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Costumes and Disguises for Undercover Pentesters

In the world of cybersecurity, staying one step ahead of hackers and cybercriminals is a constant challenge. One effective way to do this is by employing undercover pentesters – experts who assess the security of computer systems and networks by simulating attacks. To successfully blend in with the environment they are testing, these pentesters often use costumes and disguises. In this article, we will explore the importance of costumes for undercover pentesters, the various disguises they may use, and the significance of staying inconspicuous in the world of cybersecurity.

The Significance of Undercover Pentesters

Before delving into the world of costumes for undercover pentesters, it’s essential to understand why these professionals are so crucial. Undercover pentesters are cybersecurity experts hired to evaluate the vulnerabilities in a system, much like how real hackers would. Their work helps organizations identify weaknesses in their security and rectify them before malicious actors can exploit them. This proactive approach is crucial in safeguarding sensitive data and maintaining the integrity of computer networks.

The Art of Staying Inconspicuous

When undercover pentesters infiltrate a network, the last thing they want is to draw attention to themselves. Their effectiveness relies on remaining unnoticed, allowing them to uncover vulnerabilities without alerting the target system’s defenders. This is where costumes and disguises come into play.

Why Disguises Matter

Disguises serve several purposes for undercover pentesters. They help blend in with employees, contractors, or visitors, reducing the risk of being identified as a threat. Furthermore, disguises can be used to gain access to restricted areas or information. This section examines the various types of disguises and costumes pentesters might employ.

Common Disguises and Costumes

A group of undercover pentesters in various disguises.

Masters of Infiltration: Unmasking the Disguises of Cybersecurity Guardians

To maintain their cover, undercover pentesters need to adopt a range of disguises, each tailored to the specific environment they are infiltrating. Here are some common disguises and costumes they might use:

1. The IT Technician

In many organizations, IT technicians are a common sight. Pentesters can don the attire of an IT technician to gain access to server rooms, network closets, or even individual workstations. Carrying a toolkit, wearing a badge, and acting confident in their role can help them go unnoticed.

IT Technician Disguise

An essential accessory, the Tool Belt / Pouch is a convenient and practical way to carry necessary tools discreetly, contributing to the authentic appearance of an IT technician.

The Badge Holder and Lanyard add a touch of professionalism, allowing the pentester to display a badge with confidence. This subtle accessory enhances the authenticity of the IT technician persona.

A Network Installations or Repairs Tool Kit is a crucial component, providing the tools needed for common IT tasks. This toolkit completes the technician look and ensures the pentester is equipped for any scenario.

The Work Shirt contributes to the overall appearance, adding authenticity to the IT technician disguise. It enhances the professional image, making it easier for the pentester to blend into the work environment.

Pairing the Work Pants with the work shirt completes the outfit, ensuring a cohesive and realistic appearance. These pants are chosen for their durability and suitability for the role of an IT technician during penetration testing.

2. The Janitor

Janitor Disguise

Janitors have access to virtually all areas within a building, making this disguise a favorite among pentesters. Carrying cleaning supplies and a uniform, they can discreetly inspect areas and plug in devices for testing.

For situations where blending in as janitorial staff provides strategic advantages, consider the following disguise kit:


The Short-Sleeve Coverall is a versatile and practical garment for the janitorial staff persona. Its design offers comfort, ease of movement, and a professional appearance suitable for various environments.

The Janitorial Cart is a functional accessory that enhances the realism of the janitorial staff disguise. It provides a legitimate reason for being in specific areas, facilitating inconspicuous movement during penetration testing.

3. The Consultant

Consultant Disguise

A well-dressed consultant can easily blend in with office staff. This disguise allows pentesters to engage with employees, assess their security practices, and potentially gain access to sensitive information.

For scenarios where a business-oriented persona is the key to access, consider the following disguise kit:


The Business Suit is a classic choice for blending into corporate environments. Its professional appearance conveys authority and respectability, providing a seamless disguise for undercover operations.

The Briefcase is an essential accessory, adding authenticity to the executive persona. It serves both functional and aesthetic purposes, allowing the undercover operative to carry necessary tools discreetly.

4. The Delivery Person

Delivery Person Disguise

Dressed as a delivery person, pentesters can deliver packages while also surreptitiously assessing the security of the organization. This disguise is excellent for checking if employees are following proper procedures for incoming deliveries.

For situations requiring a delivery worker disguise, consider the following kit:


Black or brown coveralls provide a nondescript yet recognizable look associated with delivery workers. It’s a practical choice for blending in and gaining access to various locations.

An Amazon safety vest adds credibility to the delivery worker disguise. It’s a common and easily recognizable uniform that allows you to move inconspicuously while maintaining a low profile.

The UPS hat is a distinctive accessory that complements the delivery worker look. It adds an extra layer of authenticity to your disguise, making you blend seamlessly into environments with package deliveries.

5. The New Employee

New Employee Disguise

Pentesters can assume the identity of a new employee, complete with an orientation packet and a sense of eager curiosity. This disguise allows them to closely interact with existing staff, test employee security awareness, and assess onboarding procedures.

For scenarios where blending in as a business professional is crucial, consider the following kit:


A business suit exudes professionalism and authority. Choose a classic and well-fitted suit to enhance your overall appearance and seamlessly blend into corporate settings.

Carrying a set of folders or a portfolio gives the impression of someone attending meetings or conducting business. It’s a subtle accessory that enhances your credibility in a professional environment.

6. The Repair Technician

Repair Technician Disguise

In this role, pentesters can carry a toolbox and wear a uniform that resembles that of a repair technician for office equipment or appliances. This disguise provides access to various areas while maintaining a legitimate reason for being on-site. This covers multiple roles A/C, Electrician, Plummer, Elevator Repair, etc.

For scenarios where disguising as maintenance personnel is necessary, consider the following kit:


Short-sleeve coveralls are a common uniform for maintenance staff. They offer a practical and comfortable outfit for tasks that require mobility and protection.

Carrying a toolbox enhances the illusion of a maintenance worker. It adds authenticity to your disguise, making it easier to access restricted areas without arousing suspicion.

If you’re going to go the elevator repair tech route you might…

Watch this video:

Showout to Deviant Ollam and Howard Payne from The Core Group

Elevator Access Tools:

For professionals needing elevator access tools, consider the following kit:


This set of elevator keys is designed for fire service personnel, offering access to various elevator and escalator controls during emergency situations. It provides a comprehensive solution for emergency responders.

The pentesting master key set is a versatile collection of keys for testing and assessing physical security systems. It includes a variety of keys that may be useful for professionals in penetration testing and security assessments.

The elevator blue server test tool is an essential gadget for testing and diagnosing elevator systems. It allows professionals to simulate server interactions and evaluate the performance of elevator controls.

This nylon banner serves as a practical and easily noticeable sign, indicating that an elevator is out of service. It’s a useful tool for maintenance or testing scenarios, ensuring clear communication to building occupants.

The OTIS elevator key pack includes a set of keys designed for OTIS elevators. It provides access to various controls and panels, making it a valuable tool for professionals requiring specialized access in OTIS elevator systems.

This heavy-duty lunar elevator door key is designed for specific elevator systems. Its large and durable design ensures reliable use in scenarios where access to elevator doors is required. It’s a practical tool for professionals in the field.

7. The Guest Speaker

Guest Speaker Disguise

Pretending to be a guest speaker or presenter at a conference or workshop hosted by the organization is another effective disguise. It grants pentesters access to both employees and potentially sensitive information.

For blending into corporate environments, consider the following:


A classic business suit is a versatile choice for professionals seeking a formal and inconspicuous appearance. It provides a polished and sophisticated look, suitable for various corporate and formal settings.

8. The Intern

Intern Disguise

As an intern, pentesters can infiltrate organizations and work closely with staff. This disguise is ideal for observing internal practices and identifying security gaps.

For a polished and professional intern look, consider the following items:


A business suit offers a professional and inconspicuous appearance, suitable for blending into corporate environments. It provides a polished and sophisticated look.

A stylish notebook and pen set adds to the professional appearance. It’s practical for taking notes, maintaining a professional image, and seamlessly blending into office environments.

An intern badge can help create the illusion of a temporary staff member, making it easier to access certain areas or strike up conversations within the workplace.

A lanyard provides a practical and common accessory seen in professional settings. Use it to hold identification badges, access cards, or simply to enhance the appearance of a professional disguise.

9. The Vendor

Vendor Disguise

Dressing as a vendor or supplier gives pentesters access to loading docks, inventory areas, and supply rooms. They can observe security protocols and assess vulnerabilities.

To appear as a vendor or supplier, consider the following attire:


A blue polo shirt is a versatile and common choice for vendor or supplier attire. It offers a professional appearance suitable for interacting with staff in loading docks or supply rooms.

A red polo shirt can be an alternative color choice for a vendor or supplier disguise. It helps diversify your appearance and may align with the branding of certain companies.

Tactical work pants provide a practical and durable option. With multiple pockets, they offer utility for carrying tools or small items discreetly. They are suitable for a variety of environments.

A Pepsi hat can serve as part of a vendor disguise, aligning with the appearance of delivery personnel or vendor representatives. It helps create a consistent look when paired with a polo shirt and work pants.

A Coke hat is an alternative choice for a vendor disguise. Similar to the Pepsi hat, it contributes to the illusion of being a delivery person or supplier representative, aiding in blending into specific environments.

10. The Construction Worker

Construction Worker Disguise

Pentesters can disguise themselves as construction workers, providing access to construction sites, building areas, and equipment storage. This guise enables them to assess security measures and identify vulnerabilities.

To blend in as a construction worker and gain access to related areas, consider the following attire:


A reflective safety vest is a crucial component for visibility and safety on construction sites. It also enhances the authenticity of the disguise, making it an essential part of the construction worker attire.

A hard hat is a recognizable piece of construction attire. It not only provides safety but also completes the look of a construction worker. Consider choosing a neutral color for a more authentic appearance.

A tool belt with pouches adds realism to the construction worker disguise. It provides functionality for carrying tools or equipment and contributes to the overall appearance of a worker on a construction site.

Sturdy work boots are a key element of construction worker attire. They offer protection and durability, making them suitable for navigating construction sites. Choose a pair that aligns with typical construction footwear.

Carrying a metal clipboard adds authenticity to the disguise. It gives the appearance of having construction-related paperwork or plans, helping blend in seamlessly with actual construction workers.

This set of keys mimics those used for heavy construction equipment. While not functional, it contributes to the realism of the disguise and can be a conversation starter if questioned.

The Role of Technology

A visualization of key pentesting tools, including WiFi Pineapple, lock picking kit, and Raspberry Pi.

Arming the Guardians: Tools of the Undercover Pentester’s Trade

In addition to costumes and disguises, technology plays a significant role in the work of undercover pentesters. They utilize various tools and equipment to assess the security of a network. Some essential tools include:

1. WiFi Pineapple

The WiFi Pineapple is a versatile tool for intercepting and analyzing network traffic. Pentesters can use it discreetly, blending in with ordinary people using public Wi-Fi.

Get a WiFi Pineapple at the Hak5 Shop .

2. Lock Picking Kit

Physical security is just as critical as digital security. A lock-picking kit allows pentesters to gain access to secured areas when in disguise.

There are many lockpick sets to choose from on Amazon . However, we recommend any of the following quality sets:

3. Raspberry Pi

The Raspberry Pi is a small, inconspicuous computer that can be used to run various penetration testing tools. It’s an essential part of a pentester’s toolkit.

You can pick up a Raspberry Pi on Amazon , or alternatively get the more powerful alternative the Orange Pi .

4. FlipperZero

The FlipperZero is a versatile tool for undercover pentesters, offering a wide range of capabilities. It’s a multi-tool for security assessments, equipped with features like RFID cloning, NFC emulation, hardware hacking, and more. With its compact and inconspicuous design, pentesters can blend in while conducting various security tests.

Get the FlipperZero on the official website .

The FlipperZero is designed to support various security research and penetration testing tasks, making it a valuable addition to a pentester’s toolkit.

More Hardware Recommendations

For additional hardware recommendations, you can explore SimeonOnSecurity’s Hacker Hardware Recommendations .

Legal Compliance in Cybersecurity.

Ethical Boundaries: Navigating the Legal Landscape of Cybersecurity.

It’s important to note that the work of undercover pentesters should always be within the bounds of the law and adhere to ethical standards. Government regulations, such as the Computer Fraud and Abuse Act (CFAA) in the United States, set clear guidelines for what is legal and illegal in the field of cybersecurity. Pentesters must operate within these legal frameworks to avoid legal repercussions.


In the ever-evolving landscape of cybersecurity, staying ahead of cyber threats is paramount. Undercover pentesters play a crucial role in this battle by identifying vulnerabilities before malicious actors can exploit them. Costumes and disguises are essential tools in their arsenal, allowing them to remain inconspicuous while assessing the security of computer systems and networks. By understanding the significance of these disguises and the various roles they play, we can better appreciate the vital work of undercover pentesters in safeguarding our digital world.