Day 11 – 12 Days of Unscripted with SST

IT Horror Stories

For Day 11, we revisit Episode Eleven of Unscripted with SST, our Halloween special focused on real IT and cybersecurity horror stories. In this episode, Tracy, Beau, Josh, and Ryan share the kinds of situations that keep IT professionals awake at night, along with the lessons these incidents teach about preparation, process, and cyber readiness. Each story reinforces a simple truth: most disasters are preventable when businesses adopt proper controls, frameworks, and habits.

Josh started the episode by describing a scenario in which an unlocked, publicly accessible workstation granted access to a company’s entire Google Drive, including sensitive data. The lack of policies like automatic session locking, MFA, and proper access controls created a significant security risk. Beau discussed the dangers of performing maintenance outside scheduled windows, explaining that even redundant systems can fail when changes are made without proper planning. Ryan shared an incident involving a client whose maintenance team moved critical equipment without notifying IT, resulting in days of disruption and emergency rework. These examples showed that communication, change control, and documented procedures are just as crucial as technical safeguards.

Other stories were just as compelling. Josh described a Friday reboot gone wrong at a healthcare organization, which temporarily took down phone service until emergency support could restore it. Beau recalled a ransomware incident in which gaps in monitoring allowed attackers to regain access because not all systems were under surveillance. Tracy shared a situation in which outdated inventory information led to hours of unnecessary troubleshooting during a significant upgrade. Ryan concluded with a lesson about onboarding, where outdated software was blocked by antivirus tools until proper whitelisting could be completed.

The main message from Episode Eleven was clear. Security frameworks, maintenance windows, updated inventories, thorough monitoring, communication plans, and disciplined processes are the foundation of operational resilience. Businesses that adopt these practices lessen the chance of expensive surprises and recover more quickly when problems arise. Cyber readiness isn’t about being perfect; it’s about having structure, visibility, and a culture dedicated to doing things the right way.