Social Engineering Penetration Testing

A type of security assessment that evaluates an organization's vulnerability to deception-based attacks targeting the human element within the security framework, Social Engineering Penetration Testing simulates real-world social engineering tactics such as phishing, pretexting,  tailgaiting, and others, to assess how well employees can identify and respond to these attacks. Social engineering penetration testing is vital for organizations identifying weaknesses in their security awareness and training programs.  

People often think of cybersecurity risk purely in terms of firewalls and network protections, but that’s only one side of the issue. Human behavior can leave cyber systems just as vulnerable as physical or technical issues. Social engineering penetration testing is considered the main method to uncovering these vulnerabilities.

In this article, we’ll break down all things related to penetration testing and social engineering, from basic definitions to how the process of these tests actually operates, and the varied forms attacks can take. Understanding the risks that humans might pose to cybersecurity can help businesses build more robust protections and ultimately avoid costly attacks.

Contents

• What is a Social Engineering Penetration Test?
• Types of Penetration Testing
• What are Social Engineering Attacks? 
• The Social Engineering Penetration Test Process
• Types of Social Engineering Penetration Tests
• Social Engineering Penetration Test Best Practices
• Penetration Testing and Prescient Security

What is a Social Engineering Penetration Test?

Social engineering refers to the use of manipulative techniques on humans to gain unauthorized access to data, private networks, and other parts of a cyber system. A social engineering penetration test assesses how vulnerable an organization might be to this exploitation by simulating typical attacks of this nature.

The team performing the test will take on the role of a hacker and target people’s emotions so as to deceive or persuade them into providing access or performing actions that compromise security. For this simulation to operate effectively, it must be done with only limited knowledge of its occurrence until after the fact. That’s what ensures accurate, realistic results.

People often aren’t aware that they’re the victim of a social engineering attack until it’s too late. Performing a social engineering penetration test gives organizations a chance to play out scenarios and see exactly where their employees or users are most vulnerable so that those areas can be addressed. The goal of a penetration test is never just to show where the weaknesses are, but also to provide valuable insight and awareness so that people and systems come out stronger than before.

Types of Penetration Testing

To understand penetration testing better, here’s a look at the main types that exist:

• Wireless: This tests the security of wireless networks such as Wi-Fi and Bluetooth and checks if there are any misconfigurations or weak points that might make it easy for attackers to get in.
  
• Network: External network testing simulates an attack against public-facing aspects, such as firewalls and web servers, versus internal testing, which places an ethical hacker inside the network. The purpose of the latter is to simulate what might happen if an employee or user were to turn on the system in some way.
  
• Social Engineering: Instead of testing technical security boundaries, these tests check how well users and employees can recognize and avoid deceptive tactics from hackers.
  
• Physical: The physical component of cybersecurity is related to how well things like hardware and data centers are protected. Penetration tests will then attempt to gain unauthorized access through lock-picking, tailgating, etc., and see how well physical barriers hold up.
• Web Application: Web apps such as shopping carts and APIs can be vulnerable to security issues. Pen tests will check that there aren’t any broken authentications or other system flaws that might be leaving a gap open for attackers to get through.
  

What are Social Engineering Attacks?

Social engineering attacks can be hugely damaging. They can land organizations with massive data breaches, compliance issues, and plenty of other financial and legal consequences. We’re making a point of this upfront, not to fearmonger, but because the names that the cyber community has given to some of the most common types of social engineering attacks can sometimes undermine their seriousness.

It may read like a joke, but as we’ll explain, smishing, vishing, and phishing are nothing to be laughed at:

• Phishing: This is a broad term used to describe any kind of fake emails or messages sent with the intention to trick people into clicking on malicious links or providing private data. More often than not, the emails will appear as if sent from a trusted source, such as a cloud service provider or even a tax representative. Specific types of phishing include Spear Phishing, in which a specific individual or organization is targeted, and whaling, which is when a Spear Phishing attack goes after a “big whale,” i.e., a high-level executive like a CFO or CEO.
• Vishing: The term is a combination of “voice” and “Phishing” and refers to phishing done over the phone. A classic example is when a person calls and impersonates a trusted organization, such as a bank. They usually then try to use the false identity to extract personal identifying information, which can then be used to log into cyber systems, etc.
• Smishing: Many phishing attacks also occur via SMS, hence the term “smishing”. They usually include links to click or fake customer service numbers that, if called, turn into a Vishing attack. It’s important to remember that social engineering attacks are often sandwiched together and use multiple deceptions as they try to lure unsuspecting users in.
  
• Business Email Compromise (BEC): Attackers will impersonate a company executive or partner in this highly targeted form of phishing to trick employees into making transactions or sharing data.
• Impersonation and Pretexting: These social engineering attacks tend to go hand in hand. They involve someone creating a fabricated story (pretexting) and assuming a false identity (impersonation) to gain the victim’s trust. It can be as simple as getting a call from someone saying they’re from your workplace IT department and need to confirm your password. More elaborate examples are fake charity requests that, when they lead you to a donation page, also require personal identifying information.
• Dumpster Diving: Like a creep going through your trash, some attackers will use discarded information and deleted files to gain access to systems.
• USB drops: These attacks will leave USBs in open places with the hope that unsuspecting users pick them up and plug them, only for the USB to install malware and other threats.
• Tailgating: We’ve all had moments where we’ve walked into an office building and someone slips in behind us holding coffee cups or boxes, seemingly unable to put in their own credentials because their hands are full. Unfortunately, this is exactly how tailgating happens. Attackers slip into restricted areas under a false pretense and then gain access to security systems.
• Scareware: If you’ve ever received an email with some variation of “download this or else”, you’ve been exposed to scareware. The intent is to scare victims into downloading malicious software, and links to them often appear in Phishing emails.
• Baiting: Like a fish being lured with the promise of easy food, many cyberattacks happen because victims have been lured by the promise of free software or music that then turns out to contain malware.
• Honey Trapping: There are few cyber-attacks more disturbing than honey trapping. Attackers set up fake online profiles and use them to build a relationship with a victim so that they can trick them into sharing money or data.
• Quid Pro Quo: Attackers will sometimes incentivize victims to share information by offering services or benefits such as shopping discounts or “free” tech support.

The Social Engineering Penetration Test Process

Here’s an overview of the steps that a social engineering penetration test will typically follow:

• Reconnaissance: The testing team will gather high-level information about the organization and employees that they’ll be targeting in the simulated attack. They’ll typically look at what hackers might have access to in terms of publicly available information.
  
• Information Gathering: This is when the testing team goes a step deeper into more detailed and specific research about the organization, the people that work there, how the systems work, and potential weak points that an attacker would exploit.
• Target Selection: Based on the above, specific targets will be selected. Usually it’s because they fit the profile of certain attack types.
• Pretexting and Planning: With their targets and background files at the ready, this is when all the work goes into building a convincing pretext and plan on how to deploy the simulated attack. This is what will help ensure that the attack feels real.
• Attack Execution: A good social engineering pen test will use a few different social engineering attack tactics. They’ll execute a Phishing email campaign right alongside baiting or even honey-trapping. The cyber threats out in the real world are broad, and the testing execution needs to reflect that.
• Exploitation and Access: Any vulnerabilities exposed during the attack will then be exploited to see how far that would get a real hacker. Testers need to see how easily they can get access to sensitive information and/or systems.
• Documentation: Everything about the attack must be documented. The methods used, data collected along the way, and any particular insights gleaned by the testing team all need to be compiled for later reflection. It’s also what ensures the ethics of these kinds of tests. Though initially performed under the cover of darkness, everything is tracked and dealt with transparently by the end.
• Reporting and Analysis: A detailed report will include all the above as well as final recommendations. It should be as much a guide to potential social engineering weak spots as it is a guide on how to prevent those weaknesses from being exploited going forward.
• Remediation and Follow Up: This is when any identified vulnerabilities are followed up on and addressed. It’s by far the most crucial step, as it’s what ensures that the penetration test does its job of strengthening an organization’s cybersecurity profile.

Types of Social Engineering Penetration Tests

Social engineering tests will take different forms depending on the team providing them and the needs of the organization being tested. That said, the two main testing types usually guide the process:

• On-site Tests: These take place on-site and primarily test physical safety measures and employee vigilance. It’s the only way to test attacks like tailgating and USB dumping, and is extremely helpful in showing how ready staff and on-site security are to keep out unauthorized individuals.
  
• Off-site Tests: Remoting testing is more common as it’s what most real-life hackers are known to utilize. The tests simulate digital threats and track how well employees and users are able to spot things like phishing emails.

Social Engineering Penetration Tests Best Practices

Here’s a quick guide to best practices for social engineering penetration tests and what top cybersecurity teams should prioritize:

• Defined objectives and scope, be it in terms of the kinds of attacks being tested or the departments or people that the test should target.
• Proper authorization in the form of written approval from senior leadership. It’s also important that legal, HR, and IT representatives are included in the planning and that they approve the rules of engagement document that guides the test.
  
• Scenarios that are based on realistic threats and reflect common concerns that the organization is facing. It can’t be anything too outlandish. Realism is vital.
  
• The testing needs to use a variety of techniques in order to properly assess the organization’s security measures.
  
• Reconnaissance gathered must be done so carefully and mimic the actions of a potential hacker.
  
• The simulated attack needs to ride a very fine line: creating a real impact without causing any true harm. There can’t be any actual data loss or harm done to employees. Part of this endeavor requires a fail-safe mechanism or “safe word” that allows the test to cease if something concerning arises.

Penetration Testing and Prescient Security

The team at Prescient Security offers a wide variety of penetration testing services that can help strengthen your social engineering protections and overall cybersecurity position. We tailor the service to fit your needs so that the insights gathered are relevant and actionable.

Click here to speak to our experts and see how we can ensure that your organization isn’t left vulnerable to Phishing, Vishing, Smishing, or any other harmlessly named social engineering attacks. The names might be humorous, but the consequences are anything but.

Learn more about how your organization can fortify its security posture with Social Engineering Penetration Testing.