IT Horror Stories

About IT Horror Stories

If you’ve worked in IT, you’ve probably got a few good ghost stories. This show is dedicated to those stories and the IT heroes who survived to tell the tale. Join some of the world’s top IT leaders as they recount the most harrowing experiences of their careers. They’ll share how they found themselves in hot water, managed to escape disaster, and their best advice for making sure you don’t end up in the sequel. This is IT Horror Stories, where the call is coming from inside the office. Brought to you by NinjaOne, the leader in automated endpoint management.

Publisher

NinjaOne

Category

business · technology

Language

en

Explicit

No

First episode

27 Feb 2025

Latest episode

5 Aug 2025

Latest episodes

11 of 13 episodes have a transcript.

1. 

   5 Aug 2025TRANSCRIPT

   ITOops

   Host Jonathan Crowe interviews IT veterans who share their most terrifying and unbelievable tech support nightmares, revealing the dark side of the digital world.

2. 

   22 Jul 2025TRANSCRIPT

   Human Error

   Mark Settle, a seasoned CIO and author, recounts operational IT disasters caused by human error, offering insights into preventing future catastrophes in this interview.

3. 

   8 Jul 2025TRANSCRIPT

   Bitcoin and Brown Paper Bags

   Shelley Ma, incident response lead, explores the challenges of negotiating with cybercriminals, emphasizing the critical human element involved in cybersecurity incident response in this interview.

4. 

   24 Jun 2025TRANSCRIPT

   The Nightmare Phone Call

   Andrew Wilder recounts terrifying experiences as a security veteran, highlighting the ominous nature of interactions with certain government organizations in this interview.

5. 

   10 Jun 2025TRANSCRIPT

   Point of No Rollback

   Mahesh Guruswamy, CPTO at Kickstarter, relives the intense experience of taking down production with no rollback option, highlighting the challenges of delivering bad news while maintaining trust in this interview.

6. 

   27 May 2025TRANSCRIPT

   Crisis Clarity

   Wawa CIO and SVP John Collier discusses how design thinking informs quick decision-making during IT crises, providing valuable tactics for IT leaders seeking influence and preparedness in critical situations in this interview.

7. 

   13 May 2025TRANSCRIPT

   POS SOS

   Wyatt Hansen unpacks how a back of house server going down turns into a massive nightmare for one of his biggest retail clients, shuttering POS systems and leading to business chaos.

8. 

   29 Apr 2025TRANSCRIPT

   Confessions of an Adversary

   Dr. Chase Cunningham, aka DrZeroTrust, sheds light on what a horror story looks like from an adversarial perspective. He explores why doing the basics and applying them intelligently does matter, why people should abandon the notion of perfect security, and what controls and practices organizations can adopt and follow to make it a bad day for bad actors.

9. 

   15 Apr 2025TRANSCRIPT

   Last Out

   When COVID lockdowns loom in early 2020, it’s up to Matthew's team to prepare hundreds of laptops for an employee base that’s about to start working from home.

10. 

    1 Apr 2025TRANSCRIPT

    No Longer a Drill

    Could a robust internal process and contingency plan have prevented a disastrous fire suppression test in a data center? Mike Anderson, CDO and CIO of Netskope, describes the importance of scenario planning and proactive security in order to prevent disaster.

11. 

    18 Mar 2025TRANSCRIPT

    Dead in the Water

    When a corrupted virus definition file was distributed by a centralized management server, it was up to Jay Abbott to find a fix for the company-wide blue screen of death.

12. 

    3 Mar 2025

    Hurricanes and Diesel Fuel

    When a Hurricane causes a major power outage, Nick’s data center is pushed to run on generator power. Then the generator runs out of fuel… In the middle of a fuel shortage.

13. 

    27 Feb 2025

    Trailer

    If you’ve worked in IT, you’ve probably got a few ghost stories. This show is dedicated to those stories and the IT heroes who survived to tell the tale.

Inside a recent episode

ITOops

Published 5 Aug 2025 · Transcript excerpt

[…] I had been working with this company for about a year. So I still felt like I was getting my legs under me as the the primary like Microsoft person. I have a very small team and I am the Microsoft person who if you're if you're watching the video here, I have an Azure tattoo. So I am the Microsoft person at my job. And we are a fully remote company. We're split as to whether we're on Macs or PCs. So about half of the organization is mine that I am managing. This fleet is my baby. And then the first person that we get affected was our senior IT security person. Was the first person who reported an issue to us. […]

Who has been a guest on IT Horror Stories

Names identified in recent episode analyses. Showing up to five guests.

• IT veterans
• Mark Settle
• Andrew Wilder
• Mahesh Guruswamy
• John Collier

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

4 ratings

Spotify

5.0 / 5

10 ratings

Podcast Authority Score: 39 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

65

Social presence

0

YouTube

0

Engagement

32

Contact IT Horror Stories

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.