The Ransomware Rookie

In the lonely expanse of sun-drenched dunes, an old CRT monitor flickers with a desperate pixelated plea for ransomed data, a solitary relic broadcasting its digital distress into the silent, timeless desert.
This entry is part 10 of 10 in the series Digital Duct Tape and Prayer

The Call for Help

Zero Cool’s phone rang at 2:47 AM with the distinctive tone reserved for emergencies and disasters. The caller ID showed “Randy Martinez – Junior Developer,” which immediately triggered Zero’s rookie-disaster-detection systems.

“Zero?” Randy’s voice carried the particular strain of someone who’d just discovered that theoretical knowledge and practical crisis management were entirely different skills. “Dude, I think I need help. Like, immediately. Big time.”

“What happened?” Zero was already reaching for their laptop, muscle memory developed through months of emergency response calls.

“So I’m pulling night shift at TechStart Solutions, right? And I think… man, I think we’re getting ransomwared. Ransomhacked? What’s even the right word here?”

“Compromised by ransomware,” Zero corrected automatically. “How many systems affected?”

“That’s the thing, dude. I have literally no clue. Everything just started… breaking? File shares went dark, the main WordPress site is showing these super sketchy messages, and there’s this countdown timer saying we’ve got 72 hours to fork over bitcoin or bye-bye data forever.”

Zero felt their blood chill. Randy was twenty-three, brilliant with code, and had approximately zero experience with actual security incidents. “Randy, are you the only person there?”

“Night shift. It’s just me until 6 AM.”

“Don’t touch anything else. I’m on my way.”

Driving through empty streets, Zero couldn’t shake the feeling that this disaster was going to be uncomfortably familiar.

The Mirror Disaster

3 AM – Driving to TechStart

Zero’s phone buzzed with messages from Cipher and The Architect, who had been monitoring emergency channels and detected the TechStart incident. By the time Zero arrived at TechStart’s office, they found Randy surrounded by multiple monitors displaying various stages of digital catastrophe.

“Show me what happened,” Zero said, settling into crisis mode.

Randy walked them through the timeline. “I was updating WordPress plugins on the development server—just routine maintenance stuff you taught me last month. Everything seemed normal until I got this popup saying my files were encrypted and I needed to pay to get them back. Oh, and Derek’s parking meter system went down too, but that’s probably unrelated.”

Zero examined the affected systems and felt an uncomfortable recognition. The attack pattern, the timeline, even Randy’s response—it was eerily similar to their own first major security disaster five years ago.

“Randy,” Zero said carefully, “what exactly did you click on before this started?”

“Nothing, man! I was just updating plugins like you showed me. WP SecureGate had an update, so I clicked update, and then…” Randy paused, looking embarrassed. “There was this popup about downloading additional security tools, and I was like, more security is totally good, right? So I…”

“You downloaded and installed software from a popup.”

“Dude, it looked completely legit! It said it was from the WordPress security team!”

Zero stared at the compromised systems, experiencing the temporal vertigo of watching someone else make the exact mistakes they’d made when they were Randy’s age. Overconfidence combined with rookie enthusiasm, resulting in catastrophic security failures through well-intentioned incompetence.

This moment called for teaching, not just fixing.

Parallel Processing

Instead of simply fixing the crisis, Zero made an unusual decision. “Randy, I want you to walk me through your incident response plan.”

“My what now, dude?”

“When you realized something was wrong, what steps did you take?”

Randy looked confused. “I… totally panicked? Then I called you?”

“Before that. What did you do when you first saw the ransom message?”

“I tried to close it, but it kept popping back up like some nightmare whack-a-mole game. Then I figured restarting the server would fix it, but that just made everything way worse. Then I was like, backups to the rescue! But…” Randy’s voice trailed off.

“But what?”

“Dude, the backups were on the same network share that got encrypted. I basically nuked my own safety net.”

Zero felt the universe achieve perfect symmetry. Randy had made every mistake Zero had made during their first major incident, in the exact same order, with the exact same reasoning.

“Randy,” Zero said, pulling up a chair, “I’m going to tell you about the worst mistake I ever made. Then we’re going to fix this together.”

Learning Through Parallel Experience

Zero began narrating their own rookie disaster while simultaneously guiding Randy through proper incident response procedures. As they isolated affected systems, Zero described making the same impulsive decisions Randy had made. As they analyzed the attack vector, Zero explained their own overconfidence with security tools.

“The popup you clicked,” Zero said while examining the malware signature, “was designed specifically to target people doing exactly what you were doing—routine WordPress maintenance. It exploits the psychological moment when you’re focused on security improvements and makes malicious software look like legitimate security tools.”

“So I’m not just… like, completely hopeless at this?”

“You’re inexperienced,” Zero corrected. “There’s a difference. I fell for almost exactly the same attack five years ago.”

“No way, seriously?”

“Seriously. Except my version was disguised as a WordPress core security update, and I was so focused on keeping everything current that I installed malware directly into the site’s root directory.”

Randy looked slightly less mortified. “Dude, what happened after that?”

“Thirty-six hours of crisis response, four different security firms, one very angry client, and the most educational experience of my career. Meanwhile, Derek’s running the city’s school lunch payment system on consumer hardware and hasn’t had a single security incident. Go figure.”

Collaborative Recovery

Working together through the night

Zero and Randy systematically contained the ransomware attack. Zero provided expertise and guidance while Randy implemented the actual recovery procedures, learning through direct experience rather than theoretical instruction.

“The key,” Zero explained while Randy restored from offline backups, “isn’t avoiding all mistakes. It’s recognizing when you’ve made a mistake quickly enough to minimize damage.”

“How do you recognize mistakes?”

“Experience. And mentors who help you understand that everyone makes these mistakes exactly once.”

As they restored the final compromised system, Randy asked, “Why are you teaching me this instead of just fixing it yourself?”

Zero paused, realizing they were mentoring someone the way they wished they’d been mentored during their own rookie disasters. “Because,” they said, “someone needs to know how to handle the next Randy who calls at 3 AM with the exact same problem.”

“You think there’ll be another me out there?”

“There’s always another Randy. The goal is making sure each Randy learns enough to help the next one.”

6 AM

TechStart’s systems were fully operational with improved security configurations. Randy had learned incident response procedures, proper backup strategies, and the critical difference between legitimate security tools and sophisticated social engineering attacks.

“So,” Randy said as they documented the incident, “next time someone my age calls you with a similar disaster…”

“You’ll be the one explaining how they made the same mistakes you made, and walking them through recovery procedures you learned tonight.”

“That’s… actually kind of terrifying, dude.”

“Welcome to cybersecurity,” Zero replied. “Where yesterday’s rookie mistakes become tomorrow’s teaching opportunities.”

Randy’s phone buzzed with a message from TechStart’s CEO, thanking him for “excellent incident response under pressure” and “demonstrating professional crisis management capabilities.”

“Think he knows I totally caused the problem in the first place?” Randy asked.

“Probably,” Zero said. “But he also knows you fixed it. And learned from it. That’s way more valuable than never making mistakes.”

Morning drive home

As Zero drove through traffic, they reflected on how teaching Randy had reminded them of their own journey from chaos-causing rookie to reluctant mentor. Everyone in cybersecurity had a Randy story—the difference was whether you used that experience to help the next Randy or just to feel superior.

Their phone buzzed with a message from Cipher: “Heard you pulled an all-nighter mentoring the next generation. How’d it go?”

“Discovered I’m officially old enough to be the experienced professional,” Zero replied. “Also discovered I like teaching more than I expected.”

“Think Randy’s ready for the real world?”

“Randy’s ready to teach the next Randy,” Zero replied. “The cycle continues, but better.”

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