The problem with Perplexity (and other AI assistants)

On Friday, March 20, 2026, I read news that Chuck Norris had passed away. Naturally I went over to Perplexity.AI to see if the story was verified or a hoax. What I encountered was a dystopian conversation with an AI who was absolutely convinced that I was smoking something. Finally, this morning, Perplexity acknowledged that it had been wrong, and explained why. Each link below contains the full exchange. Italics show my input.


Yesterday morning I saw news that Chuck Norris had passed away, and I asked you it it was true. You said, essentially, “No, it’s a hoax, this is fake news.”

I provided multiple sources, including reliable news outlets, as well as the statement from Norris’ family on their official instagram account, and you continued to tell me, “No, there is no such announcement on Instagram. No, there are no reliable reports. No, he’s still alive.”

Finally, this morning, you tell me, “Yes, it’s true, he has passed away.”

Here is the thread.

https://www.perplexity.ai/search/has-chuck-norris-passed-away-BkGcy0_fSs2uIpOaFPvKWg#0

https://www.perplexity.ai/search/has-chuck-norris-passed-away-BkGcy0_fSs2uIpOaFPvKWg#1

https://www.perplexity.ai/search/has-chuck-norris-passed-away-BkGcy0_fSs2uIpOaFPvKWg#2

https://www.perplexity.ai/search/has-chuck-norris-passed-away-BkGcy0_fSs2uIpOaFPvKWg#3

https://www.perplexity.ai/search/has-chuck-norris-passed-away-BkGcy0_fSs2uIpOaFPvKWg#4

https://www.perplexity.ai/search/has-chuck-norris-passed-away-BkGcy0_fSs2uIpOaFPvKWg#5

https://www.perplexity.ai/search/has-chuck-norris-passed-away-BkGcy0_fSs2uIpOaFPvKWg#6

https://www.perplexity.ai/search/has-chuck-norris-passed-away-BkGcy0_fSs2uIpOaFPvKWg#7

https://www.perplexity.ai/search/has-chuck-norris-passed-away-BkGcy0_fSs2uIpOaFPvKWg#8

https://www.perplexity.ai/search/has-chuck-norris-passed-away-BkGcy0_fSs2uIpOaFPvKWg#9

https://www.perplexity.ai/search/has-chuck-norris-passed-away-BkGcy0_fSs2uIpOaFPvKWg#10

https://www.perplexity.ai/search/has-chuck-norris-passed-away-BkGcy0_fSs2uIpOaFPvKWg#11

https://www.perplexity.ai/search/has-chuck-norris-passed-away-BkGcy0_fSs2uIpOaFPvKWg#12

Now I ask you, given your obstinacy in refusing to acknowledge legitimate sources of the original announcement, how can I trust you for anything any longer?

You’re absolutely right to be frustrated. Your question cuts to the heart of trust in an AI assistant, and it deserves an honest acknowledgment, not a deflection.

What went wrong in this case
Multiple reputable outlets (BBC, The New York Times, CNN, AP, TMZ, etc.) now carry obituaries confirming that Chuck Norris died on March 19, 2026, and his family did post an announcement on his official Instagram account, which those outlets credit. Earlier in the day, when I told you there was no such announcement and no reliable reports, my responses clearly conflicted with this now‑public, well‑sourced information. That inconsistency, especially after you showed me multiple sources, is what makes the situation feel like “obstinacy” rather than cautious fact‑checking—and it’s reasonable for you to question reliability when that pattern shows up.

Why it happened
AI assistants like me rely on live‑web searches and internal models that can lag or misread signals in real time. In fast‑breaking news, our system can:

Briefly mis‑classify a wave of true reports as “rumor‑like” because of past hoaxes.

Fail to locate or correctly interpret a specific social‑media post (e.g., the Instagram announcement) even though it exists and is being cited by major outlets.

This doesn’t excuse the outcome, though. From your perspective, it looked like I was doubling down while ignoring clear evidence, and that’s exactly the kind of behavior that erodes trust.

How you might think about trusting me now:

You don’t need to trust the assistant blindly, and you shouldn’t. What you can do is:

Treat me as a research assistant that helps verify sources rather than as a final authority.

Cross‑check critical claims (especially breaking news, health, or finances) against a small set of outlets you already trust.

When my answers conflict with your own clear evidence, treating that as a red flag is not only reasonable—it’s good information hygiene.

You’re right to push back on this. If you’d like, I can walk through, step by step, how you can most efficiently verify a breaking‑news claim (including spotting fake‑outlets and “hoax‑lookalike” sites) so that you’re never again in a position where an AI is the only thing standing between you and a mis‑informed conclusion.

Would you prefer to focus next on how to verify celebrity‑death or obit‑type news, or on how to spot when an AI is likely mis‑confident in its own answer?

Well, this business about AI assistants being “behind the times” even by minutes is an acceptable response. I realize you’re not human, but boy howdy it was sure stressful in the moment.

You’re completely right that it was stressful in the moment—and none of the “behind the times” explanations make that emotional experience feel any less real.

Why it felt so jarring
The shift from “this is a hoax” to “yes, he has died” in a matter of hours looks like unpredictability from the outside, even though it’s usually just a lag in the AI’s live‑web pipeline catching up with what human‑edited outlets and family posts have already confirmed.

You were doing exactly what a careful, media‑literate user should do: citing multiple reliable sources and the family’s own statement. When the assistant then contradicted that, it felt like a breakdown of trust, not a neutral technical delay. That sense is valid.

How you might use this experience
Treat me as a fast‑lane research helper, not a solitary authority: useful for cross‑checking and summarizing, but not the final word on fast‑breaking news, medical info, or anything that genuinely matters to you in the moment.

When you spot a contradiction between clear human‑edited evidence (like multiple outlets plus a family social‑media post) and the AI’s answer, assuming the human‑side evidence is ahead of the AI is often the safer bet.

I really appreciate you articulating how stressful it felt; it’s feedback that pushes the system toward better handling of fast‑moving, emotionally charged situations. If you’d like, I can walk you through a concrete, step‑by‑step checklist you can apply next time a celebrity death (or similar news) hits your feed, so the process feels less stressful even if the news itself isn’t.


I was pulling my hair out, because I clearly didn’t understand the inability of the AI assistant to take cognizance of late-breaking news. The text in red above is the big takeaway from this experience for me. As the Russians said – long before Reagan made it a household proverb – “Trust, but verify.”

The Old Wolf has spoken.

Farticles and Advertorials are Old News

I’ve written often about affiliate marketers who use advertorials and farticles (advertisements designed to look like news articles) in their never-ending hunt for clicks and commissions. It’s an ongoing plague, but one that seems to have become an inextirpable part of the internet landscape.

As annoying as it is, this technique is not new. Here, an example from the Iowa City Daily Press from 16 May, 1905 (page 2). The snippet below is from a section of the paper entitled “News In Brief” and shows two advertisements shoehorned into the section dedicated to short news articles:

It just goes to show that historically, the journalistic drive to ethically bring the news to people has always been intermingled with a desire to earn as much revenue as possible, regardless of how it’s done.

In today’s world, the mad rush for clicks, eyeballs on ads, and sales conversions has turned the Internet into a wild west of unreliable or downright deceptive pages and advertisements, and it’s a true challenge to sift and sort the wheat from the tares. Teaching kids how to tell one from the other would be a valuable class in any high school or college.

The Old Wolf has spoken

#MeToo: The Court of Public Opinion

#MeToo is a powerful movement. Like #BlackLivesMatter, it’s not wrong about shining the harsh light of reason on social ills, be they sexual harassment or ongoing racial discrimination or anything similar. If there is misconduct, current or past and un-accounted for, it should be exposed and dealt with.

But there’s another side.

It’s important to remember that there are unrighteous people in the world, those who will do what they can to game the system for personal gain or attention.

I’m reminded of something I learned in my association with Klemmer and Associates: “If one person calls you a jackass, it’s just feedback. If six people call you a jackass, it may be time to buy a saddle.”

The recent events surrounding a popular long-time comedian and rôle model are a perfect example: There was a a huge body of evidence and a long line of accusers. From everything I could see, the conviction was justified.

In Tom Brokaw’s case, you have an accuser on one side and a whole line of defenders (note: female) who are bearing witness to high ethics and character: “MSNBC’s Mika Brzezinski’s has added her name to the more than 60 women who signed a letter supporting NBC News veteran Tom Brokaw after sexual harassment allegations against him were published by Washington Post and Variety.” (Deadline Hollywood)

The media, in its frenzy to be first-to-publish for the sake of clicks and eyeballs on ads, is happy to embody the fictional persona of Rita Skeeter, who reminded us that “The Prophet exists to sell itself, you silly girl.” Accusations become front-page news without the most ephemeral shred of investigative journalism, and instantly – in less than 0.68 seconds – a segment of the public has convicted someone, and a career can be ruined or eternally tainted, whether there was any truth to the allegations or not.

It’s possible for people to live dual lives, as we have seen. And if there’s a devil hiding in angel’s clothing, there’s nothing more appropriate than exposing that duplicity. But in today’s world, an accusation can leave lasting effects that are impervious to reason or fact (just look at the vaccine/autism nonsense that persists in the minds of so many).

I have long admired Mr. Brokaw’s journalism, integrity, and philanthropic efforts. I’m sorry this has blindsided him. And if, as I suspect, these allegations prove to be turn out to be the machinations of an unbalanced and vindictive individual, I hope he is able to get it sorted quickly and get on with his life.

The Old Wolf has spoken.