IT Nightmares

On IT Nightmares, host Justin Esgar hears true tales of IT terror from MSPs, sysadmins, and integrators—stories of outages, breaches, and tech disasters that still haunt the people who survived them. Enter if you dare.

#005 - Reboot of Doom | Guest Matt Rose 07/10/2026

#005 - Reboot of Doom | Guest Matt Rose In IT, few words are more deceptively harmless than “just reboot it.” Most of the time, that is the beginning and end of the fix. Other times, it is the first creak of the floorboard in a much bigger horror story. In this episode of IT Nightmares, Justin Esgar talks with Matt Rose, chief experience officer at Tech Rage IT, about a new-client onboarding that started with a routine server reboot and quickly became a lesson in when to stop troubleshooting and start recovering. /episode/index/show/579af0da-e611-409b-8fba-dcbd01f3d0ec/id/42036585

#004 - The Handoff Horror | Guest Eric Weast 07/09/2026

#004 - The Handoff Horror | Guest Eric Weast In IT, the scariest moments are not always when something breaks. Sometimes, they happen in between — between vendors, between contracts, between “we’ve got this” and “wait, who’s responsible for that?” In this episode of IT Nightmares, Justin Esgar talks with Eric Weast, president of ECW Network & Solutions, about an offboarding that went from routine to ransomware. /episode/index/show/579af0da-e611-409b-8fba-dcbd01f3d0ec/id/42028170

#003 – Municipal Mayhem | Guest Norbert Doeberlein 07/09/2026

#003 – Municipal Mayhem | Guest Norbert Doeberlein The biggest IT horrors aren’t always ransomware or failed hardware. Sometimes, it’s walking into an environment wrecked by bad processes, poor communication, and MSPs pretending to be experts. In this episode of IT Nightmares, Justin Esgar talks with Netzbahn CEO Norbert Doeberlein about the terrifying reality of municipal IT, why most MSPs approach it completely wrong, and the business-first mindset needed to survive in one of the industry’s toughest environments. /episode/index/show/579af0da-e611-409b-8fba-dcbd01f3d0ec/id/42028120

#002 – RMM Gone Rogue | Guest James Wroten 07/09/2026

#002 – RMM Gone Rogue | Guest James Wroten It started with a single call on a quiet Sunday afternoon… then another… and another. In this episode of IT Nightmares, host Justin Esgar sits down with James Wroten to relive the moment a trusted RMM tool became the attack vector. Unleashing a fast-moving ransomware event that encrypted two-thirds of his clients in minutes, what followed was weeks of exhaustion, recovery, and survival in a nightmare where the tools meant to protect you become the threat. /episode/index/show/579af0da-e611-409b-8fba-dcbd01f3d0ec/id/42028035

#001 – Mouse Unseen | Guest Justin Lewis 07/09/2026

#001 – Mouse Unseen | Guest Justin Lewis Sometimes the scariest IT problems aren’t catastrophic server crashes—they’re the tiny things that vanish without a trace. In this episode of IT Nightmares, host Justin Esgar welcomes IT consultant Justin Lewis to recount a haunting help desk call from the dial-up era, where a simple missing mouse pointer turned into a patience-testing tech horror story. In a world before screen sharing, finding that little arrow became a nightmare all its own. /episode/index/show/579af0da-e611-409b-8fba-dcbd01f3d0ec/id/42028000

IT Nightmares

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