Apple’s big Siri update is here. Now the real challenge begins

Apple CEO Tim Cook waves on stage during Apple's annual Worldwide Developers Conference in Cupertino, California, on June 8, 2026. Carlos Barria/Reuters via CNN Newsource

Siri is finally getting the big AI upgrade Wall Street has been waiting for. But it’s just the beginning.

Apple on Monday announced Siri AI, a major revamp the company hopes will thrust its roughly 15-year-old digital assistant into the spotlight alongside OpenAI’s ChatGPT and Google’s Gemini. The new assistant, which will launch in beta later this year, will help operate apps, analyze an iPhone’s screen to answer questions and incorporate personal context into responses, the company said.

• READ MORE: Apple’s Siri is finally getting a big AI upgrade

After falling behind in the AI race, Apple has been under pressure over the past couple of years to prove it has a plan to catch up. The company will soon have to prove it can leverage its AI assistant to drive iPhone upgrades, boost services revenue and power new types of products. But perhaps the most important question for investors is: Can Apple, a company known for turning nascent technologies into blockbuster products, convince people to pay for AI?

“Updates felt more evolutionary vs revolutionary, and we continue to view (Apple) as a laggard in AI with no killer apps and a questionable monetization strategy,” Barclays analysts wrote in a research note following Apple’s event.

Apple did not immediately respond to CNN’s request for comment on its monetization plans for Siri AI and Apple Intelligence.

Apple isn’t the only tech giant drawing doubts about its AI capabilities. OpenAI and Anthropic — both of which are on the verge of going public — have faced skepticism over whether they’re generating enough revenue to justify their sky-high valuations and investments.

Apple has been shielded from some of those concerns because it generates most of its revenue from iPhone sales, which have been booming. The company posted record revenue for the March quarter that was largely driven by iPhone 17 demand.

But analysts are still looking for signs that Apple’s AI ambitions will lead to more Phone upgrades, iCloud+ subscriptions or both. Morgan Stanley analysts said Apple’s announcements provided “clearer paths to monetizing AI” in a note following the event, although they also said Apple’s AI advancements will be a “marathon, not a sprint.”

Siri AI and Apple’s other AI tools are available on phones as old as the iPhone 15 Pro, which launched in 2023. But more than half of iPhones don’t support Apple Intelligence, according to estimates Bloomberg Intelligence analyst Anurag Rana previously shared with CNN. Even if those users buy new iPhones this fall, it will likely be for longer battery life or faster performance — not AI features.

“I don’t think (AI is) driving upgrade cycles in the way that manufacturers were hoping that it would,” Paul Schell, a senior analyst covering AI for research firm ABI Research, told CNN.

Still, Apple’s announcements this week provided a peek at how AI features could entice users toward pricier iPhones and subscriptions.

Certain Siri AI functions — like more accurate voice dictation and the ability to customize its voice to sound more expressive — can only be accessed using Apple’s top-tier iPhones: an iPhone Air, iPhone 17 Pro or iPhone 17 Pro Max. More than 1.3 billion iPhones currently in use don’t have the computing power or memory to run those two Siri features, according to Morgan Stanley estimates.

Some Apple Intelligence features, like higher limits on image generation and descriptions of footage from smart home cameras compatible with Apple’s HomeKit system, will require an iCloud+ subscription.

Making Siri key to the iPhone’s future

Apple is aiming to shift Siri from an assistant that answers questions to a critical tool across the iPhone’s software. Google and Samsung have been racing toward the same goal by incorporating Gemini into Android in recent years.

The use cases Apple outlined for Siri AI are meant for everyday tasks rather than office work. This is a stark contrast from ChatGPT and Anthropic’s Claude, which target businesses.

“I’m looking for something, I’m replying to a text message, I’m trying to find the address of the restaurant that my friend mentioned last week — those kind of things,” Carolina Milanesi, president and principal research analyst at Creative Strategies, said in reference to Siri AI’s main functions. “I’m not saying that people will use Siri for productivity, but that’s not really what Apple cares about.”

Apple on Monday showed how Siri could reference content from texts, so that users can ask it questions like, “Where’s Jeff’s new place?” to pull a friend’s new address from a recent message. Siri can also understand what’s on an iPhone’s screen, as Apple vice president of Siri engineering Mike Rockwell showed in another example. He asked Siri for directions to a landmark he was looking at in a photo, with a stop at his friend’s house along the way.

Apple’s current offerings aren’t enough to convince users to buy an US$1,000 iPhone or subscribe to a pricier iCloud plan yet. But in the near term, they could help Apple lock in existing iPhone users.

“It’s going to be difficult for a user to migrate from iOS to Android, with the Siri AI model understanding you, and now your personal context, and all of the history,” said Nabila Popal, a senior director at market research firm the International Data Corporation covering smartphones. “You’re going to leave that behind when you switch completely.”

Lisa Eadicicco, CNN