OpenAI buys the Sky team to bring true desktop control to ChatGPT

OpenAI has acquired Software Applications Incorporated, the small team behind Sky, a Mac app that reads what is on your screen and can take actions in your apps. OpenAI says it will bring Sky’s deep macOS integration to ChatGPT, with the full Sky team joining. This could shift ChatGPT from answering prompts to actually doing work on your desktop.

On October 23, 2025, OpenAI announced that it bought Software Applications Incorporated, maker of the Mac app Sky. Sky’s promise is simple to state and hard to execute. It understands what is on your screen, then helps you act on it using natural language. The goal is to fold that know-how into ChatGPT so the assistant can handle tasks inside the tools you already use, not just reply with text.

What is Sky and who built it

Sky is a lightweight assistant that floats over your Mac. You call it with a hotkey, describe what you want, and it looks at the current window to help. Early previews showed it summarizing documents, composing messages, moving things into Notes or Calendar, and performing multi-step actions without setting up complex flows first. Think of it as context-aware help that lives on top of your desktop.

The team behind Sky has history with Apple’s automation ecosystem. Ari Weinstein and collaborators previously built Workflow, which Apple acquired and turned into Shortcuts. That lineage matters. It blends deep platform familiarity with a taste for approachable automation.

What OpenAI actually said

OpenAI’s announcement is short and direct. It calls Sky “a powerful natural language interface for the Mac,” says the entire team is joining OpenAI, and commits to bringing Sky’s macOS integration and “product craft” into ChatGPT. The post includes a disclosure that an investment fund associated with Sam Altman held a passive stake in Software Applications Incorporated. It states the deal was led by Nick Turley and Fidji Simo and approved by the board’s independent Transaction and Audit Committees. Those details aim to address conflict-of-interest questions up front.

How this could change ChatGPT on desktop

ChatGPT already answers questions and drafts content. What it does not fully do yet is operate your computer. Bringing Sky’s model into ChatGPT would push the assistant toward an operator role. Instead of “write an email to Mia,” you could say “send this summary to Mia in Mail, attach the latest PDF, and schedule a 20-minute call next week.” The assistant would read the screen, grab the right file, open Mail, fill the fields, and confirm before sending.

In practical terms, here are five everyday Mac workflows that should get easier:

1. Turn a web page into a meeting
   “Create a calendar event from this page, invite the three people in this email thread, and add the link.”
2. Clean up a document
   “Find every section header in this Pages doc, build a table of contents at the top, and export to PDF.”
3. Inbox triage
   “Summarize the last ten unread emails from clients, draft three replies, and file the rest.”
4. Research capture
   “Pull the key specs from this review into a new Apple Note, then tag it with ‘printer tests’ and link the source.”
5. Quick reporting
   “Take the selected cells in Numbers, make a bar chart, paste it into the status doc, and share to Slack.”

These are the kinds of tasks Shortcuts can do if you wire the steps in advance. Sky’s pitch is opportunistic automation. It sees what is on screen, interprets intent, and proposes the next action without forcing you to build the flow first.

Privacy, permissions, and policy

A desktop assistant that “sees” your screen needs clear guardrails. On macOS, these apps typically rely on accessibility APIs to observe the UI and simulate actions with your consent. Sky’s early coverage points to that approach. If and when this ships inside ChatGPT, expect permission prompts, a visible indicator when the assistant is reading content, and granular toggles to limit scope by app or data type.

Teams should press for four things before rolling this out widely:

• On-device boundaries: what stays local vs what leaves the machine for model inference.
• Per-app controls: a simple way to block sensitive apps like password managers.
• Auditability: logs for what was read or clicked, exportable for compliance.
• Least-privilege defaults: no blanket access until needed, and clear revocation.

OpenAI’s announcement did not specify privacy architecture, pricing, or timing. That is normal for day-one news. It still leaves an important follow-up list for buyers and admins.

Where this leaves Apple, Microsoft, and others

Apple Shortcuts is powerful, but it still asks users to pre-define steps. Apple Intelligence promises context-aware help in Apple’s own apps, yet its reach into third-party tools can be limited. If ChatGPT gains a systemwide, model-driven layer that understands arbitrary screens and acts on them, it could become the default front door for a lot of routine work on a Mac.

On Windows, Microsoft is pushing Copilot deeper into the shell. If OpenAI’s desktop control arrives Mac-first, Windows parity will be a popular question. A credible plan here would matter for enterprise buyers who standardize across both platforms.

Third-party players like Raycast, Cursor, and Alfred may feel pressure too. Their strength is speed and customization. OpenAI’s advantage would be cross-app understanding plus a massive model behind it.

Availability, pricing, and what’s next

OpenAI did not share dates. Integrating desktop control is not a quick patch. It touches permissions, UI conventions, failure handling, and enterprise policy. A cautious read is that we will see small steps inside the ChatGPT Mac app first, then broader access as privacy and reliability mature.

Pricing is unknown. It could be included in ChatGPT Plus, gated behind a higher tier, or sold as an enterprise add-on. Compute costs for screen understanding are not trivial, so a paid tier is likely.

Signals to watch: new toggles in the ChatGPT Mac app, a beta program for “desktop control,” and developer docs that show how third-party apps can expose actions cleanly.

Pros and cons at a glance

Quick start: 5 real tasks this should make easier

• Turn a PDF invoice into a paid entry in your tracker and file the email.
• Draft a response using text shown in your CRM and send from the right account.
• Capture a research snippet into a tagged Note with source and date.
• Build a meeting agenda from a long Slack thread and attach the files.
• Rename and upload screenshots to a shared Drive folder, then notify the team.

Frequently Asked Questions (FAQs)

Is Sky replacing Shortcuts?
No. Shortcuts is Apple’s automation framework. Sky is an app that reads context and acts. They can overlap in outcomes but take different routes.

Who founded Software Applications Incorporated?
It includes veterans of Workflow, the app Apple bought and turned into Shortcuts. Ari Weinstein is listed as co-founder and CEO on the company’s page.

Is my screen data sent to the cloud?
OpenAI has not described the final privacy model. Expect permission prompts and some on-device processing, with details to follow.

When will this arrive in ChatGPT?
No date yet. Watch the ChatGPT Mac app release notes and OpenAI’s newsroom.

Will this come to Windows?
OpenAI has not said. Cross-platform plans are a key unknown.

Was there any conflict-of-interest disclosure?
OpenAI disclosed that a Sam Altman-associated fund held a passive investment in SAI and that independent board committees approved the deal.

The Bottom Line

OpenAI bought the Sky team. Sky reads what is on your Mac’s screen and can take actions in your apps. OpenAI plans to bake that into ChatGPT, shifting it from a smart answer box to a true desktop helper. The big questions now are privacy, policy, pricing, and Windows parity.

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Source: OpenAI