TechCrunch’s running list of failed AI bets covers a wide range of casualties: startups that shut down, products that were folded into larger platforms, and high-profile launches that missed expectations. Relay, an AI-powered workflow automation tool positioned as an alternative to Zapier, shut down entirely in August. It let users automate email and task workflows with AI agents, but as OpenAI, Google, and other large platforms built similar automation directly into their own tools, the five-year-old company could no longer justify existing as a standalone product. More recently, chatbot platform Character.ai filed for bankruptcy five years after launching. The article cites S&P Global Market Intelligence data showing that about 42% of AI initiatives are ultimately abandoned by their corporate parents, with reasons ranging from insufficient funding and technical challenges to competition, difficulty scaling, and weak user demand.

Even the biggest players are not immune. OpenAI, one of the most valuable private companies in the world, has had several casualties and missteps. On July 9, OpenAI redesigned ChatGPT to combine separate Chat, Codex, and Work modes, renaming the familiar version as ChatGPT Classic. The move drew widespread criticism for being confusing and cluttered, and OpenAI rolled back the change soon after. The company has also folded several standalone apps into ChatGPT, including ChatGPT Atlas, an AI-powered web browser discontinued on August 9 after less than a year, and Operator, an AI agent that browsed the web and completed tasks on users’ behalf. Image generation has increasingly been built directly into ChatGPT, shrinking the role of DALL-E as a separate destination. OpenAI‘s video-sharing platform Sora struggled with high operating costs and user-retention challenges and shut down in March 2026.

Apple’s promised AI-powered Siri, highlighted when Apple Intelligence was unveiled in 2024, faced repeated delays attributed to engineering issues and bugs. The delays contributed to a $250 million settlement over claims about how Apple marketed the iPhone 16’s AI capabilities. Siri AI finally appeared in the iOS 27 beta this past July, with the new English-language version rolling out this month and other languages expected to follow. Microsoft’s Recall, announced at Build 2024 as an AI-powered photographic memory for Windows PCs, triggered immediate privacy and security backlash over the risk of creating a searchable archive of passwords, private messages, and financial details. Microsoft delayed the feature for nearly a year to rethink protections, but controversy resurfaced when a cybersecurity researcher built a tool that could extract data Recall had captured.

Several other products illustrate the pattern. Notion Mail launched in April 2025 as an AI-focused email product, but the company found users were turning to separate AI agents to handle their inboxes; it is scheduled to shut down on September 22. Humane AI Pin, a wearable AI device, raised $230 million from investors but struggled with performance and issued a warning about a potential battery fire risk in its charging case. Humane shut down its AI Pin business in February 2025, with most assets acquired by HP for $116 million. Rabbit R1, unveiled at CES in January 2024, sold 100,000 units shortly after launch but was widely reviewed as unfinished with unreliable performance and few useful integrations. The company continues updating the R1 and has announced a new hardware project called Project Cyberdeck aimed at portable vibe-coding.

Other shutdowns include Huxe, an AI audio app built by former Google NotebookLM developers that turned written information into podcast-style audio; it shut down in May 2026 partly because larger platforms like Spotify began offering similar experiences to large existing audiences. Yupp, a free playground for comparing responses from hundreds of AI models with cryptocurrency rewards, peaked at more than 800 models from companies including OpenAI, Google, and Anthropic, but its founders said it never achieved strong enough product-market fit and shut down in March 2026. Figgs AI, which operated from 2023 to 2024, let users create and interact with customizable AI characters for role-play and storytelling; it drew over 1 million users but was shut down because keeping the service free became too expensive to sustain.