Progressive Skills Discovery: When Bigger Context Windows Aren't Enough

Progressive skills discovery is treated as solved — until your skill listing quietly drops descriptions and skills stop firing. This episode digs into how Anthropic's three-tier progressive disclosure actually works, why Claude Code truncates descriptions for your least-used skills first, and how Codex handles the same problem with different numbers. We survey the open-source landscape for auto-syncing with marketplace updates and semantic search over skill definitions, including why the one project that hit both is now abandoned. If you're maintaining a self-hosted skill catalogue behind an MCP gateway, this is the episode about whether the architecture you built has a future.

Episode 6033 — myweirdprompts.com/n/6033 (permanent short link: myweirdprompts.com/345391)