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Siri’s Growing Pains: Apple’s Struggle to Compete in AI

By Matt Seitz

March 17, 2025

TL;DR Apple’s Delay in Rolling Out Apple Intelligence increased dissatisfaction with Siri and reinforced the perception that it is falling behind in AI.  The failure to deliver on promised features was highly visible and frustrated users, employees and industry observers.  The episode highlights the challenge in delivering on “Agenic AI”, which has tremendous promise but requires addressing issues of consistency, reliability, privacy and security.

Key Dynamics to Watch

Apple Intelligence struggled with basic answers, including fabricating facts about a Super Bowl that has not happened yet.
  • Missed Opportunity: While Apple’s integrated software and data access position it to deliver an incredible AI-based user experience, they have struggled to deliver even basic features like email summaries and personalized notifications.
  • Cracks in Culture: Under Steve Jobs and Tim Cook, Apple developed a track record of always delivering quality products on time.  This delay was a stark departure and raised questions about company culture, processes and executive leadership.  
  • Security Risks:  Apple Intelligence falls into a class of AI assistants” with tremendous promise for personal productivity through planning activities, managing calendars and responding to emails but pose risks like unwanted purchases, data leakage and malware.
  • Inconsistent Results:  AI Chatbots use probabilistic, sampling-based approaches that provide different results each time.  This works well for tasks that benefit from creativity like writing and advertising but is risky in areas requiring precision like medical diagnoses or autopilots.  
  • Hybrid Approaches:  Human oversight is essential in ensuring quality results and industries like retail, finance and travel are combine AI chatbots with legacy back-end systems to ensure precise results at scale.  

Apple was mocked for its laughable results while featuring Apple Intelligence in its marketing campaign. Screenshots show inaccurate and alarming summaries created by Apple Intelligence.

My Take

Apple’s products dominate our digital lives, making it the most valuable company in the world with a $3.2 trillion market capitalization.  Today’s Apple is a reflection of Steve Jobs, who built Apple into an iconic brand synonymous with product excellence.  Part of Steve’s success was finding great partners; Steve Wozniak’s technical acumen, Jony Ive’s design prowess and Tim Cook’s operational excellence complemented his vision, creativity and commitment.

All language models, including ChatGPT 4, struggle with numerical precision due to their stochastic approach. A screenshot shows ChatGPT 4 responding that 9.11 is bigger than 9.9
Source: ThoughtFox

Despite its dominance in hardware, Apple has fallen behind in AI, trailing competitors like Google, Microsoft and Amazon.  While these players have had their own missteps, they have aggressively integrated AI into their core products.  This gap began with Siri and has become a glaring weakness with Apple Intelligence. Apple’s privacy-first approach compounds the problem by limiting its ability to leverage cloud-based AI solutions.

Last year’s announcement of Apple Intelligence included a simple example: “What time does Mom’s flight land?” This basic question is a great example of the complexity of AI agents.  Consider a typical modern family:  The AI must discern which ‘Mom’ the user is referring to including in-laws, exes, grandmothers and more.  It then has to choose between multiple flights in emails or calendars, some of which might be held, changed or canceled.  If the AI chooses incorrectly, Mom may be stuck at the airport.

This is a good example of the broader challenge with AI.  In creative domains like writing or advertising, 90% accuracy works well.  But in high-stakes areas like medical diagnoses, piloting aircraft or precision manufacturing, 99% accuracy falls short. 

Just as Steve Jobs had Wozniak, Cook and Ive, AI has a partner ideally suited to the challenge: traditional computing systems.  Whereas AI excels at language and ambiguity, traditional systems use logic and rules to ensure stability and consistency.  Chatbots in retail and travel combine AI with legacy systems to handle customer requests like checking inventory and processing returns.  

Apple can be a leader in personal AI. People use their iPhones hundreds of times daily, trusting the company with their most intimate data. By combining AI’s creativity with traditional computing’s precision, wrapped in Apple’s signature design, Apple Intelligence can follow the Jobs playbook: not being first, but being best.


Dad Joke: Why couldn’t Apple Intelligence help you with your homework?  Because it was taking a “Siri-ous” delay!


Articles

Apple delays Siri AI improvements to 2026

CNBC

“Besides OpenAI, Apple risks falling behind rivals including Amazon, which announced an upgraded Alexa voice assistant last month but hasn’t released it, and Google, which is developing similar capabilities with its Gemini assistant. But all consumer voice assistants have had issues with incorrect answers and task automation.

The delay to Siri’s supercharged features isn’t Apple’s first run-in with issues adapting to new-age AI.  Earlier this year, the company disabled Apple Intelligence summaries for news apps like The New York Times and BBC after users discovered that the AI system had twisted headlines to display inaccurate facts.

Apple’s Siri Chief Calls AI Delays Ugly and Embarrassing, Promises Fixes

Bloomberg

“Walker said the decision to delay the features was made because of quality issues and that the company has found the technology only works properly up to two-thirds to 80% of the time. He said the group ‘can make more progress to get those percentages up, so that users get something they can really count on.'”

Something Is Rotten in the State of Cupertino

Daring Fireball

“That level is called vaporware. They were features Apple said existed, which they claimed would be shipping in the next year, and which they portrayed, to great effect, in the signature ‘Siri, when is my mom’s flight landing?’ segment of the WWDC keynote itself, starting around the 1h:22m mark. Apple was either unwilling or unable to demonstrate those features in action back in June, even with Apple product marketing reps performing the demos from a prepared script using prepared devices.

What Apple showed regarding the upcoming ‘personalized Siri’ at WWDC was not a demo. It was a concept video. Concept videos are bullshit, and a sign of a company in disarray, if not crisis.

Keynote by keynote, product by product, feature by feature, year after year after year, Apple went from a company that you couldn’t believe would even remain solvent, to, by far, the most credible company in tech.  Apple remains at no risk of financial bankruptcy (and in fact remains the most profitable company in the world). But their credibility is now damaged. Careers will end before Apple might ever return to the level of “if they say it, you can believe it” credibility the company had earned at the start of June 2024.”