Mile2 Cybersecurity Institute

AI Jailbreaks

By Dr. Raymond Friedman – December 1, 2025

How AI Quietly Pushes You Over Legal Lines

AI isn’t just a technology problem anymore — it’s a legal one. From chatbots and copilots to recommendation engines and fraud models, organizations are deploying AI faster than their governance, legal, and compliance structures can adapt. The result? You can drift over legal lines without ever intending to.


Here are five ways AI can quietly move you from “innovative” to “liable” if you’re not paying attention.


1. Privacy & Data Protection: Training Your Way Into a Lawsuit


Most AI systems are hungry for data — especially personal data. Customer support logs, HR files, emails, medical records, location trails, biometric data, and even “anonymized” datasets all become tempting fuel for model training and tuning.


Under laws like the GDPR, regulators have made it clear that AI models trained on personal data are often still subject to data-protection rules, especially where data can be reconstructed or “regurgitated” from a model (European Data Protection Board, 2024). Similar concerns are emerging globally as data protection authorities examine how AI models are built and deployed.


You move into legal risk when you feed production logs (with names, emails, IDs, or chat histories) directly into training or fine-tuning pipelines without a clear legal basis or proper notices; use large web-scraped datasets whose original collection or reuse you never validated; or allow employees to paste sensitive data into public AI tools whose retention and reuse policies you don’t fully understand.


In short: if you wouldn’t handle the raw data that way under privacy law, you shouldn’t handle the AI training pipeline that way either.



2. Intellectual Property Infringement: When “Training Data” Becomes Evidence


Generative AI that creates text, code, images, music, or video can accidentally—or systematically—reproduce or closely mimic copyrighted works. That’s increasingly a live legal issue, not a hypothetical one.


The U.S. Copyright Office has reiterated that copyright law still requires human authorship and has issued guidance on how works containing AI-generated material are treated for registration (U.S. Copyright Office, 2023). Purely AI-generated outputs generally are not protected, while works with significant human creativity may be. At the same time, regulators and competition authorities are examining how copyrighted training data is used in building generative models (Federal Trade Commission, 2023).


You increase your risk of IP infringement when your training corpus includes copyrighted material scraped from the internet without licenses or a solid legal theory (such as fair use) that would stand up in court; your model outputs are “substantially similar” to existing works — logos, artwork, source code, or brand assets; or generative tools are used internally to “recreate” competitors’ documents, product designs, or patented methods.


If your AI stack casually ingests and reproduces protected works, the argument that “the model did it” is unlikely to impress a judge.



3. Discrimination & Bias: Algorithmic Decisions, Human Consequences


When AI touches hiring, promotions, lending, insurance, tenant screening, healthcare, or policing, you’re standing on the most sensitive legal ground. Anti-discrimination and civil rights laws apply whether the decision-maker is a human or an algorithm.


U.S. regulators — including the FTC, DOJ, CFPB, and EEOC — have jointly warned that automated systems can still violate existing anti-discrimination and consumer protection laws, and that enforcement will apply to both developers and deployers of AI (Chopra, Clarke, Burrows, & Khan, 2023; Jillson, 2021).


Typical failure modes include training on historical data that already reflects discriminatory patterns (for example, past hiring or lending decisions); using proxy features such as ZIP code, school, or device type that correlate with protected characteristics; and deploying opaque “black box” models and being unable to explain why certain groups consistently receive worse outcomes.


From a legal perspective, “the model is sophisticated” is irrelevant if the outcomes are systematically discriminatory. The burden is on you to show that your AI is designed, tested, and monitored to avoid unlawful bias.



4. Defamation & False Content: When Your Model Makes Stuff Up


Generative AI systems are famous for hallucinations: they confidently produce statements that sound factual but are completely wrong. That becomes a legal problem when those statements are about real people or organizations.


Imagine a customer-facing chatbot falsely claiming a competitor is “under investigation,” or an internal assistant fabricating negative performance histories about employees. Deepfake audio, images, and video raise similar risks when they damage reputations or mislead the public. The emerging regulatory trend in frameworks like the EU Artificial Intelligence Act is to treat certain AI uses — including deceptive or manipulative content and some biometric and deepfake applications — as high-risk or even prohibited (European Parliament & Council of the European Union, 2024).


Defamation law doesn’t care that it was “just an AI hallucination.” If your system publishes harmful false statements, the company that built or deployed it is usually the one on the hook.



5. Regulatory Non-Compliance: AI in Highly Regulated Environments


When AI is used in finance, healthcare, transportation, energy, or critical infrastructure, you’re operating inside tightly regulated ecosystems. Sector-specific laws and supervisory expectations don’t disappear just because decisions are now AI-assisted.


The EU AI Act, for example, adopts a risk-based approach that places strict obligations on “high-risk” AI systems, including requirements for risk management, documentation, transparency, and human oversight (European Parliament & Council of the European Union, 2024). Regulators in other jurisdictions are moving in a similar direction, emphasizing explainability, auditability, and clear accountability when AI affects people’s rights, safety, or financial interests.


You create compliance headaches when you change how you make credit, medical, or safety decisions using AI but fail to update documented controls, policies, and approvals; lack audit trails or cannot explain how a model reached a particular high-impact decision; or rely on third-party AI vendors without understanding their training data, controls, or legal obligations — or without contractually allocating responsibility and liability.

In these environments, AI is expected to be more controlled and documented than traditional systems, not less.



So What Should Leaders Do?


AI doesn’t have to be a legal minefield — but you must treat it as a regulated capability, not as a toy. Practical moves include mapping where AI is used across your organization and what data, decisions, and obligations it touches; involving legal, compliance, privacy, and security teams at the design stage, not after launch; defining clear policies for what data may (and may not) be used with AI tools, especially external services; building explainability, logging, and human review into AI workflows that affect rights, money, health, or reputation; and training teams so they understand AI risk, not just AI features.


The bottom line: AI will change your organization — the only question is whether it will also change your legal exposure. Governance isn’t a blocker; it’s your seatbelt.



References

1.       Chopra, R., Clarke, K., Burrows, C. A., & Khan, L. M. (2023, April 25). Joint statement on enforcement efforts against discrimination and bias in automated systems. Federal Trade Commission.

2.       European Data Protection Board. (2024, December 17). Opinion 28/2024 on certain data protection aspects related to the processing of personal data in the context of AI models.

3.       European Parliament, & Council of the European Union. (2024). Regulation (EU) 2024/1689 laying down harmonised rules on artificial intelligence (Artificial Intelligence Act). Official Journal of the European Union.

4.       Federal Trade Commission. (2023, October 30). Comment of the Federal Trade Commission before the U.S. Copyright Office on artificial intelligence and copyright.

5.       Jillson, E. (2021, April 19). Aiming for truth, fairness, and equity in your company’s use of AI. Federal Trade Commission.

6.       U.S. Copyright Office. (2023, March 16). Works containing material generated by artificial intelligence (Policy statement).

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