MCPInstall

context-window-management

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

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Install

Works with every agent the skills CLI supports.

npx skills add https://github.com/sickn33/agentic-awesome-skills --skill context-window-management
  1. 01

    Install

    Run the command in your project. The CLI asks which agents to install for.

  2. 02

    Describe the task

    Ask your agent for something this skill covers. It loads context-window-management automatically when relevant.

  3. 03

    Review the result

    The agent follows the SKILL.md steps, scripts and references bundled with the skill.

SKILL.md

The instructions your agent reads when the skill is triggered.

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

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

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

function buildOptimalPrompt(components: {
    systemPrompt: string;
    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

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

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.

FAQ

What does the context-window-management skill do?

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

How do I install context-window-management?

Run npx skills add https://github.com/sickn33/agentic-awesome-skills --skill context-window-management in your project. The skills CLI detects the agents you use and copies the skill into the right folder. For Claude Code you can also place the skill folder at ~/.claude/skills/context-window-management/ (personal) or .claude/skills/context-window-management/ (project).

Which AI agents can use context-window-management?

Any agent that supports the open Agent Skills format (a folder with a SKILL.md file), including Claude Code, Codex, Cursor, GitHub Copilot, Gemini CLI, Windsurf, Cline, OpenCode and more.

Is context-window-management safe to install?

No partner security audit is available yet. Skills can run commands and scripts, so read the SKILL.md and any bundled files before installing.

Who maintains context-window-management?

It is published by sickn33 in sickn33/agentic-awesome-skills. It has 1,552 recorded installs.

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