OpenAI Acquires Mac AI App Sky to Boost ChatGPT’s Desktop Capabilities

OpenAI’s Strategic Acquisition

OpenAI has acquired the team behind Sky, a Mac application that understands screen content and performs tasks through natural language, according to reports from AppleInsider. The deal, announced October 23, 2025, brings Sky’s entire team led by co-founder and CEO Ari Weinstein into OpenAI’s organization.

OpenAI’s Strategic Acquisition
How Sky’s Technology Works
Strategic Implications for AI Assistants
Competitive Landscape with Apple
Implementation Timeline and Availability

Sources indicate that Sky’s technology will be integrated into ChatGPT, providing the popular AI assistant with deeper macOS integration and user-focused design capabilities. This acquisition represents OpenAI’s continued expansion beyond web-based chatbots toward becoming integrated desktop assistants.

How Sky’s Technology Works

Sky functions as a lightweight AI layer that “floats” over the Mac desktop and operates within existing applications, the report states. Using macOS accessibility APIs, the technology can identify what appears on screen and perform actions such as writing, planning, or coding assistance without requiring users to switch between applications.

Early testers compared Sky’s functionality to Apple’s Shortcuts app combined with ChatGPT’s natural language understanding. Instead of merely asking ChatGPT to compose text, users could reportedly instruct it to send emails directly through Apple Mail or Gmail, demonstrating genuine desktop control capabilities.

Strategic Implications for AI Assistants

OpenAI Vice President Nick Turley stated that the acquisition moves ChatGPT toward becoming an active helper rather than a passive responder, according to the announcement. Analysts suggest that Sky’s deep Mac integration accelerates OpenAI’s goal of embedding AI directly into tools people use daily.

Weinstein, who previously co-founded Workflow and sold it to Apple in 2017, reportedly built Sky to make computers more intuitive and personal. He indicated that OpenAI represents the right partner to expand this vision to a broader audience., according to expert analysis

Competitive Landscape with Apple

The acquisition positions OpenAI in direct competition with Apple’s developing Apple Intelligence system, sources indicate. Apple’s approach, expected in future macOS Tahoe and iOS 26 updates, will enable Siri to understand on-screen content and perform contextual tasks.

For Mac users, this development could transform ChatGPT from a standalone application into a background assistant that understands and reacts to screen content. Power users might appreciate the deeper workflow integration, though Apple might view it as competition for Siri’s expanding role in Apple Intelligence.

Implementation Timeline and Availability

The company hasn’t announced specific dates for when Sky’s technology will appear in ChatGPT, according to reports. Based on OpenAI’s typical release patterns, new features usually debut in Plus and Team subscription plans before broader availability.

OpenAI mentioned that Sky’s integration is already in progress, suggesting users might see these capabilities in the relatively near future. If Sky’s context engine performs as promised, analysts suggest ChatGPT could evolve into a genuine desktop companion that understands and acts upon what users are doing.

References

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