Example Adaptive Phishing Simulation for Executives

Adaptive phishing simulations are must-have tools for improving executives' phishing resilience. Keepnet Human Risk Management platform offers an AI adaptive phishing simulation platform tailored to executives. Dynamically adjusting phishing scenarios to address their unique roles, behaviors, and risks.

This blog post explores how adaptive phishing simulations can help executives recognize and mitigate phishing threats, improving organizational cyber resilience.

Phishing Scenario Overview

• Target Group: C-level executives, senior leadership, directors, and managers.
• Objective: Test executives’ ability to recognize and respond to spear-phishing and CEO impersonation attempts while building awareness of targeted attack strategies.
• Attack Vector: Email phishing with executive-level context and spoofed high-level contacts.
• Difficulty Level: Advanced (escalates based on individual performance and behavior).

Phishing Test Campaign Details

Phishing attacks targeting executives leverage urgency, authority, and highly specific scenarios to appear legitimate. In this example, attackers crafted a tailored email to exploit an executive's trust in internal communication channels. Understanding the anatomy of such emails is significant for identifying red flags and avoiding compromise.

Email Content:

• Subject Line: "[Action Required] Confidential Investment Strategy Approval"
• Sender: "board@yourcompany-management.com" (spoofed domain)
• Body:

Dear [Executive Name],

Please find attached the proposed strategy document for the upcoming board meeting. As it contains sensitive financial details, we request your review and approval as soon as possible.

If you have any feedback, please reply directly to this email or contact John Smith at john.smith@yourcompany-management.com.

Best regards,

Board Secretary

Attachments:

A malicious PDF named Strategy_Document.pdf is designed to collect login credentials through a phishing site.

Phishing Indicators:

1. Spoofed domain closely resembling the legitimate company domain.
2. Reference to confidential or high-priority topics such as board meetings or investment strategies.
3. Request for quick action without proper verification channels.
4. Suspicious attachment with an unfamiliar naming convention.

Dynamic Adjustments in Phishing Scenarios

Keepnet’s platform ensures simulations evolve dynamically based on executive behavior and responses:

For Executives Who Fall for the Initial Simulation:

• Immediate Training: A short, tailored micro-learning session on identifying high-level phishing indicators is triggered.
• Simplified Follow-Up Scenarios: Future simulations emphasize basic indicators, such as domain mismatches and attachment scrutiny.

For Executives Who Report the Initial Simulation:

• Advanced Scenarios: More sophisticated simulations are introduced, such as spear-phishing emails mimicking key stakeholders or clients.
• Focus on Business-Relevant Threats: Examples include BEC (Business Email Compromise) scenarios or requests involving large financial transactions.

Role-Based Adaptation:

• Tailored scenarios mimic realistic executive responsibilities, such as strategic approvals, confidential communications, and investment decisions.

Follow-Up Phishing Simulation Example

Follow-up phishing simulation tests whether executives can apply what they’ve learned after an initial attack. These scenarios are crafted to appear even more convincing, targeting areas where vulnerabilities may still exist. This approach helps organizations assess improvements and identify ongoing training needs.

Scenario for Executives Who Fell for the Initial Simulation

This scenario targets executives who fell for the initial simulation, presenting a more urgent and convincing follow-up to assess whether they can recognize and respond to the threat.

Email Content:

• Subject Line: "[Urgent] Updated Proposal for Approval Before Submission"
• Sender: "ceo@yourcompany-group.com" (spoofed domain impersonating the CEO)
• Body:

Hi [Executive Name],

I’ve reviewed the updated proposal for our partnership with XYZ Corp. Please ensure this is approved and shared with the board by the end of the day.

I’m unavailable for calls, so reply here if you need clarification.

Thanks,

[Spoofed Name]

CEO

Attachments: A malicious PDF designed to appear as a proposal document with embedded phishing links.

Scenario for Executives Who Reported the Initial Simulation

This scenario is designed for executives who successfully reported the initial simulation, introducing a more targeted phishing attempt to test their vigilance.

Email Content:

• Subject Line: "[Follow-Up] Confidential Client Information Request"
• Sender: "partner@xyz-corporation.com" (spoofed domain impersonating a trusted business partner)
• Body:

Dear [Executive Name],

As per our agreement, please review the attached client information for our upcoming collaboration and let us know if additional details are required.

Best regards,

[Spoofed Name]

XYZ Corporation

Attachments: A malicious Excel file with macros designed to compromise system security.

Why Keepnet’s Adaptive Phishing Simulation Stands Out for Executives

Keepnet’s platform offers unique features to address the specific challenges of training senior leaders:

1. Comprehensive Attack Vectors:

Our simulations cover various scenarios, including advanced spear-phishing, CEO impersonation, business email compromise (BEC), and vendor impersonation. This comprehensive approach ensures that executives are well-prepared for any potential threat.

2. AI-Driven Personalization:

Our AI-driven phishing simulations are tailored to each individual executive based on their role, behavior, authority level, and risk profile. This personalization ensures that each executive receives training that is relevant and valuable to them.

3. Hyper-Personalization:

Scenarios are localized and contextualized, reflecting senior leadership communications' tone, language, and priorities.

4. Gamification:

Encourages engagement by rewarding executives who report phishing attempts through leaderboards and badges.

5. Real-Time Feedback and Learning:

Provides instant feedback and micro-learning opportunities to executives who fall for simulations.

6. Outcome-Driven Metrics:

Tracking outcome-driven metrics from phishing simulations, like phishing reporting rates, risk scores, dwell times, and improvements in awareness, offers a clear view of executive performance and highlights how effectively they identify, report, and adapt to phishing threats.

Below are the key metrics that provide valuable insights:

1. Click Rate: Percentage of executives who clicked on phishing links or opened malicious attachments.
2. Reporting Rate: Percentage of executives who correctly identified and reported phishing attempts.
3. Time to Report (TTR): Average time executives take to report suspicious emails.
4. Adaptation Effectiveness: This metric measures the improvements in executives’ ability to identify advanced phishing attempts over time, demonstrating the continuous learning and improvement that the simulations facilitate.
5. Engagement Levels: Tracks participation in simulations and training modules.

Learning Outcomes for Executives

By participating in Keepnet’s adaptive phishing simulations, executives will:

1. Develop heightened awareness of spear-phishing and BEC threats.
2. Learn to verify requests for confidential information or financial transactions through secure channels.
3. Gain confidence in identifying and reporting sophisticated phishing attempts.
4. Contribute to fostering a cybersecurity-first culture across the organization.

Keepnet’s Human Risk Management Platform ensures executives receive targeted, realistic, and effective training to stay ahead of evolving threats. By enhancing their ability to identify and respond to phishing attempts, organizations of any size, like yours, can protect their most critical assets and leadership communications.