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OpenAI buys Sky developer to fold macOS automation into ChatGPT

Published 24 October 2025

OpenAI said on Thursday that it has acquired Software Applications Incorporated, the San Francisco startup behind Sky, a macOS application that uses natural language to understand what is on a user’s screen and perform actions across apps. The entire Software Applications team will join OpenAI, which said it plans to fold Sky’s deep macOS integration and product craft into ChatGPT. Financial terms of the deal were not disclosed.

Sky, developed by the team that created Workflow, the app Apple bought in 2017 and transformed into Shortcuts, is designed as a context aware assistant that can generate and execute workflows on the fly from plain language prompts. OpenAI described Sky as a way for AI to work alongside people in writing, planning, coding and organizing tasks by taking action in existing apps. OpenAI said the acquisition was led by Nick Turley and Fidji Simo and was approved by the company’s independent board committees.

Software Applications cofounders include Ari Weinstein, CEO, Conrad Kramer, CTO, and Kim Beverett, product lead. The trio previously worked at Apple after that company acquired their earlier automation product. According to the startup’s technical...

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