Context Windows

Risk Level: 🟡 Caution Advised

Guide Entry

CONTEXT WINDOW (n.): The amount of text an AI can “remember” at once. Like RAM, but for conversation. When you exceed it, early information falls off the edge into the void, taking your carefully specified requirements with it.

The Problem

AI models have limited context windows:

GPT-4: ~128k tokens
Claude: ~200k tokens
Others: Varies

Sounds like a lot until:

Your codebase is 50 files
Your conversation is 100 messages
Your paste is 1000 lines

Then: context overflow.

Symptoms of Context Problems

The Forgotten Requirement

Message 1: “We’re using TypeScript strict mode” Message 50: AI generates untyped JavaScript

The Style Drift

Early: Clean, consistent code matching your patterns Later: Generic code that doesn’t fit your codebase

The Contradiction

AI: “As I mentioned earlier…” You: You mentioned the opposite earlier.

The Repetition Request

AI: “Could you remind me what framework you’re using?” You: I told you three times.

Survival Strategies

Start Fresh Often

Long conversations accumulate errors. New chat = clean slate.

Rule of thumb:
- Simple task: 1 conversation
- Medium task: 2-3 conversations
- Complex task: Multiple focused conversations

Restate Key Constraints

Periodically remind the AI of critical requirements:

"Quick reminder before we continue:
- TypeScript strict mode
- No new dependencies
- Follow existing patterns"

Use CLAUDE.md / System Context

Put project constants in a file the AI always sees:

# Project Context
- Language: TypeScript 5.0
- Framework: Next.js 14
- Style: Functional components with hooks
- Testing: Jest + React Testing Library

Chunk Large Requests

Instead of:

"Here's my entire codebase, refactor it"

Do:

"Here's file 1, refactor this"
"Here's file 2, refactor this using the same patterns"
"Here's file 3..."

Summarize Before Continuing

After complex discussions:

"Let's summarize what we've decided:
1. Using approach X
2. With constraint Y
3. Excluding Z

Confirm this is correct before we continue."

The Street Rule

“The AI’s memory is shorter than you think. Repeat important things.”

Move to Make

Check your last long conversation:

Find where the AI “forgot” something
Identify what context would have helped
Plan where to repeat key constraints next time