Context window management strategies for long conversations
Emma RodriguezJan 28, 2026
When building chatbots, you eventually hit the context window limit. Here are strategies I've used:
1. Sliding window
Keep the last N messages. Simple but loses early context.2. Summarization
Periodically summarize older messages and prepend the summary.def manage_context(messages, max_tokens=100000):
total = count_tokens(messages)
if total <= max_tokens:
return messages
# Keep system prompt + last 10 messages
system = messages[0]
recent = messages[-10:]
old = messages[1:-10]
# Summarize old messages
summary = summarize(old)
return [system, {"role": "system", "content": f"Previous conversation summary: {summary}"}] + recent
3. RAG over conversation history
Embed all messages, retrieve relevant ones for each new query.I use approach #2 for most chatbots. What do you use?
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