IT Horror Stories with Jack Smith

IT Horror Stories with Jack Smith

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We delve into the bizarre and often cringe-worthy world of IT mishaps, glitches, and the horror stories that come with it. With a sarcastic twist we recount the tales of those who somehow manage to create chaos out of the simplest tasks. We strike a balance between relatable frustration and dark humor that gets even the most cringe-inducing stories entertaining and you will find yourself laughing, cringing, and shaking their heads in disbelief as we take a wild ride through the chaotic world...
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Episode List

Raspberry Mistery

Mar 2nd, 2026 11:00 AM

A few hundred field engineers. Real humans. With vans. And jobs. All coordinated by a device roughly the size of a coaster and powered by something suspiciously similar to a phone charger. For months, it runs slow but flawlessly. Tickets dispatched. Routes optimized. Managers happy.  The tiny silicon hero hums along in its noble plastic case, bravely pretending it's not one 'apt upgrade' away from a crisis. Join us as we unravel the mystery, debate the true definition of "production-ready," and ask the question no one wanted to say out loud.   00:00 Welcome Back 01:23 Shadow IT Chaos 05:18 Major Outage 12:04 Data Center Discovery 17:59 Where's the Server? 19:58 Raspberry Pi Reveal 25:13 Migration Success 30:36 Closing Thoughts

Jack's Rants - Batch Job Blues

Feb 10th, 2026 10:58 AM

Jack's Rants dives into the world of banking mainframes and the batch jobs that quietly keep everything moving — until one of them doesn't. What starts as a routine overnight run turns into a multiple transactions on thousands of accounts that didnt happen in the real world, but the mainframe says something else. 00:00 Rant Kickoff 01:23 Transaction Glitch 03:14 Batch Job Drama 05:23 Mainframe Pros 07:33 Wrap Up  

Welcome to IT Horror Stories with Jack Smith

Feb 9th, 2026 12:37 AM

Surviving the Anonymous DDOS

Feb 2nd, 2026 11:00 AM

This episode we unpack what a DDoS attack actually is, using the specter of Anonymous as a cultural touchstone rather than a how-to villain. We talk about why high-profile groups target services, what it feels like in real time when traffic spikes and systems start gasping, and how panic can make things worse. Instead of glorifying attackers, we center on mindset: staying calm, recognizing early warning signs, and understanding the difference between noise and a true outage. The takeaway isn't technical bravado; it's preparedness. By the end of the episode, "surviving" a DDoS means knowing how to keep your service, your team, and your reputation intact when the internet decides to stress-test you all at once. 00:00 Hello & Introduction 00:51 The Anonymous Attack 06:19 Unprepared Response 13:52 DDoS Solutions 16:08 Smart Attacks 25:06 Evolution of Protection 33:11 Risk & Insurance 34:52 Podcast Wrap-Up  

Shadow IT Reports

Jan 7th, 2026 12:13 PM

We dive into the familiar chaos of Shadow IT created by the sales department — well-intentioned, fast-moving, and completely invisible until something breaks. A "quick tool" turns into a critical system overnight, contracts appear after go-live, and IT is asked to secure, integrate, and support something it never approved or even knew existed. It's a story about speed versus control, good intentions with bad outcomes, and why Shadow IT doesn't start with malice — it starts with urgency.   00:00 Podcast Kickoff 01:11 What is Shadow IT 02:44 Sales Server Disaster 12:57 Data Migration Drama 23:45 Luck and Lessons 25:15 Common Shadow IT 26:58 Management Irony 28:02 Final Thoughts

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