IT Horror Stories with Jack Smith tells real stories from the world of IT: outages, failed migrations, broken infrastructure, cybersecurity incidents, software failures, networking disasters, cloud problems, Shadow IT, and the occasional decision that seemed like a good idea at the time. Jack Smith talks with the people who were there about what happened, how they got out of it, and what others can learn from the incident. Stories are anonymized where needed, and the focus is on technology, processes, and organizations rather than blaming individuals. New episodes weekly, with Jack's Rants in between. You are one of us.
Latest episodes
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15 min
Jack's Rants - PHP, Panic, and Technical Debt - PHP2Shell: Critical PHP Flaws, Emergency Patching, and Technic…
Two critical PHP vulnerabilities. Emergency patches. Government websites going offline. And IT teams around the world suddenly discovering just how much forgotten infrastructure th…
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45 min
Wrong Person, Right Skills : Technical Hiring Failures and Why Companies Mismanage IT Talent
Companies complain that they can't find the right technical people. Technical people complain that companies have no idea who they're actually looking for. This time, Jack crosses…
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46 min
Cleared for Disaster : Air Traffic Control Technology: Outages, Failures, and Recovery
Jack talks with Harvey Scolnick about his years working with air traffic control technology and the failures that came with it. From construction work accidentally cutting a critic…
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20 min
Jack's Rants - Meshcore : Off-Grid Messaging, LoRa, Privacy, and Decentralised Networks
Someone asked us why we weren't on MeshCore yet. First we had to establish that it wasn't a new kind of thrash metal. Then we discovered an off-grid messaging network built from li…
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21 min
Cultural Differences in IT : When Global Teams Don't Work the Same Way
IT may run on the same protocols everywhere, but the people operating it certainly don't. Put teams from different countries, companies, and working cultures onto the same project…
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33 min
When UNPK Broke – Diagnosing an IBM Mainframe Hardware Failure
Texas, 1978. Robert was working at a cotton co-op running what may have been one of the world's earliest online auction systems. Farmers received punch cards representing their bal…
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38 min
Pinball as IoT : When Arcade Machines Go Online
A modern pinball machine isn't just flippers, bumpers, lights, and a very large box making expensive noises. It's a connected computer with software updates, online score tracking,…
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25 min
The Three Envelopes: Blame, Reorganize, Repeat
The Three Envelopes: Blame, Reorganize, Repeat There is an old management joke about an outgoing manager leaving three numbered envelopes for their successor. When the first crisis…
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9 min
Jack's Rants - Why You Need to Reboot : Why Rebooting Your Computer Actually Fixes Problems
Jack's Rants - Why You Need to Reboot : Why Rebooting Your Computer Actually Fixes Problems "Have you tried turning it off and on again ?" became an IT cliché for a reason. Rebooti…
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39 min
Testing Software Properly : Software Testing Done Right – Where, When and What Should You Test?
Testing software sounds simple enough. But what exactly should you test, where should those tests happen, and how do you decide which parts of a complex system need the most attent…
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25 min
Microcode Mayhem : How a Mainframe Timer Bug Slowed an Entire Development Team
One day, a busy IBM-compatible mainframe began slowing to a crawl. Hundreds of programmers noticed immediately—some even resorted to banging on the server room window whenever the…
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12 min
Jack's Rants - AI Is The New Shadow IT : Why Employees Are Quietly Building the Next IT Risk
Artificial intelligence didn't invent Shadow IT—it made it invisible. In this Jack's Rant, Jack Smith explores how AI tools like ChatGPT, Copilot and Claude have fundamentally chan…
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30 min
Melbourne Cup Meltdown : How a Betting System Crashed at the Worst Possible Moment
Every year, the Melbourne Cup pushes Australia's betting infrastructure to its limits. In 1991, a known software bug turned one of the busiest days of the year into an IT disaster.…
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11 min
Jack's Rants - The Missing Five Minutes : Why scambaiting videos leave security professionals with more questi…
Scambaiters like Kitboga, Jim Browning and Pierogi educate millions, waste scammers' time, and undoubtedly prevent people from becoming victims. As a security professional, I genui…
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38 min
One Network to Rule Them All : How a Missing VLAN Strategy Turned Smart City Infrastructure into a Cybersecuri…
Smart cities promise better transportation, connected infrastructure, and improved services—but what happens when everything is connected a little too well? In this episode, our gu…
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10 min
Jack's Rants - Can I Keep Your ID? : Privacy, Identity Theft, Data Minimization, and Why Your Driver's License…
Opening a tab at a bowling alley shouldn't require handing over your driver's license or national ID card. Yet many businesses still ask customers to leave government-issued identi…
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32 min
Cardboard Confidential : A Cybersecurity Incident, a Golf Course Conversation, and Why No Industry Is Too Bori…
No one expects a cybersecurity incident to begin in the cardboard industry. Yet as our guest Kayne McGladrey explains, cybercriminals don't care what your company manufactures—they…
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13 min
Jack's Rants - The New Change Management : ITIL Change Control, Organizational Change, and Why Project Manager…
Once upon a time, Change Management meant raising an RFC, preparing a rollback plan, and surviving the Change Advisory Board. Today, it also means stakeholder engagement, communica…
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15 min
GDPR Enters the Chat : The Day a Hiring Exercise Became an Information Security Incident
It was supposed to be a routine hiring exercise. A candidate receives a technical assignment, reviews the provided material, and prepares a solution. Then someone notices that the…
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27 min
Spooling Out of Control : Enterprise Printing Explained and Why Printing Still Breaks IT
Printing is one of those technologies everyone assumes should have been solved years ago — until someone can't print invoices, shipping labels stop coming out, or 50,000 customer l…