OpenAI Acquires Sky AI App From Former Apple Shortcuts Creators

OpenAI has acquired Software Applications Incorporated and its Sky AI application. The deal was confirmed on October 23, 2025. The acquisition brings a team of ex-Apple employees to OpenAI.

This move signals a major push to integrate advanced AI directly into desktop operating systems. The Sky team is renowned for their work on automation.

From Workflow to Sky: A Legacy of Automation

Software Applications Incorporated was founded by Ari Weinstein and Conrad Kramer. They previously created the Workflow app for iOS. Apple acquired Workflow in 2017.

The app eventually became the foundation for Apple’s system-wide Shortcuts feature. This background gives the team unique expertise in user-focused automation. According to Reuters, such talent acquisitions are highly sought after in the AI sector.

Their new project, Sky, was a Mac-based AI assistant. It could understand natural language to perform tasks in any open application. This deep system integration is a key asset for OpenAI.

Deepening macOS Integration for ChatGPT

OpenAI plans to integrate Sky’s technology directly into ChatGPT. The goal is a more intuitive and powerful desktop AI experience. All members of the Sky team will join OpenAI to work on this vision.

The acquisition follows the recent announcement of the ChatGPT Atlas browser. This new browser already includes AI Operator features to perform tasks. Sky’s technology could significantly expand these capabilities.

This strategic move places OpenAI in direct competition with other tech giants. It aims to make AI a seamless part of the everyday computing environment. The focus is on creating tools that are both empowering and deeply integrated.

The OpenAI Sky acquisition represents a significant step towards a more intuitive computing future. It merges top-tier automation talent with leading artificial intelligence. This partnership could fundamentally change how we interact with our computers.

Thought you’d like to know

What is the Sky AI app?

Sky was an AI assistant designed for Mac. It used natural language to complete tasks within any open application window. The app had not officially launched to the public.

Who founded the company behind Sky?

The company was founded by Ari Weinstein and Conrad Kramer. They are the same creators behind the Workflow app, which Apple acquired. Both are former Apple employees.

How will Sky technology be used by OpenAI?

OpenAI plans to integrate Sky’s deep macOS features into ChatGPT. This will likely enhance how the AI interacts with the desktop environment. The goal is a more seamless and powerful user experience.

Why is this acquisition important?

It combines expertise in user automation with advanced AI language models. This could lead to computers that are more intuitive and helpful. It represents a major move in the competitive AI landscape.

What was the Workflow app?

Workflow was a popular iOS automation app purchased by Apple in 2017. It allowed users to chain actions together to create custom shortcuts. Its technology now powers the Shortcuts feature across Apple devices.

Trusted Sources

Reuters