Whaling 101

The apex predator of phishing attacks - whaling. Whaling goes after the biggest catches of all: senior executives, CEOs, CFOs, and other high-value targets.

Whaling 101
Moni's Whaling Adventures

For phishing awareness training or just for a chat, get in touch with us at main@cybermonkey.net.au

Code Monkey Cybersecurity’s Phishing Awareness Training
The Basics $12.99 per person, per month $10.99 per person, per month (paid annually - save 15%) ✓ One simulated phishing email to each staff member approximately every 10 days ✓ Monthly reporting & analysis ✓ Free 1hr initial onsite education and introduction ✓ Simulated phishing attempts tailored to you based on publically

If you haven't read Phishing 101, or Spear Phishing 101, you'll want to do that.

Phishing 101
Phishing 101. What is it? Why should you care? How can training help?
Spear Phishing 101
For phishing awareness training or just for a chat, get in touch with us at main@cybermonkey.net.au Code Monkey Cybersecurity’s Phishing Awareness TrainingThe Basics $12.99 per person, per month $10.99 per person, per month (paid annually - save 15%) ✓ One simulated phishing email to each

Now for the apex predator of phishing attacks - whaling. Following our fishing metaphor, if phishing catches whatever swims by and spear phishing targets specific fish, whaling goes after the biggest catches of all: senior executives, CEOs, CFOs, and other high-value targets.

Here's my analysis of what makes whaling distinct: It's essentially spear phishing taken to its logical extreme, with even more research, sophistication, and potential payoff. The attackers aren't just personalizing the attack; they're often crafting entire campaigns around the target's business dealings, personal interests, travel schedule, and communication patterns.

The reasoning behind whaling is economically rational from an attacker's perspective. Why spend effort compromising a junior employee's account when you could compromise the CEO's? Executive accounts have broader access privileges, authority to initiate large financial transfers, access to strategic information, and their communications carry inherent authority that can be leveraged for further attacks.

What makes whaling particularly challenging from a defensive standpoint is that executives are often the hardest group to protect. They frequently bypass security protocols for convenience, use personal devices for work, communicate with a wide variety of external parties, and their assistants often have access to their accounts. They're also public figures, so information about them is readily available for attackers to use in crafting convincing pretexts.

A typical whaling attack might involve multiple stages and extreme attention to detail. For instance, an attacker might first compromise a law firm that works with the target company, spend months understanding the relationship and communication patterns, then send a perfectly-timed email about a confidential acquisition that's actually in progress, with malware disguised as a legitimate document. The executive, seeing a expected communication about a real deal from a known contact, is likely to open it without question.

The evidence from major breaches shows that whaling has been behind some of the most damaging incidents in cybersecurity history. The 2016 Democratic National Committee breach began with whaling attacks on senior staff. The Ubiquiti Networks incident resulted in $46.7 million being transferred to attackers through whaling. These aren't just security incidents; they're organizational catastrophes.

The interconnected nature of these three attack types reveals something important about cybersecurity: as defenses improve against broad attacks, attackers naturally move toward more targeted approaches. It's an evolutionary arms race where increased effort yields increased success rates, and the stakes get higher as you move up the food chain from phishing to spear phishing to whaling.


For phishing awareness training or just for a chat, get in touch with us at main@cybermonkey.net.au

Code Monkey Cybersecurity’s Phishing Awareness Training
The Basics $12.99 per person, per month $10.99 per person, per month (paid annually - save 15%) ✓ One simulated phishing email to each staff member approximately every 10 days ✓ Monthly reporting & analysis ✓ Free 1hr initial onsite education and introduction ✓ Simulated phishing attempts tailored to you based on publically