OpenAI has officially acquired Software Applications, Inc., the company behind Sky, a natural language interface built for macOS.
Sky is an AI interface designed to assist users as they write, plan, and code on their Macs.
It works alongside applications, observing what’s on the screen and performing actions based on natural language commands.
In essence, Sky turns the Mac into a more intuitive, context-aware machine; one that can execute user requests seamlessly across apps.
For example, you could ask it to organize your calendar, summarize a document, or send an email without switching between windows.
According to Software Applications co-founder and CEO Ari Weinstein, the goal was always to make computers “more empowering, customizable, and intuitive.”
He noted that large language models finally make this vision possible. “We built Sky as an AI experience that floats above your desktop to help you think and create,” he said in a statement.
Sky Founders
The Sky team is no stranger to innovation. Weinstein and co-founder Conrad Kramer previously developed Workflow, a powerful automation app for iOS.
Apple acquired Workflow in 2017 and reintroduced it as Shortcuts, a core part of iOS today.
After their time at Apple, Weinstein and Kramer teamed up again in 2023 with Kim Beverett, a former senior product manager at Apple.
Beverett had spent nearly a decade developing core software such as Safari, FaceTime, Messages, and SharePlay.
Together, they launched Software Applications, Inc. and began developing Sky.
OpenAI’s Intention
OpenAI’s acquisition of Sky aligns with its goal of embedding AI into everyday workflows.
Until now, the company’s tools, like ChatGPT, have existed mostly in browsers or standalone apps.
But Sky makes OpenAI gain the foundation to operate directly within the macOS environment.
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Agentic Computing
This acquisition aligns with OpenAI’s focus on “agentic” AI, systems that can understand context and act on a user’s behalf.
Sky is built to do exactly that. It reads on-screen content, interprets user intent, and executes commands automatically.
Capabilities like that push AI beyond text generation. They introduce an assistant that doesn’t just answer questions but performs actions in real time.
For instance, users might soon be able to say, “Draft a response to this email” or “Find my latest report and convert it into slides.”
It’s a hands-free functionality that reflects OpenAI’s long-term vision.
Apple’s AI
Apple is also ramping up its own AI efforts. The company plans to release an upgraded version of Siri with new AI features next year.
It has already introduced “Apple Intelligence,” a suite of AI tools for writing, translation, and image creation across devices.
Apple also offers a “Foundation Models” framework, enabling developers to integrate AI models locally into their apps.
However, Apple continues to emphasize user privacy. This focus could make the concept of a screen-reading, action-performing AI, like Sky, a more sensitive topic within Apple’s ecosystem.
The Deal
The financial terms of OpenAI’s acquisition have not been disclosed. However, PitchBook data shows that Software Applications, Inc. raised approximately $6.5 million from investors.
This includes OpenAI CEO Sam Altman, Figma CEO Dylan Field, and Stellation Capital.
OpenAI clarified that Altman’s investment was passive and made through an external fund.
The deal was led by Nick Turley, Head of ChatGPT, and Fidji Simo, OpenAI’s CEO of Applications. Both oversaw the integration and approval process under the company’s board.
Privacy and Security
Although Sky introduces exciting new possibilities, it also raises privacy concerns.
Because it can view a user’s screen and perform actions, some users may worry about data exposure or unauthorized access.
Agentic AI is still in early development. Security experts note that such systems require strict guardrails to prevent misuse or data leaks.
OpenAI will likely need to balance innovation with transparency to maintain user trust. For instance, users should be able to control when and how the assistant views content.
OpenAI may also need to establish strong local data processing policies to align with Apple’s privacy standards.
Expectations
OpenAI has not announced when Sky or its features will become publicly available.
Since the product had not yet been launched before the acquisition, development will likely continue under OpenAI’s internal roadmap.
In time, users may see Sky’s capabilities integrated into ChatGPT or future Mac-native products. Features could include:
- A floating assistant window that provides real-time help.
- Smart automation across apps like Mail, Calendar, and Notes.
- Context-aware task execution based on what’s visible on-screen.
- Personalized recommendations and adaptive workflows.
