
- Implement strong authentication mechanisms, such as multi-factor authentication (MFA) and biometric authentication, to prevent unauthorized access to systems and networks.
- Encrypt sensitive data both in transit and at rest to protect it from unauthorized disclosure during reconnaissance activities.
- Educate employees and raise awareness about the risks of information disclosure and the importance of practicing good security hygiene, such as avoiding sharing sensitive information online and using strong, unique passwords.
- Conduct regular security assessments and penetration tests to identify and remediate vulnerabilities before they can be exploited by attackers during reconnaissance activities.
- Stay informed about emerging threats and evolving reconnaissance techniques, keeping security defenses up to date to adapt to changing threat landscapes.
- Collaborate with industry peers and information sharing organizations to exchange threat intelligence and best practices for mitigating reconnaissance risks effectively.
4. Scanning
4.1 Network Scanning
Syn Scan recomended
This command will initiate SYN scan using Metasploit, where the tool will send SYN packets to the specified IP range to discover open ports on the target systems.
4.2 Port Scanning
This command will initiate TCP port scanning using Metasploit, where the tool will attempt to connect to TCP ports on the specified IP range to determine their status (open, closed, or filtered).
4.3 Vulnerability Scanning
4.3.1 For Windows Systems:
This command will initiate a vulnerability scan targeting WordPress sites on Windows systems to check for the WordPress Admin Shell Upload vulnerability.
4.3.2 For Linux Systems:
This command will initiate a vulnerability scan targeting WordPress sites on Linux systems to check for the WordPress Pingback Access vulnerability.
4.3.3 For Oracle Database:
This command will initiate a vulnerability scan targeting Oracle Database systems to check for default passwords.
4.3.4 For WordPress:
This command will initiate a vulnerability scan targeting WordPress sites to check for weak or default login credentials.
4.4 Scanning Tools and Utilities
- Scanning tools are essential for network reconnaissance and vulnerability assessment.
- They help identify open ports, services, and potential vulnerabilities on target systems.
- Popular scanning tools include Nmap, Nessus, OpenVAS, Masscan, and Metasploit.
- Nmap is a versatile network scanner capable of performing port scans, service version detection, OS fingerprinting, and more.
- Nessus and OpenVAS are comprehensive vulnerability scanners that can identify security vulnerabilities in systems and networks.
- Masscan is a high-speed port scanner designed for large-scale network scanning.
- Metasploit includes auxiliary and scanner modules for various types of scanning, including port scanning, service enumeration, and vulnerability assessment.
- Scanning tools should be used responsibly and with proper authorization to avoid causing disruption or harm to target systems.
- It’s essential to stay updated on the latest scanning techniques and tools to effectively assess and secure networks and systems.
4.5 Scanning Best Practices
- Obtain proper authorization before conducting any scanning activities.
- Clearly define the scope of the scan to avoid unintended consequences or disruptions.
- Notify relevant stakeholders, such as system administrators or network security teams, about the scanning activities to prevent false alarms or misunderstandings.
- Use scanning tools and techniques responsibly, ensuring that they comply with legal and regulatory requirements.
- Schedule scans during off-peak hours to minimize the impact on network performance and availability.
- Prioritize scanning based on the criticality of systems and assets, focusing on high-value targets first.
- Document and maintain records of scanning activities, including the scan parameters, results, and any actions taken.
- Verify and validate scan results to ensure accuracy and reliability.
- Keep scanning tools and systems up to date with the latest security patches and updates to mitigate potential vulnerabilities.
- Regularly review and update scanning policies and procedures to adapt to evolving threats and technologies.
- Continuously monitor and assess the effectiveness of scanning activities to improve security posture over time.