The Backup Wrap-Up

Claude deletes a company — and the internet immediately blamed the AI. But this story is really about backup design, credential management, and least privilege. An AI coding agent running Claude via Cursor deleted PocketOS's entire production database and all its backups in nine seconds. One bad design decision at a time, a startup built itself a disaster waiting to happen. Claude just happened to be the thing that set it off.
Here's what you need to understand: the AI violated the principles it was given, and that's on Claude. But Claude never should have had access to do what it did. Credentials were sitting in a plain text YAML file. The production database and its backups lived on the same volume. No least privilege. No expiration on elevated permissions. And almost certainly, no backup recovery test — ever.
In this episode, Curtis and Prasanna break down what actually went wrong with PocketOS, what Railway did to help recover the data, and what you need to do to make sure this never happens to you. Topics covered include backup isolation, the 3-2-1 rule, secrets management tools like AWS Secrets Manager and HashiCorp Vault, least privilege access, permission expiration, and credential scanning tools like TruffleHog.
Chapters:
0:00 — Intro: Meet the villain
1:50 — Welcome and introducing "the French friend"
3:48 — What Claude actually did to PocketOS
7:20 — This is a backup story, not an AI story
9:27 — The recovery: Railway, a weekend of chaos, and a lucky Twitter post
12:31 — Your data is your responsibility — not your vendor's
17:48 — Rule #1: Never store backups inside production
20:37 — The real problem: credential management
23:38 — Secrets management tools explained
25:21 — Least privilege and why permissions need expiration dates
34:59 — Finding exposed credentials with TruffleHog
37:24 — Summary and takeaways

Honeypots and canary files are two of the most underused tools in cybersecurity — and in this episode, Dr. Mike Saylor and I break down exactly how they work and why you should be using them. The short version: they're tripwires. They tell you a bad guy is poking around your network before anything gets encrypted.
Mike walks through his layered security analogy, explains the three different ways organizations use honeypots — learning attacker tactics, distraction, and testing — and then we get into canary files: what makes them different from a honeypot, how they beacon home when stolen, and why clock synchronization matters more than most people think if you ever want that evidence to hold up.
We also cover how to stand one up without a big budget, what tools are available, and why something is absolutely better than nothing. Plus, Mike and I have news about our new O'Reilly book, Learning Ransomware Response and Recovery.
0:00 - Intro and book news
1:09 - Meet the crew
3:45 - Security is all about layers
9:22 - What are honeypots and canary files?
11:00 - Three ways honeypots work for you
13:17 - Real-world examples: bait cars and glitter bombs
15:20 - Making your honeypot convincing
19:11 - Honeypot tools and options
21:13 - Something is better than nothing
24:10 - Monitoring and notifications
25:05 - Canary files explained
27:03 - How canary files beacon and track attackers
28:03 - Don't forget to sync your clocks
29:05 - Final thoughts

Network segmentation to prevent ransomware isn't just a nice-to-have — the UCSF ransomware attack proves it's what separates a contained incident from a catastrophe. UCSF got hit. Their segmented network kept the damage from spreading across their entire operation. That's the difference we're talking about in this episode.
Dr. Mike Saylor — my co-author on Learning Ransomware Response and Recovery — joins me and Prasanna to break down exactly how network segmentation works, why it matters for ransomware defense, and how to start doing it without breaking everything in the process. (Not that I've ever done that. Much.)
We cover what segmentation actually is, how VLANs make it manageable, the "need to talk" principle, and where microsegmentation fits in — and when it becomes overkill. We also get into the complexity trap: more rules and more layers don't automatically mean more protection. Sometimes they mean nobody can troubleshoot anything when the house is on fire.
If you're an IT admin trying to make the case for better network architecture, or you just want to understand what would actually stop ransomware from ripping through your environment, this is the episode.
Chapters:
00:00:00 — Intro
00:01:40 — Welcome & Guest Introductions
00:05:17 — Case Study: UCSF Ransomware Attack
00:08:13 — What Is Network Segmentation?
00:12:32 — VLANs Explained
00:19:50 — The Need to Talk Principle
00:30:54 — Complexity vs. Security
00:31:09 — Microsegmentation
00:38:55 — Action Items: Where to Start
00:42:05 — Monitoring VLAN Traffic

Stop Using VSS as a Backup Before Ransomware Deletes Your Shadow Copies
Ransomware deletes shadow copies using your own built-in Windows tools against you — and if VSS was your backup plan, you just found out the hard way that it wasn't. In this episode, W. Curtis Preston (Mr. Backup), Prasanna Malaiyandi, and Dr. Mike Saylor break down exactly what shadow copies are, why they don't qualify as a real backup, and how attackers are weaponizing vssadmin to wipe your recovery options before you even know you're under attack.
If you've got Windows systems and you've been thinking "eh, we've got shadow copies," this episode is for you. We cover the history of VSS — what it was actually designed for, why it became a crutch, and why using it as your primary backup strategy is a bad idea on multiple levels. Performance, the 3-2-1 rule, and the fact that one attacker with admin rights can delete every single copy in seconds. We also get into the living off the land angle: how attackers do recon on your shadow copies, how they use them to scope out valuable data before going full ransomware, and what you can actually do to detect and respond to this behavior using EDR tools.
The bottom line: VSS is a great tool. It was just never meant to be your backup. Get a real one.
Chapters:
0:00 — Intro
1:39 — Welcome & Book Talk
3:26 — What Are Shadow Copies and Why Do People Use Them as Backups?
9:14 — Performance Problems with VSS as a Backup
10:19 — Living Off the Land: How Ransomware Uses VSS Against You
12:36 — Can You Monitor or Lock Down VSS Admin?
14:26 — Why Shadow Copies Fail the 3-2-1 Rule (They're Not a Backup)
18:01 — How to Protect Yourself: Configuring Your EDR
21:31 — The Local Admin Problem and Security Culture
27:00 — Virtualization, Snapshots, and Shadow Copies
29:00 — Final Thoughts: Just Don't Do That

Ransomware sanctions are something most companies never think about — until they're staring down a ransom demand from a group the US government has already put on a sanctions list. In this episode, Dr. Mike Saylor walks us through a real incident involving a construction company, hundreds of millions in active contracts, and the Lazarus Group — a North Korean state-sponsored threat actor. Before that company could pay a single dollar in ransom, they had to figure out whether doing so would trigger federal penalties that dwarfed the ransom itself. We're talking fines of 10x to 100x the payment amount, and in some jurisdictions, jail time.
This is one of those episodes where the story alone is worth your time. Mike was in the room for this incident, negotiating directly with the Lazarus Group over a weekend — and yes, it turns out North Korean cybercriminals have a surprisingly functional help desk. But beyond the story, there's real actionable information here about OFAC (the Office of Foreign Asset Control), how the US Treasury tracks Bitcoin wallets to identify sanctioned actors, and what you actually need to do the moment ransomware hits your organization.
We also get into why paying a ransom paints a target on your back — 70% of companies that pay get hit again within six months — and why immutable backups are the only thing that truly keeps you out of this situation.
Chapters:
0:00 Intro
1:31 Meet the Guests: Curtis, Prasanna, and Dr. Mike Saylor
4:10 Case Study: A Construction Company and the Lazarus Group
6:34 Are These Bad Guys Sanctioned? Introducing OFAC
8:05 Why Ransomware Funds Terrorism, Drug Trafficking, and Worse
11:00 Sanctions Penalties: Fines That Can Put You Out of Business
12:24 Colonial Pipeline and Exceptions for Critical Infrastructure
13:26 How the Government Tracks Bitcoin Wallets
16:27 Global Sanctions: UK and Australia Have Their Own Rules
18:31 Pay Once, Pay Again: The 70% Re-Attack Rate
20:43 Proof of Life: Don't Pay Without It
23:38 What To Do When You Get Hit: The Right Order of Operations
25:17 Immutable Backups: The Only Real Answer
27:07 How the Construction Company's Backups Got Wiped
33:07 Build Your Team Before the Bad Day: FBI InfraGard and More