IT Nightmares

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#007 - Seven Paths to Nowhere | Guest Sean Maguire

4 Sep 2026

In IT, few things are more unnerving than a problem that disappears whenever you try to diagnose it. One minute, customers cannot access critical systems. The next, everything works again, and every provider involved insists the trouble must be somewhere else. In this episode of IT Nightmares, ...

00:17:16

#006 - The Price of No | Guest Dr. Jared Knisley

7 Ogo 2026

In IT, there is only so long you can warn a client before "we'll think about it" turns into "how did this happen?" Old firewalls, outdated systems, weak security controls — the risks can pile up quickly when every recommendation sounds like an upsell. In this episode of IT Nightmares, Justin Es ...

00:12:31

#005 - Reboot of Doom | Guest Matt Rose

10 Jul 2026

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 experi ...

00:09:35

#004 - The Handoff Horror | Guest Eric Weast

9 Jul 2026

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 Netwo ...

00:10:14

#003 – Municipal Mayhem | Guest Norbert Doeberlein

9 Jul 2026

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 ter ...

00:09:15

#002 – RMM Gone Rogue | Guest James Wroten

9 Jul 2026

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-thi ...

00:09:53

#001 – Mouse Unseen | Guest Justin Lewis

9 Jul 2026

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 mou ...

00:05:34