5 Examples of Whaling to Help you Steer Clear of Trouble

Phishing remains one of the most prevalent and dangerous cyberthreats that businesses face. In our Kaseya Security Survey Report 2023, 41% of our respondents reported phishing as the cybersecurity issue that impacted their organization the most. Among the various types of phishing attacks that employees may encounter, one stands out for its specificity and potential for significant damage: whaling, also known as CEO fraud or CEO phishing.

Unlike general phishing attacks, which cast a wide net, whaling targets high-profile individuals within an organization, such as executives or key decision-makers. This targeted approach makes whaling particularly dangerous and damaging. Take a look at these five examples of what a whaling attack might look like to learn about the red flags that may indicate trouble.

What is whaling?

Whaling is a sophisticated form of phishing aimed at senior executives, often disguised as legitimate business communication. Attackers meticulously research their targets to craft convincing emails that exploit the authority and influence of the targeted executive. The advent of artificial intelligence (AI) and its adoption in cybercrime has made it easier for bad actors to craft a convincing message that avoids many of the common indicators of phishing. The goal is often to trick the recipient into authorizing large financial transactions, divulging sensitive information or installing malware.

One factor that makes whaling attacks so insidious is that they typically feature bad actors using a stolen identity to impersonate the requisite executive or authority that is presented as the sender. Identity theft becomes easier with every major data breach, making it a cinch for cybercriminals to gain access to the information they need to pull off the con. The IBM X-force Threat Intelligence Index 2024 found a 71% increase in cyberattacks leveraging stolen identities in 2023 compared to 2022.

3 hallmarks of a whaling attack

Whaling attacks can take a wide variety of forms, making them tricky to spot. However, there are a few basic identifiers that can indicate a CEO phishing attack. Whaling attacks are typically characterized by:

1. Personalization: Emails are tailored specifically to the target, often including personal details to appear legitimate. While this is a common characteristic of phishing, in a whaling attack, the personalization is carefully tailored to mimic an executive or some other powerful player.
2. Urgency: Messages frequently convey a sense of urgency, pressuring the target to act quickly without verification. This can be especially dangerous when the message targets someone who can operate outside of an organization’s normal checks and balances.
3. Authority: The attacker impersonates a figure of authority, such as the CEO or a high-ranking executive, to compel compliance without raising too much suspicion by leveraging an employee’s fear of job loss or reluctance to displease an authority figure. AI makes it even easier for bad actors to strike the right tone.

5 examples of whaling attacks

Here are five scenarios illustrating what a whaling attack might look like:

Urgent wire transfer request

Scenario: The CFO receives an email from the CEO, urgently requesting the transfer of $250,000 to a new vendor for a confidential project. The email appears legitimate, complete with the CEO’s signature and a plausible reason for the secrecy and urgency.

Indicators: The email domain is subtly different (e.g., [email protected] instead of [email protected]) and the transfer request deviates from standard procedures.

Fake legal subpoena

Scenario: The legal department head gets an email that appears to be from a well-known law firm stating that the company is facing a lawsuit and immediate action is required. The email includes a link to download the full subpoena, which actually installs malware like ransomware.

Indicators: Unsolicited legal threats, an urgent call to action and a download link which, if scrutinized, shows an unfamiliar or suspicious URL.

Executive travel compromise

Scenario: An executive assistant receives an email from what seems to be the CEO, who is supposedly traveling. The CEO asks the assistant to purchase and send gift card codes to clients as a token of appreciation, promising reimbursement upon return.

Indicators: Unusual requests for gift cards, a sense of urgency and the use of personal email addresses.

M&A confidential information request

Scenario: During a merger and acquisition negotiation, the head of finance gets an email from the purported CEO asking for detailed financial records and projections to be sent to an external consultant’s email.

Indicators: The external email address is not previously known, and there is pressure to bypass standard confidentiality protocols.

Internal policy update

Scenario: Employees receive an email from the HR director about an urgent update to internal policies, with a link to review the changes. The link leads to a fake login page designed to capture credentials.

Indicators: The link directs to a domain that doesn’t match the company’s official URL, and the email creates a sense of urgency that discourages verification.

Tips for protecting against whaling

To mitigate their risk of falling victim to a whaling attack or CEO fraud, organizations should implement the following measures:

• Frequent education: Regularly educate employees about phishing threats and how to recognize suspicious emails.
• Phishing simulation: The best way to ensure that employees are aware of phishing threats is through phishing simulations.  
• Verification protocols: Establish procedures for verifying unusual requests, especially those involving financial transactions or sensitive information.
• Email filtering and security: Utilize advanced email filtering tools to detect and block phishing attempts.
• Incident response plan: Develop and regularly test a formal incident response plan for dealing with suspected phishing attacks.
• Comprehensive security awareness training policies: Require cybersecurity awareness training.

Whaling attacks leverage the power of authority and urgency, making them highly effective but also detectable with the right precautions. By fostering a culture of vigilance and implementing robust security measures, organizations can better protect their leaders and assets from these sophisticated threats.

Kaseya’s Security Suite helps businesses mitigate all types of cyber-risk affordably

Kaseya’s Security Suite has the tools that MSPs and IT professionals need to mitigate cyber-risk effectively and affordably. It features automated and AI-driven features that make IT professionals’ lives easier. 

BullPhish ID – This effective, automated security awareness training and phishing simulation solution provides critical training that improves compliance, prevents employee mistakes and reduces a company’s risk of being hit by a cyberattack.    

Dark Web ID – Our award-winning dark web monitoring solution is the channel leader for a good reason. It provides the greatest amount of protection around, with 24/7/365 human- and machine-powered monitoring of business and personal credentials, including domains, IP addresses and email addresses.   

Graphus – Graphus is a cutting-edge, automated email security solution that puts three layers of AI-powered protection between employees and phishing messages. It works equally well as a standalone email security solution or supercharges your Microsoft 365 and Google Workspace email security.     

RocketCyber Managed SOC – Our managed cybersecurity detection and response solution is backed by a world-class security operations center that detects malicious and suspicious activity across three critical attack vectors: endpoint, network and cloud.

Datto EDR – Detect and respond to advanced threats with built-in continuous endpoint monitoring and behavioral analysis to deliver comprehensive endpoint defense (something that many cyber insurance companies require).     

Vonahi Penetration Testing – How sturdy are your cyber defenses? Do you have dangerous vulnerabilities? Find out with vPenTest, a SaaS platform that makes getting the best network penetration test easy and affordable for internal IT teams.  

Learn more about our security products, or better yet, book a demo today!