ChatGPT maker OpenAI has acquired Software Applications Inc., a company founded by former Apple employees who worked on Workflow, the software Apple acquired in 2017 and renamed “Shortcuts.”
At Software Applications, the team has been hard at work on Sky, an AI-powered assistant that can perform actions across any app on your Mac. The acquisition should give OpenAI a leg up when it comes to integrating ChatGPT into Macs.
OpenAI snaps up the team behind Shortcuts
The high-profile acquisition comes as Apple struggles to compete in the booming world of AI. With a long-delayed Siri upgrade still in the works, and competitors poaching Apple’s top AI talent, Cupertino has been scrambling to catch up and eyeing partnerships with Google and others. Apple already integrated ChatGPT into Apple Intelligence to field queries Siri can’t handle.
Meanwhile, OpenAI seems intent on targeting Apple users. Just this week, the company launched ChatGPT Atlas, a Mac-exclusive web browser that makes it easy to access OpenAI’s popular chatbot while going about your business online. (OpenAI says it will bring ChatGPT Atlas to other platforms in the future.)
Now, Apple is facing a world in which OpenAI has gained a crucial advantage in bringing deep ChatGPT integration to Macs.
Thomas Ricouard, an iOS developer based in France, said the acquisition would allow ChatGPT to control your Mac, bypassing the Finder.
“Completely insane,” he wrote on X. “They’re literally robbing Apple in daylight. They’ll be completely integrated with macOS in a much better way that Apple will ever do. And will probably give them a good head start for building their own OS.”
Sky: An AI assistant deeply integrated with macOS
Software Applications leaders Ari Weinstein and Conrad Kramer developed Workflow, a powerful automation tool for iOS. Apple acquired Workflow and the team behind the app in 2017. It eventually renamed the app to Shortcuts and integrated it into iOS, macOS and iPadOS.
The two teamed up again after leaving Apple to form Software Applications. Earlier this year, they teased Sky, which deeply integrates with macOS and uses AI to carry out actions across apps.
The app never launched, remaining limited to a small group of alpha testers. MacStories‘ founder Federico Viticci went hands-on with Sky in May and noted that it would “fundamentally change how I think about my macOS workflow and the role of automation in my everyday tasks.”
The teaser video below from Software Applications showcases what Sky aimed to do.
It shows the AI assistant automatically adding a dinner date to Calendar, then being prompted to search for places nearby to get a drink beforehand. The assistant searches Apple Maps, and after it finds a handful of suitable watering holes, it’s instructed to message all the dinner invitees about meeting up.
The video makes the assitant look easy and natural to use, and a powerful productivity tool.
It also makes it clear why OpenAI’s acquisition of the team and the app is such a big deal.
This is what sky was supposed to launch this summer, before @OpenAI acquired them.
Apparently these are also the folks behind the workflow app that apple bought and turned into shortcuts so they have deep knowledge of the internals of macOS! https://t.co/4DUHYnyMCE pic.twitter.com/puVgWXRfx4
— Alex Volkov (Thursd/AI) (@altryne) October 23, 2025
OpenAI will integrate Sky into ChatGPT
“We’re building a future where ChatGPT doesn’t just respond to your prompts, it helps you get things done,” Nick Turley, OpenAI vice president and heads of ChatGPT, said in a press release Thursday announcing the Software Applications acquisition. “Sky’s deep integration with the Mac accelerates our vision of bringing AI directly into the tools people use every day.”
As part of the acquisition, all members of Software Applications will join OpenAI. Instead of launching Sky as a standalone app, OpenAI plans to integrate its deep macOS capabilities directly into ChatGPT.
Rajesh has been closely following and writing about the latest happenings in the world of mobile for nearly a decade now. While he prefers Android, he does not deny the superiority of Apple’s products and ecosystem.
