The cryptolocker virus was the attack that turned ransomware from a nuisance into a full-blown criminal industry — and in this episode of The Backup Wrap-up, we break down exactly how that happened. W. Curtis Preston (Mr. Backup) sits down with co-host Prasanna Malaiyandi and cybersecurity expert Dr. Mike Saylor to trace the full evolution of ransomware and explain why CryptoLocker was the turning point.

If you've ever wondered how ransomware went from fake pop-up messages to billion-dollar criminal enterprises, this is the episode for you. We start with the earliest days — scareware attacks that did nothing more than frighten you into paying — and walk through the progression of encryption methods that made ransomware increasingly dangerous. Dr. Mike Saylor breaks down the difference between symmetric and asymmetric encryption in plain language, and explains why the move to public-private key pairs made it so much harder for victims to recover without paying up.

Then we get into the cryptolocker virus itself: how it spread through fake FedEx emails, why it kick-started phishing awareness training, what Operation Tovar did to shut it down, and — just as interesting — what the bad guys learned from its failures. We cover the role of the Zeus botnet, how Bitcoin became the payment method of choice, and why ransoms started out at just a few hundred bucks. We also talk about what happened next: the rise of data exfiltration, double extortion, and even triple extortion where attackers go after the victims of the victims.

Plus, we take a side trip into the LastPass breach and pour one out for the guy who lost his crypto fortune in a landfill.

Whether you're in IT, security, or just want to understand how ransomware works, this episode gives you the full picture.

Chapters:

00:00:00 — Intro

00:01:22 — Welcome and Introductions

00:04:11 — The Three Generations of Ransomware

00:05:01 — Scareware: Fake Attacks That Did Nothing

00:05:42 — Ciphers and Decoder Ring Encryption

00:06:38 — Symmetric Encryption Explained

00:09:25 — Asymmetric (Public-Private Key) Encryption

00:12:46 — Why Asymmetric Encryption Made Ransomware Stronger

00:15:44 — What Was the CryptoLocker Virus?

00:16:25 — Lessons CryptoLocker Taught Victims and Criminals

00:18:03 — Operation Tovar Takes Down CryptoLocker

00:19:54 — Bitcoin, Ransom Amounts, and Getting Paid

00:23:20 — Botnets Explained: Networks of Zombie Computers

00:26:22 — Recap: Three Phases of Ransomware

00:27:09 — Double Extortion and Data Exfiltration

00:28:01 — The LastPass Connection

00:28:47 — The Lost Crypto Hard Drive

A history of ransomware is more than just dates and names—it's the story of how criminals evolved from mailing infected floppy disks in 1989 to running billion-dollar enterprises that cripple entire organizations. On this episode of The Backup Wrap-up, I sit down with Dr. Mike Saylor, my co-author on "Learning Ransomware Response and Recovery," to trace this evolution from the AIDS Trojan to today's sophisticated double extortion attacks.

We talk about how ransomware went from requiring physical distribution to scaling globally through the internet, how cryptocurrency made anonymous payment possible, and why the shift from tape to disk backups created vulnerabilities that attackers now exploit first. You'll learn about the wild west days when IT focused on building systems without understanding how bad guys attack, the emergence of ransomware-as-a-service that democratized cybercrime, and why modern attacks target your backups before encrypting your production systems.

If you've ever wondered why backup immutability matters or how we got to a point where ransomware is inevitable rather than hypothetical, this episode connects those dots. Dr. Mike and I also discuss why having backups is still critical even with double extortion threats, and what you need to know about defending your backup systems in today's threat environment.

Chapter Markers:

00:00:00 - Introduction

00:01:19 - Welcome and Guest Introduction

00:02:19 - Curtis's First Ransomware Memory

00:03:40 - The AIDS Trojan: First Ransomware (1989)

00:04:42 - The Wild West Era: Late 1990s Security

00:08:05 - Y2K and Budget Shifts

00:11:26 - The Transition from Tape to Disk Backups

00:15:45 - How Disk Backups Created Vulnerabilities

00:19:30 - The Rise of Cryptolocker and Bitcoin

00:23:15 - Ransomware as a Service Emerges

00:27:40 - WannaCry and NotPetya

00:31:20 - Double Extortion: The Game Changer

00:35:10 - Why Backups Still Matter

00:37:55 - Should You Just Pay the Ransom?

00:40:01 - Defending Your Backup System

Understanding how ransomware works is critical for anyone responsible for protecting their organization's data. In this episode of The Backup Wrap-up, we examine the five core objectives that drive nearly every ransomware attack - from initial access through the final ransom note delivery.

I'm joined by my co-author Dr. Mike Saylor as we kick off what's going to be a comprehensive series on our new book, "Learning Ransomware Response and Recovery." We start at the beginning: how do these attackers even get in? Mike breaks down the role of initial access brokers (IABs) - the bad guys who specialize in harvesting and selling credentials. We talk about why email phishing remains the cheapest and most statistically reliable attack vector, even with all our defenses.

From there, we walk through lateral movement and reconnaissance. Once attackers are inside your network, they're not sitting idle. They're mapping your environment, identifying your crown jewels, and figuring out where your backups live. The "phone home" phase establishes command and control, letting attackers coordinate their activities and receive instructions.

We dig into data exfiltration and the rise of double extortion. It's not enough anymore to just encrypt your data - attackers are stealing it first, threatening to publish it even if you can restore from backups. Mike shares some fascinating details about how sophisticated ransomware can be, including variants that examine file headers rather than just extensions to find valuable targets.

The encryption phase itself is resource-intensive, and Mike explains why you might actually notice your computer acting weird if you're paying attention. Your mouse hesitates, typing lags, the network slows down - these are all potential warning signs.

Finally, we cover how ransom notes are delivered today. Spoiler: it's not the old-school desktop background takeover anymore. Modern ransomware drops text files in every folder it touches, making sure you can't miss the message.

This episode sets the foundation for understanding how ransomware works, which is the first step in defending against it and recovering when prevention fails.