0

Whaling Phishing: Protecting High-Level Executives from Targeted Attacks

Cyberattack
Howard Poston
Oct 10, 2023
Whaling Phishing: Protecting High-Level Executives from Targeted Attacks

Whaling attacks take phishing techniques and target the “big fish” in the organization (hence the name). These attacks use deception, manipulation, and similar techniques to trick high-level executives into doing something that an attacker wants. For example, whalers might pretend to be another CEO looking to close a deal in exchange for a big payment.

These individuals are ideal targets for cybercriminals because they likely have the power to authorize financial transfers or take other actions that benefit the attacker. Additionally, tricking the CEO or another high-level executive reduces the chance of someone questioning an unusual transaction.

Whaling attacks are growing more prevalent because they have the potential to net significant payoffs for a cybercriminal. This article explores how these attacks work, examples of notable whaling attacks, and best practices for protecting against this threat.

Whaling Phishing: Definition and Characteristics

A whaling attack is a phishing attack targeting executive-level individuals within an organization. The attacker will use social engineering techniques personalized to the intended target to increase the plausibility of the attack and induce the target into performing a particular action.
These attacks are often highly tailored to the target executive. For example, an attacker performing a whaling attack against a CEO may pretend to be part of another organization looking to make a deal. The attacker will have researched the CEO and their company and tailored their pretext and the content of their phishing messages to maximize the chance that the attacker will believe the con and take action to close the deal.

Spear Phishing vs. Whaling vs. Phishing

Whaling is a form of phishing attack. More specifically, it is a type of spear phishing attack. The main difference between these three types of attacks is the number of potential targets of the attack.

In a general phishing attack, the attacker uses a pretext that will apply to a wide audience. While these attacks have a lower probability of success, the sheer number of potential targets means that the attacker will succeed in some cases. For example, many phishing emails will pretend to be Netflix or a similar organization and try to trick users into entering their credentials into a phishing site.

Spear phishing attacks use pretexts that are tailored to a specific target. By making the attack specific to an individual or small group, the attacker increases its believability and likelihood of success. Often, spear phishers will pretend to be the company CEO or other high-level executives and instruct an employee to perform some action that benefits the attacker.

In a whaling attack, the target is a high-level executive within an organization, such as a member of the C-suite. These attacks are often highly researched and may require more effort and interaction between the attacker and the target. This additional work can be worth it in the end due to the larger potential payoff.

How Whaling Attacks Work

A successful whaling attack is a multi-stage operation. The key steps include:

Target Selection: Whaling attacks require a great deal of effort by the cybercriminal performing them, so there needs to be a substantial potential payoff. An attacker will look for a target that makes the attack worth it. For example, the CEO of a large organization may be in a better position to pay a large amount of money to the attacker than the executive of a smaller firm.

Reconnaissance: Whaling attacks are highly tailored to their intended target. A cybercriminal will perform in-depth research into the executive and their company to determine a pretext that is likely to succeed and have the desired result. For example, the attacker may pose as a vendor offering services or products that the company is likely to want or one that has not been paid for services rendered.

Crafting Deceptive Messages: After the attacker has done their research, they can craft a personalized and convincing phishing email. These emails combine knowledge of the target with psychological manipulation to maximize the probability that the attacker will do what the attacker wants, such as sending money or sensitive data to the attacker.

Examples of Whaling Attacks

Whaling is a common attack vector that can have a significant impact on an organization. Some examples of high-profile whaling attacks include:

Levitas Captial: In 2020, a co-founder of Levitas Capital, an Australian hedge fund, fell for a whaling attack that installed malware on the company network. The whaling attack included a fake Zoom link and included an attempt to steal $8.7 million from the company via fraudulent invoices. While the attackers only successfully stole $800, the reputational damage caused the company to close after it lost its biggest client.

Mattel: In 2016, Mattel fell for a phishing attack that blended whaling and CEO fraud. The attacker, pretending to be the CEO, emailed a finance executive requesting a payment. $3 million was wired to a Chinese bank account, but, due to luck, the company was able to freeze and recover the funds because the next day was a Chinese banking holiday.

These are only a couple of examples of the potential repercussions of a successful whaling attack. Often, the goal is to steal money or data from the organization, and the high-level targets mean that the losses can be substantial.

Whaling Phishing Use Cases

Whaling attacks target high-level executives within an organization. Cybercriminals can perform these attacks to achieve a few different goals, including:

Corporate Espionage: High-level executives have control over an organization’s strategic vision and may be willing to share sensitive information with partners and vendors. Cybercriminals can take advantage of this to steal intellectual property or other sensitive company data from executives via targeted, deceptive emails.

Financial Fraud: Financial fraud is a common goal of whaling attacks because an executive may be induced to send a payment to pay an invoice or close a deal. Whaling attacks can have price tags in the millions as demonstrated by the FACC and numerous other successful attacks.

Reputational Damage: Whaling attacks can also be performed with the intent of causing reputational damage to the executive or the corporate brand. For example, if an executive is tricked into handing over sensitive data or sending a payment to an attacker, the cybercriminal could leak this information, causing embarrassment to the executive and the business.

Protecting Against Whaling Phishing

Whaling attacks target the most powerful individuals in an organization, meaning that they can have a significant impact on it if they succeed. Some steps that organizations can take to defend themselves against whaling attacks include:

Strong Authentication: Whaling attacks may be designed to gain access to executives’ online accounts via compromised credentials. These accounts could then be used to steal data or money from the organization. Implementing strong authentication — including the use of multi-factor authentication (MFA) — can make it more difficult for an attacker to use stolen credentials.

Cyberawareness Training: Executives are often a prime target of cyberattacks and also some of the most resistant to cybersecurity training. Providing targeted training on the threats that executives are most likely to face — including whaling attacks — can maximize the effectiveness of training and ensure that executives are aware of the whaling threat and common tactics used in these attacks.

Email Security Solutions: Email filtering and anti-phishing tools have the potential to identify and block attempted whaling attacks before they reach executives’ inboxes. Anti-phishing solutions using AI and natural language processing (NLP) can identify and flag email content likely to be associated with a phishing attack.

Incident Response Plans: Even with the best preparation and prevention in place, successful cyberattacks can still happen. Having incident response plans in place enables a more rapid response to successful whaling attacks, reducing the potential cost and damage to the organization.

Best Practices for Whaling Phishing Prevention

For whaling — and other social engineering threats — the best defense is proactive and preventative. Some best practices for preventing whaling attacks include:

Executing Regular Security Audits: Regular security testing can help to validate that an organization’s anti-whaling defenses are effective. For example, an organization may test fake whaling emails to see if they reach executives’ inboxes.

Establishing a Clear Chain of Communication: Clear, rapid communication is key during any security incident. Establishing communication channels in advance helps to ensure a coordinated, effective response to an incident.

Encouraging a Culture of Skepticism: Whaling and similar attacks work using trickery and deception. Encouraging executives and other employees to be skeptical of emails and other messages reduces the chances that they will fall for a scam.

Enabling User-Friendly Reporting Mechanisms: Reporting suspected phishing attacks alerts security teams of the threat and enables them to respond if someone else falls for it. Making these reporting mechanisms user-friendly increases the probability that users will report attempted attacks.

Future Trends and Preparedness

The emergence of generative AI tools such as ChatGPT has had a significant impact on phishing and social engineering attacks. Often, one of the main limitations of these attacks is the fact that grammatical errors help targets differentiate between real emails and phishing attacks.

With generative AI, phishers are able to develop much more polished emails more quickly. This increases the believability of their attacks, enables them to perform more sophisticated psychological manipulations, and allows them to scale attacks by taking advantage of automation.

As generative AI matures, whaling attacks may grow more sophisticated and difficult to attack. This fact, combined with constant innovation by attackers trying to evade detection and defenses, contributes to an ever-evolving phishing threat landscape.

A successful whaling attack can carry heavy costs for an organization, and a company can’t be certain that defenses that work today will succeed tomorrow. Organizations need to continuously adapt to the evolving whaling threat and take action to protectively block, detect, and respond to potential whaling attacks.

Conclusion

Whaling attacks go straight to the top, targeting high-level executives with personalized phishing attacks. These attacks can be designed to steal money or data from organizations.

Protecting against whaling attacks requires a proactive, defense-in-depth approach. Organizations should educate employees regarding the risks and deploy security solutions designed to identify and block attempted attacks.

It’s also best practice to put solutions in place to mitigate the potential effects of these attacks, such as compromised credentials. KelvinZero helps to protect against credential theft with a universal, phishing-resistant biometric pass. Contact us to learn more about how your organization can confidently authenticate executives and other employees while protecting against whaling and similar threats.

Howard Poston

Howard Poston is a copywriter, author, and course developer with experience in cybersecurity and blockchain security, cryptography, and malware analysis. He has an MS in Cyber Operations, a decade of experience in cybersecurity, and over five years of experience as a freelance consultant.