A model grading your agent’s output is the only thing that scales for subjective quality — and it’s a biased instrument you’re reading as a ruler. Here are the biases that actually move scores (position, verbosity, self-preference, leniency), why raw agreement with a human hides them, and how to validate and harden a judge with code — including why you should be reporting Cohen’s kappa, not accuracy.
“It works” is a demo result, not a measurement. An agent is a trajectory, not a function, and grading only the final answer throws away most of what decides whether it’s reliable. Here’s a five-layer scheme for what to measure — outcome, trajectory, cost, failure class, and stability under nondeterminism — with a small harness that computes it.
Treating the context window as append-only memory is how agents get slow, expensive, and quietly wrong. The fix is to run it like a cache with a budget and an eviction policy: decide what earns its tokens every turn. Here’s the cost math, the accuracy failure mode, and a working context manager.
The worst agent failures don’t crash — they keep working. A postmortem on loop drift: an agent that stayed busy for 40 steps without getting closer to done, why the model’s own progress reports can’t catch it, and the external signals and evals that can.
A tool schema is a contract with a caller that guesses. This is a concrete walkthrough of the four properties that separate a tool a model uses correctly from one it fumbles: legible schemas, validating boundaries, recoverable errors, and idempotency — with before-and-after code.
Retries feel cheap and local. In a multi-step agent they’re neither. A small cost model shows why 20% per-step failure can more than double your bill — and how your recovery architecture, not your failure rate, decides the multiplier.