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July 10, 2026 |

IT Nightmares #005: Reboot of doom

A routine reboot of an aging Hyper-V server turned into a two-day MSP nightmare for Matt Rose of Tech Rage IT.

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.

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About Matt Rose

Matt Rose is the co-founder and Chief Experience Officer at Tech Rage IT, an award-winning IT managed services provider. Throughout his journey, he assumed diverse roles, ranging from consultant to virtual Chief Information Officer, catering to the needs of all companies, from small to mid-sized businesses to Forbes Global 200 companies.

As a published author of Kiss Tech Rage Goodbye and more, Matt continues to significantly impact the IT landscape, empowering businesses and professionals alike with his unparalleled knowledge and expertise.

Source: LinkedIn

About 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.

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