Apple is grappling with mounting internal and external challenges as it scrambles to deliver long-promised upgrades to Siri, its voice assistant, ahead of next week’s Worldwide Developers Conference (WWDC). The delays have dampened investor expectations for groundbreaking artificial intelligence announcements, raising broader concerns about Apple’s position in the accelerating AI race.
Former employees told the Financial Times that Apple’s efforts to retrofit Siri with large language models (LLMs)—the kind powering next-generation conversational AI tools like ChatGPT and Google Gemini—have run into technical snags, particularly integration bugs. These complications have been especially frustrating given competitors like OpenAI, Google, and Perplexity are building more advanced voice assistants from the ground up, unburdened by legacy systems like Siri.
“It was obvious that you were not going to revamp Siri by doing what executives called ‘climbing the hill,’” said one former Apple executive, referring to the company’s incremental approach. “It’s clear that they stumbled.”
Siri’s revamp was meant to anchor “Apple Intelligence,” a suite of AI features introduced at last year’s WWDC as part of a broader strategy to reinvigorate hardware sales. But with several promised features—including a more conversational and screen-aware Siri—still unreleased, the pressure is now mounting.
Investor disappointment has been reflected in Apple’s stock, which is down about 18% this year—making it the worst performer among the so-called “Magnificent 7” tech giants. By contrast, the Nasdaq Composite is flat year-to-date.
Apple’s troubles are not limited to Siri. Its broader AI rollout in China has also hit regulatory roadblocks, with Beijing slowing the approval of Apple Intelligence features powered by Alibaba’s LLMs. These delays come amid heightened scrutiny of American tech in China, exacerbated by U.S. President Donald Trump’s revived trade war and tariffs.
“We’re at the point where investors already know what the good news potentially is,” said JPMorgan analyst Samik Chatterjee. “Now it’s about: let’s first have you deliver what you promised last year.”
Apple CEO Tim Cook recently acknowledged that the company’s AI features had not met its “high quality bar” and were “taking a bit longer than we thought.” The delays even forced Apple to pull television ads—featuring The Last of Us star Bella Ramsey—that promoted the enhanced Siri, triggering false advertising lawsuits.
Internal restructuring has followed. John Giannandrea, Apple’s senior vice president of AI and a former Google executive, saw Siri removed from his oversight earlier this year. The division was handed to Mike Rockwell, the executive behind the Vision Pro mixed reality headset. Insiders cite fragmented leadership and underinvestment as major reasons behind Apple’s AI lag.
Adding to the complexity is Apple’s steadfast commitment to privacy. Unlike rivals who run massive AI models on cloud servers, Apple insists on processing data on-device through smaller models to protect user data. While this reinforces its privacy brand, it also limits the power of its AI tools.
To bridge the gap, Apple recently integrated OpenAI’s ChatGPT with Siri. But that move came with its own complications. OpenAI CEO Sam Altman has since signaled his intention to compete directly with Apple, announcing a $6.5 billion acquisition of IO, the hardware startup founded by former Apple designer Jony Ive. Apple’s stock slipped 2% on the news.
Industry analysts say Apple is now years behind competitors in delivering a modern AI assistant, with Bank of America estimating a delay of “three years or more.”
As WWDC 2025 approaches, Apple’s reputation for polished innovation is being tested. The company must convince developers, consumers, and investors alike that it still has the vision—and the execution—to lead in the AI era.
