Trash Bags and Shoeboxes

Charles Herring 14 August 2026
Trash Bags
If you stuffed a year of receipts into trash bags and dumped them on your accountant every April, they would stop taking your calls. That is what our industry hands law enforcement, and then we wonder why nobody prosecutes cybercrime.

The Deterrence Delusion

Charles Herring 12 August 2026
Handcuffs on Keyboard
Ninety-two percent of business owners say they would call the police about a ransomware attack. Eighteen percent of actual victims do. The reason cybercrime feels unattributable is not physics. It is that we shred the evidence at ingest.

Hard-Earned Trust, Automated Away

Charles Herring 3 July 2026
Hard Earned Trust Lost to Automation
Someone stood up a slick "WitFoo Authorised Partner" store selling licences we never made, and the registrar's abuse desk answered with a form letter. A look at counterfeit partner programmes, the supply-chain risk they create, and what happens when we automate away the judgement that trust actually depends on.

Fish in a Box

Charles Herring 25 June 2026
Dragon 300 on launch from USS Kitty Hawk
Twenty years ago a young sailor quoted "Fish's second rule of troubleshooting" back to me, and I realised I'd been writing rules I never wrote down. This is the story of how we used AI to inventory, argue over, and ratify the norms that run WitFoo, from "The WitFoo Way" of coding all the way out to a thing we call Fish-in-a-box.

Adversarial Code Review Example with Claude

Charles Herring 18 June 2026
Adversarial Review

Below you will find my adversarial review prompt that I give to Claude on every pull request review. This is a living document that references dozens of cascading documentation. Collectively, over 1,700 norms contained in the "WitFoo Way" are reviewed. Also, the integrity of the work done by what is often a lazy or dishonest Claude session. In spite of the rigorous testing I outlined in Coding with Claude: What I've Learned Building a Cybersecurity Platform with AI , Claude finds new innovative ways to come off the rails. I use this prompt in an independent session to find shortcuts and lies from the PR session. I have run this prompt dozens of times and it has never come back without hits.

Podcast: Adventures of Alice & Bob

Charles Herring 23 April 2026
Alice and Bob Podcast with Charles Herring
In this episode, James talks to Charles Herring about what happens when an IT wizard runs away to join the Navy, works on fighter jets, and then gets thrown into cybersecurity right after 9/11? He shares his unconventional journey from the Wild West days of network defense, complete with fighting worms with worms—to being CISO during the Target breach. Plus: why trauma creates silos, why your SOC is like throwing receipts in garbage bags, and what it takes to build a "good neighborhood" in cybersecurity.

Three Prompts That Turn Your Data Lake Into an Empathetic Processor

Charles Herring 22 April 2026
Huggingface Dataset
Earlier this week, WitFoo and the University of Canterbury released 100 million labelled cybersecurity records to Hugging Face under Apache 2.0. Here's a three-prompt walk-through for putting it to work in a stack you already own (Grafana, Sentinel, Splunk, Elastic), using Empathetic Processing to translate, detect, and visualise across your own data.

Blaster, Mythos, and the Patching Tempo We're About to Need

Charles Herring 8 April 2026
Digital Storm
In 2003 at the Naval Postgraduate School, the Blaster worm taught me hard lessons about patch windows, perimeter assumptions, and the laptops that walk in from outside. With Anthropic's release of Mythos, we're about to relive a version of that August, compressed and supercharged. Here's the guidance I gave my team and what I wish I'd known in Monterey.

The Nuclear Code Fork

Charles Herring 30 March 2026
Submarine Control Room
We killed all 450 external dependencies in our analytics platform and brought every line of code in house. It took two days, ~305K tokens, and uncovered 14 vulnerabilities that were already sitting in our stack. Here's why we did it, what we found, and what it actually cost.

Lost in Space, Time and Standards

Charles Herring 16 March 2026
Southern Cross
I anticipated most of the challenges of moving to New Zealand. Immigration, housing, saying goodbyes. What I didn't anticipate was how exhausting it would be to relearn space, time and standards. When seasons run backwards, Mondays happen twice, and you find yourself whispering 'I miss inches' in bed, the cumulative toll is real. Fortunately, wonder makes a good coping mechanism

Supersonic Broken Processes: The Hazards of Automating Cybersecurity with AI

Charles Herring 15 March 2026
Speedometer
You cannot accelerate a process to supersonic speeds if it barely works at five miles per hour. Applying Anthropic's 4D Framework for AI Fluency to cybersecurity automation reveals that all four D's (Delegation, Description, Discernment, Diligence) fail when built on the same siloed, philosophy-free foundations that have plagued SECOPS for decades. The consequences in our field are uniquely severe: the AI can't go to prison when it gets it wrong.

How AI was the Best Bender of My Life

Charles Herring 11 March 2026
Lake Tekapo
I built guardrails for the code, the architecture, and the security. I forgot to build guardrails for myself. After an eight-month megasprint rebuilding 10 years of work with Claude, I ended up on bedrest for a week. Turns out AI-assisted development is the most potent productivity drug ever created, and the dose that makes it medicine and the dose that makes it poison are closer together than you'd think.

The Closing Window: AI's Value-to-Cost Ratio Is Shifting Fast

Charles Herring 4 March 2026
Sinking Tokens
In September, I burned through an entire GitHub Enterprise token allocation and barely noticed — the overages cost pennies. I rated that moment at 1,000:1. Value to cost. By February, I'm spending $2,000 a week on similar workflows. The ratio is now 600:1 and falling. The window isn't shut. But it's moving. Here's what I think is driving it, and what I'm planning for when it closes.

People > Machines (The OODA Loop Strikes Back)

Charles Herring 12 February 2026
OODA Loop
Eight years after writing "People > Machines," the thesis holds stronger than ever. AI-assisted development has turned the OODA loop into a double-edged sword: with solid devops practices, it creates virtuous cycles that compound quality at unprecedented speed. Without them, it amplifies technical debt into a death spiral. The microphone-next-to-the-speaker problem is real, and the human in the loop is the one who decides what gets amplified.
Subscribe to Newest Content