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The Ethical Hacker
assume the role of an ethical hacker tasked by law enforcement to infiltrate the network of a business known to engage in illegal activities.
The specific course learning outcome associated with this assignment is:
Conduct activities to protect IT assets and infrastructure from threats and improve incident response strategies. Scenario Imagine for a moment that you are a hacker, an ethical one. You are called upon by law enforcement to hack into the network of a business known to be engaged in criminal activity for financial gain as its primary activity. Assume you are not to be concerned with any political aspects of the job and that your actions are legal and ethically justified.
This nefarious business takes its own security seriously and, therefore, has implemented several forms of network security, including firewalls, web proxies for its web gateways, and VPNs for remote users. You also know that this business, much like any normal corporation, rents several floors of office space to accommodate between 100 and 200 employees. Also, imagine that the business's entire network topology is located on-site. Your goal is to infiltrate their security to find evidence of illegal activities in the local MSQL database. You must remain anonymous and operate within the parameters of the law.
Instructions Write a 6-10 page paper in which you:
Explain your method of attack and operation within the reasonable parameters of the law, citing specific, credible sources that support the method of attack and operation. Describe a specific malware, social engineering, or other type of attack you would deploy to achieve your desired goals, citing specific, credible sources that support deployment of the attack. Identify effective techniques for concealing executables and specific tools used for each stage of the attack. Develop a plan to overcome expected hurdles your attack must overcome to be successful, citing specific, credible sources that support the plan. Develop an anonymizing strategy, supported by specific, credible sources, that creates a false trail and minimizes the risk of detection.
Sample Answer
As an ethical hacker operating on behalf of law enforcement, my primary objective is to non-destructively penetrate the target's on-site network to exfiltrate evidence from their local MSQL database while maintaining complete anonymity and legal compliance. My method of operation, attack deployment, concealment, hurdle plan, and anonymizing strategy are detailed below, grounded in established cybersecurity principles and supported by credible sources.
I. Method of Attack and Operation
The operation will utilize a phased approach, following standard ethical hacking methodologies, focusing on exploiting the human element and physical security gaps to bypass the network's technical defenses (firewalls, proxies, VPNs). The core strategy is not a direct frontal assault on the external security perimeter, but rather a covert physical and internal network penetration.
A. Phased Operation Strategy (The Kill Chain Adaptation)
Reconnaissance (External & Physical):
External: Conduct passive OSINT (Open Source Intelligence) to map IP ranges, discover employee names/roles (LinkedIn, social media), and identify software/hardware vendors. This provides initial social engineering vectors.
Physical (Initial): Passive observation of the building, identifying high-traffic hours, entry/exit points, access control mechanisms, and, critically, the location of the server room or wiring closets relative to the leased office floors.
Source Support: The NIST SP 800-42 Guideline on Network Security Testing emphasizes reconnaissance as the foundational step for understanding the target environment and formulating effective test plans.
Initial Access (Physical and Wireless):
Physical Breach: Gain temporary, unauthorized physical access to the building (e.g., posing as a maintenance worker, delivery person, or potential client for another business in the building). The target is a temporary "staging area" near the target's network perimeter—ideally a wiring closet, an adjacent office, or an unattended common area.
Wireless Exploitation: Once physically proximate, use a high-gain antenna and tools like Aircrack-ng to passively monitor for unsecured guest Wi-Fi networks or poorly configured employee networks. However, the primary focus is the wired network.
Establish Foothold (Network Injection):
This is the critical step. An attacker will exploit the fact that the entire network topology is on-site.
A covert network implant (a small device like a Raspberry Pi or a custom LAN tap) will be physically connected to an accessible network port (e.g., an unattended printer port, an easily accessible switch/router in a wiring closet, or an Ethernet port exposed in a common area).
The implant is pre-configured to act as a transparent layer-2 device or a rogue access point for a few seconds to capture network traffic (ARP poisoning, DNS snooping) or, ideally, to simply gain an IP address on the internal network.
Source Support: The concept of "physical persistence" using small computing devices is a well-documented technique in penetration testing, often termed "Dropping a Box." The SANS Institute’s penetration testing courses routinely cover this non-destructive method for initial internal network access.
Internal Lateral Movement and Privilege Escalation:
Once on the network, standard internal penetration testing techniques apply. Tools will be used to passively map the internal network (NMAP scans are too noisy; prioritize ARP requests and DNS queries).
The focus is on locating the MSQL database server and identifying any unpatched vulnerabilities, weak credentials, or configuration mistakes that allow lateral movement.
Exfiltration:
The evidence is extracted from the MSQL database and tunneled out of the network using the covert implant over an encrypted channel (e.g., DNS or ICMP tunneling, or over HTTPS to evade proxy detection) to a securely maintained law enforcement collection server.
II. Specific Attack Deployment: Spear Phishing via Watering Hole
Given the difficulty of directly breaching firewalls and proxies, the chosen attack is a multi-stage Spear Phishing via Watering Hole attack, which bypasses the perimeter by targeting the trust of specific employees.
A. The Attack Vector: Compromising the Proxy
The web proxy is a key defense, but it can be leveraged. The business's web gateway likely grants exceptions or has less scrutiny for certain known, industry-specific websites (e.g., a shipping company’s portal, a financial news site, or a vendor’s support forum).
Watering Hole Setup: Law enforcement will legally compromise a genuine, high-trust, low-security website that the target employees are known to frequent (e.g., a small vendor's login page). This is the Watering Hole.
Malware Injection (Client-Side): A tiny, obfuscated JavaScript snippet is injected onto the Watering Hole site. This snippet profiles the visitor. If the visitor’s IP address or browser characteristics match the target network's known profile (identified during Reconnaissance), the script delivers the payload.