Essays, link dumps, and opinion pieces about current events in the software landscape, offering what I hope is new perspective.

“The reasonable man adapts himself to the world: the unreasonable one persists in trying to adapt the world to himself. Therefore all progress depends on the unreasonable man.” – George Bernard Shaw (Man and Superman)

  • NOTE: By no means should this aphorism be interpreted as meaning that all unreasonable people contribute to progress; in fact, in many cases, just the opposite (myself included).

You can reach out to me with constructive criticism or insights at infosec.exchange@lmk.

Role confusion: one more reason we can’t trust LLMs

Prompt Injection as Role Confusion is my new favorite paper about a very obvious threat in hindsight that’s hard for us humans to see because we anthropomorphize LLMs so naturally. When Obi-Won Kenobi tells the stormtroopers that “These are not the droids you are looking for” to pass the checkpoint that’s role confusion: the guards foolishly think his words are their own thoughts. The very readable blog-style writeup explains the details, but I want to focus on the threat model perspective which is my bread and butter.

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ai  security 

Normalizing cybersecurity facepalms

OpenAI writes: “Last week, Hugging Face disclosed a new kind of security incident⁠(opens in a new window) after they detected and contained an AI agent that compromised their infrastructure, something we expect to become more commonplace with the proliferation of increasingly cyber-capable models. After investigating, we now know that this particular incident was driven by a combination of OpenAI models — including GPT‑5.6 Sol and an even more capable pre-release model, all with reduced cyber refusals for evaluation purposes — while being internally tested on a benchmark⁠(opens in a new window) of cyber capabilities.”

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ai  security 

PHANTOM-B: threat modeling systems using LLMs

Opinion

Back in 1999 had STRIDE anticipated LLMs at all, much less their particular threats, it would be remembered as an unbelievable feat of prognostication rather than just categories of threats. However, even if it had predicted present day machine learning capabilities I think it plays a different role than the subject of the latest Shostack + Associates White Paper #6 titled PHANTOM-B: A STRIDE Analog for LLMs (PHANTOM-B is a tool to structure how you answer the question “What can go wrong with the LLM parts of the system?)” clearly notes: “PHANTOM-B is intended to be used as prompts, rather than categories.” By “prompts” I believe that means suggestions for (non-digital) people — not inputs to LLMs.

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Toward Better AI Legislation

“People deserve to know whether or not the videos, photos, and content they see and read online is real or original,” said Senator Schatz. “Our bill is simple – if any digital content is made by artificial intelligence, it should be labeled so that people are aware and aren’t fooled or scammed.”

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ai 

June 2026

This month the link dump continues to evolve: breaking out a few article length posts and then various links and quick thoughts to share. As always this is all quick takes so please read with a grain of salt and I’m happy to get criticism where needed.

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“Fence the ocean”

According to the recent article, ‘Very blunt approach’:

eSafety Commissioner Julie Inman Grant has expressed reservations about the social media ban for under-16s pushed by Minister for Communications Anika Wells.
“What you’re effectively asking us to do with this is fence the ocean,” she said. “We might be able to create some friction and some degree of safety, but it’s a futile exercise if you think you’re totally stemming the ocean.”

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