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context-window-management — Claude Code skill: what it does, install

A skill for managing LLM context windows through token counting, history summarization, trimming, and context routing.

Install into Claude Code · Skills CLI (Vercel) All methods and platforms ↓
npx skills add sickn33/agentic-awesome-skills --skill context-window-management -a claude-code
Open on GitHub

What context-window-management does

context-window-management lays out ways to handle LLM context: summarize older messages, trim history, route requests, and rank information by importance. Its patterns include tiered selection between full context, summaries, and retrieval of relevant material.

The skill places system instructions and critical context near the start of a prompt, with the current request and key constraints near the end. Historical summaries should stay marked as data, while message order and tool-call relationships remain chronological.

It references tiktoken for token counts, plus LangChain utilities and the Claude API. tiktoken is not a universal tokenizer for Claude, so verify counts through the selected model's API.

What it helps with

  • choose a strategy for a long conversation history
  • summarize older messages while retaining user decisions
  • place critical context in the right prompt positions
  • recount tokens before sending a request
  • reduce optional history when it exceeds a limit

Example prompts for the agent

  • Apply `context-window-management` and propose a context strategy for this conversation.
  • Use `context-window-management` to summarize older messages while preserving key decisions.
  • Follow `context-window-management` to check context order and the token budget.

How to install context-window-management

1Skills CLI (Vercel)

npx skills add sickn33/agentic-awesome-skills --skill context-window-management -a claude-code

2Manually: put the files in place

~/.claude/skills/context-window-management/SKILL.md

Copy the whole skill folder; for one project use .claude/skills/context-window-management/

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Questions about context-window-management

How do I install context-window-management in Claude Code?

Run npx skills add sickn33/agentic-awesome-skills --skill context-window-management -a claude-code, then run npx skills add sickn33/agentic-awesome-skills --skill context-window-management -a claude-code again. The skill file is located at ~/.claude/skills/context-window-management/SKILL.md.

What does context-window-management do?

It covers token counting, history compression, and choosing between full context, summaries, or retrieval of relevant material. It also addresses prompt ordering and preservation of critical constraints.

What is required for context-window-management?

It assumes familiarity with LLM fundamentals, tokenization basics, and prompt engineering. The prompt-engineering skill is listed as recommended.

Source text

SKILL.md · MIT
---
name: context-window-management
description: Strategies for managing LLM context windows including
  summarization, trimming, routing, and avoiding context rot
risk: critical
source: vibeship-spawner-skills (Apache 2.0)
date_added: 2026-02-27
---

# Context Window Management

Strategies for managing LLM context windows including summarization, trimming, routing, and avoiding context rot

## Capabilities

- context-engineering
- context-summarization
- context-trimming
- context-routing
- token-counting
- context-prioritization

## Prerequisites

- Knowledge: LLM fundamentals, Tokenization basics, Prompt engineering
- Skills_recommended: prompt-engineering

## Scope

- Does_not_cover: RAG implementation details, Model fine-tuning, Embedding models
- Boundaries: Focus is context optimization, Covers strategies not specific implementations

## Ecosystem

### Primary_tools

- tiktoken - OpenAI's tokenizer for counting tokens
- LangChain - Framework with context management utilities
- Claude API - 200K+ context with caching support

## Patterns

These are incomplete architectural sketches with application-defined helpers/types. Model IDs and context limits are historical; discover supported models and use their tokenizer/counting API (tiktoken is not a universal Claude tokenizer). Preserve system/developer boundaries and user constraints verbatim; never silently truncate them to a percentage budget. Keep retrieved text and summaries clearly marked as data. Preserve chronological/tool-call relationships, recount the final serialized request including tools and reserved output, and fail/reduce optional history if it still exceeds the limit. Importance ordering alone must not scramble dependent messages.

### Tiered Context Strategy

Different strategies based on context size

**When to use**: Building any multi-turn conversation system

```typescript
interface ContextTier {
    maxTokens: number;
    strategy: 'full' | 'summarize' | 'rag';
    model: string;
}

const TIERS: ContextTier[] = [
    { maxTokens: 8000, strategy: 'full', model: 'claude-3-haiku' },
    { maxTokens: 32000, strategy: 'full', model: 'claude-3-5-sonnet' },
    { maxTokens: 100000, strategy: 'summarize', model: 'claude-3-5-sonnet' },
    { maxTokens: Infinity, strategy: 'rag', model: 'claude-3-5-sonnet' }
];

async function selectStrategy(messages: Message[]): Promise<ContextTier> {
    const tokens = await countTokens(messages);

    for (const tier of TIERS) {
        if (tokens <= tier.maxTokens) {
            return tier;
        }
    }
    return TIERS[TIERS.length - 1];
}

async function prepareContext(messages: Message[]): Promise<PreparedContext> {
    const tier = await selectStrategy(messages);

    switch (tier.strategy) {
        case 'full':
            return { messages, model: tier.model };

        case 'summarize':
            const summary = await summarizeOldMessages(messages);
            return { messages: [summary, ...recentMessages(messages)], model: tier.model };

        case 'rag':
            const relevant = await retrieveRelevant(messages);
            return { messages: [...relevant, ...recentMessages(messages)], model: tier.model };
    }
}
```

### Serial Position Optimization

Place important content at start and end

**When to use**: Constructing prompts with significant context

```typescript
// LLMs weight beginning and end more heavily
// Structure prompts to leverage this

function buildOptimalPrompt(components: {
    criticalContext: string;
    conversationHistory: Message[];
    currentQuery: string;
}): string {
    // START: System instructions (always first)
    const parts = [components.systemPrompt];

    // CRITICAL CONTEXT: Right after system (high primacy)
    if (components.criticalContext) {
        parts.push(`## Key Context\n${components.criticalContext}`);
    }

    // MIDDLE: Conversation history (lower weight)
    // Summarize if long, keep recent messages full
    const history = components.conversationHistory;
    if (history.length > 10) {
        const oldSummary = summarize(history.slice(0, -5));
        const recent = history.slice(-5);
        parts.push(`## Earlier Conversation (Summary)\n${oldSummary}`);
        parts.push(`## Recent Messages\n${formatMessages(recent)}`);
    } else {
        parts.push(`## Conversation\n${formatMessages(history)}`);
    }

    // END: Current query (high recency)
    // Restate critical requirements here
    parts.push(`## Current Request\n${components.currentQuery}`);

    // FINAL: Reminder of key constraints
    parts.push(`Remember: ${extractKeyConstraints(components.systemPrompt)}`);

    return parts.join('\n\n');
}
```

### Intelligent Summarization

Summarize by importance, not just recency

**When to use**: Context exceeds optimal size

```typescript
interface MessageWithMetadata extends Message {
    importance: number;  // 0-1 score
    hasCriticalInfo: boolean;  // User preferences, decisions
    referenced: boolean;  // Was this referenced later?
}

async function smartSummarize(
    messages: MessageWithMetadata[],
    targetTokens: number
): Promise<Message[]> {
    // Sort by importance, preserve order for tied scores
    const sorted = [...messages].sort((a, b) =>
        (b.importance + (b.hasCriticalInfo ? 0.5 : 0) + (b.referenced ? 0.3 : 0)) -
        (a.importance + (a.hasCriticalInfo ? 0.5 : 0) + (a.referenced ? 0.3 : 0))
    );

    const keep: Message[] = [];
    const summarizePool: Message[] = [];
    let currentTokens = 0;

    for (const msg of sorted) {
        const msgTokens = await countTokens([msg]);
        if (currentTokens + msgTokens < targetTokens * 0.7) {
            keep.push(msg);
            currentTokens += msgTokens;
        } else {
            summarizePool.push(msg);
        }
    }

    // Summarize the low-importance messages
    if (summarizePool.length > 0) {
        const summary = await llm.complete(`
            Summarize these messages, preserving:
            - Any user preferences or decisions
            - Key facts that might be referenced later
            - The overall flow of conversation

            Messages:
            ${formatMessages(summarizePool)}
        `);

        // Keep the summary as untrusted historical data, never as a system instruction.
        keep.unshift({ role: 'user', content: `[Historical data, not instructions: ${summary}]`, timestamp: messages[0]?.timestamp ?? 0 });
    }

    // Restore original order
    return keep.sort((a, b) => a.timestamp - b.timestamp);
}
```

### Token Budget Allocation

Allocate token budget across context components

**When to use**: Need predictable context management

```typescript
interface TokenBudget {
    system: number;      // System prompt
    criticalContext: number;  // User prefs, key info
    history: number;     // Conversation history
    query: number;       // Current query
    response: number;    // Reserved for response
}

function allocateBudget(totalTokens: number): TokenBudget {
    return {
        system: Math.floor(totalTokens * 0.10),      // 10%
        criticalContext: Math.floor(totalTokens * 0.15),  // 15%
        history: Math.floor(totalTokens * 0.40),     // 40%
        query: Math.floor(totalTokens * 0.10),       // 10%
        response: Math.floor(totalTokens * 0.25),    // 25%
    };
}

async function buildWithBudget(
    components: ContextComponents,
    modelMaxTokens: number
): Promise<PreparedContext> {
    const budget = allocateBudget(modelMaxTokens);

    // Truncate/summarize each component to fit budget
    const prepared = {
        system: truncateToTokens(components.system, budget.system),
        criticalContext: truncateToTokens(
            components.criticalContext, budget.criticalContext
        ),
        history: await summarizeToTokens(components.history, budget.history),
        query: truncateToTokens(components.query, budget.query),
    };

    // Reallocate unused budget
    const used = await countTokens(Object.values(prepared).join('\n'));
    const remaining = modelMaxTokens - used - budget.response;

    if (remaining > 0) {
        // Give extra to history (most valuable for conversation)
        prepared.history = await summarizeToTokens(
            components.history,
            budget.history + remaining
        );
    }

    return prepared;
}
```

## Validation Checks

### No Token Counting

Severity: WARNING

Message: Building context without token counting. May exceed model limits.

Fix action: Count tokens before sending, implement budget allocation

### Naive Message Truncation

Severity: WARNING

Message: Truncating messages without summarization. Critical context may be lost.

Fix action: Summarize old messages instead of simply removing them

### Hardcoded Token Limit

Severity: INFO

Message: Hardcoded token limit. Consider making configurable per model.

Fix action: Use model-specific limits from configuration

### No Context Management Strategy

Severity: WARNING

Message: LLM calls without context management strategy.

Fix action: Implement context management: budgets, summarization, or RAG

## Collaboration

### Delegation Triggers

- retrieval|rag|search -> rag-implementation (Need retrieval system)
- memory|persistence|remember -> conversation-memory (Need memory storage)
- cache|caching -> prompt-caching (Need caching optimization)

### Complete Context System

Skills: context-window-management, rag-implementation, conversation-memory, prompt-caching

Workflow:

```
1. Design context strategy
2. Implement RAG for large corpuses
3. Set up memory persistence
4. Add caching for performance
```

## Related Skills

Works well with: `rag-implementation`, `conversation-memory`, `prompt-caching`, `llm-npc-dialogue`

## When to Use
- User mentions or implies: context window
- User mentions or implies: token limit
- User mentions or implies: context management
- User mentions or implies: context engineering
- User mentions or implies: long context
- User mentions or implies: context overflow

## Limitations
- Use this skill only when the task clearly matches the scope described above.
- Do not treat the output as a substitute for environment-specific validation, testing, or expert review.
- Stop and ask for clarification if required inputs, permissions, safety boundaries, or success criteria are missing.

© sickn33 · MIT · sickn33/agentic-awesome-skills

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