Whaling: How To Shield Your C-suite from Whaling Phishing

Whaling: How To Shield Your C-suite from Whaling Phishing

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The ethos behind whaling is "Go straight to the top of the organization". Cybercriminals who target high-level executives are attempting to catch the "big phish". These sophisticated, highly targeted attacks based on phishing and social engineering are costly and disruptive. Some companies lose millions of dollars and, often, their company reputation in whaling attacks.

What is Whaling and Who is Targeted?

What is Whaling and Who is Targeted?

The word "whaling" describes the targets of a whaling attack, who are typically C-level executives, like a CEO or CFO. However, senior managers who have access to sensitive network areas and data repositories can also be targeted. Other potential targets include board members with insider information on business deals and insider knowledge of Intellectual Property (IP).

These prestigious targets are chosen because of their access to sensitive information and critical data and their control of resources, including finances. Whaling aims to manipulate and deceive high-level targets into performing a task that benefits the attacker. Typical outcomes of a whaling attack include the following:

  • Transfer of large sums of money to a hacker's bank account.
  • Access to sensitive areas of a network and executive accounts.
  • Theft of sensitive corporate data, such as intellectual property (IP), company secrets, and sensitive corporate information.
  • Manipulation of corporate policies and processes to cause harm to the business and its systems.

What Happens During a Whaling Attack?

A whaling attack aims to exploit an executive or other senior-level company representative.

What Happens During a Whaling Attack?

Reconnaissance and Intelligence

Research is the key to a successful whaling campaign. The fraudsters will spend time gathering intelligence on a target, finding out their company and personal details, corporate structure, and business associates/supply chain vendors. Research often uses Dark Web forums and marketplaces to locate the data needed for a successful attack. This research allows the attacker to create highly believable campaigns that are difficult to identify as a scam.

Create the Whaling Campaign

Whaling attacks focus on executive or senior management-level relationships. The goal of whaling is to convince the victim to send a large sum of money or share company IP or other proprietary or sensitive data. The intelligence gathered in the initial reconnaissance step provides the details needed to identify the most effective relationship to exploit. Whaling attacks can happen inside a company and between associated companies. For example, whaling attackers may impersonate the CFO of a trusted supply chain provider to manipulate the CEO of the customer company. The attackers pretend to be the CFO, sending spoof emails or using a compromised account to send social engineering emails to an executive requesting payment for a service.

Execute the Whaling Campaign

Whaling attacks rely on building trust between the attacker impersonating a trusted person and the targeted executive. Typically, whaling phishing emails are used to develop the relationship to the point of the execution of the scam. As such, they do not use the typical elements of a phishing email, so red flag warnings are absent. Once the victim begins to show signs they are comfortable with the attacker posing as a trusted associate, the attacker will start manipulating the executive into performing the final deed, e.g., transferring money.

Collect the Results of the Campaign

The money or company resource is transferred to the attacker. This is what happened to an energy company. The attackers used a deepfake voice call, sounding exactly like the company's CEO, to trick the company's UK managing director into transferring $243,000; the funds went to a fraudster's bank account.

The plausibility of whaling phishing is made more effective by using generative AI to create hyper-personalized emails based on the intelligence gathered. The emails are designed to socially engineer the victim into performing actions to benefit the attacker.

Whaling attacks are continually evolving. They take advantage of deepfakes for social engineering and use evasive tactics, like bypassing MFA (multi-factor authentication), to remove security barriers.

The Financial Impact Of a Whaling Attack

Whaling attacks hit the financial heart of an organization, many of the attacks focusing on stealing corporate funds. High-profile whaling attacks talk of companies transferring tens of millions of dollars to attackers, believing the transaction to be legitimate. However, there are several other impacts caused by a whaling attack:

Data Loss

This includes IP and company secrets. Competitors may recruit cybercriminals using the Dark Web to target a company. The loss of a competitive edge costs a company more than direct financial losses.

Operational Disruption and Recovery

The aftermath of a major security breach, like a whaling attack, leads to downtime during the response phase. Downtime reduces productivity and can cause the loss of business opportunities. Research shows that an SMB loses around $8,000 – $20,000 for every day of downtime.

Reputation Damage

A business executive who has been part of a whaling attack can see their personal and business reputation impacted. A loss of trust can lead to a loss of customers. Research shows that 75% of consumers prefer not to do business with a company that has suffered a security breach.

Business Email Compromise (BEC)

BEC scams can be part of a whaling attack. BEC attacks cost US companies an average of $137,132 per incident, according to FBI data.

Whaling Signals

Whaling Signals

The red flag signals associated with phishing do not apply to whaling. This type of cyber-attack is low volume and highly targeted. The email and other communication channel exchanges are based on gathered intelligence on the target. The communications are designed to impersonate an executive closely so that the victim, typically another senior executive, can be socially engineered.

AI is making whaling even more difficult to detect. The application of offensive AI to create hyper-personalized whaling campaigns allows phishing communication channels, like emails and deepfake communications, to go under the radar.

The Part the Dark Web Plays in Whaling Attacks

The Dark Web plays an integral part in the development of whaling campaigns. The Dark Web provides the following opportunities to create compelling whaling attacks:

The Part the Dark Web Plays in Whaling Attacks

Intelligence Gathering

Attackers use the Dark Web forums to identify targets and locate intelligence on those targets. Generative AI interfaces can be used to automate intelligence gathering.

Impersonation and Social Engineering

Dark Web generative AI apps like FraudGPT and DarkBard are available to generate hyper-personalized and believable communications between the impersonated C-level executive and the victim. A study from Kaspersky found almost 3,000 Dark Web posts discussing "the use of ChatGPT and other LLMs for illegal activities".

Development of Malicious Content

The Dark Web provides as-a-service and Vibe coding options to develop malicious content, including malware and spoof websites, as required.

Data Handling

Dark Web marketplaces and forums handle the sale and transfer of stolen data, including login credentials that can be used in highly targeted whaling attacks.

How Important is Security Awareness Training to Prevent Whaling?

How Important is Security Awareness Training to Prevent Whaling?

Prevention of a whaling attack requires a multilayered approach. However, a fundamental layer is security awareness training. All employees, particularly C-level board members and other senior management, must be educated about the dangers of whaling. Staff should be made phishing aware, including the safe use of social media. Deepfake awareness is now an essential ingredient in any security awareness program. Regular program reviews and updates are essential. Behaviour-led security awareness training helps to modify training based on individual needs. Phishing simulations are typically deployed during training. The simulations generate real but fake emails that replicate the type of social engineering used by whaling attackers.

However, whaling attacks are notoriously difficult for anyone to detect, so security awareness training must be augmented using other email fraud prevention measures.

Other Cybersecurity Measures that Help Prevent Whaling Attacks

Dark Web Monitoring

Dark Web monitoring tools, like Sentinex, search the Dark Web for evidence that cybercriminals are targeting your company. The tools monitor stolen company information, including login credentials, corporate credit cards, and other sensitive company data.

AI-Powered Email Security Solutions

Advanced email security that uses AI, including Natural Language Processing (NLP), can identify subtle signals of social engineering in email communications.

Robust Identity and Access Management (IAM)

Enforcing the right level of access control to sensitive and critical data and apps helps prevent a successful whaling attack. Strong authentication measures, like MFA, can help when used with other layers of protection.

FAQs

FAQs

Is Whaling the Same as Spear-Phishing?

Whaling targets high-level organizational personnel, like a CFO or CEO. It is highly sophisticated and relies on deep intelligence about a company, corporate structure, and business associates. Spear-phishing is also targeted and is often used to steal login credentials of employees with high access privileges, like an administrator.

Is CEO Fraud the Same as Whaling?

CEO fraud and whaling are often used interchangeably, but refer to different attack strategies. As per CEO fraud, the cybercriminal impersonates a CEO and then manipulates any employee. Whaling attackers specifically target a high-level executive, like a CEO, by impersonating a trusted third party, like a vendor, but the target may not necessarily be a CEO.

What's the Difference Between Business Email Compromise (BEC) and Whaling?

BEC can be thought of as a subset of whaling. However, whaling is a broad type of cyberattack that targets executive-level personnel and has various outcomes. BEC scams are financially motivated. BEC attacks may impersonate an executive, like a CEO, and target an employee in accounts payable, manipulating that person into transferring money that ends up in a hacker's bank account.

Why are High-Level Executives Targeted in Whaling Attacks?

High-level executives like CEOs and CFOs typically have access to sensitive corporate information and IP. C-level executives also have power and control in a business and can issue commands that other employees must follow. This power and control, coupled with access to company secrets, make C-level executives an ideal target.

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