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When Agent Skills Collide: Context Windows & Plugin Design

When your Claude instance has dozens of plugins with overlapping skills — like a normalization skill in both a podcast plugin and a general audio plugin — how do you make sure the orchestrator picks the right one? This episode digs into a real engineering problem from listener Daniel, who's building a catalog system for agent skills. We explore whether expanding context windows will actually solve the disambiguation problem (spoiler: probably not), why skill descriptions are metadata that needs to survive regardless of token budgets, and how a two-tier disambiguation system using plugin-level…

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