OpenAI has acquired the team behind Sky, a Mac app designed to understand and act on what’s happening on your screen, marking its latest move to build AI that genuinely helps people get work done. The deal, announced on October 23, 2025, brings Sky’s entire team—led by co-founder and CEO Ari Weinstein—into OpenAI. The technology will be folded into ChatGPT, combining Sky’s deep macOS integration with OpenAI’s conversational intelligence.
What Sky Brings to ChatGPT
Sky is a lightweight AI layer for macOS that “floats” above the desktop, working seamlessly within users’ existing apps. It can interpret on-screen content and perform tasks like writing, planning, or coding, all without forcing users to switch contexts. Rather than behaving like a separate chatbot, Sky integrates directly with the operating system, responding to natural language commands in real time.
OpenAI Vice President Nick Turley said the acquisition accelerates ChatGPT’s transformation from a passive responder into an active digital assistant. He credited Sky’s tight Mac integration with advancing OpenAI’s goal of embedding AI into everyday workflows.
Weinstein—who previously co-founded Workflow, later acquired by Apple in 2017—said Sky was built to make computers more intuitive and personal. “OpenAI is the ideal partner to bring that vision to millions more people,” he added.
How Sky Works
Sky runs as a desktop overlay using macOS accessibility APIs to recognize on-screen elements. It can summarize content, automate actions, and control apps through natural language. Early testers have described it as a hybrid between Apple’s Shortcuts app and ChatGPT’s reasoning power.
For instance, instead of asking ChatGPT to write an email, a user could tell Sky to send an email directly through Apple Mail or Gmail—without leaving the current app. Its ability to detect windows, menus, and app states could finally give ChatGPT genuine desktop awareness, something OpenAI’s plug-ins and custom GPTs have only achieved partially.
OpenAI hasn’t announced when Sky’s features will appear in ChatGPT, though the company typically releases new functionality to its Plus and Team subscribers before expanding to the general user base.
Why the Acquisition Matters
The move underscores OpenAI’s growing emphasis on user-facing products. ChatGPT already runs on the web and mobile, but it still feels separate from the operating systems people use daily. By infusing Sky’s contextual awareness, OpenAI aims to make ChatGPT function as a true built-in assistant—seeing what users are doing and offering help directly within their workflow.
That effort mirrors Apple’s own ambitions with Apple Intelligence, rolling out in macOS Tahoe and iOS 26. Apple’s forthcoming system will enable Siri to understand on-screen content and handle contextual tasks such as responding to messages or editing photos.
The Bigger Picture
For Mac users, ChatGPT may soon evolve from a standalone app into a quiet on-screen companion—one that reacts intelligently to what’s happening on the desktop. Power users could benefit from a more frictionless experience, while Apple might see this as a challenge to Siri’s expanding role within the Apple ecosystem.
OpenAI has not disclosed financial details of the deal but confirmed that integration work is already underway. If Sky’s context engine performs as promised, ChatGPT could take a major step toward becoming the always-present AI assistant users have long imagined.