Apple Intelligence Struggles as Tim Cook Faces AI Execution Crisis

Apple is preparing for a transformative 2026, with major product launches expected including a foldable iPhone and significant upgrades to its struggling AI platform, Apple Intelligence. However, CEO Tim Cook faces mounting criticism over the company’s AI execution, with analysts pointing to artificial intelligence as his “Achilles’ heel.”

Forrester analyst Dipanjan Chatterjee told Business Insider that while Apple showed early ambition in AI, “the shortfall lies in execution.” The company has struggled to establish Apple Intelligence as a household name, despite Cook’s efforts to position Apple as a competitive player in the rapidly evolving AI landscape.

A key component of Apple’s AI strategy involves a more conversational, AI-powered Siri assistant. Apple first teased this upgraded version at WWDC 2024, featuring advanced contextual awareness that could recall information from past texts and calendar entries. However, when Apple Intelligence launched in fall 2024, this promised Siri functionality was notably absent. In an unusual move for the secretive tech giant, Apple delayed the launch in March 2025, confirming to Tom’s Guide in June 2025 that the new AI-powered Siri would arrive sometime in 2026.

Beyond AI developments, Apple is expected to launch its first foldable iPhone in 2026, according to renowned Apple analyst Ming-Chi Kuo of TF International Securities. The device is projected to retail for over $2,000, with Bloomberg’s Mark Gurman reporting similar timelines and pricing. While competitors like Samsung and Huawei have offered foldable phones for years, Chatterjee believes Apple’s market dominance could make the form factor mainstream, similar to how the company catalyzed smartwatch adoption despite Samsung’s earlier entry.

Additionally, Apple is reportedly developing a more affordable MacBook priced below the current $999 MacBook Air. This budget-friendly 13-inch model would be the first MacBook to run on an iPhone chip, with mass production expected in late 2025 or early 2026.

Apple’s Services business, including its subscription offerings like Fitness+, continues showing steady growth. The company recently updated Apple Fitness+ with new workout programs and features, demonstrating its commitment to diversifying revenue streams beyond hardware sales.

Key Quotes

Many will point to AI as Cook’s Achilles’ heel — and that critique is not misplaced, though not for lack of early ambition. The shortfall lies in execution.

Forrester analyst Dipanjan Chatterjee provided this assessment to Business Insider, highlighting that while Apple showed early interest in AI development, the company has failed to effectively implement and commercialize its AI capabilities under Tim Cook’s leadership.

Apple will, like it has done before in the smartwatch business, where Samsung moved first, be a catalyst for growth in the category.

Chatterjee made this observation about Apple’s expected foldable iPhone launch, suggesting that despite being late to the foldable phone market, Apple’s massive market share could mainstream the technology similar to how it popularized smartwatches after Samsung’s initial entry.

Our Take

Apple’s AI struggles represent a rare misstep for a company known for polished, market-defining products. The delayed Siri upgrade and Cook’s inability to make Apple Intelligence resonate with consumers suggest deeper organizational challenges in adapting to the generative AI era. Unlike previous technology transitions where Apple successfully played the “fast follower” strategy, AI requires continuous innovation and rapid iteration—areas where Apple’s secretive, perfectionist culture may be a liability. The company’s decision to publicly delay Siri’s AI features is particularly telling, indicating either technical difficulties or strategic uncertainty. As competitors integrate increasingly sophisticated AI into their ecosystems, Apple risks losing its premium positioning if it cannot deliver compelling AI experiences. The 2026 timeline for both foldable iPhones and enhanced AI capabilities makes this a make-or-break year for demonstrating that Apple can still lead in transformative technologies.

Why This Matters

This story highlights critical challenges facing one of the world’s most valuable technology companies as it navigates the AI revolution. Apple’s struggles with Apple Intelligence execution represent a significant vulnerability for a company that has historically dominated through superior user experience and seamless integration.

The delayed launch of AI-powered Siri and Cook’s difficulty establishing Apple Intelligence as a competitive AI brand signal that Apple may be falling behind rivals like Google, Microsoft, and OpenAI in the generative AI race. This matters because AI is rapidly becoming the defining technology of the decade, influencing everything from smartphone functionality to enterprise productivity.

For businesses and consumers, Apple’s AI challenges could impact the ecosystem of millions of devices and services that depend on Apple’s platforms. The company’s ability to deliver on its AI promises in 2026 will likely determine whether it maintains its premium market position or cedes ground to more AI-capable competitors. The foldable iPhone and affordable MacBook launches show Apple attempting to diversify its innovation portfolio, but AI execution remains the critical test of Cook’s leadership in the post-Steve Jobs era.

Source: https://www.businessinsider.com/apple-2026-expected-product-launches-2026-1