What actually drives your Claude bill: cache misses, quadratic context, and prepaid retries

The per-token rate on Anthropic’s pricing page is real, but it’s the least useful number for predicting your actual invoice. Three multipliers move the bill far more than model choice does — a cache that silently misses, a transcript that grows quadratically with run length, and a best-of-N pattern that prepays for latency you may not need. Here’s the arithmetic on all three, combined, with real numbers.

August 20, 2026 · 8 min · 1565 words · Loop & Retry

The transcript is a log, not an index: retrieval for long-running agents

Eviction and summarization keep a long-running agent’s window small, but the summaries themselves still accumulate in the linear transcript — and on a run long enough, that accumulation becomes the new quadratic. Past a few hundred steps, the fix isn’t a better compaction policy inside the window. It’s moving history out of the window entirely and querying it like a database instead of replaying it like a log.

August 5, 2026 · 7 min · 1348 words · Loop & Retry

Prompt caching: what actually gets cached, and when it silently misses

Prompt caching can cut your input-token bill by 90% on the reused part of a request — or do nothing at all, with no error to tell you which. It’s an exact-prefix match with a short TTL, and small, common mistakes in how agents build requests break it silently. Here’s what actually gets cached, the five ways real agents lose the discount without noticing, and how to check whether yours is.

July 20, 2026 · 8 min · 1596 words · Loop & Retry

Your token bill is the cheap part: dimensioning the real cost of an agent

Everyone budgets the token bill because the provider hands you an invoice for it. But an agent in production spends across five other axes that never show up on that invoice — wall-clock latency, orchestration, tool-call fees, human review, and idle polling — and for a lot of workloads the tokens are the smallest line. A model that sums all six so you can see which one you’re actually paying.

July 14, 2026 · 8 min · 1534 words · Loop & Retry

Why a long agent run costs O(N²) tokens — and how to flatten it

A naive agent’s token bill doesn’t grow with the number of steps — it grows with the square of them, because every step re-reads the whole transcript that every previous step appended to. A small cost model shows the curve, and four structural moves turn the quadratic back into something close to linear without dropping information the agent actually needs.

July 13, 2026 · 6 min · 1145 words · Loop & Retry

The context window is a cache, not a memory

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.

July 7, 2026 · 9 min · 1826 words · Loop & Retry

Retry budgets: why 20% per-step failure doubles your token bill

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.

July 5, 2026 · 8 min · 1651 words · Loop & Retry