Sherwood News

Apple is behind in AI — maybe it can buy its way to the top?

Hey Siri, ask Perplexity whether this is a good idea.

6/23/25 10:21AM

Apple hasn’t taken AI as seriously as some of its peers, and now, it seems that the company’s top brass are considering writing a very large check to catch up in the space.

Though the company is yet to formally discuss a deal with Perplexity, some of Apple’s top decision-makers, including head of mergers and acquisitions Adrian Perica and Services chief Eddy Cue, have reportedly held internal discussions about making a bid for search engine Perplexity AI, according to Bloomberg News on Friday.

The consideration comes as the tech giant awaits the final ruling for Google’s antitrust trial, which will decide if Apple’s long-standing search partnership with Google — which was revealed to be worth $20 billion in 2022 — will be allowed to continue in any form.

Amid a recent series of Apple Intelligence failures and delays in Siri upgrades, the company is clearly keen to explore all options on the table, and Perplexity, which received 780 million queries in May, is growing at light speed. (It’s also racking up lawsuits at a pretty remarkable clip.)

But any potential deal would represent a major change to Apple’s M&A strategy. Unlike some of its more acquisitive peers, like Alphabet, Apple has typically preferred to make smaller acquisitions and grow products and teams organically. The company has made only three publicly reported transactions worth more than a billion dollars in its history.

With Perplexity recently completing a funding round that valued it at $14 billion — a figure that would likely only be a floor for any price negotiations — Apple would have to be willing to splurge. Of course, if any company can afford it, it’s Apple: the iPhone maker spent nearly $50 billion buying back its own stock over the past two quarters.

Note: A previous version of this article stated that Apple had spent nearly $50 billion buying back its own stock in the last quarter. This has been corrected. We regret the error.

Chris Stokel-Walker

Bot bias

6/17/26

Companies are getting AI chatbots to smear their competitors

The race to influence AI chatbots is leading to some companies to adopt shady competitive tactics.

Tom Jones6/17/26

Prediction markets have, predictably, been given a boost by the summer of sports

Major platforms like Kalshi and Polymarket have seen huge upticks in users of late, thanks in no small part to what’s felt like a recent sporting smorgasbord, with major competitions across hockey, basketball, and soccer soaking up fans’ time (and spending, clearly) at the outset of summer.

While gaming industry groups may not like it, there’s been a huge change in the methods people are using to put money on the big games, with everyone from fortunate NYC bar owners, to a far less fortunate Spanish supporter, turning to prediction markets to try and turn their sports know-how into cold, hard cash.

According to a new report from Adam Blacker for apptopia, that shift might have been even more seismic than imagined in the wake of the NBA and NHL finals and around the 2026 World Cup kicking off.

2026 World Cup Reverses Seasonal Lull for Sports Betting Apps

According to a new report from Adam Blacker for apptopia, that shift might have been even more seismic than imagined in the wake of the NBA and NHL finals and around the 2026 World Cup kicking off.

South by Southwest Conference and Festivals

Gold Tesla Cybercabs are piling up, but they’re not picking up passengers yet

Low-volume production started in April. Now people are noticing them more and more in the wild.

Rani Molla6/15/26

Millie Giles

TAKING ACCOUNTS

6/15/26

Britain announces social media ban for under-16s starting early 2027

The UK government plans to use the same model for the restrictions as Australia — but how successful has that case study been so far?

UK Prime Minister Announces Under-16s Social Media Ban

Jon Keegan6/15/26

Anthropic pulls Fable and Mythos access worldwide after Trump administration bars their use by foreign nationals

Only days after releasing two versions of its next-gen AI model, Anthropic has disabled them for users worldwide.

Anthropic says it received a Friday night order from the Trump administration to suspend access to the models for any foreign national (anywhere in the world) — a group that included some Anthropic employees. In response, the company turned off access to everyone.

Last week, the company released to the public its much-anticipated Claude Fable 5 model (and its restricted version Claude Mythos 5, which is still being tested with trusted partners). Anthropic said in a blog post announcing the action that officials cited national security concerns with the new models, while offering few specific details.

The post said that the government gave the company “verbal evidence of a potential narrow, non-universal jailbreak” of the public Fable 5 model. A jailbreak is a means by which users can evade restrictions built into the code to unlock prohibited functionality. Anthropic downplayed the significance of the attack, and said other major models, such as OpenAI’s GPT-5.5, could also be affected by the technique described.

Fears of these first Mythos-class models being misused are running high, after Anthropic warned the cybersecurity world in May that the advanced cyber capabilities of Mythos have rapidly discovered thousands of vulnerabilities in ubiquitous software, leading to the decision to restrict the full version of the model to a close group of trusted partners for testing.

This morning, Axios reported that Anthropic technical staff have flown to Washington to meet with White House officials to resolve the issue.

The Wall Street Journal is reporting that the Trump administration’s decision to take action against Anthropic was prompted by discussions that Amazon CEO Andy Jassy had with officials, including Treasury Secretary Scott Bessent. According to the report, Amazon researchers said they had been able to evade some of Fable 5’s security restrictions using specific prompts. Amazon is a major investor in Anthropic.

Anthropic is currently suing the US government to fight the Pentagon’s blacklisting of the company on national security grounds.

Statement on the US government directive to suspend access to Fable 5 and Mythos 5