Your Mac’s productivity potential just got a major upgrade—whether you wanted it or not. OpenAI quietly acquired Software Applications Incorporated, the creators of Sky, an unreleased AI assistant that watches your screen and controls your apps through natural language commands.
The Workflow Dream Team Strikes Again
The minds behind Apple Shortcuts now work for OpenAI, bringing proven Mac automation expertise.
This isn’t just another acqui-hire. The Sky team includes Ari Weinstein, Conrad Kramer, and Kim Beverett—the same trio who built Workflow and sold it to Apple, where it became the foundation for Shortcuts. Now they’re bringing that deep Mac integration knowledge to OpenAI’s ecosystem.
Sky operates as a contextual AI layer that floats over your desktop, capable of writing, coding, and planning across multiple applications simultaneously. The financial terms remain undisclosed, but the entire team joins OpenAI as part of the deal.
Privacy Meets Productivity in a Staring Contest
Screen-watching AI promises efficiency but raises questions Apple’s privacy-first approach doesn’t.
Here’s where things get interesting. Sky’s core functionality involves monitoring everything on your screen to understand context and execute commands across apps. That level of comprehensive system access offers powerful productivity potential for Mac users willing to embrace it.
But it’s also the exact opposite of Apple’s privacy-focused AI strategy, which emphasizes on-device processing and minimal data collection. OpenAI disclosed that CEO Sam Altman had invested $6.5 million in Sky through a fund, though the company’s independent board approved the acquisition according to OpenAI’s announcement.
The Race for Your Desktop
This acquisition positions OpenAI directly against Apple’s upcoming AI-powered Siri overhaul.
The timing isn’t coincidental. Apple is preparing major AI enhancements for Siri and its “Apple Intelligence” features, but those emphasize privacy over comprehensive system control. OpenAI’s strategy suggests they’re betting users will accept broader AI access for significantly more capable assistance. Sky represents what industry observers call “agentic AI”—systems that don’t just respond to queries but actively manipulate your computing environment based on observed context.
Your Mac experience may fundamentally change faster than Apple intended. The question is whether you’re ready for an AI that observes everything you do—and whether the productivity gains justify that level of access.
