OpenAI Acquires Mac AI Interface Sky to Deepen Desktop Integration for ChatGPT

OpenAI announced on October 23, 2025, its acquisition of Software Applications Incorporated, the company behind Sky, a powerful natural language interface designed for Mac computers. This strategic move aims to integrate Sky's deep macOS capabilities directly into ChatGPT, transforming the AI from a conversational tool into a proactive desktop assistant. The entire Sky team, known for their expertise in system-level automation, will join OpenAI to facilitate this integration.

Sky, though not publicly launched, was developed to work alongside users, understanding on-screen context and taking action within applications for tasks such as writing, planning, coding, and day management. This functionality aligns with OpenAI's vision to move beyond text-based responses and enable ChatGPT to "help you get things done," as stated by Nick Turley, VP and Head of ChatGPT at OpenAI. The acquisition closely follows OpenAI's release of ChatGPT Atlas, an AI-powered browser for Mac, signaling a concerted effort to establish a dominant presence in the desktop computing interface.

The team behind Sky includes co-founders Ari Weinstein and Conrad Kramer, who previously created Workflow, an automation app acquired by Apple that became the foundation for Apple's Shortcuts feature. Their background provides OpenAI with significant experience in developing system-adjacent software and navigating the complexities of macOS integration. Ari Weinstein expressed excitement, stating, > "We’ve always wanted computers to be more empowering, customizable, and intuitive. With LLMs, we can finally put the pieces together. That’s why we built Sky, an AI experience that floats over your desktop to help you think and create. We’re thrilled to join OpenAI to bring that vision to hundreds of millions of people."

While specific financial terms of the acquisition were not disclosed, Software Applications Incorporated had previously raised $6.5 million from investors, including OpenAI CEO Sam Altman, who held a passive interest through an investment fund. The deal was led by Nick Turley and Fidji Simo, OpenAI's CEO of Applications, and approved by the company's board. This acquisition positions OpenAI to directly challenge Apple's own AI ambitions, particularly with the anticipated overhaul of Siri and the development of Apple Intelligence.