OpenAI Buys Shortcuts Creators: ChatGPT Breaks Out of Chat Window

OpenAI acquires Sky's automation team, turning ChatGPT into a proactive desktop agent and intensifying the AI race with Apple.

October 23, 2025

OpenAI Buys Shortcuts Creators: ChatGPT Breaks Out of Chat Window
In a strategic move that signals a significant push towards more integrated and proactive artificial intelligence, OpenAI has announced the acquisition of Software Applications Incorporated (SAI), the development team behind the innovative Mac automation application, Sky.[1][2][3] This acquisition will see the entire SAI team integrated into OpenAI, with the explicit goal of embedding Sky's deep macOS integration and user-centric design into ChatGPT.[4][5][3] The move is widely seen as a pivotal step in transforming ChatGPT from a conversational AI into a powerful, action-oriented assistant capable of operating directly within a user's digital environment.
The team at Software Applications Incorporated brings a formidable track record in the realm of user automation. They are the same minds that originally developed Workflow, an iOS automation tool that was acquired by Apple in 2017 and subsequently evolved into the widely used Shortcuts app.[2][4][6] This history lends significant weight to their expertise in creating intuitive and powerful automation tools. Their latest creation, Sky, has been described as a natural language interface for the Mac that functions as an AI assistant, capable of understanding on-screen context and executing tasks across various applications.[1][7] Essentially, Sky acts as an intelligent layer that "floats" over the desktop, allowing users to issue commands in plain language to perform multi-step actions, such as summarizing a webpage and sending the summary to a contact via a messaging app, all without manual intervention.[5][7]
OpenAI's acquisition of this specialized team and their technology is a clear indicator of the company's ambition to create more "agentic" AI systems—that is, AI that can take actions on a user's behalf.[2] In a statement, OpenAI's Vice President and Head of ChatGPT, Nick Turley, emphasized this vision, stating, "We're building a future where ChatGPT doesn't just respond to your prompts, it helps you get things done."[1][4][3] The integration of Sky's capabilities is expected to accelerate this vision by allowing ChatGPT to break out of the confines of a chat window and interact directly with the tools and applications people use daily.[1][4] This deeper integration into the operating system represents a fundamental shift in how users might interact with AI, moving from a question-and-answer paradigm to one of delegation and autonomous task completion.[5][8]
This acquisition does not occur in a vacuum and has significant implications for the broader AI industry, particularly in the escalating competition between major tech players. Apple, which previously acquired the SAI team's first creation, is reportedly working on its own advanced AI features for its operating systems, including an overhauled version of Siri with similar in-app action capabilities, though its release is not expected until 2026.[2][6] OpenAI's move to absorb a team with proven expertise in Apple's ecosystem can be seen as a direct competitive maneuver, aiming to establish a strong foothold in on-device, integrated AI assistance. The acquisition is part of a larger trend of OpenAI expanding its footprint, coming on the heels of the release of its own web browser, ChatGPT Atlas, and other strategic acquisitions aimed at building a comprehensive AI stack, from infrastructure to hardware.[2][9] This strategy suggests a long-term goal of positioning OpenAI not just as a provider of AI models, but as a central platform in the future of computing, potentially even evolving into a form of AI-driven operating system.[10][11]
In conclusion, OpenAI's acquisition of the team behind the Sky Mac automation app is a significant development that underscores the industry's shift towards more capable and integrated AI assistants. By bringing the creators of what became Apple's own Shortcuts into its fold, OpenAI is not only acquiring cutting-edge technology but also a wealth of experience in creating seamless user automation. The planned integration of Sky's features into ChatGPT promises to transform the popular AI into a more proactive and powerful tool, capable of bridging the gap between conversation and action. This move intensifies the competitive landscape, particularly with Apple, and signals a clear ambition for OpenAI to become a foundational element in the next generation of personal computing, where AI is not just an application, but a core component of the operating system itself.

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