Simon Willison — 2026-05-28#

Highlight#

Anthropic’s release of Claude Opus 4.8 brings welcome improvements to model honesty and prompt caching, which Simon immediately put to the test using his newly updated llm-anthropic CLI plugin to generate SVGs of pelicans riding bicycles.

Posts#

Claude Opus 4.8: “a modest but tangible improvement” Simon highlights Anthropic’s refreshing honesty in marketing this release as an incremental upgrade, noting the model’s decreased hallucination rate achieved by simply abstaining when uncertain. Key technical changes include a reduced prompt cache minimum of 1,024 tokens and the ability to insert system messages mid-conversation, which preserves cache hits and reduces input costs in agentic loops. He tested the model by generating SVG pelicans riding bicycles at different thinking levels via his LLM CLI, using Opus 4.8 to build the rendering HTML tool and relying on GPT-5.5 as a “code security blanket” to patch XSS vulnerabilities.

Engineering Reads — Week of 2026-04-02 to 2026-04-10#

Week in Review#

This week’s reading reflects a fundamental inflection point: raw LLM intelligence is no longer the bottleneck in software development. Instead, the industry is pivoting toward the hard systems engineering required to constrain probabilistic models—whether through strict data ledgers, living specifications, or formal verification harnesses. The dominant debate centers on how we preserve architectural taste, mechanical sympathy, and system ethics as the mechanical act of writing code becomes increasingly commoditized.

Simon Willison — Week of 2026-04-04 to 2026-04-10#

Highlight of the Week#

Anthropic’s decision to delay the general release of their highly capable Claude Mythos model under “Project Glasswing” marks a significant turning point in the AI industry. The move underscores a massive shift in frontier model capabilities, as models evolve from generating text to autonomously chaining multiple minor vulnerabilities into sophisticated exploits, requiring a new level of security safeguards before release.

Engineering Reads — Week of 2026-04-08 to 2026-04-16#

Week in Review#

This week’s reading is dominated by the tension between raw, AI-driven generation and the enduring necessity of classical engineering discipline. As AI commoditizes rote code generation, the defining characteristics of engineering are migrating from writing syntax to exercising architectural taste, writing clear specifications, and deliberately bounding probabilistic systems with human constraints. The consensus is clear: creating output is increasingly trivial, but owning the execution mechanics and maintaining systemic intuition requires a conscious, hands-on imperative.

Simon Willison — Week of 2026-04-11 to 2026-04-17#

Highlight of the Week#

This week’s most striking revelation came from Simon’s infamous “pelican riding a bicycle” SVG generation benchmark, where a 21GB quantized local model (Qwen3.6-35B-A3B) unexpectedly outperformed Anthropic’s brand-new Claude Opus 4.7 flagship. Running locally on a MacBook Pro via LM Studio, Qwen generated a better bicycle frame and even won a secret unicycle backup test, leading Simon to conclude that his joke benchmark’s long-standing correlation with general model utility has finally broken down.

Simon Willison — Week of 2026-04-18 to 2026-05-01#

Highlight of the Week#

The alpha release of llm 0.32a0 marks a foundational architectural pivot for Simon’s ecosystem of CLI tools. By moving away from a simple text-in/text-out abstraction to one that natively models complex message sequences and typed streams, the library is now future-proofed to handle the realities of modern frontier models. This opens the door for seamless integration of server-side tool calls, multi-modal inputs, and reasoning tokens.

Engineering Reads — Week of 2026-05-07 to 2026-05-15#

Week in Review#

This week’s engineering discourse reflects a mature industry grappling with system boundaries and human intent. From constraining unpredictable AI integrations into strictly bounded functional workflows to leveraging organizational psychology to structure open-source compiler architecture, practitioners are aggressively reclaiming control over non-determinism. We are seeing a distinct pushback against buzzword-driven hype in favor of operational stability, rigorous domain modeling, and trusting native web standards over heavyweight abstractions.

Simon Willison — Week of 2026-05-08 to 2026-05-15#

Highlight of the Week#

The standout development this week is Simon’s rapid adaptation to the latest frontier model capabilities, most notably releasing llm 0.32a2 to expose and visualize the new interleaved reasoning tokens of GPT-5 class models directly in the terminal. This perfectly pairs with his hands-on explorations of embedding LLM calls deeply into developer workflows, such as executing prompts via script shebangs and leveraging models to output rich HTML rather than just Markdown.

Simon Willison — 2026-05-27#

Highlight#

Simon makes a compelling case that April 2026 marks a new inflection point where frontier AI labs have found true product-market fit with coding agents. By analyzing sudden enterprise pricing pivots, sales hiring sprees, and massive inference compute deals, he illustrates how the enterprise adoption of AI agents is finally turning massive usage into real revenue.

Posts#

I think Anthropic and OpenAI have found product-market fit Simon argues that the sudden shift by OpenAI and Anthropic to charge enterprise customers full API token prices for agent usage signals true product-market fit. He notes that heavy coding agent users easily burn thousands of dollars in token equivalents, prompting labs to pivot away from middlemen like Cursor or Copilot to capture this enterprise value directly. The piece features some classic Simon dogfooding—using Claude Code and Datasette Agent to analyze AI lab job listings—and highlights a SpaceX S-1 filing revealing Anthropic’s staggering $1.25 billion monthly compute spend.

Simon Willison — 2026-05-26#

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Today’s updates emphasize the dual-edged sword of AI in security, contrasting how AI tools are overwhelming open-source maintainers with a flood of valid vulnerability reports while simultaneously introducing novel data exfiltration risks in enterprise agentic systems like Microsoft Copilot.

Posts#

The pressure · Source Daniel Stenberg highlights the unprecedented toll that high-quality, AI-assisted security reports are taking on the curl project’s team. The volume of credible vulnerabilities has surged to over one report per day—double the rate seen in 2025—leading to severe work-life balance issues for maintainers. Fortunately, because curl is well-architected, these AI-discovered flaws are almost exclusively categorized as LOW or MEDIUM severity, with no HIGH severity issues found since late 2023.