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PODCAST

IT Horror Stories with Jack Smith

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,

technology management

All Episodes

33:00

The Failover That Failed Successfully - Lessons from...

IT Horror Stories with Jack Smith ·

2026/04/06

Conducted during a busy release weekend, the failover test exposed gaps not in the technology itself, but in coordination and communication. While production ultimately stayed unaffected, the situation quickly escalated as subcontractors weren't aligned, assumptions didn't match reality, and information didn't flow when it mattered most. We unpack how a well-intentioned test turned into a coordination challenge, where timing, dependencies, and unclear responsibilities created confusion across teams

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11:42

Jack's Rants - IT Hiring Chaos – The Strange State of...

IT Horror Stories with Jack Smith ·

2026/03/12

In this short episode, Jack takes a look at the current state of the IT hiring market — where job postings seem plentiful, but actual opportunities often feel strangely elusive. From "entry-level" roles asking for a decade of experience to companies searching for the mythical full-stack, cloud, DevOps, security expert all in one person, we discuss the growing gap between job descriptions and reality. With a bit of sarcasm and a lot of firsthand observation, we unpack what's going on in tech hiring

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32:18

Raspberry Mistery - 200 Techs Using A Single...

IT Horror Stories with Jack Smith ·

2026/03/02

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

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09:15

Jack's Rants - Batch Job Blues

IT Horror Stories with Jack Smith ·

2026/02/10

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

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0:57

Welcome to IT Horror Stories with Jack Smith

IT Horror Stories with Jack Smith ·

2026/02/09

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35:59

Surviving the Anonymous DDOS

IT Horror Stories with Jack Smith ·

2026/02/02

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

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30:16

Shadow IT Reports

IT Horror Stories with Jack Smith ·

2026/01/07

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

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28:20

The DevOps Royale With Cheese

IT Horror Stories with Jack Smith ·

2025/12/01

In this episode, we return to Finland, where an international burger chain suddenly found itself cut off from the one thing every fast-food operation needs to function: real-time operational data. A third-party data supplier pulled the plug without warning, leaving kitchens blind, dashboards empty, and the entire workflow stuck on "please wait." What followed was a truly Nordic-speed DevOps rescue mission — rapid troubleshooting, frantic config changes, un-authorized workarounds, and a race to

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29:26

Y2K vs Y2K38 - The Rematch

IT Horror Stories with Jack Smith ·

2025/11/03

We revisit the original digital apocalypse — the year 2000 - looking back at what Y2K really was, how an army of COBOL coders saved the world before midnight, and why most people never even noticed. But the clock is ticking again: Y2K38 is coming, and this time it's 32-bit. Different date, same panic waiting to happen as UNIX time doesn't heal — it overflows into a negative.

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43:07

SAP Happens

IT Horror Stories with Jack Smith ·

2025/10/06

SAP sits quietly at the heart of most global businesses, running everything from payroll to procurement, logistics to finance. It’s the system nobody brags about, but everybody depends on. And when someone says “just check SAP,” you know you’re in for more than a click or two. In this episode, we explore how SAP became the invisible backbone of enterprise life, why it inspires equal parts respect and frustration, and the strange comfort of knowing it’s always there whether you want it to be or not

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34:28

Paris Rooftops

IT Horror Stories with Jack Smith ·

2025/08/31

Installing a 5G antenna on a rooftop in downtown Paris sounds simple enough - until reality sets in. In this episode, we walk thru the saga of a project that required not one, not two, but multiple site visits before the antenna finally worked as expected. Permits, building access, scheduling delays, unexpected power requirements - each visit brought a new twist, each delay a new story. Was it bureaucracy? Weather? Or just the uniquely French way of doing things? Join us on the rooftops of Paris for

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33:24

IT and Global Politics

IT Horror Stories with Jack Smith ·

2025/08/04

A pharmaceutical sales team is detained at an international border. On their tablets: standard product brochures that end up in an escalation into allegations of industrial espionage. In this episode, we unpack how a well-intentioned directive to preload sales materials onto devices as per strategic choices made in boardrooms can unravel on tarmacs and in detention rooms. Back home, the IT team is asleep—until the CIO calls in the middle of the night and it’s on IT to contain the fallout of a crisis

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37:32

"Fun" With Domain Names

IT Horror Stories with Jack Smith ·

2025/07/01

We’re unpacking the critical steps behind migrating a domain name — a process that can disrupt everything from search engine indexing and referral traffic to email deliverability and authentication. Join us together with an industry expert and let's explore the technical risks, from broken redirects to, yes — forgetting to update your SPF records and wondering why your emails end up in spam (don’t worry, you’re not the first). In the end it’s all about executing that clean, strategic transition that

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41:01

Crashing Helsinki Airport

IT Horror Stories with Jack Smith ·

2025/06/02

Join us as we explore the intersection of Nordic tech innovation, modern infrastructure, and the evolving world of DevOps : Finland ! From smart cities to smarter code and crashing airport parking systems with those nasty edge cases in your test scenario.

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31:28

Our First Data Center Fire

IT Horror Stories with Jack Smith ·

2025/05/06

What happens when a data center goes up in smoke—literally? In this episode, we sift through the potential ashes of a not-so-great day. Join us as we chat about servers, batteries, paperwork and holidays, and the surprisingly flammable side of computing. It's a smoky mess, and we’re here for it.

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35 results

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