AI-Enhanced Insider Threats: When Employees Use ChatGPT to Steal Data

SHILPI MONDAL| DATE: MAY 20,2025

In today’s digital landscape, data protection companies and cybersecurity firms face an evolving challenge: insider threats supercharged by generative AI. Tools like ChatGPT, designed to assist with productivity, are now being weaponized by malicious insiders to bypass Data Loss Prevention (DLP) systems by rewriting sensitive data into seemingly benign text.

How Generative AI Helps Insiders Evade Detection

DLP solutions are designed to flag and block unauthorized transfers of sensitive information—credit card numbers, intellectual property, or confidential documents. However, generative AI can rephrase, summarize, or even encode this data in ways that evade traditional detection methods.

Rewriting Sensitive Data into "Safe" Text

An employee could feed proprietary code into ChatGPT and ask it to "reword this for documentation purposes." The output may retain the original meaning while bypassing keyword-based DLP filters.

Financial data can be disguised as "fictional case studies" or "training examples," making it appear innocuous to security tools.

Encoding Data for Stealthy Exfiltration

AI can convert sensitive information into base64, steganography, or even poetry, allowing data to slip past DLP undetected.

Attackers may use AI-generated phishing emails (crafted to mimic legitimate communications) to exfiltrate data via email without triggering alerts.

Exploiting Browser Vulnerabilities

Recent research reveals data splicing attacks, where insiders use browser-based AI tools to split and reconstruct sensitive files outside corporate oversight, bypassing cloud DLP controls.

Detection and Mitigation Strategies

To combat AI-powered insider threats, cybersecurity & data privacy teams must adopt advanced detection methods:

Behavioral Analytics & AI-Powered Monitoring

User and Entity Behavior Analytics (UEBA) can detect anomalies, such as an employee suddenly querying large datasets into ChatGPT.

AI-driven anomaly detection identifies unusual data reformatting or exfiltration patterns.

Enhanced DLP with Context-Aware AI

Modern DLP solutions now integrate natural language processing (NLP) to detect paraphrased or obfuscated data.

Real-time content inspection flags AI-manipulated text, even if keywords are removed.

Penetration Testing & Threat Simulation

Red teaming exercises simulate AI-assisted insider attacks to identify weak points in DLP systems.

Vulnerability assessments should include AI-specific threat modeling to anticipate novel exfiltration techniques.

Employee Training & Awareness

Cybersecurity awareness training should cover AI misuse risks, teaching staff to recognize suspicious AI-driven data manipulation.

Managed service providers (MSPs) can help small businesses implement AI-aware security policies.

Conclusion: Staying Ahead of AI-Driven Threats

As generative AI becomes more accessible, cybersecurity risk management must evolve. Organizations should:

Upgrade DLP systems with AI-driven contextual analysis. Conduct regular penetration testing to uncover AI-assisted attack vectors. Train employees on the risks of AI misuse. Leverage managed security providers for advanced threat detection.

By integrating AI-powered cybersecurity solutions, businesses can defend against next-generation insider threats while maintaining data integrity and compliance.

Citations

1. Sestito, K. (2025, January 8). Prompt injection attacks on LLMs. HiddenLayer | Security for AI. https://hiddenlayer.com/innovation-hub/prompt-injection-attacks-on-llms/

2. ITNS Consulting. (2025, March 7). AI Cyber Threats in 2025: A guide for small business owners. https://itnsconsulting.com/ai-cyber-threats-in-2025-a-guide-for-small-business-owners/

3. Mitchell, S. (2025, April 16). Researchers reveal data splicing attacks bypassing DLP. SecurityBrief UK. https://securitybrief.co.uk/story/researchers-reveal-data-splicing-attacks-bypassing-dlp

4. SentinelOne. (2025, April 6). AI threat detection: Leverage AI to detect security threats.SentinelOne.https://www.sentinelone.com/cybersecurity-101/data-and-ai/ai-threat-detection/