What Is Whaling Phishing? How to Prevent and Report Executive Email Attacks

How Does a Whaling Phishing Attack Work?

A whaling attack involves a fraudulent email or web page that masquerades as authentic and urgent. Whaling messages are crafted to look like critical business emails from someone with legitimate authority.

A whaling attempt may look like a link to a regular, familiar website. When you click on a malicious link, it will direct you to a website posing as a real landing page, which will likely prompt you to either log in and provide a username and password. Upon submitting this information, a message will say your credentials are incorrect, and to attempt again. This message is your proof that the login credentials you have entered have been sent directly to the attacker, who now has access to your account.

Other whaling attempts may trick you into downloading a malicious program to view a document or image. The program can track everything you type or delete files from your computer.

These attacks are highly dangerous because threat actors conduct in-depth research on their victims. They gather information such as birthdays, pictures, hobbies, promotion announcements, and relationships via social media, the Internet, or compromised email accounts to craft convincing campaigns. Learn more about what information these attackers look for and how to protect your inbox in our guide on phishing.

This level of targeting has had an immense financial impact. The FBI reports that since 2013, over $12 billion has been sent unknowingly by 78,617 companies in the U.S., UK, and Europe through successful whaling phishing campaigns targeting CFOs and finance leaders.

Did you know? Since the anatomy of a spear phishing attack is a highly targeted variation of phishing, whaling phishing is often considered a form of spear phishing.

 

​​Whaling Phishing and Its Impact on Executives

Whaling attacks are a threat to businesses of all sizes across all industries. In one notorious 2016 whaling attack, a Snapchat email scam was underway when an employee received an email from a threat actor pretending to be the CEO. The employee thought the email was legitimate and sent over payroll records for current and former staff. When the mistake was uncovered, Snapchat alerted the FBI and offered two years of identity theft protection to those affected. This breach shows how convincing whaling attacks can be, using trust and authority to reach sensitive company data.

Another high-profile whaling attack was at Seagate Technology in March of 2016, when an employee was tricked into delivering the W-2 tax forms of all current and former U.S.-based employees to an unapproved third party. These forms were easy targets for identity theft and bogus tax returns because they included private data like salary and Social Security numbers. The phishing email was interpreted by the employee as a valid internal request. Seagate quickly alerted federal authorities to the intrusion and provided two years of free identity theft protection to anybody who was impacted. This instance emphasizes how dangerous whaling attacks can be, even for big businesses. 

How to Recognize a Whaling Phishing Email

Whaling emails, also called executive phishing or CEO fraud attacks, are crafted utilizing advanced social engineering tactics to target and deceive users; however, there are various best practices for recognizing whaling phishing emails that individuals should implement to increase their chances of identifying these dangerous messages:

• Evaluate the sender’s email address: Does it look correct? Are there added letters and/or numbers within the username? Does it use the correct domain? Suspicious addresses are a common indicator of whaling phishing.
• Unusual or misspelled email addresses are often a sign of whaling phishing, also called Business Email Compromise (BEC). Spelling mistakes or clumsy grammar in the subject line or body can point to the same problem. When a message seems off, the best move is to pick up the phone and confirm with the sender. That quick step can stop an attacker from slipping through and is one of the simplest ways to prevent email spoofing.
• If an email appears suspicious in any way, be proactive and make a phone call to the sender to confirm the message's legitimacy. This is a crucial step in preventing email spoofing.

The image below is a whaling email that was identified and quarantined by Guardian Digital EnGarde Cloud Email Security. At first glance, it may look like a legitimate email from a CEO or CFO to an employee; however, there are multiple “red flags” that indicate this is a whaling phishing email. Some indications that this is a fraudulent email include:

 

 

• Suspicious “Reply to” address
• Urgent tone: trying to convince the recipient to act without thinking things through
• No signature

There are several indications that this is not a legitimate email—many users may not be aware of them or remember to check for them in every message. Thus, an advanced, threat-ready cloud email security solution is imperative to effective whaling attack prevention for businesses. Using the best email security solutions for executives helps detect these examples of whaling phishing attacks before they cause damage.

Best Practices to Prevent Successful Whaling Phishing and CEO Fraud Attacks

• Check carefully for spoofed email addresses or names. Make sure that the sender’s email address perfectly matches the company name and format.
• Be aware of what you click on. Stop and think before responding to any email you receive to reduce the risk of Business Email Compromise (BEC).
• Review all URLs you receive via email in your web browser. By determining whether anything looks suspicious, you can greatly decrease your chances of falling victim to executive phishing or whaling attacks.
• Prioritize effective email security awareness training.
• Review existing processes, procedures, and separation of duties for financial transfers and other important transactions, such as sending sensitive data in bulk to outside entities, to mitigate whaling risks.
• Consider new policies related to “out of band” transactions or urgent executive requests to strengthen whaling attack prevention for businesses.
• Review, refine, and test your incident management and phishing reporting systems to detect examples of whaling phishing attacks early.
• Be wary of any communication that is exclusively email-based and establish a secondary means of communication for verification purposes.
• Be mindful of phone conversations. Some victims of whaling say they received phone calls from attackers asking for personal details. The goal was to make the request sound legitimate. Cases like these demonstrate why executive phishing awareness is crucial.
• Executives should be cautious with what they share online. Birthdays, job titles, promotions, hobbies, or even travel updates on LinkedIn, Twitter, or Facebook can be collected and used to build a convincing CEO fraud attack.
• Stronger defenses also help. A managed cloud email security service with tools like DKIM, SPF, and DMARC can stop many whaling and Business Email Compromise (BEC) threats before they cause harm.

Do you know how SPF, DKIM, and DMARC protect your inbox against sender fraud? 

 

How to Report Whaling Phishing and Business Email Compromise (BEC)

If you receive any type of phishing email, report it immediately. The information you give is critical in fighting scammers. Follow these steps to report a whaling phishing email:

Step 1. If you received a phishing email, forward it to the FTC at This email address is being protected from spambots. You need JavaScript enabled to view it. and to the Anti-Phishing Working Group at This email address is being protected from spambots. You need JavaScript enabled to view it.. 

Step 2. Report the phishing attack to the FTC at ftc.gov/complaint.

Why Executives Are Prime Targets for Whaling Phishing

The truth is, it is extremely common for managers and executives to fall for whaling phishing scams. In the notorious 2008 FBI subpoena whaling campaign, approximately 20,000 CEOs were attacked, and about 2,000 of them fell for the whaling scam by clicking the link in the email. They were convinced that doing so would download a special browser add-on to view the entire subpoena. The linked software was really a keylogger that secretly recorded the CEOs’ passwords and forwarded those passwords to the attackers. As a result of this successful attack, each of the 2,000 compromised companies was hacked even further once the threat actors had obtained the information they were after.

And this trend hasn't stopped. In August 2025, Milford Entities, a prominent New York City firm managing luxury properties, was scammed out of nearly $19 million due to a phishing email. The fraudulent email disguised itself as correspondence from the Battery Park City Authority, leading to a large sum being wrongly transferred to a fake TD Bank account. The funds, intended as ground-lease and PILOT (Payment In Lieu Of Taxes) fees, were collected from over 2,000 residential units the firm manages. The Department of Homeland Security is leading a multi-agency investigation into the incident.

Executives are often the main targets of whaling phishing attacks. These schemes grow more advanced each year. As tactics evolve, businesses need to stay informed and choose security measures that give the strongest protection against these phishing threats.

Whaling Phishing Trending FAQs:

1. What are the financial impacts of a whaling phishing attack?
Whaling phishing attacks can cost businesses millions. They often target executives to trick them into authorizing wire transfers. The resulting losses include stolen funds, recovery costs, and potential damage to the company’s reputation.

2. How do deepfake technologies enhance whaling phishing attacks?
Attackers now use deepfake technology to imitate CEOs or CFOs. These realistic audio and video messages make whaling attacks harder to spot. A single audio clip can be manipulated to sound like a direct request from a higher executive, without them knowing. 

3. What role does social media play in facilitating whaling phishing attacks?

Social media is a hub of valuable, personal information that attackers can exploit. From birthdays to where someone works, all it takes is a simple Google search and anyone can be one step closer to figuring out a passcode you may have, or simply having enough source material to impersonate you.

4. How can your business recover from a whaling phishing attack?

Containing the breach will be key to the recovery process. Your company should always start by investigating the attack to better understand how the breach was successful. Then, notify affected parties and strengthen email security solutions moving forward. Email spoofing training is a necessity for every member of the company, not only for prevention but for proper education. 

5. What are the emerging trends in whaling phishing attacks for 2025?
Attackers are using AI-driven phishing campaigns and multi-channel attacks. Remote executives are targeted more often. Companies need advanced email security solutions and ongoing training to prevent whaling attacks.

Conclusion: Staying Ahead of Whaling Phishing Threats

Whaling phishing is one of the most damaging email threats businesses face, and executives remain prime targets. The good news is these attacks can be stopped with the right mix of awareness and strong defenses. Training employees to recognize the signs, enforcing clear processes for high-risk transactions, and investing in smarter email security all go a long way in keeping your company protected.

Ready to add an extra layer of protection? Guardian Digital’s multi-tiered security policy controls give you the tools to detect and block executive phishing attempts before they do damage. It’s a smarter, safer way to stay ahead of whaling phishing.