OpenAI has acquired Software Applications Incorporated, the company behind the unreleased AI app Sky, in a move that signals deeper integration between ChatGPT and Apple’s macOS ecosystem. The deal brings on board several former Apple engineers known for creating Workflow—the automation app that evolved into Apple’s Shortcuts feature—along with founders Ari Weinstein and Conrad Kramer.
Weinstein and Kramer’s history with automation tools runs deep. Their earlier app, Workflow, gained widespread popularity for letting users link and automate tasks across iOS apps before Apple purchased it in 2017. Following the acquisition, Workflow became the foundation of Apple’s Shortcuts, now a central feature across iPhone, iPad, and Mac devices. Kramer left Apple in 2019, while Weinstein departed in 2023, leading the pair to launch Software Applications Incorporated and begin development on Sky.
Although Sky never reached public release, the project focused on a Mac-native AI assistant capable of understanding natural language and executing commands within any active macOS window. It effectively blended the flexibility of a desktop assistant with contextual awareness—something that traditional macOS automation tools lack.
By acquiring the company, OpenAI gains both the Sky technology and its experienced engineering team. Weinstein, Kramer, and their colleagues will join OpenAI to expand ChatGPT’s functionality on macOS. The company says it plans to integrate Sky’s deep system-level features into ChatGPT, allowing the AI to interact more seamlessly with desktop applications and workflows.
In a statement, Weinstein described the acquisition as the realization of a long-held goal to make computers “more empowering, customizable, and intuitive.” He added that large language models now make it possible to combine automation and natural language in a way that’s both accessible and powerful.
The acquisition comes just one day after OpenAI announced ChatGPT Atlas, its AI-powered browser built to perform real-time tasks online. Together, Atlas and Sky suggest a broader strategy: extending ChatGPT beyond the web and into native computing environments. If successful, the move could allow ChatGPT to serve as a unified interface—capable of performing actions, organizing workflows, and navigating both web and desktop experiences with conversational input.
For Apple users, the addition of Sky’s macOS integration could make ChatGPT a far more practical desktop assistant, potentially rivaling or complementing Apple’s own automation tools. While OpenAI hasn’t provided a timeline for rollout, this acquisition sets the stage for ChatGPT to become more than a chatbot—evolving instead into a true operating-layer AI companion.
