Evaluating agents in production with trajectory metrics

Evaluating Agents in Production: Trajectory Metrics, Not Just Final Answers

TL;DR Endpoint evals miss the failure mode that hurts in production - an agent can reach the right answer through a reckless path: wrong tool first, lucky recovery, ignored constraints that did not bite this time Trajectory evaluation scores the run: which tools were called, in what order, with what arguments, and whether each step satisfied policy The minimum viable setup: 50–200 real examples, per-step rubrics, 10+ runs per example, statistical regression tracking, and a held-out set you never tune against Replay harnesses let you re-run a captured trace against a new model or policy without re-hitting production systems This is the measurement layer that connects broken public benchmarks to agent security - you cannot harden what you cannot observe AI Evals Are Broken argued that leaderboard numbers stopped measuring production capability. Securing AI Agents argued that the tool layer must enforce policy the model cannot be trusted to enforce. This post is the bridge: how you measure whether an agent actually behaves before and after you ship. ...

June 14, 2026 · 6 min · James M
World Models - What Comes After the Language-Only Era Banner

World Models: What Comes After the Language-Only Era

TL;DR Language-only models do not contain a reliable simulator of physical reality - they contain a statistical shadow of one, good enough for many tasks and dangerously wrong for others. A world model is a system that learns to predict how an environment evolves and can plan inside that prediction - not just describe it in text. The gap matters for agents that must act in physical space, manipulate objects, or reason about counterfactuals where the answer is not in the training corpus. The 2026 frontier includes generative world simulators, vision-language-action models for robotics, and sim-to-real pipelines - not one breakthrough but a stack assembling in parallel. For builders today: language agents with MCP tools are the right architecture for knowledge work. World models are the path to agents that can competently act in the physical world. Almost everything I have written about AI agents assumes a model whose understanding of the world arrives through text. That assumption has carried the field a long way. Context engineering, tool use via MCP, memory across sessions - all of it sits on top of language models that read, reason, and call APIs. ...

June 13, 2026 · 9 min · James M
What I'm Researching in AI Right Now Banner

What I'm Researching in AI Right Now - And Where I'm Going Next

TL;DR I treat my own learning like a research agenda - a small set of questions I am actively chasing, not a reading list I feel guilty about The work I have been deep in clusters into four areas: agent reliability and non-determinism, context engineering and memory, the economics of intelligence, and the open-weight and small-model frontier The areas I have decided to move into next are the ones where I keep hitting questions I cannot answer well: securing agents that hold real tool access, evaluating agents on their trajectory rather than their final answer, world models beyond the language-only era, and the machine-to-machine agent economy I treat AGI timelines less as a forecast to win and more as a planning input - what changes for an engineer if capable autonomous systems arrive in three years rather than fifteen I am deliberately not chasing every frontier. Quantum machine learning and neuromorphic hardware sit on my watch list, not my work list, and being honest about that line is the whole point Most people consume AI news. I used to do the same - a feed of model releases, benchmark claims, and launch threads that left me feeling informed and changed nothing about what I could actually build. ...

June 8, 2026 · 12 min · James M
Trust series - deploying AI agents in production

Trust: Conditions for Deploying AI Agents in Production

TL;DR The Trust series is my answer to one question: what has to be true before you can hand a non-deterministic system a real job and walk away? Read in this order: research map → evals → security → world models → trajectory evaluation Supporting posts cover reliability, context engineering, and safety foundations Full series index: /series/trust/ Start here What I’m Researching in AI Right Now - the research map and trust through-line AI Evals Are Broken - why public benchmarks stopped measuring real capability Securing AI Agents - MCP hardening, confused deputy, and what I run on my home stack World Models: What Comes After the Language-Only Era - when text-only agents hit their ceiling Evaluating Agents in Production: Trajectory Metrics - step-level scoring, not just final answers Supporting reading AI Agents That Actually Work - patterns from real projects The Agent Reliability Problem - debugging non-deterministic systems Context Engineering - curating the window across a whole agent run AI Reliability Is Weird - why testing LLMs breaks familiar QA AI Safety From First Principles - engineering safety vs speculative scenarios Related paths Home Agent Stack - build the stack these defenses protect AI Dev Tooling - the coding-agent side of the same problem Related Reading AI Economics and Hardware: A Reading Path - cost and infrastructure decisions that constrain what you can actually deploy Expertise and Work in the Age of AI - how trust and accountability reshape what human expertise is for Agent Protocols in 2026: MCP, A2A, and ACP - the protocol layer where many trust boundaries live Structured Outputs and Schema Design for LLMs - making agent behaviour predictable enough to evaluate

June 8, 2026 · 2 min · James M
Context Engineering - The Discipline That Replaced Prompt Engineering Banner

Context Engineering: The Discipline That Replaced Prompt Engineering

TL;DR Prompt engineering optimised the wording of a single human-written request. Context engineering optimises the entire set of tokens in the model’s window across a whole run - system prompt, tool definitions, retrieved documents, tool results, conversation history, and memory The shift happened because of agents. The window is no longer one prompt you wrote - it is an accumulation that grows on every step, and most of it is produced by the system, not by you More context is not better context. Research on “context rot” and the older lost-in-the-middle effect show model accuracy degrades as the window fills, even well below the advertised limit The four levers are retrieval (what you pull in), memory (what persists across runs), tool results (what tools dump back), and compaction (what you summarise and discard) Treat the window as a budget. Measure its token composition, design tools to return terse output, curate rather than accumulate, and keep the static prefix stable so prompt caching still works For a few years, “prompt engineering” was the named skill of working with language models. It meant finding the wording, the framing, the few-shot examples, and the role instructions that coaxed the best answer out of a single request. It produced a small industry of prompt libraries, prompt marketplaces, and job titles. And in 2026 it is mostly gone, absorbed into something larger and harder. ...

May 20, 2026 · 11 min · James M
AI dev tooling reading path

AI Dev Tooling: A Reading Path for 2026

TL;DR Start with What Actually Belongs in My AI Dev Stack in 2026 - the canonical stack essay Then An AI Tooling Learning Path - phased skill-building order Deep dives below cover comparisons and spec-driven workflows; single-tool posts are briefs, not entry points Canonical essays What Actually Belongs in My AI Dev Stack in 2026 An AI Tooling Learning Path: Logical Phases for 2026 Context Engineering - the production skill behind reliable coding agents Spec-Driven Development - when the brief becomes the product Deep dives Claude Code vs Cursor: A 6-Month Comparison GitHub Spec Kit and Spec-Driven Development GitHub Spec Kit in 2026: SDD Goes Mainstream My AI-Augmented Design Workflow When to Fine-Tune vs When to RAG Briefs (moment-in-time) These are useful snapshots, not the starting point: ...

May 20, 2026 · 2 min · James M
AI economics and hardware reading path

AI Economics and Hardware: A Reading Path

TL;DR Cost is a design constraint, not an afterthought - model tier, context size, and deployment location are economic decisions Read the essays below in any order; start with Token Economics if you only have time for one Pairs with open-weight models and local inference guides Core essays Token Economics: Why the Cost of AI Isn’t Going Down GPU Servers vs AI API Credits: The Real Cost Breakdown Local AI vs Cloud AI: The Tradeoff Landscape in 2026 The AI Energy Crisis: Why Data Center Power Will Define the Next Decade Cerebras, Groq, SambaNova: The Inference Hardware Insurgents Adjacent The State of Open-Weight Models in 2026 - when open weights beat closed APIs on price Prompt Caching - the quiet latency and cost win The Token Efficiency Mindset - curating spend per conversation Is the $20 AI Subscription Era Over? We Are Learning to Buy Intelligence Related Reading AI Dev Tooling: A Reading Path for 2026 - canonical path for coding agents and stack decisions that depend on these cost constraints Home Agent Stack: From Mac Studio to Secured MCP Tools - building the hardware and software layer these economics govern Reasoning Models in 2026: What Changed and What Didn’t - why reasoning models carry a different cost profile than base models The Free Intelligence Era - the macro argument for where intelligence costs are headed

May 18, 2026 · 2 min · James M
Home agent stack reading path

Home Agent Stack: From Mac Studio to Secured MCP Tools

TL;DR This path walks through the full stack I run on a Mac Studio: local models → MCP tools → memory → remote access → security Almost no other blogs document the build and the hardening layer together Finish with Securing AI Agents before giving the agent real filesystem or mail access Part of the broader Trust series Read in order Which Mac Studio Should You Buy for Running LLMs Locally? - hardware and model sizing Giving Your Home AI Agent Real Tools: MCP Servers on a Mac Studio - wiring the tool layer Giving Your Home AI Agent Memory That Lasts - persistence across sessions How to Phone Your Home AI Agent - remote access when you are away Securing AI Agents - least privilege, confirmation gates, audit logs Adjacent guides Running AI Models Locally with Ollama - lighter-weight local inference option Agent Protocols in 2026: MCP, A2A, and ACP - the protocol layer Local AI vs Cloud AI - when to host vs call APIs DGX Spark vs Mac Studio - if you are sizing a dedicated inference box Related Reading AI Economics and Hardware: A Reading Path - token costs, GPU sizing, and energy constraints behind every hardware decision AI Dev Tooling: A Reading Path for 2026 - the coding and development layer that sits above the agent infrastructure Open WebUI: A Self-Hosted LLM Interface - web interface layer to pair with local inference Agent Protocols in 2026: MCP, A2A, and ACP - the protocol layer connecting agents to tools

May 15, 2026 · 2 min · James M
The Agent Reliability Problem Banner

The Agent Reliability Problem: Debugging Non-Deterministic Systems

The conventional reliability engineering toolkit was built for systems that behaved the same way each time given the same input. AI agents do not behave the same way each time given the same input. The classic tools - unit tests, integration tests, deterministic replay, traditional monitoring - all assume a property that the systems being operated do not have. This mismatch is not a small operational annoyance; it is the central challenge of running AI agents in production, and the patterns for handling it are still being worked out. ...

May 15, 2026 · 7 min · James M
Multimodal AI in 2026 Banner

Multimodal AI in 2026: Vision + Text + Audio - What's Actually Useful

TL;DR Document understanding is the unglamorous killer application - invoices, contracts, and scanned PDFs that were painful to extract data from are now tractable without dedicated pipelines Vision models still under-deliver on precise spatial reasoning, object counting, and subtle medical or scientific imagery - these remain jobs for specialist models Audio is the modality with the most upside: beyond transcription, it carries tone, pace, and hesitation that text loses, enabling fault detection, emotional analysis, and richer inputs The teams getting real value treat multimodal as an invisible enabling capability within a workflow, not a feature to demo - and they verify high-stakes outputs just as they would text The right question when evaluating multimodal is not “can we use this” but “what specific user problem becomes tractable that previously was not” When the first multimodal frontier models shipped, the demos were genuinely impressive. A photo of a fridge interior with the model suggesting a recipe. A handwritten napkin sketch becoming working code. A short audio clip of a meeting being transcribed, summarised, and structured. It looked, briefly, like the boundary between modalities had collapsed and we were entering a new regime in which models could reason fluidly across text, images, and sound. ...

May 9, 2026 · 10 min · James M