Glenn Wilkinson on the hacker mindset, the first AI-orchestrated ransomware attack, and why every shiny new threat still trips over the same old fundamentals.
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Featuring Glenn Wilkinson, co-founder & CEO of Agger Labs · Hosted by Sam Dickison
Some guests bring a war story. Glenn Wilkinson brings a stage show. Early in this episode he tells us about Snoopy — a tool he built during his time at SensePost that quietly profiled audience members’ phones during a live theatre production about privacy. As people reached for the venue Wi-Fi, Snoopy pieced together names, home addresses and travel histories from thin air. At the finale, the show’s star turned it all back on the room from the stage: welcome, John from Boston — and here’s a picture of your house.
Glenn still lights up recalling the actor who fronted it crossing the room to introduce himself — “you must be the hacker” — and being disarmingly kind about the whole thing. It’s a fitting way in, because everything Glenn does runs on the same instinct: this says I can’t. Let’s see about that.
Anarchist or engineer?
Glenn traces the instinct to a childhood in Zimbabwe, where a first computer was a precious, irreplaceable thing — break it and there was no replacement. He got bored of the hardware fast and fell for software instead: the demo games that shipped on magazine cover-CDs, locked to one level. With no way to buy the full versions, he taught himself to bypass the copy protection just to keep playing. Early reverse engineering, dressed up as a kid wanting more game.
That, he says, is the whole thing in miniature. The hacker mindset has two parts: a love of tinkering and puzzles, and a healthy disdain for authority. Or, as he puts it: are you an anarchist or an engineer? It’s a distinction the show keeps landing on with different guests — IT is about understanding how something works; hacking is about understanding how something breaks.
“This says access denied. That’s interesting. I wonder if I can get past that—or make it do something different.”
Glenn Wilkinson
These days that instinct has a business behind it. Glenn is co-founder and CEO of Agger Labs, an anti-ransomware startup born out of a simple frustration: when his team pulled apart the existing EDR and antivirus tools, none of them were much good at stopping novel ransomware. Their answer is a lightweight endpoint agent that runs entirely locally — no signatures, no cloud lookups — and judges every program by its behaviour. Because ransomware has to act like ransomware, the agent lays deception traps for it to trip over, which keeps false positives near zero. It was also engineered from day one to be near-impossible to tamper with; customers now ask it to stand guard over their EDR, backup and logging servers too. Like a little bodyguard, Glenn says.
The first AI-orchestrated ransomware attack
Which brings us to the reason this episode is so timely. Sysdig’s threat research team recently documented what’s being described as the first observed end-to-end agentic ransomware attack — a campaign given the excellent name Jade Puffer. Glenn’s honest first reaction? “Wow, that’s so cool” — before catching himself, the way a virologist might admire a nasty new strain before remembering whose side they’re on.
The important nuance: the ransomware itself wasn’t magically “AI-powered.” What was new is that the intrusion — the reconnaissance, the break-in, the lateral movement, the escalation — appears to have been orchestrated by an AI model. “The important word,” Glenn stresses, “is orchestrated.” At the low end, that might be nothing more than someone proxying commands through a model with its guardrails stripped off, asking what should I do next? and pasting the answers into a live target.
How did anyone know it was AI? It got sloppy. The logging was verbose, and the Python payloads were littered with comments that exposed the model’s own reasoning — the kind of housekeeping a seasoned human attacker would have scrubbed before deploying. Glenn suspects it may even have been botched: the encryption key possibly never made it back to the attacker, which raises the grim possibility it was a test, a ransomware-as-a-service dry run, or thinly veiled wiperware dressed up as ransomware.
The part worth sitting with
This cutting-edge, AI-driven attack got its foot in the door through a Langflow server carrying a roughly year-old, unpatched remote-code-execution vulnerability.
Every new layer of technology just finds a new way to exploit the fundamentals.
The black piano fallacy
This is Glenn’s drum, and he beats it everywhere — including on BBC Breakfast, where his advice to eight million viewers was simply: get your basic cyber hygiene right. He borrows a line from his friend Dominic White to explain why people get this wrong. Picture walking down a dodgy street at night, worrying that a piano might fall on your head. Your risk register is skewed: you should be thinking about getting mugged, not about the one-in-a-million piano. Security teams do the same thing — they get excited and anxious about the exotic new threat while the attackers quietly walk through the front door the basics left open.
So what does AI actually change? Not the playbook — the clock. The timelines defenders used to enjoy (days, weeks, months to react to a new vulnerability, because human attackers are relatively slow) can collapse when a model helps reverse-engineer a patch and weaponise it at speed. The fundamentals don’t matter less in that world. They matter more, and faster. If anything, Glenn and Sam agree, that’s an argument for more skilled defenders, not fewer — someone still has to patch the box and keep the inventory honest.
We’ve seen this rush before
Glenn has been in the game long enough to recognise the pattern. Dot-com. Cloud. IoT. Web3 and crypto. Each time, the same story: everyone rushes to adopt the shiny new thing, and security is a problem for later. AI is simply the current chapter. Fools rush in where angels fear to tread — and hackers love it, because every rushed rollout means a bigger attack surface and more complexity to hide in.
The Langflow box is the archetype. Somewhere, someone was told “we need to do AI,” stood up a server, left the default credentials in place, skipped the updates, and moved on. Quite possibly shadow IT the sysadmins didn’t even know was running. Layer upon layer of ordinary risk, created by the pressure to move fast.
Tools, not jobs
For all that, Glenn is not a doom-monger — and he’s pointed about the anxiety the hype is causing. He gets graduates coming up after talks asking whether they should abandon cybersecurity for a plumbing diploma. His answer, drawn from watching tools come and go for decades (he remembers the same end-of-the-world panic when Metasploit first landed): AI will replace tools, not people.
“Be the AI wrangler. Maybe in five years you manage fifty agents — but you’re the one in charge.”
Glenn Wilkinson, on advice for the next generation
And a neat economic backstop for the anxious: if all the humans are replaced, who’s putting cash into the economy to buy what’s being built?
He’s just as sharp on why the guardrails around these models keep failing. Prompt engineering is now a genuine skill — and so is prompt injection. The reason jailbreaks are such an endless game of whack-a-mole, he explains, is structural: the industry largely tamed SQL injection by learning to separate data from commands. Large language models put your instructions and your data in the very same channel. Until that’s solved, tricking a model into confusing the two will remain frustratingly doable.
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