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Context Windows in AI Applications

Master the constraints of LLM working memory. Learn to calculate token usage with Tiktoken, explore strategies for importance-based message pruning, and understand how to implement recursive summarization for long-term coherence.

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Context Hub

Memory management.

Quick Quiz //

Which of these is the most accurate way to reliably count tokens before sending a prompt to an OpenAI model?


An AI doesn't have a hard drive; it has a 'Reading Desk'. If the desk is full, you can't add more papers without taking some away.

1The Boundary of Intelligence

Think of an AI model like a brilliant assistant who unfortunately has a very strict limit on how much they can hold in their working memory. This critical constraint is called the Context Window.

If you accidentally dump too much text and exceed the model's hard token limit, the API will immediately reject your request and return a harsh 400 error. As a professional engineer, you must strictly utilize specialized tokenizers like OpenAI's tiktoken to mathematically calculate exactly how many tokens your massive prompt contains BEFORE you send it.

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import { get_encoding } from 'tiktoken';

// Always count tokens before sending
function checkTokenLimit(promptText, limit = 8192) {
  const encoder = get_encoding('cl100k_base');
  const count = encoder.encode(promptText).length;
  encoder.free(); // clear memory
  
  if (count > limit) {
    throw new Error(`Token limit exceeded: ${count} / ${limit}`);
  }
  return true;
}
localhost:3000
Context Limit Monitor
Input text: 'Hello World'
Counted before sending -> Token Count: 2

Context Used: 125,000 / 128,000
Status: [CRITICAL_WARNING]

2Pruning & Truncation

When you finally hit that inevitable token limit, you are forced to 'Prune' the conversation. The absolute simplest, most brute-force method is FIFO (First-In, First-Out) Truncation, where you literally just delete the oldest messages in the chat array.

However, simple FIFO has a massive flaw: if you delete the very first message, the AI forgets its core instructions. To solve this, we use Importance-based Pruning. We permanently pin the critical System Prompt to the top of the array so it is never deleted.

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// Importance-based Pruning
function pruneMessages(messages, maxRetained = 5) {
  // Keep the critical system prompt (index 0)
  const systemPrompt = messages[0];
  
  // Keep only the N most recent user/assistant messages
  const recentMessages = messages.slice(-maxRetained);
  
  // Reconstruct the array
  return [systemPrompt, ...recentMessages];
}
localhost:3000
Pruning Engine
[PINNED] System Prompt (Never Deleted)

[DELETED] Message 1 (Oldest)
[DELETED] Message 2

[KEPT] Message 3
[KEPT] Message 4 (Newest)

3Recursive Summarization

For truly long-form interactions, the absolute gold standard architecture is Recursive Summarization. Instead of violently deleting old messages and losing them forever, we periodically ask the AI to summarize its own previous thoughts into a single, dense paragraph.

We then inject that summary back into the prompt. This saves massive amounts of space while preserving the core context, minimizing the brutally expensive unit costs of sending 100,000 tokens per request.

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// Recursive Summarization strategy
async function compressHistory(oldMessages) {
  const historyText = oldMessages.map(m => m.content).join('\n');
  
  const summary = await ai.generate({
    model: "gpt-4o-mini", // Use cheap model for summarization
    prompt: `Summarize the following conversation:\n${historyText}`
  });
  
  return [{ role: 'system', content: `Context: ${summary}` }];
}
localhost:3000
Compression Engine
Compressing...

[50 Long Messages]
โฌ‡๏ธ
[1 Short Summary Paragraph]

Saved: 4,000 Tokens
Cost Reduction: ACTIVE

?Frequently Asked Questions

Pascual Vila

Pascual Vila

Frontend Instructor // Code Syllabus

Lesson Glossary

[01]Context Window

The total amount of text (tokens) a model can consider when generating a response.

Code Preview
The AI Desk Space

[02]Tiktoken

A fast BPE (Byte Pair Encoding) tokenizer for use with OpenAI's models.

Code Preview
Token Calculator

[03]Truncation

The act of cutting off part of a text or conversation to fit within a limit.

Code Preview
Manual Cut

[04]Recursive Summarization

A method where an AI summarizes its own history to save space in the context window.

Code Preview
Compression via Text

[05]FIFO

First-In, First-Out: A strategy where the oldest information is removed first.

Code Preview
Queue Logic

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