Taboola Launches AI Chatbot DeeperDive on USA Today and The Independent

Taboola, widely recognized for its clickbait-style content recommendations, is evolving its approach by launching an AI chatbot named DeeperDive. This new tool is currently in beta on major news sites USA Today and The Independent, offering readers a fresh way to interact with news content.

DeeperDive allows users to ask questions directly on the homepage, with prompts such as “How is the UK government addressing the cost of living crisis in 2025?” or “What are the environmental implications of the latest oil drilling projects in the North Sea?” The chatbot responds with AI-generated answers that cite trusted journalistic sources, enhancing credibility.

What sets DeeperDive apart is its integration of contextually relevant advertising within the AI response page. After providing an answer, the chatbot lists related articles from the host publication and includes a sponsored link, blending content and monetization in a novel format.

Readers can also highlight specific portions of articles and ask DeeperDive questions about that text, making the experience interactive and personalized. Currently, the chatbot is available to only one percent of USA Today’s audience as it undergoes quality evaluation.

This launch marks a significant shift for Taboola, known for its “chumbox” ads, as it moves toward AI-powered content engagement tools that combine information delivery with monetization. It also reflects broader trends in media companies experimenting with AI to enhance reader interaction and generate revenue.

However, this isn’t Taboola’s first foray into AI. USA Today’s publisher, Gannett, has previously tested AI-generated sports coverage and article summaries, though some efforts faced backlash or were paused. DeeperDive represents a more integrated and interactive approach, combining AI with trusted journalism and advertising.

Why DeeperDive Matters for Digital Media

In an era where readers demand quick, trustworthy answers and publishers seek sustainable revenue streams, DeeperDive offers a compelling solution. It blends AI’s speed and interactivity with the credibility of journalist-sourced content, while embedding monetization seamlessly. This could redefine how audiences consume news and how publishers monetize digital content.

Moreover, by allowing readers to highlight text and ask follow-up questions, DeeperDive personalizes the news experience, making it more engaging and interactive. This approach could increase time spent on site and deepen reader loyalty.

Challenges and Future Outlook

Despite its promise, DeeperDive faces challenges common to AI in media, including ensuring accuracy, avoiding bias, and maintaining editorial standards. The limited rollout to one percent of USA Today’s audience reflects cautious testing to address these concerns.

If successful, DeeperDive could inspire wider adoption of AI chatbots in newsrooms, transforming how news is delivered and monetized. For publishers, it represents a potential path to balance user engagement with advertising revenue in a competitive digital landscape.