OpenAI buys Sky, an AI interface for Mac (techcrunch.com)

OpenAI has acquired Software Applications, Inc., the startup behind Sky — an unreleased AI-powered natural-language interface for macOS that “floats” over the desktop, can read what’s on your screen, and take actions inside apps (writing, planning, coding, etc.). The small team includes Workflow/Shortcuts alumni Ari Weinstein and Conrad Kramer plus ex-Apple product manager Kim Beverett; the startup had raised $6.5M from investors including an investment vehicle tied to Sam Altman, Figma’s Dylan Field and others. The deal was led internally by Head of ChatGPT Nick Turley and Applications CEO Fidji Simo; financial terms were not disclosed. Technically and strategically, the acquisition accelerates OpenAI’s push to embed agentic assistants directly into everyday Mac workflows — bringing screen-reading, cross-app automation and real-time assistance to desktop users. That capability could make OpenAI a major player in consumer and enterprise Mac software, but it also raises privacy and safety questions: agentic systems that view and manipulate user interfaces introduce new attack surfaces and data-handling concerns, and early reviews of AI browsers highlight safety risks. The move also sets up a closer interplay with Apple’s AI efforts (Apple Intelligence, local Foundation Models, and Siri fallbacks to ChatGPT) and may pressure Apple to evolve its privacy-centric approach to comparable agentic features.