Understanding Phishing in Red Team Engagements: Insights from TryHackMe's 'Phishing' Room

Introduction: Phishing remains one of the most prevalent and effective methods of cyber-attacks. In red team engagements, understanding and simulating phishing attacks can provide valuable insights into an organization's vulnerabilities and preparedness. This guide delves into the art of phishing, from crafting convincing emails to setting up realistic simulations.

Intro To Phishing Attacks:

Definition and Impact:

• Broader Scope: While commonly associated with emails, phishing can also occur via other communication forms like text messages, social media, or phone calls. The essence of phishing is deception; attackers masquerade as trustworthy entities to extract sensitive information or deliver malware.
• Tactics Used: Attackers often use urgent or enticing language to prompt immediate action. The emails might appear to come from banks, service providers, or even colleagues, containing links to fake websites or attachments harboring malware.
• Impact on Individuals and Organizations: The consequences of phishing can range from financial loss and identity theft for individuals to significant data breaches and reputational damage for organizations. Phishing is also a common entry point for more complex cyber attacks.

Relevance in Red Teaming:

• Simulating Real-World Threats: In red team engagements, simulating phishing attacks helps organizations understand how their employees respond to real-life phishing scenarios. This is critical since the human factor often is the weakest link in cybersecurity.
• Assessing Vulnerability and Awareness: Phishing simulations conducted by red teams can gauge the level of security awareness among staff and identify areas where additional training is needed.
• Refining Defense Strategies: By analyzing the results of these simulations, red teams can provide targeted recommendations to strengthen an organization's human and technical defenses against social engineering attacks.
• Continuous Evolution: Phishing techniques are constantly evolving, and red teams must stay abreast of the latest trends and tactics to effectively test and train an organization's personnel.

Writing Convincing Phishing Emails:

Crafting the Email:

• Believable Sender Address: This is crucial for the initial trust. Phishers often use email addresses that closely resemble legitimate ones, with subtle changes that can be easily overlooked.
• Compelling Subject Line: The subject line should be attention-grabbing, relevant, and create a sense of immediacy or importance. Common tactics include pretending to be urgent messages from banks, warnings about account security, or confirmations for fictitious transactions.
• Content Strategy: The body of the email should be crafted to maintain the illusion. This includes using the right language, tone, and even the branding that matches the entity being impersonated. The content often plays on human emotions like fear (e.g., account compromise), curiosity (e.g., unusual activity), or greed (e.g., unexpected rewards).
• Call to Action: A clear call to action, such as clicking on a link or downloading an attachment, is typically included. These actions should seem natural within the context of the email.

Mimicking Legitimate Communications:

• Studying Target Communications: Successful phishing requires understanding how the impersonated entity communicates. This could involve studying the language, format, and type of content typically sent by these entities.
• Attention to Detail: Attention to detail is paramount. This includes the use of logos, email signatures, and even the type of language and greetings used. Small discrepancies can alert a vigilant recipient.
• Adapting to Target’s Habits: Understanding the target's habits can increase the success rate. For example, if the target is known to frequently receive and respond to work-related emails, a phishing email could be crafted to resemble a communication from a colleague or supervisor.
• Dynamic Content: Advanced phishing emails might include dynamic content that changes based on the recipient, making the email seem more personalized and convincing.

Phishing Infrastructure:

Setting Up:

• Reliable Hosting Environment: Choosing the right hosting service is crucial for phishing operations. It needs to be reliable to handle the traffic and sophisticated enough to avoid being blacklisted quickly by anti-phishing tools.
• Email Sending Capabilities: The ability to send out a large number of emails while avoiding spam filters is essential. This often involves setting up SMTP (Simple Mail Transfer Protocol) servers or using email services that allow for bulk sending without raising red flags.
• Tracking and Analyzing Responses: Incorporating tools or software that can track if the emails were opened, links were clicked, or attachments were downloaded is vital for assessing the effectiveness of the campaign. This data helps in understanding the behavior of the targets and refining future phishing attempts.
• Creating Convincing Landing Pages: If the phishing email includes links, the landing pages they lead to must be convincingly similar to legitimate ones. This includes mimicking the look, feel, and behavior of real websites.

Securing the Infrastructure:

• Anonymity and Traces: Ensuring the phishing infrastructure cannot be easily traced back to its origin is crucial, especially in red team operations. This involves using methods to mask IP addresses, using domain privacy services, and potentially utilizing VPNs or Tor networks for additional layers of anonymity.
• Robust Security Measures: Just as with any other server, the infrastructure used for phishing needs to be secured against intrusions. This is crucial because compromised phishing infrastructure can be turned against the red team or lead to legal and ethical violations.
• Regular Updates and Monitoring: Keeping the software and hardware up to date with the latest security patches is essential. Regular monitoring for any unusual activities or breaches is also a key part of maintaining a secure infrastructure.
• Legal Compliance: Ensuring that all activities are within legal boundaries and comply with any regulations or ethical standards set by the organization or the red team community.

Using GoPhish:

About GoPhish:

• Toolkit Overview: GoPhish is a powerful, open-source phishing toolkit. It's favored for its user-friendly interface and comprehensive features that cater to both businesses and penetration testers.
• Campaign Simulation Features: The toolkit allows users to design and simulate entire phishing campaigns, from crafting emails to creating landing pages that mimic legitimate websites.
• Success Tracking: One of GoPhish's key features is its ability to track the success of phishing campaigns. It provides detailed reports on various metrics like click rates, submitted data, and opened emails, offering valuable insights into the effectiveness of the campaign.

Implementing Campaigns:

• Campaign Setup: Users can set up campaigns by defining the target email addresses, designing the phishing email, and creating a landing page. GoPhish supports HTML emails, allowing for sophisticated and realistic email designs.
• Landing Page Creation: The platform enables the creation of custom landing pages that can closely resemble the look and feel of legitimate websites. This is crucial for convincing the recipient of the email's authenticity.
• Credential Capturing: GoPhish can be configured to capture credentials entered on the landing pages. This feature is particularly useful for penetration testers to demonstrate how easily credentials can be obtained through phishing.
• Testing and Launching: Before launching the campaign, users can test the emails and landing pages to ensure they work as intended. Once satisfied, the campaign can be launched directly from the GoPhish dashboard.
• Data Analysis and Reporting: After the campaign, GoPhish offers comprehensive analytics. This data includes who clicked on the links, who submitted data on the landing page, and other behavioral metrics. These insights are crucial for understanding the campaign's impact and for planning future tests or training exercises.

Ethical and Legal Considerations:

• Consent and Authorization: When using tools like GoPhish for red team exercises or corporate training, it's imperative to obtain explicit authorization from the organization's leadership or relevant authorities. This consent ensures that all simulated phishing activities are legally sanctioned and ethically sound. Unauthorized phishing simulations, even if well-intentioned, can lead to legal issues and ethical dilemmas.
• Data Handling: The data collected during phishing simulations, such as captured credentials or personal information, must be handled with utmost care. This involves ensuring that the data is stored securely, used only for the intended educational or security-enhancing purposes, and disposed of responsibly. Compliance with data protection laws like GDPR or HIPAA, where applicable, is crucial to maintain privacy and trust.

Droppers:

• Purpose and Use: Droppers in phishing are essentially delivery mechanisms for malware or other malicious payloads. They are often disguised within seemingly harmless files or links in phishing emails. Once opened or clicked by the unsuspecting recipient, they can install malware, ransomware, or other harmful software onto the user's system.
• Incorporation into Phishing Emails: Droppers can be embedded in various file formats or linked to via URLs. The effectiveness of a dropper often depends on its ability to evade detection by antivirus software and the user’s vigilance.

Choosing A Phishing Domain:

• Criteria for Selection: The choice of a domain name for phishing simulations is critical. It should be convincing enough to not raise immediate suspicion but should also avoid infringing on trademarks or impersonating real entities too closely, as this could constitute illegal activities like domain squatting or fraud.

Using MS Office In Phishing:

• Leveraging Familiar Tools: Microsoft Office files are commonly used in legitimate business communications, making them effective vehicles for phishing. Attackers embed malicious code or links in Word or Excel documents. When opened, these documents can execute the code or prompt users to visit malicious sites, thus appearing more credible due to their familiar format.

Using Browser Exploits:

• Exploitation Techniques: Browser exploits take advantage of vulnerabilities in web browsers. In phishing, links in emails can lead to websites that exploit these vulnerabilities to install malware or perform other malicious actions. These techniques require a deep understanding of browser security and are often used in more sophisticated phishing operations.

Phishing Practical:

• Real-World Simulation: Conducting a mock phishing campaign involves planning the attack, crafting the emails, setting up the infrastructure, and executing the campaign. After the simulation, it's important to analyze the results to understand the effectiveness of the attack and the level of awareness among the targets. This practical experience is invaluable for understanding the dynamics of phishing and for training purposes, but it must be done within the bounds of ethics and legality.

Summary: Phishing is a critical component in red team engagements, offering insights into potential vulnerabilities and user awareness within an organization. This guide equips red team professionals with the knowledge and tools to conduct effective phishing simulations, enhancing their ability to safeguard against real-world attacks.