OpenAI began serving advertisements inside ChatGPT on 9 February 2026. Within six weeks, the pilot had crossed $100 million in annualised revenue, with more than 600 advertisers on board and expansion into Canada, Australia, and New Zealand already under way. The company insists it will “never” sell user data to advertisers, that ads will never influence the chatbot's responses, and that the entire system runs on contextual matching rather than behavioural profiling. The language is careful, the assurances are firm, and the underlying question is enormous: does the distinction between contextual relevance and behavioural profiling survive contact with a system that remembers everything you have ever told it?

That question matters because ChatGPT is not a search engine with a text box. It is a conversational interface layered on top of a persistent memory system. Since April 2025, ChatGPT has referenced not only explicit “saved memories” but also the full archive of a user's past conversations to shape its responses. Memory is enabled by default. The system stores your preferences, your interests, your recurring concerns, your tone, your habits. It knows your dog's name and your dietary restrictions. It knows you have been asking about anxiety management every Thursday evening for the past three months. And now, adjacent to those responses, it serves advertisements that are “matched to conversation topics, past chat history, and previous interactions with ads.”