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IT Horror Stories with Jack Smith
IT Horror Stories with Jack Smith
Author: Jack Smith
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© 2024-2026
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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.
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.
40 Episodes
Reverse
What happens when a company rushes into AI adoption without understanding what it actually costs? Ankit Mishra joins Jack Smith to share a firsthand incident involving an AI-powered sales lead generation platform, shared API access, and thousands of dollars in unexpected usage charges. What started as a promising business automation project became an expensive lesson in API budgets, cost monitoring, and the importance of understanding the technology before putting it into production. We expand into the challenges of enterprise AI adoption, from AI fluency and employee training to human oversight, unreliable outputs, and the pressure to deploy new technology faster than organizations can adapt. Also explored are the economics behind AI services, the importance of keeping humans involved in critical decisions, and why slowing down might be the smartest move when everyone else is racing to automate everything. Find out more about Ankit Mishra on https://ankitmishra.ca Want even more info ? Read our show notes and related blog post related to this episode : https://blog.ithorrorstories.eu/episode-29-the-cost-of-rushing-ai/ 00:00 Introduction 01:20 AI Horror Story 05:58 AI Fluency Concept 08:07 AI Levels Explained 12:26 Certification Ideas 19:10 Token Costs & Efficiency 23:25 Hardware Costs 29:22 Critical Thinking 32:10 Lessons Learned 35:22 Speed of AI 37:36 Conclusion
Call Center Down : If Only AI Could Diagnose Network Traffic Problems What happens when hundreds of call center employees suddenly find their systems grinding to a halt, only for everything to return to normal at 5 pm? And why does the same problem return at 9 am the next morning? Wolf O'Rourc joins Jack Smith to revisit a network incident where an overloaded Cisco backbone brought customer service operations to a near standstill. Finding the cause became an exercise in troubleshooting, escalation, and detective work defining the culprit to be quite an unexpected source. Find out more about Wolf O'Rourc at https://www.wolforourc.com/ Want even more info ? Read our show notes and related blog post related to this episode : https://blog.ithorrorstories.eu/episode-28-call-center-down/ 00:00 Introduction 01:09 Networking Issues 05:41 Communication Breakdown 10:37 Unauthorized Streaming 19:29 Resolution and Learnings 35:11 Future of IT
Two critical PHP vulnerabilities. Emergency patches. Government websites going offline. And IT teams around the world suddenly discovering just how much forgotten infrastructure they're responsible for. But the real horror story isn't PHP itself. It's the years of technical debt, unsupported software, missing documentation, and Shadow IT that turn a security update into a business crisis. Because you can't patch a server you don't know you have. Want even more info ? Read our show notes and related blog post related to this episode : https://blog.ithorrorstories.eu/jacks-rant-php-panic-and-technical-debt/ Sources and further reading : https://www.php.net/supported-versions.php https://thephp.foundation/blog/2026/10/21/todays-php-security-release-and-how-were-strengthening-php-security/ https://openai.com/index/coordinated-disclosure-of-critical-vulnerabilities/ https://www.php.net/supported-versions.php 00:22 Introduction 00:39 PHP Security Flaw 02:00 RCE Dangers 02:35 Patch Release Chaos 05:01 Identifying Vulnerable Systems 06:54 Widespread Impact 09:04 AI in Discovery 09:15 GitLab Joins Chaos 09:32 Addressing Technical Debt 11:22 Possible Exploits 11:58 Emergency Wrap-up 12:48 The Real Horror 14:26 Conclusion
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 to the other side of the table with Ashley Randall to find out why both might be right. We look at how organizations turn operational problems into job descriptions, why they search for impossible unicorns, and what happens when the person they hire has the right skills for a job that doesn't actually exist as advertised. From HR screening and mismatched expectations to KPIs, management workshops, organizational silos, and the eternal question of whether HR is really there for you, we explore what happens when technical specialists and the business speak very different versions of the same language. Sometimes the problem isn't the person you hired. It's the job you thought you were hiring them for. To find out more about Ashley Randall and Aspiring Redirection, visit: Ashley Randall: https://www.linkedin.com/in/ashley-randall7/ Aspiring Redirection: https://www.linkedin.com/company/aspiring-redirection/ Want even more info ? Read our show notes and related blog post related to this episode : https://blog.ithorrorstories.eu/episode-27-wrong-person-right-skills/ 00:00 Introduction 00:43 Business Perspective 02:03 Hiring Challenges 04:48 Evaluating Talent 07:02 Structural Issues 08:52 Role Mismatches 13:24 Miscommunication Effects 17:15 Improving Processes 24:00 Culture and Metrics 33:43 HR and Employee Relations 39:23 Conclusion
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 critical cable and knocking an air traffic control facility offline, with systems unavailable and aircraft still in the sky, to the people on the ground having to fall back on procedures, neighboring facilities, and some very human problem-solving. In addition, we look at the redundancy behind air traffic control, what recovery looks like when safety-critical infrastructure fails, and why even carefully designed systems can still be brought down by something remarkably mundane. Want even more info ? Read our show notes and related blog post related to this episode : https://blog.ithorrorstories.eu/episode-26-cleared-for-disaster/ Find out more about Harvey Scolnick : https://www.scolnickatc.com/ 00:00 Introduction 00:55 Harvey's Journey 02:13 Becoming ATC 05:34 Airways and Radar 07:03 Separation Standards 11:21 Busy JFK 14:33 Iconic Aircrafts 21:12 Technology Upgrades 29:27 Preventative Measures 38:10 AI and Future 41:27 Weather Challenges 43:57 Conclusion








