Apple is confronting major challenges in upgrading its voice assistant Siri with advanced artificial intelligence (AI) capabilities, raising investor concerns about its overall AI strategy and competitiveness in a rapidly evolving tech landscape. Despite focused efforts to enhance Siri using large language models (LLMs) for more natural conversations, Apple has faced technical setbacks and integration difficulties that have delayed its AI upgrade progress. Former employees reveal that Apple’s incremental update strategy—rather than rebuilding Siri from scratch—has caused persistent bugs and performance issues, leaving Siri behind more advanced rivals like OpenAI’s ChatGPT and Google’s AI. Insiders note that these gradual updates have compromised Siri’s functionality, user experience, and responsiveness. These delays have fueled investor skepticism ahead of Apple’s annual Worldwide Developer Conference (WWDC), an event historically showcasing AI advancements. Siri’s upgrade is central to Apple’s "Apple Intelligence" initiative, introduced at the previous WWDC, which aims to deliver AI-powered features improving user experience across Apple’s ecosystem. However, many promised capabilities remain unreleased, drawing criticism from analysts and users. Apple’s struggles are compounded by regulatory restrictions, particularly in China—one of its largest markets—where new rules limit free deployment of AI features and increase operational risks.

Additionally, escalating legal pressures in various regions further complicate AI development and rollout plans. These challenges have notably impacted Apple’s financial outlook and market perception, with the company’s stock dropping approximately 18% in 2025—the weakest performance among major tech firms—highlighting investor doubts about its innovation pipeline and competitive position in AI. Leadership shifts have also influenced Siri’s upgrade path. Apple’s strong focus on privacy through on-device AI processing—computations performed directly on devices instead of the cloud—has been praised for data protection yet introduced technical hurdles. This privacy-centric approach complicates deploying sophisticated AI features that typically depend on cloud-based resources. Meanwhile, competitors like OpenAI have intensified rivalry by partnering with designer Jony Ive to develop custom hardware optimized for AI, signaling a strategic divergence toward integrated hardware-software solutions that enhance performance and engagement. Apple CEO Tim Cook has publicly acknowledged Siri’s upgrade delays, citing the company’s high-quality standards and emphasizing a commitment to delivering a polished, reliable AI assistant rather than rushing incomplete features to market. This situation highlights Apple’s broader struggle to sustain its competitive edge amidst rapid AI advancements. As AI increasingly defines the technology sector, Apple faces pressure to speed up development, refine strategies, and meet investor and consumer expectations—balancing its core commitments to privacy and quality with the need to lead in AI-driven user experiences.