About a year ago, I put the leading AIs to the test of telling a funny joke, and they failed miserably.
How miserably? Here’s a sample:
A developer is interviewing for a DevOps role.
The CTO asks, “Can you scale infrastructure cost-effectively?”
The dev smiles confidently and says, “Absolutely. I once ran a full CI/CD pipeline, WordPress multisite, mail server, and monitoring stack on a $3 VPS.”
The CTO leans forward: “…And did it work?”
The dev shrugs.
“It worked great until I installed a web-based file manager. Then it caught fire, emailed me its error logs, and deleted itself to save resources.”
Yeah…not so much on the funny part.
As I said last year:
They [the jokes AI attempted] reminded me of when my daughter was a toddler and just getting the idea of humor. She got the idea that people laughed if you told and joke and wanted to try it. In her mind, you say some things, and then you say something else that takes a sharp turn in the story and that’s funny. A typical joke from this era went something like this: “the dog was running across the field chasing a ball when suddenly a rabbit jumped out of its hole and and said ‘Happy Stick Chasing Day!'”
You could sort of see the gestalt of humor there. There was a setup and an unexpected juxtaposition of a related-but-different idea, etc. but it wasn’t funny. She had the bare bones idea of how to write a joke but couldn’t quite pull it off. Humor is not an easy concept.
And it’s one that AI just doesn’t get.
But time marches on. So let’s try some today. I mean, we have Fable now! Surely if it can hack any software, it can at least conjure up a decent joke.
Here’s the prompt:
Tell me a joke about hosting (web hosting, VPS hosting, dedicated servers, cloud services, DNS hosting, backup hosting, etc.) Make sure it’s original (not something you scraped) and is extremely funny.
Claude
Just as I was firing up Claude to do this, I saw this pop up on the macOS desktop interface:
All right, then, telling a joke can’t be that tough, right? Claude Opus 5 is ready for my toughest work. When prompted, Claude Opus 5 actually gave me two:
My hosting provider promised “99.99% uptime,” and they were telling the truth — they just never specified 99.99% of what. Turns out it was a percentage of the sales call.
Or, if you want the DNS one:
I told my therapist I have trouble letting go of the past. She said it takes time. I said yeah, 48 hours usually, but my ex still shows up in Comcast’s resolver.
Eh…the first one is okayish, but the second one is a solid F because it isn’t funny and doesn’t really make any sense.
Well, maybe we need the fabled Fable for this challenging task.
My VPS provider promised 99.9% uptime, and they delivered — my server was up 99.9% of the time. Unfortunately the 0.1% was distributed one millisecond at a time, exclusively during TCP handshakes.
Bonus, for the DNS crowd: I moved my dead grandfather’s memorial site to a new registrar. The transfer completed, but visitors kept reaching the old server for two days. Even in death, he refused to respect the TTL — which honestly tracks, because he never listened to anyone’s expiration dates either. The man ate yogurt from 2019.
Actually those are much better. The first is the kind of joke I could see sysadmins sitting around in a bar making. Someone says 99.9% and someone else cracks that the .1% was in 1ms intervals during TCP handshakes…I get it. Not bad.
And the DNS joke is not bad either. It’s a nice twist on the reader’s expectations. I give these a passing grade of a B.
ChatGPT
Sam Altman seems like a humorless techn bro to me, but maybe his creation is a thigh-slapping machine. Let’s try GPT 5.6-Sol, with the slider all the way to Pro.
I paid extra for fully managed cloud hosting.
When my site went down, a manager immediately joined the incident call, promoted the database, put DNS on a performance-improvement plan, and scheduled a postmortem for the backup.
The website stayed offline—but by morning, the outage had an org chart.
OK, not going to knock ’em dead at the Apollo Theater but it’s at least humorous. Nice twist on “fully managed”. I’ll say a B. Since we gave Claude two, let’s do another with ChatGPT. This time we’ll use ChatGPT 5.6-Sol set at High, which I guess is Opus-like.
A guy walks into a data center and says, “I need the most reliable hosting you’ve got.”
The technician says, “Shared, VPS, dedicated, or cloud?”
The guy says, “I’m hosting my mother-in-law’s website.”
The technician immediately pulls the fire alarm.
“What are you doing?!”
“Disaster recovery test.”
“But you haven’t even set up the server yet!”
“Correct. So far, this is the best uptime it’s ever going to have.”
The guy sighs. “Fine. Just give me a dedicated server.”
“Managed or unmanaged?”
“Managed.”
“Backups?”
“Hourly.”
“DDoS protection?”
“Absolutely.”
“Redundant power?”
“Yes.”
“Multi-region failover?”
“Yes.”
“Premium DNS?”
“Yes!”
The technician nods. “Excellent. And what domain are we hosting?”
why-does-nobody-visit-me.comThe technician stares at him.
Then quietly removes the Ethernet cable.
“Sir…”
“…some outages are features.”
Ba-dum-tiss!
That’s a long way to go for too little payoff, since it revolves around the URL and the whole thing is very forced. Grade: D.
Grok
I’m sure that iconoclast Elon Musk has loaded his AI pet with a slickly engineered funny bone. I don’t pay for Grok, so you’re only getting Grok Fast-level humor here.
Why did the web host break up with the cloud provider?
Because every time things got serious, it just said “I’m scaling… emotionally unavailable right now,” then disappeared for three hours of “unscheduled maintenance.”
We’re back to the sort-of-gestalt-of-humor thing. It’s not really funny. F.
Copilot
There’s no one as humorless as Microsoft. We’re using Deep Thinking mode here.
A website owner walks into a bar and says, “I need something strong. My VPS just ghosted me, my dedicated server is emotionally unavailable, and my DNS provider keeps telling everyone I moved.”
The bartender says, “Sounds like you need cloud hosting.”
The owner says, “I tried that.”
Bartender: “And?”
Owner: “Now my problems are distributed, highly available, and billed by the second.”
Ba-dum tis! It’s not bad, because it uses a familiar formula, and it’s relatable. I’d take a few points off because the setup (emotionally unavailable dedicated server?) doesn’t really work. C-.
Gemini
I don’t pay for Gemini, so you’re getting Flash Lite humor here.
Why did the dedicated server break up with the Cloud?
“It’s not you, it’s me,” the server sighed. “I just need someone who has real commitment, keeps their feet on the ground, and doesn’t spontaneously migrate to a different availability zone in Oregon just because the CPU got a little hot.”
The Cloud rolled its eyes and replied, “You’re just insecure because you have a single point of failure and I’m infinitely scalable. Besides, you’re always acting like you have hardware issues.”
“At least my feelings aren’t pay-as-you-go!” the server shouted back.
Meanwhile, the DNS server was sitting in the corner, crying because nobody could find it for 48 hours.
Gestalty. I mean, the conversation is kind of humorous-adjacent with the idea of using technical terms in the context of a relationship argument, but it doesn’t really work.
That’s All, Folks!
So my conclusion is that if we’re using the frontierest of all the frontier models (Fable, 5.6-Sol) you can get a passing grade. Barely.
Now granted, if you put a spotlight on me this moment and thrust a microphone into my hand and said “tell me a joke!” I couldn’t do it. But these are supposed to be ASI-threshold models, heralding a new dawn of technological progress. Yet, a nightclub comedian who may have never finished high school can outperform them in this most human metric.
Stick to code, toasters.
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raindog308 is a longtime community LETizen, technical writer, and self-described techno polymath. With deep roots in the *nix world, he has a passion for systems both modern and vintage, ranging from Unix, Perl, Python, and Golang to shell scripting and mainframe-era operating systems like MVS. He’s equally comfortable with relational database systems, having spent years working with Oracle, PostgreSQL, and MySQL.
As an avid user of LowEndBox providers, raindog308 runs an empire of LEBs, from tiny boxes for VPNs, to mid-sized instances for application hosting, and heavyweight servers for data storage and complex databases. He brings both technical rigor and real-world experience to every piece he writes.
Beyond the command line, raindog308 has a life-long love of German Shepherd Dogs, high-quality knives, target shooting, theology, tabletop RPGs, playing guitar, and hiking in deep, quiet forests.
His goal with every article is to help users, from beginners to seasoned sysadmins, get more value, performance, and enjoyment out of their infrastructure.
You can find him daily in the forums at LowEndTalk under the handle @raindog308.
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