Plaintext with Rich

Roll for Security: What D&D Teaches About Cyber Defense

Plaintext with Rich

Show Notes

The fighter absorbs hits up front. The rogue finds traps before the party walks into them. The cleric keeps everyone alive when things go wrong. And the bard convinces the people with resources to actually fund the quest. Nobody does everything. Everybody has a role. Now replace the dungeon with your company's network. This episode maps cybersecurity roles to D&D character classes, SOC analysts as fighters, pen testers as rogues, incident response as clerics, security architects as wizard...

More from Plaintext with Rich

Oct 23, 2026

Task scams can make an evening of online assignments feel like money earned. Then the withdrawal request turns into another demand, and the balance you've been watching starts to mean something different. Rich traces the sequence described in the Federal Trade Commission's August 2025 warning, from unexpected work offers to supposed commissions and deposit demands. The conversation explores why a polished app can display earnings without establishing that the money exists or belongs to you. I...

Oct 16, 2026

Device-code phishing starts with an uncomfortable possibility: the sign-in address you checked really does belong to Microsoft. The document you're expecting comes with a code, the page looks right, and the question that matters is still hiding in the request. Plaintext with Rich follows the approval from the person entering that code to the software waiting on the other end. A television sign-in and a parcel collection slip help explain device-code flow without turning your commute into a te...

Oct 9, 2026

Browser extensions can stay in your working day long after you've forgotten why you installed them. That tiny toolbar icon may represent a bigger arrangement than you remember making. Rich explores what extension permissions describe, from website data to other browser capabilities, and why broad access deserves context rather than automatic suspicion. Socket's August 2026 investigation supplies a concrete example of useful extensions acquiring malicious behavior, including some bought from l...

Oct 2, 2026

You came for a conference agenda, and the website wants proof you're human. ClickFix can hide behind that familiar check, with instructions that deserve a much closer look. Rich follows the moment a fake CAPTCHA, a test meant to distinguish people from automated visitors, changes what it asks you to do. Microsoft's August 2026 TerminalFix analysis provides a concrete example involving an imitation Cloudflare screen and commands pasted into Windows Terminal or PowerShell. CERT Polska's Februar...

Sep 25, 2026

Episode 4: When the Phones Woke Up Finding one another doesn’t fix the city. There are still people waiting for news, families searching for loved ones, and neighborhoods trying to function without the systems they depend on. Then the phones begin waking up. In the final chapter of Last Seen, messages arrive out of order, maps fill with roads again, and everyday convenience returns almost as quickly as it disappeared. But after seeing what happens when one damaged connection affects nearly...

See all episodes →