Not long ago, ChatGPT and other generative AI technologies made their way into the public domain and took the world by storm. Ever since, GenAI has become a trusted assistant for many, including cybercriminals. Hackers are using GenAI tools the way everyday users do, but with a malicious intent. They are leveraging these tools to research targets, write malicious code, or generate targeted phishing emails, all with the goal of speeding up turnaround and carrying out attacks at scale.
One of the big advantages for hackers lies in social engineering. For years, bad grammar or awkward phrasing were telltale signs of a phishing email. In fact, in a report, 61% of people said they spot scam or phishing emails by their poor spelling and grammar. Now, however, AI can produce polished, human-like content with technically sound grammar, making this common phishing red flag less reliable.
However, while the language may have improved, social engineering behavioral tactics remain consistent. So, in this blog post, we will break down the behavioral signs that can help you recognize an AI-generated phishing email.
How hackers are using GenAI for phishing
Hyper-personalized emails
Tools like ChatGPT, WormGPT, and FraudGPT allow attackers to generate emails that mimic the tone, style, and context of employees.
These emails are free of grammatical errors and often reference real projects, job roles, or recent events, making them highly convincing and believable.
Many phishing and business email compromise (BEC) messages appear to come from a company’s CEO, CFO, or trusted vendors. This is not hard to put together since a lot of the information attackers need like leadership names, employee updates, hires, and partnerships already live on company websites and social media like LinkedIn. GenAI tools help accelerate this reconnaissance, letting attackers pull public information together and craft far more believable, targeted phishing or BEC messages at speed.
In fact, academic research even shows AI-generated automated spear-phishing performs on par with human-crafted attacks in click-through rates.
Deepfake audio & video
AI-generated voices and videos impersonate C-Level Executives or managers, instructing employees to transfer funds or share credentials. These are used in vishing (voice phishing) and video phishing attacks, often following up on a phishing email to add legitimacy.
AI-generated phishing websites
Attackers use AI-powered website builders to clone legitimate sites (e.g., online banking portals, regulatory portals, etc.) in seconds. These sites are used to collect sensitive data like account credentials, payment information and or internal confidential data.
Malicious chatbots
Chatbots impersonate call center staff or recruiters, engaging victims in long conversations to build trust before delivering a malicious link or verbal request to reveal sensitive information.
Automated A/B testing
GenAI enables attackers to test different subject lines, email formats, and call-to-actions to optimize click-through rates, making phishing campaigns more effective.
Behavioral red flags of AI-generated phishing emails
Despite the sophisticated language, the tone and other behavioral patterns of the phishing email can give it away. These red flags show up in what the sender is asking you to do, how they create a sense of urgency, and the emotional tricks they use to rush your response.
Urgency or pressure to act
Attackers rely on creating a sense of urgency or time pressure to bypass your judgment.
AI models now blend this urgency into polished, professional language. For instance, a message may say, “To avoid any disruption to your service, please verify your details by the end of the day.” The tone sounds calm, but the demand is the same: act now.
Requests that break normal process
If an email asks you to bypass a standard approval step or payment workflow, that’s a big phishing red flag, even if the request sounds reasonable.
“Can you process this wire directly for me? I’ll handle the documentation later.” GenAI can tailor the language to make these requests sound authentic, referencing your real projects or vendors, but legitimate instructions rarely skip established processes.
Mismatched intent vs. channel
Appeals to authority
One of the most effective tricks AI enables is impersonating leadership. Attackers use publicly available information like names, titles, tone of voice to generate emails that look and sound like they’re from your company’s CEO, CFO, or VP.
“Hi, I’m traveling and need you to process this transfer right away. Please keep this confidential until I’m back.” This kind of request can feel intimidating, especially for new or junior employees. It plays directly on hierarchy and the pressure to please leadership.
What you can do to tackle AI-generated phishing
The best defense against these kinds of AI-enhanced phishing tactics is your people. Security awareness training needs to go beyond spotting typos or grammatical errors and focus on recognizing behavioral cues like false urgency or inconsistent requests. Employees, especially new hires or those in junior roles, should be reminded that it’s always okay to slow down and verify requests, even if they appear to come from senior leaders.
Additional considerations include advanced email filtering using AI-based filters that analyze behavior and context, not just content, can be useful. Lastly, digital fingerprinting & verification tools that verify sender identity and detect anomalies in communication patterns can be effective.
Just as important, reporting a suspicious email should be simple. A ‘Report Phish’ button or a direct channel to IT can help. When employees know the right process and feel supported for speaking up, they are far more likely to trust their instincts and follow company policy.
Stay one step ahead of GenAI phishing
GenAI has made social engineering smarter, faster, and harder to spot. But with the right mix of awareness, tools, and strategy, your organization can stay ahead.
Our information security services are designed to do just that: from security awareness training and security tools to incident response planning, we help you build resilience across every layer of your business.
If you’re looking to strengthen your defenses or simply assess how prepared your team is, contact us today to get started!
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