TL;DR: OpenAI is picking a fight—hiring an outside law firm to prepare “possible legal action” against Apple over the companies’ ChatGPT-Siri integration, Bloomberg reported Thursday. OpenAI hoped the partnership would turn hordes of iPhone users into paid ChatGPT subscribers, but that hasn’t happened. The tension reflects a recurring question in Big Tech: What does relying on Apple’s platform for growth get you, anyway?

What happened: OpenAI’s lawyers could send Apple a breach of contract notice without escalating to a lawsuit. No decision has been made, and it’s unlikely to make a move until it’s done with another high-profile legal fight: the Musk vs. Altman trial.

When the deal launched in 2024, no money changed hands; Apple’s pitch was distributing ChatGPT to hundreds of millions of iPhone users whom OpenAI could then convert to subscribers—with Apple getting a cut of subscription revenue it generated.

Nobody’s happy: OpenAI thinks the integration is buried and that Apple never adequately promoted the integration. It’s also disappointed that the billions in subscription revenue it anticipated hasn’t materialized. “We have done everything from a product perspective,” an unnamed OpenAI exec told Bloomberg. “They have not, and worse, they haven’t even made an honest effort.”

OpenAI has also run into Apple’s notorious secrecy culture. Apple reportedly wouldn’t give OpenAI execs details on the integration and said the startup “needs to take a leap of faith and trust us,” per Bloomberg’s source. Questions around what, exactly, Apple promised could be central to any legal case.

The hurt feelings appear to be mutual: Apple has concerns about OpenAI’s user privacy standards, is peeved about its $6.5 billion acquisition of Jony Ive’s hardware startup io—which aims to compete with Apple on devices—and is reportedly also upset about OpenAI poaching dozens of engineers.

OpenAI’s headaches are building ahead of its IPO, from the Musk trial to Anthropic’s growth and questions around CEO Sam Altman’s honesty. Does it really need to pick a legal fight with a tech heavyweight right now?

Apple’s house, Apple’s rules: OpenAI isn’t alone in feeling burned by Apple, which famously swapped out Google Maps, a flagship iPhone feature, in 2012 and then apologized. The EU also fined Apple $2 billion over antitrust allegations involving music streaming competitors like Spotify.

But it’s Apple’s world, and the rest of the tech industry is living in it. Apple is expected to unveil iOS 27’s new Extensions system in June, giving OpenAI’s competitors access to Apple Intelligence. And, in yet another bad sign for OpenAI, Apple inked a $1 billion-per-year deal with Google for Gemini to power Siri.

Bottom line: Apple owns our screens, giving it control over how partners’ products are featured. OpenAI is just the latest company to learn this lesson the hard way. —JG

Also at OpenAI…

• Here’s what comes next in the Musk vs. Altman trial, which heard closing arguments yesterday.
• Codex is now in the ChatGPT mobile app on iOS and Android.
• If you use ChatGPT on Mac, you will be forced to update your app after hackers got access to some of OpenAI’s systems.

What AI can (and can't) do for your finances

AI shouldn't replace your financial advisor or make trades on your behalf. But it can help you understand your full financial picture well enough to ask smarter questions and make better decisions—and that's more useful than it sounds.

What any AI can do right now:

• Analyze your spending if you share your latest statements (just make sure to crop or redact identifying info before you do)
• Help you understand the tradeoffs between two financial options
• Explain concepts like expense ratios or mortgage points in plain English
• Build a savings plan around your specific numbers

It's a surprisingly good thinking partner for financial decisions—as long as you're the one making the final call. One caveat: Financial information is data-heavy, so if you're doing a deep-dive session, create summaries as you go (I covered how in the April 17 edition) so your chatbot doesn't start losing the thread.

Using AI for financial help also got a lot more interesting today, with OpenAI rolling out a new feature called ChatGPT Finances that can connect your bank accounts directly to the chatbot through Plaid (with read-only access). Once linked, you can ask questions based on your actual account data. Here are a few examples of what OpenAI says it can handle:

• I feel like I've been spending more recently. Has anything changed?
• What credit card will get me the most reward value based on my spending?
• What's the biggest risk in my portfolio?
• Look at my subscriptions and help me choose what to cancel.

ChatGPT says that financial memories are kept separate from your regular Memory, and you can "view or delete them at any time from the Finances page." The feature is rolling out to Pro subscribers (which starts at $100/month) in the US today, with the OpenAI team telling Tech Brew it plans to give access to Plus subscribers in the future. —SM

Software developers pushed to use AI tools to write code seem to be realizing that there’s truth to the whole excellence-is-not-an-act-but-a-habit maxim. Devs who spoke to 404 Media anonymously said that forced AI use is actively making them worse at their jobs.

“It’s making me dumber for sure,” one fintech software dev said. ”And supposedly I tell myself I’ll just use it for inspiration but it ends up being my only thought. It gives you the illusion of productivity and expertise, but at the end of the day, you are more divorced from the output you submit than before.”

Cognitive atrophy from offloading tasks to AI is “by now a well-studied phenomenon.” And while those still employed say they’re hastening their own cognitive decline, Big Tech companies are citing AI-driven efficiencies to rationalize sizable rounds of layoffs—which means fewer people to clean up the mess.

“We're building a rat's nest of tech debt that will be impossible to untangle when these models become prohibitively expensive,” another dev told 404. —AS

Chaos Brewing Meter: /5