OpenAI acquires Sky.app

https://openai.com/index/openai-acquires-software-applications-incorporated

by meetpateltech • 9 months ago

250 168 9 months ago

I've personally known Ari, the guy behind Sky, since the mid 2000s when he was a frequent visitor to the forum insanelymac.com, back when OSx86 was a big deal. Even back then, he really stood out and I'm glad he's continuing to make waves.

rpwilcox• 9 months ago

To jog people's memory about Sky: yes this is the app created by former Shortcuts/Workflow.app people

mentalgear2• 9 months ago

And another consolidation in the space to make the big players even bigger, when actually it's hard time to break up the tech feudalism party.

jimmydoe• 9 months ago

Amreicans want to make the economy looks good, so they have to fake AI growth. To do that, they have to give OpenAIs a lot of money.

OpenAIs have so much money they have to make bets.

The best ways to make bets are: (a) do what others do: social video, app store, online shopping... (b) buy out other small promising companies so investors have no where else to look.

mentalgear2• 9 months ago

btw: Don't know what they think their competitive advantage is going to be with this. Either apple will just clone it, or more likely and quicker (and probably already done) there will be a better open-source version of this that let's you freely choose your local/cloud LLM model provider.

tyre• 9 months ago

Apple's AI adoption and execution has been atrocious. Siri still makes so many mistakes, Homepod can't answer anything substantial without "I've sent a link to your iPhone". If they simply let Claude back Siri, they'd be light years ahead of where they are now.

TeMPOraL• 9 months ago

We're still where we were for the past 2 years: by far the best voice assistant available on the market is... Home Assistant wired to a SOTA LLM via API key.

fnordsensei• 9 months ago

There is precedence for Apple waiting for technologies to mature before using them (last mover advantage), and then dominating by being the platform owner.

Sometimes, it seems that this just makes parts of their offering seem aged though, while they (presumably) sit around being discontent with the currently available alternatives. Especially now with LLMs which age faster than anything.

consumer4512• 9 months ago

My entirely unsubstantiated theory is that Apple is a company that would not want to release a product it can't control 100%. You can't control an LLM 100%, so here we are.

"Hey Apple, why was Steve Jobs considered to be such a jerk?" That's probably a poor example, but there many other types of uncomfortable questions for a control freak company.

Does that sound plausible to anyone else?

joomla199• 9 months ago

I wanted to look up Japanese vocab easily with my voice while running. Wouldn’t let me do it (it could show me dictionary pages but wouldn’t speak the translation into my AirPods). However, I could look up English words just fine.

So I had to set my Siri language to Japanese, and now I can look up English translations of Japanese words…though I do have to speak Japanese.

bossyTeacher4• 9 months ago

Apple's AI adoption and execution has been atrocious.

Plenty of us are glad. Look at Microsoft and Google tried to force feed users inmature broken LLM tech no one asked for

skygazer• 9 months ago

I’ve noticed very recently (last several weeks) Siri (via my HomePod) is able to competently answer some very nuanced world knowledge questions that are sourced to random but still reputable websites — it appears to paraphrase enough to appear to be directly answering your question and then cites the source website. It only seems to get fouled up if it’s possible to confuse the question for something supposedly actionable that it chokes on. I have an Amazon Echo in the same room and usually direct such questions to Alexa, but trial Siri every so often to check for progress. And suddenly Siri just started giving appropriate answers with citations. It’s like they just hooked up something new to the Siri knowledge graph, and it’s pretty good.

krackers• 9 months ago

Either apple will just clone it

They've had two years to do so, and haven't done anything. Their decision to completely abandon applescript has come back to bite them.

Also I wonder if the current dev team for macOS even knows much about the features that exist. Since mac os 9 apple has included a "summarize" service, you'd think this would be the first thing to be sprinkled with LLM magic. Instead they've just left that to rot and added a new layer for this

seyyid235• 9 months ago

I don’t know how this will help but okay.

an0malous• 9 months ago

Disclosure: An investment fund associated with Sam Altman held a passive investment in Software Applications Incorporated.

colesantiago• 9 months ago

Were there any revenue numbers for this acquisition?

saagarjha3• 9 months ago

Sky was never publicly available.

airstrike• 9 months ago

We’ve always wanted computers to be more empowering, customizable, and intuitive.

Agreed

With LLMs, we can finally put the pieces together.

I think this is true

That’s why we built Sky, an AI experience that floats over your desktop to help you think and create.

Never mind, hard pass

wiseowise• 9 months ago

So it begins, they’ve acquired the first half. Now they just need to buy or fork .Net from Microsoft.

geor9e• 9 months ago

i honestly thought it was the entire joke of the headline and all the comments would be mentioning skynet

but ctrl-f says net appears once

dang2• 9 months ago

Discussed (a bit) here. Others?

The Sky's the limit: AI automation on Mac - https://news.ycombinator.com/item?id=44179691 - June 2025 (71 comments)

Sky, Natural Computing for the Macintosh - https://news.ycombinator.com/item?id=44121891 - May 2025 (4 comments)

samfriedman• 9 months ago

https://news.ycombinator.com/item?id=44179691

dang2• 9 months ago

Added. Thanks!

stopachka3• 9 months ago

Interesting! The folks who built this made what became Shortcuts on iOS. They are great hackers.

MisterTea• 9 months ago

There are a few other comments like yours but it it doesn't mean anything to someone who doesn't use iOS. I had to look it up and it lets you create automated tasks using different iOS apps.

stopachka3• 9 months ago

Yes.

Some more interesting background:

The founders originally built Shortcuts as a separate startup. From memory I think both were under 20 at the time. They were acquired by Apple, and turned their startup into a default application that people actually like.

One of my younger teammates got into programming thanks to their app.

bossyTeacher4• 9 months ago

Which afaik is something that has been in Android for ages. What's so special about the iOs implementation?

big_toast• 9 months ago

macOS exposes a lot of affordances to code/xrpc/services/etc that Shortcuts (and previously automator) used. They let you do basically anything you'd want on macOS programmatically, without going through accessibility frameworks, code signing and sand-boxing issues. iOS as well to some extent.

Presumably if OpenAI is dog-walked/locked out of these by Apple at some point, they would be stuck in the Chrome/Chromebook feature jail. My guess is this gives OpenAI a team to put in charge to give them a chance to wedge themselves into the OS before Apple changes their mind or puts scare-box dialogs everywhere.

Either that or there's nothing so complicated and OpenAI just wants to re-build this stack inside ChatGPT as quickly and well as they can.

trenchpilgrim• 9 months ago

Shortcuts is the strangest programming "language" that I make useful things in.

My favorite is an automation that triggers when I turn on my motorcycle helmet's bluetooth module, it checks the time of day and starts playing my favorite type of music for riding at that time - hard rock at daytime, EDM/synthy music at night.

dmix2• 9 months ago

I've tried Shortcuts but I found the settings app really confusing. They really don't do a good job of explaining how to use them.

shuckles5• 9 months ago

Workflow / Shortcuts was a neat idea that never really worked or expanded beyond a small group of users. I don't think you can really extrapolate "great hackers" from that. The programming interface they exposed was truly awful and the tools around it weren't much better.

why_only_15• 9 months ago

I'm not really sure but my recollection from talking to them in 2019 was that it was quite difficult to get features shipped because of e.g. hacking risk.

brandly• 9 months ago

Thiel Fellows too.

troupo• 9 months ago

OpenAI is rapidly skating to where Apple should be, and isn't.

johnzim• 9 months ago

Wow! I was wondering why they were so quiet! Great news

yahoozoo• 9 months ago

Next step towards AGI?

tartoran• 9 months ago

Perhaps Artificial General Illusion?

luma• 9 months ago

I'm not an IOS guy so I'm trying to track this - from the thread I'm to gather this allows robotic process automation on IOS which I guess isn't easy to do? I could see the use case if you're trying to build an agent that can navigate and use apps on IOS.

Here's the question - why is this difficult on IOS? What "magic" does Sky bring to the table to make this happen?

technocrat80802• 9 months ago

Sky is macOS only. It essentially gives an LLM access to various system APIs coupled with a floating user interface that you can access on command.

toephu2• 9 months ago

"Software Applications Incorporated"... what a very generic company name

jasonjmcghee• 9 months ago

here's their website https://software.inc/

YAndreaRusso• 9 months ago

thats a cool website. thanks for sharing

geoffpado• 9 months ago

Between this and The Browser Company of New York (Arc, Dia) it seems like having a generic name is the way to get acquired these days.

WorldPeas2• 9 months ago

I've been thinking more recently, do you think that an OpenAi-Apple merger will happen this cycle as it did with AOL-TimeWarner in the past? The thought being that an aging gatekeeper attempts to merge with an up-and-coming company when they feel it's too late to be relevant only for there to be another paradigm shift that obsoletes that decision. Though that is very much speculation.

fourseventy• 9 months ago

I wonder how that would even work with OpenAI's weird 'non profit' shenanigans.

WorldPeas2• 9 months ago

MS was sizing them up a short time ago, I would imagine it'd be something strange like laying everyone off then hiring them again, or moving the IP to a child corporation Firefox-style

username223• 9 months ago

That would be wild: a cash furnace merges with a pile of cash. I had forgotten just how late in the dot-com bubble AOL/TW happened. I think it's far more likely that Microsoft lets OpenAI hang, then pillages the corpse, while Apple goes on to boringly make giant piles of money from hardware.

gtirloni2• 9 months ago

I actually think it's smart of Apple to play it safe, considering all the hype and insanity around LLM's. Also, OpenAI's valuation is not grounded in actual revenue so I doubt it's a good deal to buy them right now. Don't they have something like >400 P/E?

rvz• 9 months ago

The AI grift must continue.

technocrat80802• 9 months ago

Seems pretty obvious Sky.app's functionality will land in the macOS ChatGPT app at some point. I wonder how Atlas fits into that story.

ignoramous• 9 months ago

Atlas will evolve to collect data for training. There's a bunch of context and content bots can't process or access, but a browser not only gives the mothership a closer look at all the walled-garden services and virals a user consumes but also a residential IP address.

gigatexal• 9 months ago

Maybe this is what smart actually useful Siri could become?

mrtksn• 9 months ago

Congrats to the Sky app developers, so OpenAI believes that the future is in computer assistants?

I don't buy this, it doesn't make sense to me that tools and interfaces made for human comfort and consumption is the right place to plug the AI to automate our lives.

IMHO the computing is ripe for a re-do with everything already being enshitified and putting another lay to cover all the shit we are in isn't going to help anybody.

rco8786• 9 months ago

What IS Sky? Their landing page is just about the acquisition and I can't infer much from the OpenAI announcement.

mikeiz404• 9 months ago

Not sure if you saw the demo video but the blue "Trailer" button at the bottom of their page pops it up to watch.

https://sky.app/

isaacremuant• 9 months ago

Thoroughly unimpressed. Every one of these assistant apps always go to "send message/add something to calendar".

Hopefully the actual features and interoperability prove the ad wrong and there's a game changing UX behind it.

gurjeet• 9 months ago

Archive link to the video, in case it disappears : :-) https://web.archive.org/web/20251024095740/https://sky.app/s...

dmix2• 9 months ago

The 2nd paragraph in the article

Sky is a powerful natural language interface for the Mac. With Sky, AI works alongside you, whether you’re writing, planning, coding, or managing your day. Sky understands what’s on your screen and can take action using your apps.
We will bring Sky’s deep macOS integration and product craft into ChatGPT, and all members of the team will join OpenAI.

So it's probably a https://www.raycast.com/ competitor

righthand2• 9 months ago

Clippy. It’s Clippy’s the whole way down.

kokanee• 9 months ago

That's what I was gonna say. All of these companies are desperate to make Clippy work.

sxg• 9 months ago

https://www.macstories.net/stories/sky-for-mac-preview/

This is what you need to know.

shuckles5• 9 months ago

It's a demo of how macOS accessibility APIs and app intents can be used to provide context aware AI agent.

rcarmo2• 9 months ago

In a way Apple itself was unable to do: https://taoofmac.com/space/blog/2025/06/03/2155

Bombthecat• 9 months ago

It watches your screen, sends the screenshot to the company and the ai decides what's the next step or good for you.

I see nothing wrong with this! What could go wrong?

guluarte• 9 months ago

it's a revolutionary app the let's you create calendar events to have dinner with your friends

the_duke2• 9 months ago

The recent prioritisation of the Apple ecosystem is interesting.

Sorra, Atlas, buying Sky.

There have been signs that Apple is going with Anthropic instead of OpenAI for integrating AI features.

This may partially be an aggressive strategic push to take the wind of out such a potential partnership.

Jianghong94• 9 months ago

My take is that it's a standalone business consideration: Apple users are more inclined to pay for software (definitely the case for iPhone vs. Android, although I haven't found a source for Windows).

notatoad• 9 months ago

just from my own anecdotal experience, it's easy to prioritize apple because apple users are not only more inclined to pay for software, they're more inclined to use it.

even on web apps that are exactly the same across platforms my experience is you might more signups from windows users because somebody told them "hey, you should check this out", but the metrics on actual usuage usually favor the mac users.

locusofself• 9 months ago

I was surprised by the launch of the chatGPT desktop app for mac only, and then Sora only for iOS. Kinda seems like a middle-finger to Microsoft, which is strange considering how closely MS and OpenAI were aligned not long ago.

radicaldreamer• 9 months ago

The first version of Microsoft Office was Mac only.

the_duke2• 9 months ago

Kinda seems like a middle-finger to Microsoft

I think it might be more the opposite!

They could be staying away to not intrude into Microsoft's "turf". MS is also pushing lots of AI integrations.

DeathArrow2• 9 months ago

I think MS wants to roll their own AI stuff even if they might also using OpenAI in the backend. If we look at Github Copilot it can use multiple LLMs.

marcellus232• 9 months ago

The ChatGPT app for Mac seems to be based on the same codebase as their iOS app (either using Catalyst or SwiftUI), so the lift to bring it to Mac was probably much less than creating a fully-native Windows app. Even today their "Windows" app is a wrapper around a web view.

mohsen1• 9 months ago

I think Apple will acquire Anthropic soon. It makes a lot of sense for both sides

ef2k• 9 months ago

Comes to prove that a great UI/UX can work wonders for users. This is what Alfred back in the day was dabbling with, except that Sky seems to have a modern natural language spin to it.

notepad0x907• 9 months ago

This is..disturbing.

When a company uses acquisition as a strategy to develop features, it is stagnating. Maybe that's not the right word? At least it's past it's peak.

Consider the efforts and costs of merging a new team with yours, getting different cultures and people to work together, integrating an entirely new code base with your own.

Bigger and established companies take the risk and it does mostly pan out ok in the end. But, they generally tend to use this strategy going forward.

Think of it this way, even with lots of capital on hand, will a company just poach/hire the other companies engineers or guy it out right for it's "IP"?

I find it concerning because OpenAI's failure will have a cascading effect. And failure doesn't mean collapse, just a declining stock, an out-competed company. Its leadership must feel like they're big enough to where buying out the competition or to add new product lines is a good strategy, but they haven't (as far as I know) turned a healthy profit yet? They already have so many skeptics that claim OpenAI could never raise enough revenue to match its valuation.

And it's not like they have any shortage of competition. Alphabet alone can play the acquisition game and win more readily. ChatGPT and Sora are great, but not they don't have enough of a difference for it to be a moat.

I don't know, I just hope it isn't consultants and MBA's making decisions now over there.

And Sky.app is for MacOS? Shouldn't they be locking in a stronger partnership with Apple and get a stake in Siri instead of competing against Siri and Apple Intelligence?

I guess I just don't get business enough, I'm sure this all makes sense to entrepreneurs.

atonse2• 9 months ago

Seems like an acquihire. Honestly, I'm shocked that Apple didn't purchase them, given that Apple has nearly ZERO to show after three years since ChatGPT.

I mean, this seems to be exactly the sort of thing Apple was trying to sell us, right? And they still haven't pulled it off.

notepad0x907• 9 months ago

Apple is the smart one then maybe. You don't need to hire all the non-technical people, that's what causes issues/stagnation. They could have poached all their people instead. Or, they could have developed a competitor in less than a year (imho). I doubt they'll integrate it with their core-brand any sooner anyways.

My concern is, Sam Altman is now thinking "meh, let's just buy that company" instead of "damn, we need to dig in and beat these small guys".

koolala• 9 months ago

Maybe it is the opposite of microservice architecture. Buying a company is like a macroservice.

TheOtherHobbes• 9 months ago

Technically, it's macrodata refinement.

stackskipton• 9 months ago

Bigger and established companies take the risk and it does mostly pan out ok in the end. But, they generally tend to use this strategy going forward.

Having been in several companies that been bought, disagree it's mostly pans out. Most of time, it's just a sub company that does whatever it was doing before and names on paychecks change.

However, revenue rarely increases to point purchase probably made sense or synergy is there.

notepad0x907• 9 months ago

That's why I said "ok" instead of "great" lol. sometimes it is a disaster, most of the time it's a minor loss or a break-even. when you consider that they could have just hired people and competed directly instead, it's usually a failure though.

It's a sign of executives feeling like they don't have enough control and influence over their own company to enable similar innovation and inventiveness like the competition.

cnnlives733• 9 months ago

When a company uses acquisition as a strategy to develop features, it is stagnating.

That’s a gross over-simplification. M&A has been the modern way to grow for decades.

notepad0x907• 9 months ago

For startups? OpenAI hasn't been public for long enough to no longer be considered a startup.

theideaofcoffee• 9 months ago

I had nearly the same reaction to the headline, I feel like they’re hitting a wall in terms of the things they can innovate on in house and are flailing and are looking for the next hit, in more ways than one. This is just a suggestion of that.

stopachka3• 9 months ago

When a company uses acquisition as a strategy to develop features, it is stagnating.

Google in it's heyday acquired: (a) Android (b) Google Maps (c) Youtube. It was anything but stagnating at the time.

From what I can tell, OpenAI is following a similar strategy.

notepad0x907• 9 months ago

Has Google made anything as impactful as Gmail and Chrome since those acquisitions? Stagnant doesn't mean unprofitable.

Google videos was a thing, it died. Google had an awesome modular phone project (Ari?), it died too. I can imagine they could have done something like M-series apple chips and an actual modular phone and phone OS that was superior to Apple products.

saurik2• 9 months ago

When a company uses acquisition as a strategy to develop features, it is stagnating. At least it's past it's peak.

I feel like you might just be ignoring tons of acquisitions... back in 2004, Goole went on a spree and acquired a bunch of companies. I happen to know the founders of what later became Google Photos, but I think Google Maps was even more important... was it already past its peak?

Microsoft acquired Powerpoint in 1987. I don't think they peaked until long after that, but, hell: Microsoft acquired DOS in 1981, and there is no way in hell they had peaked before that point, lol.

I mean, you comment even talks about Siri... do you know that Apple bought that one in 2010? (They also bought the Shortcuts feature, acquiring a company called Workflow... which happens to be made by the same team as Sky ;P. But, I totally appreciate that 2017 might be considered after Apple "peaked", though I imagine most people would disagree, as Apple Silicon has been a massive market disruption... though, arguably, they bought PA Semi to pull off that project, lol.)

This is just how companies work.

notepad0x907• 9 months ago

I think Siri is a bad example, apple was around long before 2010. But you have a good point and I mostly concede. The only counterargument I have is that I don't think the culture of acquisition was the same pre '08 (just spitballing there)? Or maybe I'm just unaware. But these days I hear about companies acquired by capital-heavy bigcorps and just fizzle out, the company acquiring them being profitable but stagnant in terms of new innovations.

Look at Apple, their software game is mediocre now because of that culture, but they're at the top of their hardware game because instead of outsourcing and acquiring, they built in-house.

Others said this is an acquihire, and that might be the case, but are the new hires going to easily follow OpenAI's vision or try to interpret things according to what they're used to? If OpenAI is trying to do something major in the Apple world, why are they not building in-house? They can attract the talent and have the capital and the undertaking does not seem relatively big. OpenAI is also over-hyped, so it needs to show that it can churn out value on its own much more than Google in '04 or Microsoft in '81.

I'll conclude with this: so long as this is a tactical decision, you/others are 100% and I'm wrong. But if it is a strategic decision, then I'm bearish on the count of their strategy being flawed and timed poorly.

jononor• 9 months ago

I suspect OpenAI wants the user data from Sky/Atlas, and Apple does not want to give it. Also, Apple are probably wanting to keep their options open wrt other AI providers - after all, it is increasingly clear that OpenAI is not the only game in town for thd core LLM tech.

ndneighbor• 9 months ago

I think this acquisition makes a lot of sense and it's good business. Finding good MacOS developers who know the system level APIs more so than the docs is a tough go. It would make a lot of sense that OpenAI would just go ahead and hire out this expertise as they try to get their Mac app and their iOS app to get closer and closer to the system.

geoffbp• 9 months ago

First I’ve heard of this app

Interesting..

jlarocco• 9 months ago

Why didn't they "vibe code" their own version?

reilly3000• 9 months ago

Aqui-hire?

crossroadsguy• 9 months ago

I'd guess that's where PC's "vibe code" part aimed to quip at?

giancarlostoro3• 9 months ago

My guess is they wanted to snatch all their existing customers? Not familiar with the app. It seems to me ChatGPT wants to replace Cora and Siri. The Jarvis of AI.

whilenot-dev• 9 months ago

There are no existing customers of a yet unreleased product.

jhatax• 9 months ago

Surprised that Apple didn’t acquire Sky. Raycast might be an acquisition target if their code can become a service / extension for Spotlight in macOS. Usability win for macOS users if done right and Apple puts the right guardrails & privacy protections in place.

Lorenzo45• 9 months ago

Maybe they tried but the founders rejected. The founders created another company that was acquired by Apple and worked there for a few years. Probably not a fun place to work for ambitious engineers who want to build AI products.

giancarlostoro3• 9 months ago

I feel like they just wanted to work on new thing to make macOS better with no guard rails. If Tim Pool was worth his salt he would hire them to let them do that, Apple needs a skunkworks for macOS. They should “overpay” them for it. If it yields superior internal products whats not to love?

joshstrange• 9 months ago

Apple _should_ have acquired them. They've worked with the people behind it before (Shortcuts) and the demo videos I saw a few months ago were light years ahead of what Apple has demoed.

davidkunz• 9 months ago

One step closer to Skynet

DeathArrow2• 9 months ago

Why is this important?

gtirloni2• 9 months ago

Because it helps OpenAI justify its insane valuation by showing the market... something (which is better than the almost nothing we've seen lately).

testfrequency• 9 months ago

OAI wants to build an OS don’t they? Am I wild for assuming this?

Everything to me now from them appears to be a moonshot to be the replacement for - not an addition to.

Obviously they are not there yet with many of their products, but they all feel…weirdly intentional steps to overtake existing ecosystems.

podgietaru• 9 months ago

Not surprising. The AI in her was considered an operating system, and OpenAI are creatively bankrupt.

seanthemon• 9 months ago

A mobile OS most likely, or at least a complete cover over all of our applications, this is the only way for them to get more real training data.

sumedh• 9 months ago

Their biggest fear is that Apple or Google or MS can take away their users.

rramon• 9 months ago

It almost seems like OpenAI being a stealth operation by Apple with Altman becoming the new Jobs in an Nextstep like aquisition move.

Ive/Altman.jpg, the focus on Macs, Apples unexplainable AI strategy and getting devs snatched by Meta. Why put up a fight if you already own the biggest player..

Hendrikto• 9 months ago

getting devs snatched by Meta. Why put up a fight if you already own the biggest player.

Why match 100 million pay packages when nobody is actually making money? Apple is profitable. Big AI is not.

Zufriedenheit• 9 months ago

Probably not easy to build this type of deep integration as a third party developer. Apple could easily cripple the access for „security“ reasons and build a much better competitor themselves with first class integration into the os.

nightfox1• 9 months ago

I feel like this will also put a lot of gpt voice models into more dominance.

nektro• 9 months ago

yet another sign OpenAI doesn't quite have the moat they'd like you to think they do

dzink• 9 months ago

From Hackathons, to Workflow, Apple Shortcuts, Sky and now OpenAI… Congratulations Ari! His team knows Apple software better than anyone, but will Apple allow third parties access to all functionality under the pretext of sandboxing or security?

fadedsignal• 9 months ago

I don't think it's a meaningful acquisition. I am wondering how much cash OpenAI is holding. They literally bought dozens of startups/companies while they were/are still not profitable.

ActionHank• 9 months ago

I would be looking to see who is benefiting from their investments and acquisitions right now.

They know enterprise is not seeing the gains expected and that the average joe likes the product if it is basically free. Neither means meaningful revenue for them let alone enough to keep shovelling money into the gpu furnace.

They are going to be looking for ways to extract what liquid cash they can now.

andy_ppp• 9 months ago

I hope Apple allows me to do all this locally... I've no desire to be sending all this stuff to OpenAI.

OpenAI acquires Sky.app

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