OpenAI is reportedly so dissatisfied with Apple over a ChatGPT integration that failed to generate the expected subscribers and visibility that it is now actively considering legal action against the iPhone manufacturer, according to a Thursday report from Bloomberg News, which cited sources familiar with the situation. Bloomberg indicated that OpenAI has retained an external law firm to evaluate its options, which could include issuing a formal breach-of-contract notice to Apple without necessarily escalating to a full lawsuit—at least for now. Any legal steps are likely to be postponed until after the conclusion of OpenAI's ongoing trial with Elon Musk. Nonetheless, this situation underscores how challenging Apple can be as a partner for major software companies. The iPhone represents an immensely attractive platform for growth, but it remains entirely under Apple's control, and companies that build on it are merely guests. From Google to Adobe, there is a long history of Apple showing these guests the door when they appear to be getting too comfortable.

The partnership, announced at Apple's Worldwide Developers Conference in June 2024, integrated ChatGPT into Apple's operating systems as an option within Siri and as part of the iPhone's Visual Intelligence feature—allowing users to use their camera to analyze their surroundings and send photos to ChatGPT with related questions. OpenAI, along with industry observers, anticipated that the deal could eventually funnel billions of dollars in new subscriptions its way and give the company prime real estate across one of the world's most-used mobile ecosystems. Instead, Bloomberg reports, OpenAI has grown increasingly frustrated, complaining that the integration has been buried, its features are hard to find, and revenue from the tie-up is far below projections. "They basically said, 'OpenAI needs to take a leap of faith and trust us,'" one OpenAI executive told Bloomberg. "It didn’t work out well."

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Apple, for its part, has its own grievances, including concerns about OpenAI's privacy standards and, according to Bloomberg, irritation over OpenAI's push into hardware—an effort led by former Apple executives, including ex-design chief Jony Ive. Either way, OpenAI is hardly the first Apple partner to regret hitching its wagon to the company. Apple has a long history of embracing partners and then alienating them. The most famous case is Google Maps, which was a flagship feature of the original iPhone. It was so central to the device's appeal that its removal in 2012—replaced by Apple's markedly inferior Apple Maps product—became one of the biggest tech fiascos of the decade, prompting a rare public apology from CEO Tim Cook. The friction between the two companies had been building for years at that point, due to the rollout of Google's Android phone a year after the iPhone's 2007 debut; after Google's then-CEO Eric Schmidt stepped down from Apple's board in 2009, that rivalry only intensified.

Adobe also bears some scars. Steve Jobs refused to support Flash on the iPhone and iPad, publishing a famous open letter in 2010 explaining why and effectively dooming the technology. Flash never recovered its footing on mobile. Then there's Spotify, which spent years arguing that Apple leveraged its control over the App Store to disadvantage rival music streaming services after launching Apple Music in 2015. The European Commission agreed, fining Apple nearly €1.8 billion in March 2024. Sometimes these rifts can be overcome in the name of commercial interests. Google is now Apple's AI infrastructure partner, having struck a multiyear deal in January to power the next generation of Apple Intelligence with Gemini models. Apple is paying Google roughly $1 billion a year.

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In the meantime, OpenAI has had its own share of strained relationships lately. Elon Musk's lawsuit against the company—which accuses OpenAI of abandoning its nonprofit founding mission and operating in bad faith—is currently at trial. The company has also reportedly navigated tensions with Microsoft, its biggest backer and infrastructure partner, as it pushes for greater independence ahead of its own IPO ambitions.