There is a con called the Spanish Prisoner. A letter arrives from a stranger: a wealthy man sits in a foreign jail, and for a small advance to free him, he will reward you many times over. The trick is at least four hundred years old. It is also, give or take a few details, the email sitting in your spam folder this morning. I keep that in mind whenever someone tells me cybercrime is a technology problem. The tools change. The mark does not. We are still robbed through the same prehistoric wiring: a flash of fear, a moment of greed, a decision made in panic before the slow part of the brain wakes up. That is the thread I pulled on with Sarah Armstrong-Smith at InfoSecurity Europe. Sarah spent nearly thirty years in cyber and crisis leadership, was Chief Security Advisor at Microsoft, and now runs Secure Horizons. She has written two books on the human side of all this and sits on the UK Government Cyber Advisory Board. After all of it, she says the thing most people in her position will not say out loud: whatever we are doing is not working. More tools, more money, more people, more AI, and the problem keeps getting worse. Attack, wake-up call, attack, wake-up call. How many wake-up calls, she asks, does anyone need? I asked what keeps her up at night. She described an industrial accident on the scale of 9/11, triggered through a network: the first time a cyber incident kills people in numbers. We have been lucky so far. She doubts luck is a plan. The industry loves a big number, and the number is exactly where the human disappears. X million records stolen, Y terabytes gone. The day before, my friend Geoff White sat in this same chair and described a ransomware attack that shut down a hospital, which meant a woman missed the cancer appointment she had counted on. That is an Armageddon, and it has a name and a face. Sarah, as it happens, knows Geoff’s work well enough to carry a line from him on the back of her book. The human element keeps finding the same small circle of people willing to talk about it. So how do we move this from a line item to a fact of society? Her answer is collective resilience. There is no prize for being the last one standing, because we are all wired into the same supply chain, the same dependencies, the same brittle web. And the smallest businesses, the ones without a war chest to ride out the storm, are the ones we discuss the least. Then a statistic. Close to half of all crime in the UK is now fraud or cyber. Around one percent of policing is pointed at it. Read those two numbers again. We fund what we can see, and we want officers on the street because a visible patrol both deters the thief and reassures the neighbourhood. The crime that actually empties our accounts happens somewhere we have agreed not to look. Follow the money, Sarah says, and you rarely stop at one criminal’s pocket. It pays for the next thing: drugs, weapons, and more often than people imagine, the trafficking of human beings. Will AI save us? She did not flinch. Whatever you build to detect, the other side uses to evade. The asymmetry holds. Technology is part of the answer and never the whole of it, because the problem was never only technical. So what do we carry forward, and what do we leave behind? We carry the person behind the number: the one who misses the appointment, the small shop that never reopens. We leave behind the fantasy that a clever enough machine will spare us the harder work, which is teaching a whole society to recognize the Spanish Prisoner when it arrives, wearing this year’s technology. Sarah’s books are linked below, with a second edition on the way. Geoff’s conversation is part of this same coverage. And if you want more of these, the newsletter lives at marcociappelli.com. Let’s keep thinking. — Marco Co-Founder ITSPmagazine & Studio C60 | Creative Director | Branding & Marketing Advisor | Personal Branding Coach | Journalist | Writer | Podcast: An Analog Brain In A Digital Age ⚠️ Beware: Pigs May Fly | 🌎 LAX🛸FLR 🌍 About Marco Marco Ciappelli is Co-Founder & CMO of ITSPmagazine, Co-Founder & Creative Director of Studio C60, Branding & Marketing Advisor, Personal Branding Coach, Journalist, Writer, and Host of An Analog Brain In A Digital Age podcast. Born in Florence, Italy, and based in Los Angeles, he explores the intersection of technology, society, storytelling, and creativity — with an analog brain, in a digital age. His on-the-ground event coverage is produced with ITSPmagazine co-founder Sean Martin under the On Location With Sean Martin And Marco Ciappelli banner. 🌎 marcociappelli.com | itspmagazine.com | studioc60.com About the Guest Sarah Armstrong-Smith is one of the most recognized voices in cybersecurity and crisis leadership, with nearly three decades on the front line of major incidents, beginning with the Millennium Bug. She served as Chief Security Advisor for Microsoft EMEA from 2020 until 2025, and earlier led business resilience and crisis management at the London Stock Exchange Group, with senior roles at Fujitsu, EY, and AXA. She is now Executive Director of Secure Horizons. A Fellow of the British Computer Society and a member of the UK Government Cyber Advisory Board, she is the author of two Kogan Page books — Effective Crisis Management (2022) and the Amazon No. 1 bestseller Understand the Cyber Attacker Mindset (2024), with a second edition on the way. Her work centers on the human element of security: the psychology of attackers, the people behind the headlines, and what it takes to build collective resilience. 🔗 LinkedIn: linkedin.com/in/sarah-armstrong-smith Website: saraharmstrong-smith.com More from this event: Full InfoSecurity Europe 2026 coverage: ITSPmagazine InfoSecurity Europe 2026 All ITSPmagazine event coverage: Technology & Cybersecurity Conference Coverage Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
