IT Horror Stories – NinjaOne

ITOops

Joel Newcomer — Tue, 05 Aug 2025 14:00:40 +0000

In the spine-tingling finale of IT Horror Stories, host Jonathan Crowe is joined by a fearless lineup of IT veterans who have stared into the digital void and lived to tell the tale. Guests Kallum Kyle, Senior Sysadmin at Storable; Josh Adcock, Director of Client Services at The Tech Doctor; and Adam Walter, Founder of Humanize IT, recount their most harrowing experiences from the trenches of tech. They relive moments when end users were their only hope, when vulnerable software lurked like ghosts on forgotten networks, and when automation backfired so badly it cost them their jobs. These stories aren’t just frightening—they’re all true!

Human Error

Eduardo Pereira — Tue, 22 Jul 2025 14:37:15 +0000

IT isn’t just wires and widgets. It’s a minefield of lurking disasters waiting to strike. Few know that better than Mark Settle, 7-time CIO and author, who’s survived more operational horrors than most dare imagine. In this episode, Mark takes us into the shadowy corners of enterprise IT, where outdated processes haunt progress, bad news festers in silence, and AI ignorance prowls like a predator in the dark. He shares battle-tested wisdom from a career spent defusing digital disasters and building resilient, process-driven teams that can take a punch.

Bitcoin and Brown Paper Bags

Eduardo Pereira — Tue, 08 Jul 2025 14:00:26 +0000

Think haunted houses are scary? Try stepping into a breach in progress. In this spine-chilling episode, we sit down with Shelley Ma, Incident Response Lead at Coalition, to guide us through the real-world horrors of cybersecurity. Shelley doesn’t just face the darkness for a living — she negotiates with it. Confronting cybercriminals head-on, keeping her cool when it counts, beating burnout and more, Shelley explores what it’s really like being on the front lines when the alarms start screaming.

The Nightmare Phone Call

Joel Newcomer — Tue, 24 Jun 2025 14:00:41 +0000

Things are bound to go sideways in the world of IT and security, but there are certain three-letter government organizations that you never want to hear from. In this episode, long-time security veteran and Chief Security Officer at Vetcor, Andrew Wilder, joins us to unpack several harrowing encounters with bad actors and local law enforcement – ranging from chasing down unknowing internal payments to known hackers and cracking down on vulnerable vendors. Andrew explores why establishing relationships with your local law enforcement before bad things happen is key in a world where so much often goes awry, and how to translate risks into opportunities for growth.

Point of No Rollback

Joel Newcomer — Tue, 10 Jun 2025 14:00:55 +0000

When a huge cloud platform migration stalls out mid-flight with no hope of changing course, panic lunges to take the wheel. In this episode, Mahesh Guruswamy, CPTO at Kickstarter and author of How to Deliver Bad News and Get Away with It, recounts the night he took down production and had no other choice but to push through. Tune in for the blow-by-blow — from anxiously watching the clock as queries time-out to the tightrope walk of breaking bad news without breaking trust. You’ll leave with the brutally simple playbook Mahesh now swears by to make sure your next migration doesn’t become an IT horror sequel.

Crisis Clarity

Joel Newcomer — Tue, 27 May 2025 14:00:26 +0000

When blueprints start to smolder, true leaders draft new ones on the fly. In this episode, former architect turned Wawa CIO & SVP John Collier reveals how his background in design thinking has helped him make split-second judgments when even the most unforeseeable crises hit. From war-room gut-checks made in the dark to culture-defining decisions that outlast the chaos, John shares hard-won tactics for IT leaders who want a real seat at the table — and who want to be ready when all eyes turn to them.

POS SOS

Joel Newcomer — Tue, 13 May 2025 14:00:15 +0000

In this episode, Wyatt Hansen, Vice President of Information Technology Services at LeaderOne Financial, sits down with host Jonathan Crowe to discuss an IT horror story that he experienced early on in his career while working at an MSP. He 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. He also explores the upsides of having a nontraditional career path, learning on the job and having room to fail, and why clear communication and documentation are the best ways to counteract crisis.

Confessions of an Adversary

Joel Newcomer — Tue, 29 Apr 2025 14:00:39 +0000

In this episode, Dr. Chase Cunningham, aka DrZeroTrust, joins us to shed light on what a horror story looks like from an adversarial perspective. In drawing on his extensive red teaming and NSA background, 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.

Last Out

Joel Newcomer — Tue, 15 Apr 2025 14:00:53 +0000

In this episode, information security analyst in the professional sports world, Matthew Schuster, joins host Jonathan Crowe to discuss Matthew’s harrowing IT horror story from the early days of the Covid pandemic. Matthew shares how his small but mighty team chased down and shipped out laptops to support his organization’s quick transition to fully remote work (cutting a 12-month planned rollout down to just three days), how a dedicated leadership team helped his team knock it out of the park, and lessons learned from operating under pressure.

No Longer a Drill

Joel Newcomer — Tue, 01 Apr 2025 14:00:41 +0000

In this episode, Mike Anderson, CIO & CDO at Netskope, joins Jonathan to discuss several IT horror stories that have stuck with him throughout his career – including a fire suppression test gone wrong, how he helped his organization quickly recover from a ransomware attack in his first tenure as CIO, and now as a more seasoned CIO, how he thinks about taking calculated risks, investing in people, and depositing in relationship accounts to drive business forward.