TLDRs:
- OpenAI acquires Sky, a Mac automation app, integrating natural language control into ChatGPT.
- Sky reads windows across macOS apps, enabling AI-driven on-screen actions.
- IT oversight and security measures will be crucial as agentic AI reaches desktops.
- Sky launch expected this summer with a waitlist; pricing details remain undisclosed.
OpenAI has taken a significant step toward enhancing its AI ecosystem by acquiring Software Applications Incorporated, the creators of Sky, a natural language interface for Mac computers.
The acquisition was confirmed in a Thursday blog post by OpenAI, which revealed that the Sky development team will now join the AI powerhouse. This move is expected to integrate Sky’s Mac automation capabilities directly into ChatGPT, allowing users to control their Macs through natural language commands.
Sky has already garnered attention for its ability to read and interact with open windows on macOS.
By leveraging Apple’s AppKit, SwiftUI, and Electron frameworks, Sky goes beyond simple screenshots, understanding the actual content of applications. Users can run commands referencing what is on-screen, streamlining workflows and offering a more intuitive interface for desktop automation.
How Sky Reads Your Mac
The technology behind Sky is particularly notable. It captures a combination of screenshots and textual representations of windows, enabling AI to comprehend and manipulate the user interface.
Actions within system apps require explicit permissions, and multi-step commands prompt manual confirmation to ensure users maintain full control over automation.
This level of interaction is expected to be extended to ChatGPT, allowing the AI to operate with context from users’ desktops. OpenAI’s acquisition highlights a growing trend toward agentic AI, where systems can act autonomously on behalf of users while maintaining transparency and oversight.
Implications for Enterprise IT
The introduction of agentic AI on company-managed Macs carries significant implications for enterprise IT departments. OpenAI’s plans suggest that ChatGPT, enhanced with Sky, could perform actions directly on employee desktops, accessing data and interfacing with applications.
This capability will necessitate robust oversight, including audit trails documenting which AI actions were taken and what data was accessed. Companies will likely require integration with security platforms to enforce policies that prevent unauthorized AI interactions with sensitive systems, such as financial apps or customer databases.
Providers of integration platforms and security solutions now face an opportunity to develop controls for agentic AI, ensuring organizations can leverage AI productivity gains while maintaining regulatory and data security compliance.
Launch Plans and Accessibility
Sky is scheduled to launch this summer, with a waitlist already open for early adopters. While pricing details have not yet been disclosed, OpenAI has indicated that a free component will likely be available.
The Sky acquisition is part of OpenAI’s broader strategy to embed AI more deeply into everyday software, giving users smarter tools to interact with technology seamlessly.
An interesting side note: an investment fund linked to OpenAI CEO Sam Altman previously held a passive stake in Software Applications Incorporated. The acquisition underwent approval from OpenAI’s independent transaction and audit committees, highlighting careful governance and transparency in the deal.

