Ari Weinstein and Conrad Kramer were two of the folks behind Workflow, which Apple bought in 2017 and turned into Shortcuts. The pair left Apple a couple of years ago and launched a startup named Software Applications Incorporated. Today, thanks to an exclusive story over at MacStories, we know what they’re up to. Here’s Federico:
What sets Sky apart from anything I’ve tried or seen on macOS to date is that it uses LLMs to understand which windows are open on your Mac, what’s inside them, and what actions you can perform based on those apps’ contents. It’s a lofty goal and, at a high level, it’s predicated upon two core concepts. First, Sky comes with a collection of built-in “tools” 1 for Calendar, Messages, Notes, web browsing, Finder, email, and screenshots, which allow anyone to get started and ask questions that perform actions with those apps. If you want to turn a webpage shown in Safari into an event in your calendar, or perhaps a document in Apple Notes, you can just ask in natural language out of the box.
At the same time, Sky allows power users to make their own tools that combine custom LLM prompts with actions powered by Shortcuts, shell scripts, AppleScript, custom instructions, and, down the road, even MCP. All of these custom tools become native features of Sky that can be invoked and mixed with natural language.
If this sounds too good to be true, well, let me explain and show you how it works.
Sky looks like it will deliver a Mac-centric AI-powered assistant long before Apple gets its act together.
Linking macOS and LLMs is one thing, but building in support for the Mac’s existing automation tools is next-level, as Ticci writes:
In addition to built-in integrations, you can make your own tools in Sky and use them as native features of the app with natural language. Custom tools can be AppleScripts, shell scripts, and – of course – shortcuts. This is where things go even deeper: custom tools can also be custom prompts for the LLM that tell it to run one or more tools when a specific word or expression is used. Essentially, by virtue of Sky being both an LLM and a desktop app deeply integrated with macOS as opposed to a chatbot living in a web browser, you can make Sky your own by creating any kind of tool you want… with natural language.
What sets Sky apart from traditional chatbots is that it’s the epitome of this concept of hybrid automation I’ve been theorizing about so much lately. In a way, it is reminiscent of the vision behind the agentic Apple Intelligence that was mocked up last year, but it’s available today (well, at least for me) without App Intents. The LLM layer understands what you’re typing and asking; Sky contextualizes it and acts as the glue between the LLM and tools; tools perform actions and pass back results to the LLM. In this virtuous cycle, the result is a personalized, efficient assistant that relies on the smarts provided by an LLM and ties them to the apps you use on your Mac. And it goes even deeper than that: if a tool you want is not available – perhaps because you haven’t created a shortcut for it – Sky can leverage Claude to create its own brand-new tools in the form of shell scripts and AppleScripts.