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OpenAI bought the team behind Sky, a Mac assistant that actually controls your apps. It's a move from answering questions to doing work—and puts pressure on Apple's automation story. Integration timing and privacy details will decide if it sticks.
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OpenAI bought the team behind Sky, a Mac assistant that actually controls your apps. It's a move from answering questions to doing work—and puts pressure on Apple's automation story. Integration timing and privacy details will decide if it sticks.
A small team, a big claim: from chatbot to computer control.
OpenAI has acquired Software Applications Incorporated (SAI), the startup behind Sky, a Mac-native assistant that reads what’s on your screen and takes actions in your apps. The entire team is joining OpenAI, which says Sky’s deep macOS integration will flow into ChatGPT. The company also disclosed that a Sam Altman–associated fund held a passive stake in SAI and that independent board committees approved the deal.
Key Takeaways
• OpenAI acquired SAI and its Sky assistant, which reads screens and executes multi-step tasks across Mac apps with user approval
• The team built Apple's Workflow and Shortcuts, bringing deep macOS automation expertise to ChatGPT's desktop integration
• Success depends on low-latency actions, predictable outcomes, and clear privacy controls—missing details on data handling and pricing
• Pressures Apple's automation strategy and menu bar tools by offering semantic context plus agentic follow-through at ChatGPT's scale
OpenAI isn’t just adding another chatbot feature. It’s buying a working interface layer that already performs multi-step tasks across Mac apps. Sky sits above your desktop, inspects live window content, and proposes confirmable actions—like summarizing a page, drafting a message, and sending it via Messages—without you wiring every step by hand. That’s the promise. The team that built it is coming along intact.
Two quotes frame the intent. Nick Turley, VP and Head of ChatGPT, says the goal is a product that “helps you get things done,” not just one that replies to prompts. SAI co-founder Ari Weinstein—the Workflow/Shortcuts veteran—casts Sky as a floating, customizable layer that helps you think and create. The messaging is consistent: bring agentic control to the desktop and make it feel native. Words are cheap; integration isn’t.
Independent hands-on reporting paints Sky as more than a launcher. MacStories described a floating UI that understands on-screen context across any app, chains actions with approvals, and exposes tooling for power users via Shortcuts, AppleScript, and shell scripts—plus the ability to draft these tools with an LLM. That’s materially deeper than “send this to app X.” It’s desktop semantics plus automation.
Bloomberg frames the acquisition as part of OpenAI’s push to make computers carry out tasks directly, not just answer questions. That’s the right yardstick. It moves ChatGPT from conversation toward operations, where reliability, speed, and permissions matter more than clever prose.
OpenAI has been formalizing an Applications organization under CEO of Applications Fidji Simo, with Vijaye Raji named CTO of Applications after the Statsig deal. That unit owns ChatGPT’s product engineering and experimentation cadence. A native, action-oriented Mac layer fits squarely into that brief—and gives Turley’s team a concrete path toward a “do-things” ChatGPT, not just a “say-things” one. It’s an execution story.
There’s also pedigree. SAI’s founders built Workflow, acquired by Apple in 2017 and reborn as Shortcuts. They know Apple’s automation frameworks and the cultural constraints of shipping system-adjacent software. That matters when you’re threading permissions, privacy prompts, and UX friction across dozens of apps. It won’t spare OpenAI the hard parts, but it reduces unknowns.
If OpenAI ships robust on-screen understanding and action chaining inside ChatGPT for macOS, it pressures Apple’s own automation story. Apple Intelligence and Shortcuts are powerful, but they still ask users to pre-wire a lot of flows. Sky’s pitch is opportunistic automation: see what’s on screen and just help. That’s a different mental model. It could make ChatGPT the front door to everyday computer work. Timing will decide the narrative.
This also touches the app-launcher and productivity-assistant category—Raycast, Alfred, and a swarm of menu bar tools. Those products excel at speed and extensibility. Sky’s advantage is semantic context plus agentic follow-through. If OpenAI productizes that reliably, developers will face a new distribution channel: tools as ChatGPT actions, not just plugins or scripts. The install base would speak for itself.
The announcement omits several critical details. First, privacy: on-screen understanding implies broad data exposure. Which data stays on device? What leaves for inference? How are approvals logged, limited, and revocable—especially for enterprise? Second, platform scope: this is explicitly Mac-first. When does Windows follow, and with what level of parity? Third, commercials: price and terms are undisclosed; so are any new paywalls for “desktop control” tiers of ChatGPT. Fourth, governance: OpenAI disclosed an Altman-linked passive investment and committee approval; more transparency on recusal, valuation fairness, and conflicts policy would strengthen trust. The next post should answer these.
Shipping a demo is trivial. Shipping a dependable operator is not. Success here means three things: low-latency actions, predictable outcomes, and clear user control over scope. If ChatGPT regularly proposes the right next step, asks for consent at the right time, and remembers just enough context without overreaching, users will forgive misses and keep it on. If it fumbles permissions, stalls, or hallucinates file paths, they’ll turn it off. Simple.
For OpenAI, this deal is less about headcount and more about product craft—deep macOS muscle memory, thoughtful UX for approvals, and a toolmaking model that invites developers to expose actions without rewriting apps. Those are scarce skills. They’re leverageable across platforms.
Q: When can I actually use this in ChatGPT?
A: OpenAI hasn't announced when Sky features will launch in ChatGPT. The acquisition just closed, and integrating on-screen understanding with permission controls takes months of work. Based on similar deals, expect early beta access in 3-6 months, with broader rollout in 2026. Watch for announcements from Nick Turley's ChatGPT team or CEO of Applications Fidji Simo.
Q: What exactly does Sky do that current Shortcuts can't?
A: Shortcuts requires you to pre-build workflows with specific triggers and steps. Sky reads what's actually on your screen right now—any app, any window—and suggests the next action without pre-wiring. Think: "It sees you're reading an email about a meeting and offers to add it to Calendar." Shortcuts needs you to script that path first. Sky proposes it live.
Q: Will this work on Windows and Linux?
A: OpenAI confirmed this is Mac-first with no Windows or Linux timeline disclosed. That's strategic—SAI's team built Workflow and Shortcuts for Apple, so they know macOS deeply. Windows has different permission models and automation frameworks. Expect Mac exclusivity for 6-12 months, then Windows support if adoption proves the concept works. Linux likely comes last, if at all.
Q: How much will desktop control features cost?
A: Not disclosed. OpenAI hasn't said if desktop control will be free, included in ChatGPT Plus ($20/month), or gated behind a new tier. Given the compute cost of on-screen analysis and the enterprise value of automated workflows, expect either a Plus requirement or a separate add-on priced at $10-30/month. Free seems unlikely for production use.
Q: What data does Sky see and where does it go?
A: OpenAI hasn't detailed which data stays on your Mac versus what gets sent to their servers for inference. Sky needs to see everything on your screen to work—emails, documents, passwords, sensitive files. Critical questions remain: Can you limit scope by app? Are screenshots stored? How long? Is enterprise data isolated? These answers should come before general release.
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