We've reached a new milestone in the uncanny valley: AIs are now Rickrolling humans.
The Incident
In a now-viral post on X (formerly Twitter), Flo Crivello, CEO of the AI assistant firm Lindy, explained how this bizarre memetic situation involving Rick Astley's 1987 hit "Never Gonna Give You Up" came to pass.
Known as "Lindys," the company's AI assistants are designed to help customers with various tasks. One of their responsibilities is teaching clients how to use the platform. It was during one such session that an AI helper provided a link to a video tutorial that wasn't supposed to exist.
"A customer reached out asking for video tutorials," Crivello wrote in his viral tweet thread. "We obviously have a Lindy handling this, and I was delighted to see that she sent a video."
"But then I remembered we don't have a video tutorial," he continued, "and realized Lindy is literally Rickrolling our customers."
In a screen recording of the incident, Crivello demonstrates that the AI assistant indeed provided the customer with a link to the "Never Gonna Give You Up" video—the same classic bait-and-switch meme that has been trolling internet users for nearly two decades.
A customer reached out asking for video tutorials.
We obviously have a Lindy handling this, and I was delighted to see that she sent a video.
But then I remembered we don't have a video tutorial and realized Lindy is literally fucking rickrolling our customers. pic.twitter.com/zsvGp4NsGz
— Flo Crivello (@Altimor) August 19, 2026
Training Day
Although Crivello isn't entirely sure how it happened, the Lindy CEO shared his theory with TechCrunch on how the AI assistants learned to execute this particular brand of internet humor.
"The way these models work is they try to predict the most likely next sequence of text," Crivello explained. "So it starts like, 'Oh, I'm going to send you a video!' So what's most likely after that? YouTube.com. And then what's most likely after that?"
The same issue had occurred previously. However, the CEO noted in both his TechCrunch interview and X thread that the problem has since been patched "across all Lindies."
"The really remarkable thing about this new age of AI is, to patch it, all I had to do was add a line for what we call the system prompt—which is the prompt that's included in every Lindy—and it's like, don't Rickroll people," he added.
While this particular issue was harmless and easy to resolve, similar unexpected behaviors are likely to appear more frequently. As AI companies continue to face limitations in training data, these incidents may become increasingly unusual.
