Conversational Phishing: When Scammers Chat Like Real People

• Conversational Phishing
• AI Email Scams
• Cybersecurity

AI chatbots are being used in phishing emails to hold realistic conversations and steal data. Learn how to spot and stop these high-tech scams.

The Rise of Conversational Phishing

Phishing emails have entered a new era. Gone are the days when a scam ended after the first message. Now, if you reply to a suspicious email, you might find yourself in a full conversation—with an AI-powered chatbot pretending to be a real person.

This tactic is called conversational phishing. It’s a growing threat, and it’s unsettlingly effective.

How AI Makes It Work

These phishing bots are trained on large datasets of business emails and customer service chats. They’ve learned how to write, respond, and even sound helpful—complete with polite language, contextual references, and personalised details. They adapt to your tone and style, even referring back to details you’ve shared.

What makes them so dangerous is how real they feel. Victims often believe they’re talking to an actual colleague, supplier, or IT support staff member.

What These Bots Try to Do

• Send fake invoices: You’re guided to process a payment or click a link that leads to a cloned banking portal.
• Request password resets: The bot may ask you to share a reset code or click a link to update your login info.
• Install malicious software: The bot might claim compliance software or a secure document viewer needs to be installed.

Because these emails evolve in real-time based on your replies, they easily bypass traditional spam filters that scan for static threats.

Red Flags of Conversational Phishing

• Unusual sender behaviour: A new contact appears helpful but avoids phone calls or video chats.
• Hyper-personalised details: The email includes references to internal documents, dates, or tone that mimic your company culture.
• Multiple back-and-forth replies: A phishing scam that drags out over several emails is likely AI-driven.
• Insistence on urgency or secrecy: You may be asked not to discuss the issue with others “due to policy.”

How to Stay Safe

• Verify before you act: Don’t click, download, or pay until you’ve verified the sender through a separate channel.
• Use multi-factor authentication (MFA): Even if credentials are stolen, MFA can stop unauthorised access.
• Slow down the exchange: Scammers rely on urgency. Take time to question and verify the details.
• Train staff regularly: Awareness is key. Make sure your team knows how to recognise AI-driven conversations.

Final Word

AI-powered conversational phishing is one of the most sophisticated scams in circulation today. These bots aren’t just sending emails—they’re pretending to be people, gaining trust, and walking victims into traps over days or weeks.

Always pause, verify, and report anything that feels slightly off. If it’s too natural, too helpful, and too smooth—it might just be too fake.