Conversational Phishing: Defending Against the Most Human Cyber Threat Yet
The Age of Human-Sounding Cyber Attacks
Cybercriminals have always relied on deception, but the rise of generative AI has elevated their tactics to unsettling new heights. Today, phishing messages don't just look legitimate - they sound authentic. We're now facing a wave of attacks that feel eerily personal, familiar, and contextually believable. Welcome to the era of conversational phishing.
At Jericho Security, we understand that defending against this new breed of phishing attack requires tools and training just as sophisticated. Our latest innovation - a self-service, agentic AI-powered phishing defense platform - delivers this capability to organizations of every size, instantly. This blog unpacks what conversational phishing is, why it works, and how we're empowering the front line of cybersecurity to respond.
What is Conversational Phishing?
Conversational phishing is a highly personalized form of social engineering that leverages generative AI to craft believable, natural-sounding communications. Unlike generic spam emails, these messages are crafted to feel like real conversations. They can be sent via email, SMS, chat, or even voice - and they’re often part of a multi-step interaction.
Whereas traditional phishing may rely on misspellings, urgency, or suspicious links, conversational phishing is more insidious. It mimics the tone, style, and even cadence of workplace dialogue. These attacks often reference real people, companies, or workflows and are designed to slip past both filters and human suspicion.
This threat is especially difficult to detect because it no longer adheres to predictable patterns. Attackers may scrape social media or data leaks to impersonate trusted figures and insert themselves into seemingly authentic interactions.
Why It Works: The Psychology Behind the Threat
Conversational phishing is effective because it hijacks trust - not just technology. It leverages the cognitive shortcuts we use in daily communication. When we see a message that sounds natural and references familiar people or processes, we’re more likely to act without questioning it.
Human-Like Language and Tone
Using large language models, attackers can generate emails with perfect grammar, context-awareness, and an understanding of business communication norms. The language feels human - often more polished than internal emails - and it bypasses the traditional markers of phishing.
Thread Hijacking and Multi-Step Attacks
Some attackers employ what’s known as barrel phishing: a two-step approach where an initial benign message ("Hi, just checking in") establishes credibility, followed by a malicious follow-up. Others hijack real threads through compromised email accounts - a tactic known as conversation hijacking.
Psychological Manipulation
The use of urgency, authority, or familiarity compels recipients to act. Attackers often impersonate executives, HR reps, or vendors to get recipients to approve wire transfers, disclose credentials, or open malicious links. It’s not just what is said - it’s how and when it’s said that makes these attacks so dangerous.
Real-World Variants of Conversational Phishing
These sophisticated attacks come in many forms, each tailored to bypass specific security controls and exploit organizational weaknesses:
|
Type |
Description |
Common Tactic |
|
Business Email Compromise (BEC) |
Impersonates executives or finance leaders to request urgent transfers or approvals |
"Please process the attached invoice today" |
|
Vendor Spoofing |
Fakes emails from known suppliers or partners asking for payment or contract changes |
"Here’s the new billing info for last month’s PO" |
|
Internal HR Impersonation |
Pretends to be an employee changing personal details or benefits info |
"I've updated my direct deposit info. Can you confirm?" |
|
Conversation Hijacking |
Joins existing threads using compromised accounts |
"Adding my input here - looks good to me." |
These attacks blur the line between external and internal communication, which is exactly what makes them so successful.
New Defense, Built for the AI Era
To address this growing threat, Jericho Security launched a self-service, agentic AI platform in May 2025. This platform empowers security teams to simulate, detect, and defend against conversational phishing attacks at scale - and without complex onboarding.
Frictionless Access to Powerful Defense
Companies can now start using Jericho’s platform with no demo, no contract negotiation, and no delay. With Jericho Lite, Plus, and Premium tiers, organizations of any size can instantly run phishing simulations tailored to their real-world communication patterns.
Multi-Vector Training
Simulations go beyond email - including voice, SMS, and chat-based phishing. Employees are trained across multiple mediums to ensure comprehensive preparedness.
Behavior-Based Risk Scoring
Our proprietary agentic AI analyzes how users interact with simulated threats, building a dynamic risk profile for every team member. This enables personalized, role-specific training that evolves as threats do.
Customization and Performance Analytics
Organizations get control over their training content and frequency, with in-depth analytics showing employee improvement, high-risk behaviors, and real-time progress.
"We’re giving companies immediate access to the same high-fidelity simulations that Fortune 500s rely on - with a frictionless way to try, buy, and grow." - Sage Wohns, CEO, Jericho Security
Why Jericho Security Leads the Way
Our approach isn’t just about technology - it’s about making enterprise-grade security accessible, scalable, and user-friendly. This commitment has been recognized by the cybersecurity community:
At RSA Conference 2025, Jericho Security was awarded:
- Market Innovator – AI Security Solution
- Trailblazer – Anti-Phishing
- Most Advanced – Cybersecurity Training
- Trailblazing – Cybersecurity Awareness
We’re proud to lead the industry in next-gen threat response, and our mission is simple: to equip every organization with the tools to fight back against human-like threats.
Best Practices to Defend Against Conversational Phishing
Even with the best technology, employee awareness is crucial. Here are proven strategies to improve resilience:
- Simulate Regularly - Run phishing simulations that reflect current attacker strategies, including conversational techniques.
- Empower Employees with Training - Go beyond annual checklists; provide contextual, adaptive learning based on real behaviors.
- Deploy AI-Powered Detection Tools - Use tools that evaluate content based on tone, behavior, and linguistic style - not just keywords.
- Monitor Communication Integrity - Track domain spoofing attempts and email anomalies.
- Use Multi-Step Approval Processes - Don’t approve financial or credential-related requests based on a single email.
Ready to Try It?
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