OpenAI has acquired Software Applications Incorporated (SAI), the team behind Sky, an AI-powered natural language interface for Mac computers. The acquisition, announced on Thursday, marks a pivotal move in OpenAI’s strategy to deeply integrate ChatGPT into everyday workflows on Apple’s ecosystem. All 12 members of the SAI team will join OpenAI, with the company focusing on advancing Sky’s technology to enable seamless, context-aware AI assistance across Mac applications. Sky, still unreleased to the public, is designed to act as a persistent AI assistant that understands user context, monitors screen activity, and performs actions across apps—such as drafting emails, writing code, managing schedules, or organizing tasks—through natural language prompts. Unlike traditional chatbots, Sky operates directly on the desktop, interacting with the user’s environment in real time. OpenAI’s Nick Turley emphasized that the acquisition accelerates the vision of embedding AI directly into the tools people use daily, making computing more intuitive and empowering. The SAI team brings significant technical expertise. Co-founders Ari Weinstein and Conrad Kramer previously founded Workflow, a popular automation app that Apple acquired in 2014 and rebranded as Shortcuts. Kim Beverett, Sky’s third co-founder and COO, spent nearly a decade at Apple in key product roles, including work on Safari, Messages, Mail, and FaceTime. Their experience in building deeply integrated, user-centric automation tools positions them well to advance OpenAI’s ambitions in agentic AI. OpenAI CEO Sam Altman had previously invested in Sky through a personal investment fund, contributing to its $6.5 million seed round alongside investors like Figma CEO Dylan Field and Context Ventures. The acquisition was led by Nick Turley and Fidji Simo, OpenAI’s CEO of Applications, and approved by the company’s board. Deal terms were not disclosed. This move fits into OpenAI’s broader acquisition spree, including the $6 billion purchase of Jony Ive’s AI hardware startup io and the $1.1 billion acquisition of Statsig, a product development platform. The Sky acquisition signals OpenAI’s intent to build not just conversational AI, but intelligent agents capable of autonomous, context-aware action—what some call “agentic AI.” Apple, meanwhile, is playing catch-up in the AI race. While it has introduced Apple Intelligence features like writing helpers, live translation, image generation, and visual search, its AI strategy emphasizes privacy and on-device processing. Apple’s upcoming Siri overhaul, expected next year, will incorporate AI, and the company has already begun routing complex queries to ChatGPT. However, Apple’s privacy-first approach may slow its ability to deliver an agentic system like Sky, which requires AI to observe screens and take actions—raising potential concerns for users wary of surveillance risks. Sky’s ability to see and act across apps represents a significant leap in AI usability, but also introduces new safety and ethical challenges. Early AI browsers have faced criticism for security vulnerabilities and unintended behaviors. As OpenAI integrates Sky’s capabilities into ChatGPT, it will need to balance innovation with robust safeguards. Ultimately, this acquisition strengthens OpenAI’s foothold in personal computing and underscores its ambition to become the backbone of intelligent, proactive digital assistants across platforms—starting with Mac users. With the SAI team’s expertise and OpenAI’s resources, the integration of Sky could redefine how users interact with their computers, turning AI from a chat tool into a true digital collaborator.