Google’s ad network has begun showing advertising within the flow of conversations with chatbots — part of Alphabet Inc.’s efforts to keep its edge in digital advertising as generative artificial intelligence takes off. Earlier this year, Google’s AdSense for Search network, which traditionally shows ads within the search results of other websites, expanded to include conversations with chatbots operated by AI startups. Google made the move after conducting tests last year and earlier this year with a handful of startups, including AI search apps iAsk and Liner, according to people familiar with the matter who asked not to be identified discussing private information. Showing ads alongside its own search results is the heart of Google’s business, bolstered by a business that serves up advertising across much of the web. That empire has come under threat as new entrants like OpenAI and Perplexity AI seek to siphon off the search giant’s audience with products aiming to help users find what they are looking for more quickly. Running experiments with AI startups will allow the company to test the waters for advertising in the relatively new world of AI chats. Generative AI startups are increasingly exploring advertising-based business models to offset the high costs of answering users’ questions with artificial intelligence. For example, before inviting users to ask follow-up questions, iAsk shows ads below its AI-generated responses. In addition to Google, startups such as Koah Labs have begun allowing brands to serve ads to the chatbot audience. AI search startup Perplexity, one of the most prominent players using AI to reshape internet services, establishes relationships directly with brands that want to buy ads on the site, according to a person familiar with the matter. Perplexity allows brands to sponsor follow-up questions to users’ queries.