OpenAI Acquires Sky To Bring ChatGPT Closer to the macOS Ecosystem

OpenAI has announced the acquisition of Software Applications, Inc., the company behind Sky—a Mac-based AI interface built by former Apple engineers. The deal marks a major step in OpenAI’s efforts to integrate ChatGPT more deeply into desktop environments, particularly within the macOS ecosystem.

“With Sky, AI works alongside you, whether you’re writing, planning, coding, or managing your day. Sky understands what’s on your screen and can take action using your apps,” the company shared in a blog post announcing the acquisition.

The Apple Connection Behind Sky

Founded in 2023 by former Apple engineers Ari Weinstein, Conrad Kramer, and Kim Beverett, Software Applications drew on deep macOS and iOS design experience. Weinstein and Kramer were part of the team that built Workflow, later acquired by Apple and transformed into the Shortcuts app that powers automation across iPhones and Macs.

Their expertise in creating intuitive, system-level interfaces makes Sky a natural fit for OpenAI’s growing product vision. “We’ve always wanted computers to be more empowering, customizable, and intuitive. With LLMs, we can finally put the pieces together,” Weinstein said.

The acquisition reflects OpenAI’s goal to transform ChatGPT from a chatbot into an intelligent desktop companion—an “everything app” capable of operating across platforms.

Nick Turley, Head of ChatGPT at OpenAI, noted, “Sky’s deep integration with the Mac accelerates our vision of bringing AI directly into the tools people use every day.”

Sky’s system-level access allows users to prompt AI to manage files, generate code, or perform in-app actions—ushering in a new phase of context-aware computing where ChatGPT doesn’t just respond but acts.

OpenAI’s recent string of acquisitions—including partnerships with Jony Ive’s design firm—suggests that the company is building toward a physical AI interface. The goal: create a device or ecosystem where AI becomes seamlessly embedded in everyday computing.

Apple’s design-first ethos appears to influence OpenAI’s approach. While OpenAI’s Atlas browser brings AI into web workflows, Sky’s integration could extend that experience to native desktop environments—an essential step toward closing the gap between conversational AI and real-world productivity tools.

Balancing Privacy and Power

Despite the promise of seamless integration, the acquisition also raises important privacy questions. Apple’s strict privacy architecture could pose challenges for AI systems that monitor screens or access user data. For security-conscious users, this tension could determine how fast such integrations roll out.

OpenAI has not disclosed financial details of the acquisition, though it confirmed that Sky’s entire team will join OpenAI. The transaction was approved by OpenAI’s independent Transaction and Audit Committees, with oversight to ensure transparency.

Sky’s inclusion marks more than a product acquisition—it’s a signal that OpenAI envisions a world where AI assistants are embedded directly into operating systems. The future of ChatGPT may not lie in browsers or apps alone, but in how intuitively it interacts with our desktops, devices, and everyday workflows.

If OpenAI can merge ChatGPT’s intelligence with Sky’s design and macOS fluency, it could reshape how users experience computing—making the interface itself intelligent, adaptive, and human-like.