MacRumors, on June 20:

Apple executives have been discussing the possibility of the company making a bid to acquire Perplexity AI, according to Bloomberg’s Mark Gurman. Perplexity is one of the leading AI startups that has proven popular as an AI-infused web search engine.

From that Bloomberg report by Gurman:

Adrian Perica, the company’s head of mergers and acquisitions, has weighed the idea with services chief Eddy Cue and top AI decision-makers, according to people with knowledge of the matter. The discussions are at an early stage and may not lead to an offer, said the people, who asked not to be identified because the matter is private.

Such a deal would help Apple develop an AI-based search engine, part of efforts to cope with the potential loss of a longstanding arrangement with Google. That partnership, which involves making Google the default browser on devices, generates roughly $20 billion a year for Apple — and is now under threat from US antitrust enforcers.

To date, Apple executives haven’t discussed a bid with Perplexity management. Bloomberg News reported earlier Friday that Meta Platforms Inc. tried to buy Perplexity earlier this year.

“We have no knowledge of any current or future M&A discussions involving Perplexity,” the AI startup said in a statement. Apple declined to comment.

I think, reading between the lines of Apple’s prepared remarks and Tim Cook’s and CFO Kevan Parekh’s answers to analyst questions last week after announcing quarterly earnings, that it doesn’t sound like they believe Apple needs to make a big acquisition in this space. Apple could probably acquire Perplexity for a lot less than it would cost to acquire other companies in the space, but that’s partly because Perplexity doesn’t develop or train its own models. Perplexity primarily puts up its own front end atop models from OpenAI, Anthropic, Mistral, Google, and xAI. I really don’t see what buying Perplexity would gain Apple.

But even putting that aside, it just seems like Perplexity is sketchy. This whole thing where Cloudflare seemingly caught them redhanded ignoring robots.txt directives and masquerading their user-agent makes the company seem like a poor cultural fit for Apple. I can see why Meta, a company without a moral compass, approached Perplexity to sniff around regarding an acquisition. That seems like a good cultural fit.

I can’t see why Apple would want to get involved with a company like this though. Gurman’s report makes it sound like his sources are inside Apple, but man, this “Apple + Perplexity” thing feels more like something Perplexity would be seeding than one that Apple executives would be leaking.

The Cloudflare blog:

We are observing stealth crawling behavior from Perplexity, an AI-powered answer engine. Although Perplexity initially crawls from their declared user agent, when they are presented with a network block, they appear to obscure their crawling identity in an attempt to circumvent the website’s preferences. We see continued evidence that Perplexity is repeatedly modifying their user agent and changing their source ASNs to hide their crawling activity, as well as ignoring — or sometimes failing to even fetch — robots.txt files.

The Internet as we have known it for the past three decades is rapidly changing, but one thing remains constant: it is built on trust. There are clear preferences that crawlers should be transparent, serve a clear purpose, perform a specific activity, and, most importantly, follow website directives and preferences. Based on Perplexity’s observed behavior, which is incompatible with those preferences, we have de-listed them as a verified bot and added heuristics to our managed rules that block this stealth crawling. [...]

Our multiple test domains explicitly prohibited all automated access by specifying in robots.txt and had specific WAF rules that blocked crawling from Perplexity’s public crawlers. We observed that Perplexity uses not only their declared user-agent, but also a generic browser intended to impersonate Google Chrome on macOS when their declared crawler was blocked.

Perplexity has responded, accusing Cloudflare of incompetence and publicity-seeking:

Because Cloudflare has conveniently obfuscated their methodology and declined to answer questions helping our teams understand, we can only narrow this down to two possible explanations.

1. Cloudflare needed a clever publicity moment and we–their own customer–happened to be a useful name to get them one.
2. Cloudflare fundamentally misattributed 3-6M daily requests from BrowserBase’s automated browser service to Perplexity, a basic traffic analysis failure that’s particularly embarrassing for a company whose core business is understanding and categorizing web traffic.

Whichever explanation is the truth, the technical errors in Cloudflare’s analysis aren’t just embarrassing — they’re disqualifying. When you misattribute millions of requests, publish completely inaccurate technical diagrams, and demonstrate a fundamental misunderstanding of how modern AI assistants work, you’ve forfeited any claim to expertise in this space.

Perplexity’s response makes it sound like Cloudflare just doesn’t get how leading-edge AI chatbots work, and what users expect of them. But going back to Cloudflare’s post, they specifically cite OpenAI as an exemplar in respecting the directives of website publishers:

When we ran the same test as outlined above with ChatGPT, we found that ChatGPT-User fetched the robots file and stopped crawling when it was disallowed. We did not observe follow-up crawls from any other user agents or third party bots. When we removed the disallow directive from the robots entry, but presented ChatGPT with a block page, they again stopped crawling, and we saw no additional crawl attempts from other user agents. Both of these demonstrate the appropriate response to website owner preferences.

And nothing in Perplexity’s response attempts to explain Cloudflare’s accusation that Perplexity is adopting a false generic user-agent when their own declared user-agents are disallowed. Seems shifty to me.

Coming March 17, 2026:

In time for Apple’s 50th anniversary, “CBS Sunday Morning” correspondent David Pogue tells the iconic company’s entire life story: how it was born, nearly died, was born again under Steve Jobs, and became, under CEO Tim Cook, one of the most valuable companies in the world.

The 600-page book features 360 full-color photos, new facts that correct the record and illuminate Apple’s subversive culture, and 150 fresh interviews with the legendary figures who shaped Apple into what it is today.

Antonio G. Di Benedetto:

Part of me still can’t believe it, but Lenovo did the thing: it took a bonkers concept for a laptop with a rollable screen and built the tech into something you can actually own and use like a normal computer. Except, as conventional as the ThinkBook Plus Gen 6 can be, it’s far from a normal computer. It’s a $3,300 laptop with a screen that expands from 14 inches to 16.7 inches at the push of a button.

Oh, and it’s actually good. Not just good, but very good. I still can’t believe it.

Di Benedetto, as you can see, is enthusiastic for the laptop. I think it’s a clever idea, but this first instance seems pretty compromised:

As with a foldable phone, you can see some creases and ripples in the screen’s lower third — the part that rolls up — especially at oblique angles. If I look closely while working on a bright-white document, I can sometimes make out a faint shadowy strip, but I rarely see it, even when staring at that spot. The motorized screen takes about eight seconds to extend or retract, and it’s no louder than the fans on an average gaming laptop. People right near you in a quiet space will hear it, but even ambient sounds like a TV in the background easily mask the motor.

Alexandra Steigrad, reporting for The New York Post:

The new publication will be headquartered in Los Angeles and feature a robust staff of editors, reporters and photographers dedicated to covering news, entertainment, politics, culture, sports and business — all with a distinctly California perspective.

The California Post will be supported by the team in New York providing national and international news. The content will appear in a daily print edition and will have its own dedicated homepage for Californians with stories being published across multiple other platforms, including video, audio and social media.

Who says print is dead?