OpenAI Acquires Software Applications Incorporated: The Team Behind Apple Shortcuts Brings Sky to ChatGPT

On October 23, 2025, OpenAI announced a strategic acquisition that could fundamentally change how millions of people interact with their Mac computers. The company has acquired Software Applications Incorporated, the creators of Sky a powerful AI assistant that understands what’s on your screen and takes action across your apps.

This isn’t just another tech acquisition. The team behind Software Applications Incorporated previously created Workflow, which Apple bought in 2017 and transformed into the now-ubiquitous Shortcuts app. Now, they’re joining OpenAI to bring Sky’s deep macOS integration directly into ChatGPT.

Breaking: OpenAI Buys Sky Maker in Strategic Mac Push

What Happened on October 23, 2025

OpenAI confirmed it has acquired Software Applications Incorporated in its entirety. All 12 team members, including co-founder and CEO Ari Weinstein, will join OpenAI to integrate Sky’s capabilities into ChatGPT. The acquisition accelerates OpenAI’s vision of making AI work seamlessly within the tools people already use every day.

“We’re building a future where ChatGPT doesn’t just respond to your prompts, it helps you get things done,” said Nick Turley, OpenAI’s VP and Head of ChatGPT. “Sky’s deep integration with the Mac accelerates our vision of bringing AI directly into the tools people use every day.”

Financial Terms and Deal Structure

Financial terms were not publicly disclosed. However, the acquisition was reviewed and approved by independent board committees at OpenAI. Notably, OpenAI CEO Sam Altman previously held a passive investment stake in Software Applications Incorporated through an associated investment fund a fact the company disclosed transparently in its announcement.

This follows OpenAI’s aggressive 2025 acquisition strategy, which includes the $1.1 billion Statsig purchase and a nearly $6.5 billion acquisition of Jony Ive’s AI hardware startup. Both previous deals were all-stock transactions.

What Is Software Applications Incorporated?

The Company Behind Workflow and Shortcuts

Software Applications Incorporated was founded in 2023 by former Apple employees who played instrumental roles in creating the technology behind iPhone’s Shortcuts app. The team’s pedigree speaks for itself: they built Workflow, an iOS automation tool that Apple acquired in 2017 for an undisclosed sum.

After Apple transformed Workflow into Shortcuts and integrated it system-wide across iOS, iPadOS, and macOS, several key team members eventually left Apple to pursue their next vision one that would leverage large language models to reimagine desktop automation.

From Apple Acquisition to Independent Startup

Ari Weinstein and Conrad Kramer, two of the original Workflow creators, co-founded Software Applications Incorporated alongside Kim Beverett. The company raised a $6.5 million seed round, with Sam Altman among its investors.

Their goal was ambitious: create an AI assistant that doesn’t just respond to queries but actively understands your screen context and takes action across any Mac application not just the ones with built-in integrations.

Sky App Explained: Natural Language Meets Mac Automation

How Sky Works on macOS

Sky operates as a lightweight overlay that “floats” above your desktop. Users invoke it with a hotkey, bringing up a minimal chat interface. But unlike typical AI chatbots, Sky has deep awareness of what’s happening on your screen.

The app uses macOS accessibility APIs to identify open windows, read on-screen content, and understand the current context. It can then take actions across multiple applications using a combination of technologies: built-in app integrations, Shortcuts actions, AppleScript, shell scripts, and natural language understanding from large language models.

What does Sky app do on Mac?
Sky is an AI assistant that understands what’s on your Mac screen and performs actions across your apps using natural language commands. It can summarize webpages, send messages, create calendar events, organize files, and automate complex multi-app workflows all without switching between applications.

Key Features and Capabilities

Sky ships with built-in tools for common Mac applications:

• Calendar: Create events from conversations or emails
• Messages: Send summaries, links, or responses
• Notes: Capture and organize information
• Safari/Browsers: Summarize pages, extract data
• Finder: Organize files based on content
• Mail: Draft and send emails with context
• Screenshots: Capture and annotate automatically

But the real power lies in Sky’s ability to chain actions together. For example, you could ask Sky to “summarize this webpage and send it to John via Messages with my meeting availability for next week.” Sky would parse the page, generate a summary, check your calendar, compose a message with available times, and queue it for your approval all in seconds.

Integration with GPT 4.1 and Claude

Sky leverages both OpenAI’s GPT 4.1 and Anthropic’s Claude models for natural language understanding and reasoning. This dual-model approach allows Sky to choose the best AI for each task, balancing capabilities like long context windows, reasoning depth, and response speed.

Power users can also create custom tools by combining natural language prompts with technical automation. Sky can even use Claude to generate AppleScripts or shell commands based on your plain-English descriptions.

Why This Acquisition Matters for ChatGPT Users

From Chatbot to Desktop Companion

Currently, ChatGPT lives primarily in browser tabs and mobile apps. While useful for conversations and content generation, it remains disconnected from your actual work environment. Sky changes that equation dramatically.

By integrating Sky’s technology, ChatGPT could evolve from a conversational assistant into an active desktop companion that sees what you’re working on and takes meaningful action. Instead of copying and pasting between ChatGPT and your apps, the AI could directly manipulate files, send emails, schedule meetings, and coordinate complex workflows.

Planned Integration Timeline

OpenAI has not announced specific integration timelines, stating only that the team is “getting to work” on bringing Sky’s capabilities into ChatGPT. Based on OpenAI’s typical rollout patterns, we can expect:

1. Initial testing: Private beta for Plus and Team subscribers (likely Q4 2025 or Q1 2026)
2. Limited release: Mac-only features for paid tiers
3. Broader rollout: Gradual expansion to more users and capabilities
4. Platform expansion: Potential Windows support following Mac release

What Changes for Mac Users

For Mac users who are already ChatGPT subscribers, this acquisition promises several transformative changes:

• Contextual awareness: ChatGPT will understand what’s on your screen without manual copying
• Direct app control: Issue commands that execute across macOS applications
• Workflow automation: Chain complex tasks with simple natural language
• Reduced context switching: Work within your existing apps while AI assists in the background

The key question remains: Will this integration feel seamless, or will it require extensive permissions and setup? OpenAI will need to balance powerful automation with user privacy and security.

The Team: Workflow Creators Return to the Spotlight

Ari Weinstein’s Journey

Ari Weinstein’s career arc tells a compelling story about the evolution of automation and AI. After building Workflow with Conrad Kramer, he joined Apple when the company acquired the app in 2017. During his time at Apple, Weinstein worked on integrating Shortcuts system-wide, making automation accessible to millions of iOS users.

But as large language models emerged, Weinstein saw an opportunity that Apple wasn’t pursuing: combining LLM intelligence with deep system access to create truly intelligent automation. In 2023, he left Apple to build Sky.

“We’ve always wanted computers to be more empowering, customizable, and intuitive,” Weinstein said in OpenAI’s announcement. “With LLMs, we can finally put the pieces together. That’s why we built Sky, an AI experience that floats over your desktop to help you think and create. We’re thrilled to join OpenAI to bring that vision to hundreds of millions of people.”

Sam Altman’s Prior Investment Disclosure

Transparency matters, especially when CEOs have financial stakes in acquired companies. OpenAI disclosed that an investment fund associated with Sam Altman held a passive investment in Software Applications Incorporated before the acquisition.

This disclosure is significant for several reasons:

• It demonstrates OpenAI’s commitment to transparent governance
• It shows Altman’s early recognition of Sky’s potential
• It raises questions about how the investment influenced the acquisition decision

The deal was reviewed by independent board committees, a governance safeguard designed to prevent conflicts of interest. Still, Altman’s prior involvement adds an interesting dimension to the acquisition story.

OpenAI vs Apple: The Desktop AI Battle Heats Up

How Sky Compares to Apple Intelligence

Apple announced Apple Intelligence at WWDC 2024, promising deep app integration, contextual understanding, and proactive assistance. But delivery has been slower than anticipated. Advanced Siri features that would allow on-screen awareness and cross-app actions have been delayed until at least Spring 2026.

Sky, by contrast, already demonstrates many capabilities that Apple has only promised:

• Understanding screen content across any application
• Executing multi-step workflows with natural language
• Working with third-party apps without special integrations
• Customizable automation without programming knowledge

The irony is palpable: Apple acquired the Workflow team to build Shortcuts, then watched as key members left to create something more advanced which is now owned by one of Apple’s biggest AI competitors.

Siri’s Delayed Advanced Features

Apple’s slow progress on advanced Siri capabilities stems from several factors:

• Privacy constraints: Apple’s commitment to on-device processing limits model sophistication
• Legacy architecture: Siri’s underlying infrastructure predates the LLM era
• Internal politics: Organizational silos within Apple may have hindered development
• Different philosophy: Apple prioritizes privacy and control over bleeding-edge capabilities

Meanwhile, OpenAI has no such constraints. By processing in the cloud with user consent, ChatGPT can leverage the most powerful models available. Sky’s acquisition gives OpenAI native Mac integration without the philosophical baggage.

Competitive Implications

This acquisition intensifies the AI desktop war on multiple fronts:

For Mac users: They now face a choice between Apple’s native (but delayed) AI features and OpenAI’s more capable (but cloud-dependent) alternative.

For Apple: The company must decide whether to accelerate its AI timeline or risk losing power users to third-party solutions.

For the industry: Sky’s approach proves that deep system integration doesn’t require OS-level access accessibility APIs and clever engineering can achieve similar results.

Comparison Table: Sky vs Apple Intelligence

Feature	Sky (via ChatGPT)	Apple Intelligence
Screen understanding	Available now	Coming Spring 2026
Cross-app automation	Any Mac app	Limited to supported apps
Natural language control	GPT 4.1/Claude	Limited Siri capabilities
Privacy model	Cloud-based	On-device preferred
Customization	Extensive	Limited
Mac availability	Now (separate app)	macOS Tahoe+
Integration depth	Accessibility APIs	Native OS integration
Cost	ChatGPT subscription	Free with compatible devices

OpenAI’s 2025 Acquisition Spree

Statsig Purchase ($1.1 Billion)

In September 2025, OpenAI acquired Statsig, a product development and testing startup, for $1.1 billion in an all-stock deal. Statsig provides A/B testing, analytics, and feature flagging tools that help companies ship products faster.

The acquisition signals OpenAI’s focus on product velocity and data-driven development capabilities critical as ChatGPT evolves from a research project into a consumer platform.

Jony Ive’s AI Hardware Venture ($6.5 Billion)

OpenAI completed its largest acquisition in May 2025: a nearly $6.5 billion deal for io, an AI hardware startup co-founded by former Apple design chief Jony Ive. The acquisition brings world-class industrial design expertise to OpenAI’s hardware ambitions.

Combined with the Sky acquisition, OpenAI now has both the software intelligence and hardware design capabilities to create native AI devices that could compete directly with Apple’s ecosystem.

Strategic Pattern Analysis

Looking at OpenAI’s three major 2025 acquisitions reveals a clear strategy:

1. Statsig: Product development infrastructure
2. io/Jony Ive: Hardware design and manufacturing capability
3. Software Applications Inc: Native OS integration and automation

These pieces fit together like a puzzle. OpenAI isn’t just building better AI models it’s constructing a complete stack to compete with tech giants on their home turf. The company is assembling talent and technology to create AI-native hardware and software experiences that could rival Apple’s integrated ecosystem.

Privacy and Security Considerations

Screen Access Permissions

Sky’s core functionality requires extensive permissions that give it visibility into everything on your screen. This raises legitimate privacy questions:

• What data is captured? Sky needs to see screen content to provide contextual assistance
• Where is data processed? LLM inference happens in the cloud, meaning screen contents are transmitted
• How long is data retained? Retention policies will be critical for user trust
• Can users audit access? Transparency tools will determine comfort levels

Data Handling Policies

OpenAI has not yet released specific data handling policies for Sky’s integration with ChatGPT. However, based on existing ChatGPT policies, we can anticipate:

• Opt-in model: Users will likely need to explicitly enable screen access
• Selective sharing: Options to limit which apps or windows ChatGPT can see
• Enterprise controls: Business plans with enhanced privacy guarantees
• Data retention: Configurable retention periods for screen-based interactions

What Mac Users Should Know

Before enabling Sky-powered features when they become available:

1. Understand the tradeoff: Powerful automation requires giving AI access to your screen
2. Review permissions carefully: Don’t grant blanket access without understanding implications
3. Be mindful of sensitive content: Consider disabling features when working with confidential information
4. Check enterprise policies: Businesses may restrict these capabilities for security reasons
5. Wait for security audits: Let early adopters and security researchers test the implementation

Expert Reactions and Industry Analysis

Mac Community Response

The Mac power user community has responded with cautious enthusiasm. Federico Viticci of MacStories, who tested Sky extensively before the acquisition, called it “incredible potential for a new class of assistive AI.”

However, some community members express concerns:

• Privacy implications: Giving any company screen access feels uncomfortable
• Apple ecosystem fragmentation: Reliance on third-party AI could weaken macOS cohesion
• Subscription fatigue: Another paid service in an already crowded market

Competitive Response from Apple

Apple has not issued an official statement regarding the acquisition. However, the timing is awkward for the company:

• Apple Intelligence features are delayed
• Former Apple employees are building competing products
• OpenAI is aggressively targeting the Mac platform
• The acquisition highlights Apple’s slower AI execution

Internally, this acquisition likely serves as a wake-up call. Apple may need to accelerate its AI timeline or risk ceding mindshare to third-party solutions.

Market Impact

The acquisition reinforces several broader industry trends:

1. AI companies want platform control: Cloud AI isn’t enough; native OS integration matters
2. Talent is the bottleneck: Acquiring experienced teams is faster than building from scratch
3. Desktop AI is underexplored: Most AI focus has been on mobile; desktop represents opportunity
4. Automation is the killer app: Beyond chatbots, taking action is where AI creates real value

What’s Next for Sky and ChatGPT

Integration Roadmap

While OpenAI hasn’t shared a detailed roadmap, we can reasonably expect:

Short term (Q4 2025 – Q1 2026):

• Internal testing with OpenAI employees
• Private beta for select ChatGPT Plus users
• Basic screen understanding and simple actions

Medium term (Q2-Q3 2026):

• Public beta for Mac ChatGPT users
• Expanded app integrations beyond Sky’s original scope
• Custom automation tools for power users
• Refined privacy controls and transparency features

Long term (2026+):

• Full ChatGPT integration on Mac
• Potential Windows version using different technical approaches
• Hardware integration with Jony Ive’s devices
• Enterprise editions with enhanced security

Feature Predictions

Based on Sky’s current capabilities and ChatGPT’s direction, integrated features will likely include:

• Persistent context: ChatGPT remembers what you’re working on across sessions
• Proactive suggestions: AI recommends actions based on screen activity
• Workflow recording: Learn from your patterns to automate repetitive tasks
• Voice integration: Combine ChatGPT’s Advanced Voice Mode with desktop control
• Collaborative AI: Multiple users working with shared AI context

Release Timeline Expectations

Realistic expectations for Mac users:

• Don’t expect immediate availability: Integration will take months, not weeks
• Phased rollout: Paid tiers first, then gradual expansion
• Mac exclusivity initially: Windows and Linux support will come later
• Feature parity with standalone Sky: Some capabilities may be simplified initially
• Ongoing development: This will be an evolving platform, not a one-time release

Key Takeaways and Next Steps

OpenAI’s acquisition of Software Applications Incorporated marks a pivotal moment in the desktop AI race. By bringing in the team behind Workflow and Shortcuts, OpenAI gains both technical capabilities and design expertise to make ChatGPT a true desktop companion.

Key points to remember:

• Software Applications Inc’s 12-person team, including Workflow creators, joins OpenAI
• Sky’s screen understanding and cross-app automation will integrate into ChatGPT
• Integration timeline is uncertain but likely spans late 2025 through 2026
• Privacy considerations are significant; users should carefully evaluate screen access permissions
• The acquisition intensifies competition with Apple in the desktop AI space
• OpenAI’s 2025 acquisition strategy reveals ambitions beyond chatbots

What you can do now:

1. Stay informed: Monitor OpenAI’s blog for integration announcements
2. Evaluate your needs: Consider whether screen-aware AI would improve your workflow
3. Review privacy settings: Familiarize yourself with ChatGPT’s existing data policies
4. Explore alternatives: Check out other desktop AI tools like Anthropic’s Claude or Raycast AI
5. Join the conversation: Follow Mac community discussions to learn from early adopters

Frequently Asked Questions

Source: OpenAI