Hackers love to score a significant breach to help build their online reputation. Targeting and breaching a CEO, a board of directors member, or other high-level executives within a small or global 1000 company is a significant accomplishment for any hacker wanting to boost their online presence.
Spear phishing, similar to whaling, targets individuals within an organization. However, their target differs from that of the C-suite or the board. They will target administrators, department managers, or recently hired employees.
Stopping phishing attacks, including whaling, requires organizations to invest in advanced artificial intelligence (AI) and machine learning (ML) email security platforms. Legacy secure gateways or first-generation behavior-based solutions cannot match the adversarial AI hackers now used to attack the C-level.
Trustifi, a global provider of AI-powered advanced email security, continues to provide world-class protection for its clients, including several CEOs and executive board members.
Introduction to Whaling Attacks
Whaling attacks have one apparent goal: to breach and compromise executive leaders through email, physical connection, or voicemail. Hackers and cybercriminals know CEOs and high-profile targets possess valuable information, including trade secrets, investor contacts, pending lawsuits, and up-and-coming mergers and acquisitions with other high-ranking executives.
Hacktivists focus on whaling attack emails or hacking into corporate websites, wanting to punish corporate executives for their decision not to support global warming initiatives, green energy, or stopping the war in the Middle East.
Understanding Whaling Attacks
Malicious activities targeting a C-level executive start with the hacker creating a series of attack vectors, forming a kill chain. These types of cybersecurity threats have been around for several years. A kill chain includes several attack vector steps within a single campaign. Whaling tactics are rarely a single-thread attack. Hackers will use several vectors to attack several potential vulnerabilities, including:
- Denial of Service attack against the CEO’s organization (Weak infrastructure)
- Impersonate a fellow CEO and attempt contact through social media (Social engineering)
- Get hired at the CEO’s company as a contractor or employee (insider threat)
- Create AI-powered email phishing message impersonating someone close to the CEO (Human error or weakness)
- Attempt to place an Apple Tag near the CEO’s car, laptop bag, or on the person. (Malicious purposes)
Hackers know the value of compromising a CEO or executive. Often, whaling attacks will lead to extortion, blackmail, and substantial financial windfall.
Recently, CEOs have become victims of “CatPhish.” Hackers create a small yet effective kill chain combining catfishing and email phishing, claiming to be the parent of a child they didn’t know existed. The hacker sends fake baby pictures with a request for a payment of $100,000. This type of whaling attack lures its primary targets into paying the funds to prevent public disclosure.
Identifying the Vulnerable Targets
Hackers realize that, when going after a whale, they must invest a considerable amount in researching their target. Many often targeted CEOs, including Elon Musk, Bill Gates, Mark Zuckerberg, and Jamie Dixon, usually shield themselves physically and digitally from the public. However, even their personal, well-cloaked email addresses, cell phone numbers, and social media identities become available on the dark web. Hackers use social engineering tactics to contact people close to these executives. These potential targets include personal assistants, family members, or college friends.
These executives are often in the news and draw much attention from the media and activists. The hackers know these executives control a considerable amount of money and wield great power with their roles. Standard phishing attacks rarely work because of the digital shield surrounding these high-profile company executives, their families, and close friends.
Adversarial AI continues to make it difficult for executives to know who they are communicating with. Deepfake voicemails, AI-generated emails, and even well-crafted text messages sent to their secure private phones make it challenging for CEOs to trust the person messaging them.
Common Tactics and Examples of Whaling Attacks
Each CEO targeted with a whaling phishing attack brings a different result or reward. Targeting Mark Zuckerberg or Jamie Dixon could have a different expected outcome than going after Donald Trump.
Here are three examples of the whaling attack all CEOs should know.
Internal CEO Impersonations
Hackers impersonating the CEO emailed the HR department requesting access to employees’ home addresses, personal phone numbers, and dates of birth. The hacker claimed in the phishing email that executive leadership wanted to send out personalized “Birthday cards” to all employees.
Business Email Compromise
A primary attack vector that continues to be effective against CEOs is business email compromise (BEC). BEC scams are attempts by a hacker or cybercriminal to trick the executive into approving past-due fraudulent invoices and executing a wire transfer. Often, BEC attacks involve the hacker successfully posing as a known executive to the target. The impersonated CEO could be a close friend, business partner, or rival.
Within the BEC email, hackers use several other phishing tactics to increase their chances of success, including clone phishing. Clone phishing uses actual content from a previously compromised email account to help sell the whaling attack. The targeted CEO reading the BEC email, recognizing previous correspondence with their name, will mostly not question its contents.
Technical Aspects of Whaling Attacks
Whaling attacks require some technical executions before the message is sent to the targets. The hacker must first create or steal the CEO’s identity. This attack could be an initial spear phishing attack attempting to lure the CEO to click on a malicious link, leading to a change in password.
After this initial account takeover, the hacker can access the CEO’s personal information. This initial account takeover could expose the CEO’s social media accounts, giving the hacker access to personal and professional contacts.
In the next phase, the hacker impersonating the CEO sends emails using the stolen identities to personnel close to their impersonated executives. The hacker could send a similar malicious email from the previous successful whaling attack with an urgent request for sensitive information, including the new target’s bank account information and social security number.
Reality: Social engineering techniques work. CEOs receiving an email from a known associate from a recognized email address rarely think twice about replying or fulfilling the request made within the message.
How to Prevent and Defend Against a Whaling Attack?
Preventing whaling attacks starts with deploying several cybersecurity countermeasures:
Security Awareness Training
Dynamic security awareness training based on actual security telemetry information provides the CEO with real-world knowledge of whaling attacks and what steps they can take to help stop them. Organizations can customize their training specifically for their CEO and executive team while creating a broad security training program for the rest of the organization.
The executive-level security awareness training could include content:
- Executive impersonation
- Internal impersonation
- Manipulating information
- BEC/Social engineering
For the entire organization, the following security awareness content could be beneficial:
- Fake login pages
- quishing attacks
- Attachment phishing
- Punycode attacks
- Typosquatting
- Link spoofing
Multi-factor Authentication (MFA)
Attaching multi-factor authentication (MFA) with a passcode or password is a valuable way to prevent hackers from sending out impersonated emails even after the initial credentials were compromised. Email security platforms like Trustifi can require, through policy enforcement, all outbound messages to contain MFA. This policy will block the hacker’s ability to send these rogue emails.
Execute Whaling Attempts Simulation
Embedded within the Trustifi security awareness training modules is the ability for organizations to run well-crafted whaling simulated attacks. These real-world simulated whaling attacks help organizations train their employees to identify suspected email phishing attacks and provide guidance on how to stop the attack.
Trustifi Value: Trustifi is one of the few security awareness and attack simulation providers that offers exceptional explanations of the attack simulation message.Trustifi offers several whaling attack templates based on actual attack telemetry information. These templates help organizations roll out whaling attacks quickly and efficiently. Trustifi frequently updates these templates to give clients access to the latest attack vectors.
Deployment of Advanced Email Security Solutions Powered by AI and ML
Stopping any attack, including whaling, requires more than enabling inbound email filtering. Comprehensive email encompasses several layers of protection, fully integrated and centrally managed. All events correlate to the same monitoring module, and all email security policy creation and enforcement become enabled within the same console.
- An inbound email filter powered by AI and ML is critical in stopping well-crafted whaling messages from reaching the CEO and executive team. The AI filter also provides advanced malware protection (AMP) embedded with attachments or malicious links inside the email.
- Outbound filtering, including data loss prevention (DLP), email encryption, and data tokenization, is critical in protecting intellectual property, outbound whale phishing attacks, and data exfiltration.
- Account Takeover prevention must prevent an organization’s executives and high-profile employees’ accounts from becoming compromised and later used in a fraudulent wire transfer scheme or another whaling scam.
- Organizations operating in regulated sectors like finance, healthcare, and defense must archive all email messages.
What Organizations Policies Should Be in Place?
Along with deploying advanced email security protection platforms, organizations must create and enforce email security policies to meet compliance and cyber insurance requirements. These policies include:
- All outbound messages need to have MFA enabled.
- All outbound messages need to be encrypted by the user or system.
- All email messages need to be archived for a period based on the organization’s data retention strategy.
- Enabling DLP policies is necessary to ensure that authorized organization data can be sent through email.
- Account passwords need to be changed periodically to prevent account takeover.
- Employees should complete security awareness training on a quarterly and annual basis.
- Security teams should perform at least one email attack simulation every month.
How Critical is SecOps Incident Response and Reporting?
Organizations are taking a more proactive approach to email security, preventing whaling attacks and other potential threats. They must enable a security platform with advanced automation capabilities to do this. The rise of adversarial AI changed the dynamic of SecOps. Organizations can no longer staff security engineers to investigate every security incident or maintain cases.
Automation for security monitoring, incident response, threat modeling, and reporting is essential for organizations to stop next-generation email attacks. Legacy solutions rely on manual signature updates or behavioral analytics that take months to compile and bring little or no value to the organization’s email security strategy.
What is the Future of Whaling Attacks?
The future of whaling attacks is already upon us. Adversarial AI continues to be part of the whaling attack vector.
Hackers use AI and recorded voice prints from the impersonated executive to email the targeted executive. This attack, combined with social engineering, the initial whaling phishing email message, cloned phishing content embedded, and now a fake voice message, makes for a very effective kill chain.
Social Engineering
Social engineering will continue to be a threat as executives, including high-profile employees, CEOs, and CIOs, become very public people. They speak at industry events and meet with investors and the media. This human contact isn’t going away. Hackers know this will. They will continue improving their social engineering attacks with deepfake capabilities, extortion, and impersonation attacks.
Harpoon Attacks
The rise of harpoon attacks also will continue to challenge SecOps teams.
Just like whaling, harpoon whaling involves researching specific targets before attacking. Attackers gather detailed info on individuals based on their expertise. The critical difference is how attackers gather info and group their victims. Whaling attacks require manual work, while harpoon whaling needs automation to balance phishing victims and high revenue per attack.
Conclusion
Phishing remains the ultimate weak spot within the organization’s security posture. Even with advanced security awareness training, incident response automation, and continuous updates of threat intelligence information, whaling attacks will continue to be a force organizations must take seriously.
Organizations that do not invest in next-generation email security strategies like Trustifi will continue to face an increase in successful whaling phishing attacks, fines, compliance violations, and a loss of trust from their customers and business partners.
Why Trustifi?
Trustifi continues to drive innovation within the advanced email security market by delivering new features within its cloud-based platform that resonate with clients’ needs. A significant success factor with Trustifi continues to be its ease-of-use, cost-effective model tailored for the SMB, and growing list of happy customers.
Powered by AI, Trustifi’s ability to detect and prevent whaling and several other phishing attack vectors and deliver several layers of email security establishes it as a gold standard for the small-to-medium business sector. Regulated and unregulated organizations trust Trustifi with their email security, message encryption, data loss prevention (DLP), and compliance reporting requirements.
Get Started With Trustifi Today – Easy, Affordable, and Comprehensive
Whether you are looking for an extra layer of protection in your existing email environment or a full-suite solution, the expertise and simplicity Trustifi offers will exceed your expectations. Let’s discuss pricing and a customized email security plan for you.
