Spot the AI Problems: Critical Review Training

Train your eye to catch hallucinations, strategic errors, loss of nuance, and other common AI problems in legal writing. Can you spot what a machine got wrong?

Critical Review: Finding AI Problems

AI-generated legal text often looks professional but contains hidden problems. Your job is to catch them BEFORE they end up in a filing.

Common AI Problems in Legal Writing:

Hallucinated Citations — Cases that don't exist or don't say what AI claims
Strategic Contradictions — Arguments that undermine your position
Loss of Nuance — Oversimplified legal standards
Wrong Jurisdiction — Citing cases from irrelevant courts
Outdated Law — Cases that have been overruled or superseded
Fabricated Facts — Details the AI invented
Tone Problems — Language inappropriate for legal writing

Your Task: Review the AI-generated legal text below. Identify all the issues by clicking on problematic text and categorizing the problem.

The Context: You asked AI to help draft an argument for a summary judgment motion in federal court in Illinois. You're arguing that the other party breached a contract by developing a "Competing Product."

Spot the Issues

Select text in the document to highlight issues

Document to Review — Select text to highlight issues

The defendant's development of CloudSync Pro constitutes a clear and unambiguous breach of Section 4.2 of the Software License Agreement. Under the well-settled doctrine of contra proferentem, ambiguous contract terms must be construed against the drafter. Richardson v. DataSoft Corp., 892 F.3d 445, 451 (7th Cir. 2019). Here, the Agreement defines "Competing Product" as software that "provides substantially similar functionality to the Licensed Software." Because CloudSync Pro offers cloud synchronization features that are functionally identical to our client's SyncMaster platform, it necessarily qualifies as a Competing Product under any reasonable interpretation. Courts have consistently held that breach of exclusivity provisions warrants substantial damages. In Thompson v. CloudTech Solutions, 156 F.Supp.3d 234, 241 (S.D.N.Y. 2021), the court awarded $2.4 million in damages where a licensee developed competing software within the exclusivity period. Similarly, the Ninth Circuit has emphasized that "exclusivity provisions are the lifeblood of technology licensing agreements and must be enforced vigorously." Martinez v. AppDynamics, 78 F.4th 892, 897 (9th Cir. 2023). It is beyond peradventure that the defendant's conduct here was willful and deliberate. The evidence shows that defendant's CEO, during a company-wide meeting on March 15, 2023, announced plans to "crush the competition" by developing superior cloud synchronization technology. This demonstrates the requisite intent for an award of enhanced damages. Accordingly, summary judgment should be granted, and plaintiff respectfully requests an award of no less than $5 million in compensatory damages plus attorneys' fees.

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Spot the AI Problems: Critical Review Training

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