Tokens & Context Windows Cheat Sheet

What counts, what it costs, and what falls out of the window

Tokens are the unit of both billing and memory. Estimating them well is most of cost control and all of context management.

Intermediate 1 min read 14 Entries Version 1.0 Sabir Updated 2
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Estimating tokens

Content Rough tokens Note
English prose ~1 token per 4 characters About 0.75 tokens per word
Code ~1 token per 3 characters Punctuation and indentation are dense
JSON Higher still Braces, quotes and keys all cost
Non-Latin scripts 2–3× more per character Budget generously for CJK and Arabic
An A4 page of text ~500–700 tokens Useful for sizing document pipelines

What occupies the window

  • The system prompt — every single turn It is re-sent with each request, not remembered
  • The full message history you choose to send The API is stateless; you own the memory
  • Tool and function definitions Their JSON schemas are prompt text
  • Tool results fed back in Often the largest single contributor
  • The reply being generated Input and output share the window

Truncation strategies

Strategy Keeps Loses
Sliding window The last N turns Anything agreed early on
Summarise-and-drop A rolling summary plus recent turns Detail, gradually
Pinned + recent Explicitly marked turns, plus recent Needs someone to choose the pins
Retrieval over history Whatever matches the current turn Continuity between turns

Frequently asked questions

Does a bigger context window mean I can stop managing context?
No. Cost scales with what you send, latency grows with it, and retrieval accuracy over a very long context is not uniform. A big window buys headroom, not a free pass.
Why does my token count differ from my word count?
Tokens are sub-word pieces. English prose runs about 0.75 tokens per word; code, JSON and non-Latin scripts run considerably higher because punctuation and rare characters split into more pieces.

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