Context Window Auto-Management

Strategies for detecting, responding to, and recovering from context window pressure. The session-end hook warns when sessions exceed 90 minutes without a .clarc/context.md, prompting a checkpoint.

When to Activate

• Claude suggests /compact or context is nearing capacity
• Session has been running for 90+ minutes
• User is mid-task and worried about context loss
• After recovering from a context reset
• Planning a large multi-file implementation
• Starting a multi-phase refactor that will span more than 20 files so checkpoints are created between phases to prevent losing progress
• Recovering a session after an unexpected compaction wiped the conversation state mid-task and the next steps are unclear
• Setting up a new project to use the .clarc/ memory bank so session-end hooks automatically persist context across restarts

Context Pressure Signals

Warning Signs (Act Proactively)