Chicago Tribune Escalates AI Copyright Disputes with Lawsuit Against Perplexity

Rising Legal Scrutiny on AI Content Retrieval Practices

The Chicago Tribune has initiated legal action against the AI-powered search engine Perplexity, accusing it of copyright infringement through unauthorized use of journalistic content. Filed on December 4, 2025, in a federal court in New York, the lawsuit highlights growing tensions between traditional media outlets and AI technologies that aggregate and summarize online information.

Allegations Center on Unauthorized Content Scraping and RAG Systems

The complaint details how the Tribune’s legal team approached Perplexity in mid-October 2025 to inquire about the use of its articles in AI operations. Perplexity responded that it did not incorporate Tribune material into its model training processes but acknowledged potential receipt of “non-verbatim factual summaries.” However, the Tribune contends that Perplexity’s outputs include verbatim reproductions of its content, violating copyright protections. A key focus of the suit is Perplexity’s use of retrieval augmented generation (RAG), a technique designed to enhance AI accuracy by pulling from verified data sources to minimize errors or “hallucinations.” The Tribune alleges that Perplexity scrapes its paywalled articles without permission to fuel these RAG systems. Additionally, the company’s Comet browser is accused of circumventing paywalls to generate and deliver detailed article summaries directly to users.

• Core Claims:
• Direct reproduction of Tribune articles in search results.
• Unauthorized scraping for RAG integration, potentially undermining content monetization models.
• Browser tools enabling paywall evasion, reducing traffic and revenue for publishers.

This case marks a shift in AI litigation, moving beyond model training disputes to scrutinize real-time content retrieval methods. While RAG aims to improve reliability—drawing only from accessible, relevant sources—its reliance on web-scraped data raises questions about consent and fair use in dynamic search environments.

Broader Implications for AI and Media Industries

The Tribune’s action fits into a pattern of escalating legal challenges against AI firms by news organizations. As part of Tribune Publishing and MediaNews Group, the outlet previously joined 17 other publications in an April 2025 lawsuit against OpenAI and Microsoft, targeting the use of copyrighted works in AI training datasets. That case remains unresolved, with an additional nine suits filed against the same defendants in November 2025. Perplexity faces parallel pressures from other entities:

• Reddit initiated a lawsuit in October 2025 over the scraping of user-generated posts.
• Dow Jones has also filed claims related to content misuse.
• Amazon issued a cease-and-desist letter last month, addressing AI-driven browsing that allegedly infringes on e-commerce protections, though no formal suit has followed.

These developments underscore a critical juncture for the AI sector, where rapid adoption of tools like RAG—projected to underpin 70% of enterprise AI applications by 2027, according to industry analyses—clashes with intellectual property frameworks established decades ago. Publishers argue that such technologies erode incentives for original reporting, potentially leading to reduced investment in journalism amid declining ad revenues (down 15% year-over-year for U.S. newspapers in 2025).

"Perplexity’s systems are not just summarizing; they are replicating our work verbatim, stripping away our ability to control distribution," the Tribune's legal filing states, emphasizing the direct economic harm.

The absence of an immediate response from Perplexity to the suit or related inquiries leaves uncertainties about its defense strategy, particularly regarding RAG’s legal boundaries. Courts have yet to establish clear precedents on whether real-time retrieval constitutes infringement akin to training data usage, which could influence future AI development standards. As AI search engines capture an increasing share of online queries—estimated at 25% of global searches by late 2025—media companies may push for regulatory reforms, such as mandatory licensing for content aggregation. This could reshape market dynamics, favoring AI providers that invest in ethical data partnerships while pressuring others to adapt. Would you integrate RAG tools into your content workflows while navigating these emerging legal risks?