Advertising Inside the Answer

Search engines have sold advertising beside results since the late 1990s, a history covered in Before AI Search.¹ When chatbots and AI summaries began to answer questions directly, the first question for their owners was where a sponsored message could sit without damaging the answer. Four companies tested four different arrangements between 2023 and 2026, and a fifth, Anthropic, declined to run ads at all. This chapter follows them in date order.

March 2023: Microsoft Explores Ads in Chat

On March 29, 2023, Microsoft told publishers that it was exploring placing ads in the chat experience of the new Bing and sharing the revenue with partners whose content contributed to the response.² The early Bing chat period is covered in The ChatGPT Shock.

May to October 2024: Google Puts Ads in AI Overviews

At Google Marketing Live in May 2024, Google demonstrated how Search and Shopping ads would appear directly within AI Overviews when relevant to both the query and the response. On October 3, 2024, it announced that ads in AI Overviews were live, starting with mobile users in the United States.³ Google's example was a person asking how to get a grass stain out of jeans, with Shopping ads for stain removers appearing inside the overview. Ads kept the "Sponsored" label.³

Google Announces Ads in AI Overviews

TechCrunch noted that one format, a carousel of sponsored product results, was embedded in AI summaries in a position that pushed nonsponsored content below the fold.¹⁰ The organic side of AI Overviews, which launched in May 2024, is covered in Google Answers Back.

November 2024: Perplexity Sells Sponsored Questions

On November 12, 2024, Perplexity said it would begin showing ads in the United States as "sponsored follow-up questions," placed to the side of answers and labeled as sponsored. Indeed, Whole Foods Market, Universal McCann, and PMG were among the first participants. Perplexity wrote that advertising was needed to fund its publisher revenue-sharing program, because subscriptions alone did not generate enough revenue, and that the answers to sponsored questions would still be generated by its AI and not written or edited by the brands.⁴

Digiday reported on November 18, 2024, that several marketers were not yet convinced. Three executives said they had seen CPMs from $30 to $60, and the ads were sold on a CPM basis, not on cost per click. One search specialist told Digiday that a CPM model suggested people would not click out of the experience, unlike traditional search.¹¹ The Perplexity Publishers' Program that the revenue was meant to support is covered in The Citation Economy.

March to June 2025: Microsoft Builds Ad Formats for Copilot

On March 5, 2025, Microsoft Advertising said ads in Copilot had ramped fully in all English, French, and German speaking markets, with Spanish and Japanese coming that month. By taking into account the signals of whole conversations, it reported, ad relevance metrics in Copilot were 25 percent better than in traditional search. The same post announced the first ad formats designed for Copilot: Showroom ads, an immersive, conversational product experience, and Dynamic filters, which narrow the products shown without the user typing another question.⁵

Microsoft Advertising Announces Copilot Ad Formats

On June 12, 2025, at Cannes Lions, Microsoft said it had started a Showroom ads pilot in the United States and was developing the format with Mercedes-Benz USA and other clients through the summer. It also introduced Brand agents, which are assistants trained on a brand's product catalog and guidelines, with Brava Fabrics as the first to go live.¹² Microsoft's documentation states that ads in Copilot are created automatically from a campaign's existing assets, that eligible campaigns are opted in, and that advertisers cannot opt out of serving in Copilot or count on a placement.¹³

May 2025: Google Brings Ads to AI Mode

On May 21, 2025, at Google Marketing Live, Google announced that it was expanding ads in AI Overviews to desktop and bringing ads to AI Mode.⁶ Google's help documentation states that existing Search, Shopping, and Performance Max campaigns are eligible automatically, without a separate budget, and that ads appear in sections labeled "Sponsored." Google matches ads either to the query directly or, for longer exploratory questions, to the query and the AI response together. Google also says paid advertising does not influence the organic responses generated by Google AI.¹⁴

On May 20, 2026, Google announced two Gemini-built formats for AI Mode. Conversational Discovery ads create ad copy tailored to a person's specific question, and Highlighted Answers make eligible ads appear in an AI Mode list of recommendations. Both carry an independent AI explainer written by Gemini, along with the "Sponsored" label, and Google said it was also launching AI-powered Shopping ads that write a product-match explainer.¹⁵ Google's help page says advertisers cannot write, edit, approve, or opt out of the explainers.¹⁴

October 2025 to February 2026: Perplexity Steps Back

On October 9, 2025, Adweek reported that Perplexity was no longer accepting new advertisers, with a Perplexity executive saying that ads were not on the roadmap for its Comet browser. The report noted the August departure of the head of ad sales.⁷ On February 18, 2026, The Verge reported that Perplexity had begun phasing out ads in late 2025 and was not pursuing new ad deals. An unnamed executive was quoted as saying that with ads "a user would just start doubting everything," while another did not rule out a return.¹⁶

The Verge Reports Perplexity Is Moving Away From Ads

January to October 2026: ChatGPT Ads

On January 16, 2026, OpenAI said it would test ads in ChatGPT for logged-in adults on the Free tier and a new Go tier priced at $8 per month, while Plus, Pro, Business, and Enterprise would stay ad-free. It listed five principles, including that ads would not influence answers, that conversations would not be shared with advertisers, and that users would have choice and control. Ads would appear at the bottom of answers, labeled, and would not be shown to people under 18 or near sensitive topics such as health, mental health, and politics.⁸

Anthropic published its own position on February 4, 2026: Claude would remain ad-free, with no sponsored links beside conversations and no advertiser-influenced responses. Anthropic wrote that ads in conversations with Claude would be incompatible with its goal for the assistant to be genuinely helpful.¹⁷ The Verge described the industry as dividing between companies that embraced ads and companies, including Perplexity and Anthropic, that did not.¹⁶

The ChatGPT test began in the United States on February 9, 2026.¹⁸ Adweek reported that OpenAI wanted advertisers to pay at least $200,000 for the early pilot, and that Omnicom Media said more than 30 of its clients had secured placements.¹⁹ Dentsu announced on the same day that it was an early test partner, with clients in consumer goods, grocery, hospitality, retail, software, and travel.²⁰ Updates to OpenAI's post on March 26 and May 7 listed the next markets, and an August 11 update said ads had launched in the United Kingdom, Mexico, Brazil, Japan, and South Korea.¹⁸

OpenAI Announces Its Approach to Advertising

On May 5, 2026, OpenAI opened a beta self-serve Ads Manager, added cost-per-click bidding to its cost-per-thousand-impressions pricing, and listed Dentsu, Omnicom, Publicis, and WPP as agency partners and Adobe, Criteo, Kargo, Pacvue, and StackAdapt as technology partners.²¹ OpenAI's help page says ads are ranked on relevance and advertiser bids, that the systems that choose ads are separate from the chat model, and that advertisers receive aggregated reporting.²²

On October 5, 2026, OpenAI began testing a visual ad format that appears during image generation and added measurement integrations, including attribution partners such as AppsFlyer, Triple Whale, and DV Rockerbox, and incrementality partners Haus, Measured, and WorkMagic. It published partner-reported results, among them a cost per acquisition for WeightWatchers that DV Rockerbox found was 15.3 percent below a paid search benchmark.²³ On October 21, 2026, OpenAI said that more than 100,000 advertisers had used ChatGPT Ads in the just over eight months since launch and that ads were expanding to 26 more countries, for a total of 89.⁹ TGA publishes a ranking of agencies by public evidence of ChatGPT ads work and a dated list of the integrations OpenAI has announced.^24,25

Anthropic Says Claude Will Remain Ad-Free

The Line Between Paid and Organic

Each company that sells placements inside answers has described the boundary between paid and organic content in similar terms. OpenAI said ads do not influence answers and are separate from the model.^8,22 Google says paid advertising does not influence the organic responses of its AI.¹⁴ Perplexity said sponsored answers would be generated by its AI and not edited by brands.⁴ Microsoft described Showroom ads as complementing Copilot's organic answers.¹² The practices that earn unpaid mentions in these answers are described in The Citation Economy.

Key Organizations