OpenAI acquires Software Applications Inc., bringing Mac automation app Sky into ChatGPT

OpenAI has acquired Software Applications Incorporated, the team behind Workflows (the iOS automation app that evolved into Apple’s Shortcuts) and the new Mac automation app Sky. The startup’s staff will join OpenAI as the company plans to fold Sky’s deep macOS integration into ChatGPT to enable apps to take more direct actions on users’ devices.

Sky is positioned as an agentic automation tool: it understands what’s on your screen and can carry out multi‑step tasks across apps, similar to the way automation apps like Shortcuts operate — but with tighter OS integration and AI‑driven decision making. OpenAI says it will use Sky’s macOS product craft to expand ChatGPT’s ability to act inside desktop apps and workflows.

Why OpenAI bought Sky

• Agentic capabilities: Sky focuses on AI that performs actions on behalf of users, which complements OpenAI’s push into agent tools and app integrations.
• macOS integration: Sky’s deep hooks into the Mac ecosystem make it useful for bringing app‑level actions to ChatGPT on desktop platforms.
• Talent acquisition: The entire Software Applications team will join OpenAI, accelerating product work without rebuilding those integrations from scratch.

Context and competition

Apple has been developing similar features for an updated Siri that can act in third‑party apps, and it recently demoed those ideas — though the new Siri is expected later. OpenAI’s acquisition follows other recent moves, including the release of ChatGPT Atlas (its web browser) and other small acquisitions aimed at expanding ChatGPT’s capabilities.

Benefits and concerns

Potential benefits include smoother automation, fewer repetitive tasks and a more powerful assistant that can complete workflows across apps. But the move raises privacy and security questions: agentic AI with access to apps and screens requires careful permissioning, transparency and robust safeguards to prevent unwanted actions or data exposure.

What to watch next

• How OpenAI integrates Sky into ChatGPT and which platforms (macOS, iOS, Windows) gain support first.
• Privacy and permission controls OpenAI introduces for agentic features.
• Apple’s response and how Siri’s roadmap will compete with AI assistants that execute app actions.

Read official announcements and follow updates from OpenAI as the integration progresses.

Discussion: Would you let ChatGPT automate tasks inside your apps if you had clear controls and safeguards, or do the risks outweigh the convenience?