AI at Risk: Final Developer Conference for Cook’s Legacy

Apple heads into next week’s Worldwide Developers Conference with its stock trading near record highs, recovering iPhone momentum, and one crucial question poised to define Tim Cook’s tenure as CEO and the company’s future: Can Apple finally deliver a compelling artificial intelligence experience that lives up to its long-standing promise?

The anticipated highlight of WWDC is a significant overhaul of Siri, Apple’s much-maligned voice assistant. Industry analysts anticipate a more sophisticated Siri, potentially featuring a standalone chatbot interface, enhanced contextual understanding, on-screen awareness, the capability to handle complex, multi-step commands, and deeper integration with external AI models, possibly including Google’s Gemini.

For investors, WWDC represents a critical juncture to ascertain if “Apple Intelligence” can genuinely become a primary upgrade driver for the iPhone. This is vital for justifying Apple’s current valuation, which already presumes the company will remain the preferred device for consumers accessing AI, irrespective of the underlying models used.

For developers, the conference is a test of whether Siri can evolve into a robust platform within the burgeoning agentic era, making it a valuable ecosystem to invest in and build for.

And for Tim Cook, this WWDC carries significant legacy weight. As John Ternus prepares to assume the CEO role, this represents one of the final major developer stages for the company to showcase a cohesive and potent AI strategy.

Dan Newman, CEO of The Futurum Group, characterized Apple Intelligence as “one of the big black eyes” of Cook’s leadership. “This is clearly the moment that Apple can say, ‘Hey, we are capable of taking advantage of our multi-billion-user install base,'” Newman stated, emphasizing Apple’s need to prove to developers that Siri is “something to build on.”

Analysts at MoffettNathanson observed this week that Apple’s stock performance has “done all the work the AI story has yet to do.” The company enters WWDC at an all-time high, with a valuation reflecting robust execution, a strong iPhone cycle, a resurgent China market, and consistent services growth.

“The question for WWDC26 isn’t ‘will Apple announce a better Siri?’ It almost certainly will,” MoffettNathanson wrote. “The question is ‘does a better Siri justify a multiple that already assumes it works?'” For the current valuation multiple to hold, Siri must demonstrably move from a simple command interface to a truly agentic assistant capable of reliably executing multi-step tasks across various applications. This hinges critically on third-party developers embracing Apple’s App Intents framework, enabling Siri to perform actions within their apps.

This presents a classic “chicken-and-egg problem”: Siri’s utility depends on widespread developer adoption, while developers may hesitate to invest significant effort until they see demonstrable consumer engagement. MoffettNathanson notes that Apple has reportedly secured early App Intents partners, including prominent players like Uber, Amazon, Temu, YouTube, WhatsApp, Facebook, Threads, and AllTrails. However, the firm cautions that developers might remain apprehensive about ceding further control to Apple, given historical tensions surrounding App Store economics. This makes WWDC a pivotal event, requiring Apple to not only showcase compelling AI advancements to consumers but also to convincingly position Siri as a viable and attractive platform for developers.

“Cook has totally missed on AI in some ways, but by spending efficiently and not overcommitting to capex and still owning that surface layer, they’re actually in a position where they can continue to miss for some time and still, at some point in the future, succeed,” Newman commented. He underscored that this WWDC is “really the last hurrah” for Cook to ignite a critical inflection point before Ternus takes the helm.

While tech giants like Microsoft, Alphabet, Amazon, and Meta are deploying tens of billions of dollars annually into AI infrastructure, Apple has largely abstained from this capital-intensive race. The company’s strategy appears to be centered on leveraging its vast device-level distribution, stringent privacy standards, and a more model-agnostic approach. This measured approach could prove advantageous, allowing Apple to bridge the AI gap through strategic partnerships rather thanShouldering the immense data center expenditure burden faced by its competitors.

Reports suggest Apple’s revamped Siri is slated for a September launch and may partially operate on Google Cloud, utilizing Nvidia chips, although these details remain unconfirmed by independent sources. This potential reliance on cloud infrastructure and third-party hardware would signify a notable departure for Apple, a company historically inclined to control its core technologies. However, investors might readily accept this trade-off if it accelerates the delivery of a functional and competitive AI product.

Newman posits that such a partnership could be mutually beneficial for Google, as significant token usage from Apple’s user base would provide a crucial validation for Gemini and bolster an already lucrative search partnership. Nonetheless, questions persist regarding whether Apple has sufficiently invested in AI innovation.

Stephanie Link, chief investment strategist at Hightower, notes Apple’s historical conservatism with its capital, often favoring share buybacks over aggressive acquisitions or substantial R&D investments. While this discipline has benefited profit margins, Link expresses frustration over Apple’s limited participation in what rivals describe as a generation-defining technological shift.

“Apple has been ridiculously late on AI,” commented Dan Niles, founder of Niles Investment Management. While Niles commends Cook’s prowess in supply chain management and political acumen, he points to the Vision Pro as an example of a recent ambitious product that has not achieved widespread success. He remains cautiously optimistic, however, acknowledging Apple’s increased R&D spending and highlighting the critical importance of future product execution.

Link expresses reservations about the setup for Apple shares heading into WWDC, given the stock’s recent run-up and its current valuation. “It’s not like I hate the stock. It’s just that it’s had a nice run, and I’m just not sure we’re going to get something big at WWDC.” She points out that Apple is trading at approximately 34 times forward estimates, with projected growth around 10%. Link is uncertain whether the company will announce developments substantial enough to significantly move the stock. Her current Apple position is minimal, significantly below the company’s weighting in the S&P 500, due to valuation concerns and uncertainty surrounding investor expectations for the developer conference.

“I don’t think WWDC is going to be that much of a catalyst,” stated Jim Lebenthal, partner at Cerity Partners. “I can’t see something momentous coming out of this Worldwide Developer Conference. I just don’t see it.” Lebenthal maintains a market-weight position in Apple but expresses a lack of strong enthusiasm for WWDC as a catalyst. He believes the stock is trading at the high end of its valuation range and, while not selling, finds it difficult to initiate new purchases.

UBS anticipates Apple will focus on AI at the event but does not foresee WWDC serving as a significant positive catalyst for the shares, barring any unexpected announcements. The firm highlighted anticipated features such as Gemini integration, third-party model connectivity via “Extensions,” a dedicated Siri app, iCloud syncing for conversations, personalization features, and on-screen awareness. UBS maintained its iPhone estimates unchanged, suggesting that while these features may offer convenience, they are unlikely to materially drive demand.

Conversely, Goldman Sachs expressed a more optimistic outlook. The firm believes that the new Siri, if effectively leveraged by developers, could become a key demand driver for the iPhone and a significant contributor to services growth. “I know that Tim Cook wants to go out on a high,” Link told CNBC. “But I would say that he went out on a high at the quarter. The quarter was good and better than expected.”

The true consumer test will unfold in September with the expected launch of the new iPhone lineup, which will likely feature the upgraded Siri experience. Gene Munster, managing partner at Deepwater Asset Management, anticipates potential stock dips around WWDC but believes this would not derail the long-term thesis if Apple effectively demonstrates its understanding of AI’s trajectory. “They don’t have to get it right,” Munster told CNBC. “They just have to show that they get it — and that they know where this is going. That means AI products people actually want to use, which they don’t have right now, and products that take advantage of what is uniquely Apple.”

Munster asserts that the bar is “surprisingly high” for a company that has not yet demonstrated AI proficiency. At a minimum, Apple must present a chatbot experience on par with Gemini or ChatGPT. More critically, the company needs to showcase how deep integration with its hardware can enhance AI’s personalization and utility. “We can’t have Genmoji 2.0,” Munster cautioned, emphasizing that such an iteration would be unacceptable.

This places Cook in a precarious position heading into WWDC. A demonstrably more capable Siri could significantly reshape Apple’s AI narrative and bolster the iPhone upgrade cycle into the fall. Conversely, any announcements perceived as incremental, delayed, or overly reliant on external partners risk rekindling concerns about past execution missteps. For a CEO who transformed Apple into a global technology titan through operational excellence, supply chain mastery, and services expansion, his final developer conference may hinge on a less familiar frontier: making Siri feel like the undeniable future.