OpenAI bought Software Applications, Inc., the startup behind Sky, a context-aware AI interface for Mac. The unreleased product promises a “float over your desktop” assistant that can make sense of what appears on your screen and take actions inside apps for you — marking OpenAI’s movement from chat windows into everyday workflows on the desktop.
The deal also extends OpenAI’s consumer reach, and aligns it with a new race on who will define agentic computing on macOS in advance of Apple Intelligence — an Apple-publicized AI shift with improved Siri. Terms of the deal were not disclosed, but the acquisition brings aboard an experienced team with some rare Apple-grade product instincts.
Why Sky Matters to Mac Users and Everyday Workflows
Sky is a powerful, persistent AI layer that sees what’s on the screen and can munge input/output to applications: composing emails from notes, transforming data in spreadsheets, refactoring code in an IDE, assembling a brief from documents.
Consider it the desktop-native equivalent to AI browsers, except that it resides in Finder, Mail, and Xcode itself.
The strategic bet: When an AI can “see” everything you see, it has the capacity to flatten what is today a hot-mess hierarchy of task-switching. Rather than duplicating information between applications, users narrate the desired result and leave it to the agent to coordinate clicks and keystrokes. Early attempts at web agents have demonstrated meaningful productivity improvements when it comes to mundane tasks, but reliability and guardrails continue to be make-or-break features for mainstream success on people’s personal computers.
A Team with Apple-Grade DNA Behind Sky for Mac
Sky was founded by Ari Weinstein and Conrad Kramer, who were known for having developed Workflow, the popular automation app that Apple purchased and incorporated into its ecosystem as Shortcuts; it comes baked into iOS, iPadOS, and macOS today. Their third co-founder, Kim Beverett, worked for nine years at Apple on Safari, WebKit, Privacy, Messages, Mail, and Phone/FaceTime; more relevant to Sky’s work is the SharePlay initiative they helped lead.
That lineage matters. And creating a system that reliably syncs actions between Mac apps is more about raw model power, less about OS integration and permissioning, and a thousand other pragmatic UX decisions. This is a team that has already rolled out automation to hundreds of millions of Apple customers.
Strategic Implications for OpenAI and Apple
For OpenAI, Sky bolsters its macOS ChatGPT app with a brand of agency on the screen, instead of chat-first help. It also provides OpenAI with an authentic response to productivity tools integrating more AI, such as Raycast and Cursor, up to Arc’s agentic browsing.
For Apple’s ecosystem, the timing is significant. As part of the upgrade, Apple Intelligence is also introducing writing tools, image generation, and on-device reasoning while the company is routing some unanswerable Siri questions to ChatGPT. Apple also provides a Foundation Models framework that enables developers to create AI features on-device. Sky’s model — watching and acting across apps — pushes into new territory, setting a higher bar for what desktop assistants can do on macOS.
Privacy and Safety Considerations with Agentic AI
An assistant reading your screen and controlling apps is a service that should have higher standards of security and transparency. History is replete with cautionary tales: Microsoft’s Recall feature for Windows, which recorded detailed on-screen activity to inform search and assistance, attracted growing scrutiny and was overhauled with stronger opt-ins and protections after security researchers warned of the risks.
Industry guidance is veering toward stricter guardrails for agentic systems. Data minimization, user consent, strong sandboxing, and building safeties against prompt injection and data exfiltration are key, if not best practices, from both the NIST AI Risk Management Framework and OWASP’s Top 10 for LLM applications. For enterprise Macs — where compliance and auditability are table stakes — expect administrators to request policy controls, local processing options, and transparent logs for AI-initiated actions.
Deal Terms, Investors, and What to Watch Next
The purchase price was not disclosed by OpenAI. Software Applications had raised $6.5 million from investors like Sam Altman (via a passive fund interest), along with investor Dylan Field, Context Ventures, and Stellation Capital, PitchBook noted. The deal was led by the Head of ChatGPT, Nick Turley, and CEO of Applications, Fidji Simo, with approval from the board, OpenAI said.
Longer term, keep an eye out for Sky capabilities to appear inside OpenAI’s Mac app and perhaps even as APIs that developers can call into to perform safe, auditable desktop actions. The test of durability that will matter the most is reliability amidst real-world messiness — multiplexed app states, flaky permissions, edge-case data. If OpenAI can fit its models to the Workflow team’s hard-won automation craft, Mac users might be on their way to their first widely trusted desktop AI — and an agent that seems more like a capable coworker sharing your machine than a chatbot.
