OpenAI has acquired Software Applications Incorporated, maker of Sky, a Mac app that understands what’s on your screen and can take actions in your apps. The Sky team will join OpenAI and integrate into ChatGPT.
📌 Key Takeaways
- Sky is a natural-language interface for Mac that can see your screen and act in apps.
- OpenAI will bring Sky’s deep macOS integration into ChatGPT; the full team is joining.
- Deal terms weren’t disclosed; Sky had raised $6.5M, including a passive Altman-linked fund stake.
- Acquisition led by Nick Turley and Fidji Simo, approved by independent board committees.
- Sky’s creators previously built Workflow/Shortcuts, Apple’s automation system.
What Was Announced, And Why It Matters
OpenAI says Sky is a powerful natural-language interface that helps with writing, planning, coding, and daily tasks while understanding on-screen context. It will be folded into ChatGPT to make the assistant more action-oriented.
This shifts ChatGPT from outputting text to doing things on your Mac. Screen understanding plus app control is the missing layer between conversational answers and real desktop workflows.
We’re excited to share that… pic.twitter.com/DfBPs0dIu6
— Sky (@skybysoftware) October 23, 2025
Who Built Sky, And What They’re Bringing
Sky was created by veterans behind Workflow, later acquired by Apple and reborn as Shortcuts. That heritage shows in Sky’s emphasis on native automation and user-friendly control surfaces.
The team joins OpenAI to infuse ChatGPT with deep macOS behavior. The goal is an assistant that lives beside your apps, understands state, and executes tasks without constant copy-paste.
What Sky Adds To ChatGPT On macOS
Sky can see what’s on your screen and take actions in your apps through natural language. Think “send this draft by Mail,” “rename these files,” or “summarize that PDF” from any window.
It runs as an overlay that works with macOS, rather than as a separate chatbot. Early previews emphasized on-screen context and direct app control as the core experience.
Permissions, Privacy, And Safety Notes
Because Sky understands on-screen content, it relies on macOS accessibility APIs and related permissions to identify windows and perform actions. You’ll grant or revoke these at the system level.
OpenAI frames the acquisition as building an assistant that “helps you get things done.” Expect visible prompts and OS dialogs as features ship, so control stays with the user.
Availability, Terms, And Leadership
OpenAI did not share a public rollout date. It confirmed the entire Sky team is joining and that Sky’s capabilities will be integrated into ChatGPT.
Deal terms weren’t disclosed. PitchBook data cited in coverage shows $6.5M raised previously, and OpenAI disclosed a passive Altman-associated fund stake, with the deal led by Nick Turley and Fidji Simo.
How To Get Ready On Mac
Here’s a short bridge: these features will appear inside ChatGPT once integration lands. You can prepare your Mac so that setup is quick when it arrives.
- Keep ChatGPT For macOS Updated: Install updates promptly to receive Sky-powered capabilities when they ship.
- Review Permissions On First Use: When prompted, allow Accessibility or screen-content access only for tasks you want ChatGPT to perform. You can revoke later in Settings.
- Test Common Tasks: Try summaries, file actions, and Mail drafts from active windows once features roll out, verifying results before wider use.
- Admin Prep: If you manage Macs, plan policy exceptions for Accessibility-based automation and document permission guidance for teams.
Context: Product Direction And Comparable Moves
OpenAI recently emphasized application-level ownership, acquiring companies to deepen ChatGPT’s product stack and control interfaces. Sky fits this arc by anchoring desktop agency.
The Shortcuts pedigree helps translate complex automation into approachable flows. That’s crucial if ChatGPT is to become a background helper instead of a destination app.
Two Numbers In The Proper Context
Sky’s maker previously raised $6.5M, signaling early conviction around native desktop AI. OpenAI explicitly disclosed the Altman-linked passive investment and named the executives who led the deal.
Separately, OpenAI’s recent product acquisitions underline a strategy of faster capability infusion into ChatGPT rather than relying only on plugins or third-party bridges.
Conclusion
OpenAI is bringing Sky’s Mac-native context and app actions into ChatGPT, aiming for an assistant that understands your screen and executes tasks with clarity and control. That’s the step from answers to outcomes.
Rollout details will follow, but the direction is clear: ChatGPT is becoming a first-class macOS helper, designed by the team that popularized workflow automation on Apple platforms.
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