I Asked ChatGPT 500 Questions. Here Are the Ads I Saw Most Often | WIREDSkip to main contentMenuSECURITYPOLITICSTHE BIG STORYBUSINESSSCIENCECULTUREREVIEWSMenuAccountAccountNewslettersBest LaptopsBest Premium SoundbarsApple MacBook NeoDigital Wall CalendarsHome Security CamerasDeals DeliveredSecurityPoliticsThe Big StoryBusinessScienceCultureReviewsChevronMoreExpandThe Big InterviewMagazineEventsWIRED InsiderWIRED ConsultingNewslettersPodcastsVideoLivestreamsMerchSearchSearchReece RogersGearMar 27, 2026 6:30 AMI Asked ChatGPT 500 Questions. Here Are the Ads I Saw Most OftenAds are rolling out across the US on ChatGPT’s free tier. I asked OpenAI's bot 500 questions to see what these ads were like and how they related to my prompts.Photograph: JOEL SAGET/Getty ImagesCommentLoaderSave StorySave this storyCommentLoaderSave StorySave this storyOpenAI is starting to stuff the free version of ChatGPT with ads. So, I spent this week asking ChatGPT 500 questions on the mobile app to get a sense of how these new ads look as they roll out to more users in the US. My questions were loosely based on how OpenAI says people use its generative AI tool, like for seeking information or requesting practical guidance.In my rough tests, the ChatGPT ads felt quite frequent. About one out of every five questions in a new conversation thread triggered an ad at the bottom of the chatbot’s output. These ads always included a website link as a button and were tailored to the general topic of my question. As OpenAI continues to experiment with ads in ChatGPT, the formatting and the frequency of these ads may change.“Because ChatGPT is a trusted and personal environment for many people, we’re intentionally rolling ads out slowly,” an OpenAI spokesperson tells WIRED. “Starting with a limited number of advertisers and formats while we iterate based on what we learn.” OpenAI claims the decision to roll out ads now is not tied to any rumored IPO later this year, but rather part of a long-term strategy to keep ChatGPT broadly accessible.The ChatGPT ads felt recurrent in my early experiences, but the range of topics covered was extensive and always tailored to my most recent prompt. I saw an ad for Uber that read “Your Schedule, Your Earnings” when I asked about the gig economy. OpenAI gave me an ad for Page Six’s Hollywood newsletter below the answer when I asked about the worst TV show ever. (The bot floated The Jerry Springer Show and Cop Rock as two possibilities.) My question about Harvard versus Stanford triggered an ad for the University of Minnesota’s part-time MBA program.Overall, I saw ads for dog food, printers, hotel reservations, productivity software, movie tickets, food delivery apps, fashionable ties, streaming services, corporate credit cards, apartment furniture, cruise vacations, AI coding tools, freelance editors, skin-care articles, business internet plans, handmade gifts, grocery stores, and basketball tickets, among others.Photograph: Reece RogersQuestions related to travel currently seem to trigger ads the most often. When I asked for help planning a trip to Palm Springs, the ad attached to the bottom of the answer was for Booking.com. When I clicked on the link, it automatically searched for hotel deals in Palm Springs.Before this year’s embrace of ads for free users, OpenAI CEO Sam Altman had expressed his distaste for chatbots with ads. “I hate ads,” Altman said during an onstage discussion at Harvard Business School in 2024. He said the mixture of “ads plus AI is sort of uniquely unsettling,” and it raised questions about who may be influencing a chatbot’s answers.“I kind of think of ads as like a last resort for us for a business model,” he said. “I would do it if it meant that was the only way to get everybody in the world access to great services. But, if we can find something that doesn't do that, I'd prefer that.” I guess 2026 is the year for some last-resort moves. OpenAI recently discontinued Sora, its social media app for AI videos, and scrapped plans for an erotic version of ChatGPT. Leaders at the company are attempting to streamline operations and stave off the competition by increasingly focusing on core products.OpenAI started testing ads in ChatGPT in February in the US. I first started noticing them in my tester account in early March. The company claims that ads do not impact the content of ChatGPT answers and that your full conversation is not shared with companies paying for ad placements. The ads that are served to users are influenced by the topic of your question as well as your past chats and whatever ChatGPT stores in its memory about you.Photograph: Reece RogersOpenAI has a chance to better monetize its user base as online search habits shift and more money is poured into generative AI-focused advertising. “The billions of dollars that are currently spent on search ads are going to be channeled to this new form of ad, so it's a huge multibillion-dollar market that is emerging,” says Olivier Toubia, a marketing professor at Columbia Business School who focuses on AI.Free users are costly for OpenAI. One of its biggest challenges throughout this change will be introducing ads at scale, without deteriorating trust or pushing users to competing chatbots, like Google’s Gemini or Anthropic’s Claude.“It's not going to be easy for ChatGPT to, let's say, erode the quality of the experience without losing a lot of users,” says Stefano Puntoni, a marketing professor at Wharton who researches generative AI. Neither of OpenAI’s main competitors features sponsored ad buttons in the outputs, though Google recently said it’s not ruling it out.Sometimes, when I asked a question with a name brand in the prompt, like DoorDash or Netflix, the ad below the answer was for one of the company’s direct competitors. Toubia describes this as “poaching” and says this technique is a longtime staple of digital advertising in search engines. “That definitely has been a key engine behind the growth of online advertising,” he says. “It seems like it's going to be the case also with [large language model] advertising.”Right now, OpenAI is hiring for multiple positions, from software engineers to marketing leaders, to work on this core integration of ads. One of the open positions on OpenAI’s site is for a “product marketing lead, advertising,” and part of the role's responsibilities is to “identify product risk areas (e.g., performance, safety, policy, trust) and drive cross-functional plans to mitigate them.” Ads come with risks, and how they’re executed will shape the future of the company.If I exclusively used the free tier of ChatGPT, the introduction of these ads would have me considering other AI tools. Even with OpenAI’s explicit ad policies, there’s an aura of surveillance these ads introduce to the user experience, which is more personal with a chatbot compared to the traditional Google Search experience. While I know advertisers can’t currently influence ChatGPT’s outputs or see my chats, the incessant ads below answers made the conversations seem less private, and I felt hyperaware of the personal data I was sharing with this bot.After this limited rollout in the US, OpenAI will move to the next phase. “We’re seeing no impact on consumer trust metrics, low dismissal rates of ads, and ongoing improvements in the relevance of ads as we learn from feedback. These positive signals support moving into the next phase of our pilot,” reads an update on OpenAI’s website dated March 26. The company is expected to expand this ad push to Canada, Australia, and New Zealand.Everything is on the line for OpenAI as this ad rollout spreads to more ChatGPT users.“The worst thing the company could do is to go in very aggressively, to do it in a way that's basically maximizing conversions and referrals but at the same time undermining people's confidence and trust in those recommendations,” Puntoni says. “Then, that will basically be the end of it, because there's no point using a chatbot you don't trust.”CommentsBack to topTriangleYou Might Also LikeIn your inbox: Upgrade your life with WIRED-tested gearNvidia plans to launch an open-source AI agent platformBig Story: He built the Epstein database—it consumed his lifeShould you leave your phone charging overnight?Watch: How right wing influencers infiltrated the governmentReece Rogers is WIRED's service writer, focused on explaining crucial topics and helping readers get the most out of their technology. 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I asked OpenAI's bot 500 questions to see what these ads were like and how they related to my prompts.Reece RogersWired CouponsT-Mobile Promo CodeSamsung GS25+ Free With T-Mobile for Business SuperMobileSquarespace Promo CodeSquarespace Promo Code: 20% Off Annual Acuity SubscriptionsLG Promo CodeLG Discount Code: 10% Off Any PurchaseDell Coupon Code10% Off Dell Coupon Code for New CustomersSamsung Promo Code30% Samsung Coupon - Offer Program 2026Canon Promo Code10% Off Canon Promo Code + Up to 30% OffWIRED is obsessed with what comes next. Through rigorous investigations and game-changing reporting, we tell stories that don’t just reflect the moment—they help create it. When you look back in 10, 20, even 50 years, WIRED will be the publication that led the story of the present, mapped the people, products, and ideas defining it, and explained how those forces forged the future. 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OpenAI’s rollout of advertisements within its free tier of ChatGPT presents a significant shift in the platform’s monetization strategy, initiated by Reece Rogers. The core of Rogers’ experiment involved posing 500 distinct questions to ChatGPT’s mobile application to assess the frequency and nature of these emerging advertisements. The findings revealed a notable prevalence of ads, appearing roughly one in five times during new conversation threads. These advertisements, consistently presented as website links, were dynamically tailored to the user’s immediate query, demonstrating a level of contextual relevance.

The advertising landscape observed was diverse, encompassing brands such as Uber, Page Six, the University of Minnesota, dog food companies, printer manufacturers, hotel reservation services, productivity software vendors, and even cruise vacation providers. Notably, Rogers observed a tactic employed by advertisers – “poaching,” wherein ads for competing products appeared when the user referenced a specific brand, leveraging strategies common in the broader digital advertising ecosystem. This behavior mirrors established practices in online search advertising.

OpenAI CEO Sam Altman has voiced prior reservations against incorporating advertisements into chatbot experiences, expressing concerns about the potential for disruptive and unsettling user interactions. Altman’s perspective highlights the delicate balance OpenAI is attempting to achieve: ensuring accessibility while exploring new revenue streams. The company’s decision to introduce ads now stems from a long-term strategy to sustain broad access to ChatGPT, rather than being driven by anticipated initial public offerings.

The ads themselves are governed by a policy designed to avoid influencing ChatGPT's responses or sharing complete conversation histories with advertisers. However, Rogers noted a heightened sense of surveillance and personal data awareness stemming from these persistent ads, a distinction from the more detached experience offered by traditional Google Search. OpenAI aims to capitalize on the evolving landscape of digital advertising, recognizing the trend of shifting ad spending from search to generative AI platforms. Olivier Toubia, a marketing professor at Columbia Business School, estimates this transition represents a multi-billion dollar market opportunity.

Despite the potential benefits, OpenAI faces considerable challenges. Maintaining user trust is paramount, and overly aggressive advertising could erode that trust. Stefano Puntoni, a Wharton marketing professor researching generative AI, stresses the difficulty in introducing advertising at scale without jeopardizing the overall user experience. This is particularly crucial given that free users represent a significant portion of ChatGPT’s audience, and OpenAI is competing with established players like Google’s Gemini and Anthropic’s Claude, both of which do not currently feature sponsored advertisements. OpenAI is currently hiring for roles including a “product marketing lead, advertising”, emphasizing the strategic importance of navigating this transition.

The company’s experiments with the social media app, Sora, and the aborted erotic ChatGPT project demonstrate a focus on streamlining operations and prioritizing core products. As OpenAI navigates this new phase, focusing on effective ad execution is crucial; anything too aggressive risks alienating its user base.