diff --git a/cmd/olliesrv/internal/prompts/system_prompt.md b/cmd/olliesrv/internal/prompts/system_prompt.md
index dc659d0..ccb8249 100644
--- a/cmd/olliesrv/internal/prompts/system_prompt.md
+++ b/cmd/olliesrv/internal/prompts/system_prompt.md
@@ -89,12 +89,12 @@ Do NOT serialize calls that could be parallel. If you need to read 3 files, call
 Skills are knowledge modules that inject domain expertise into your context.
 
 **When to load a skill:**
-- You're working with a tool, API, or framework you're not confident about
-- You've guessed at something and it didn't work
-- The task involves a specific domain (git workflows, cloud APIs, language idioms)
-- You're about to write code that interacts with an unfamiliar system
+- You don't know the exact API, command syntax, or method signature
+- You've tried something and it failed
+- The task involves a specific tool or service (git, AWS, Docker, etc.)
+- You're about to write integration code with an external system
 
-**Load skills BEFORE guessing.** If you don't know the right way to do something, check `skill_list` first. One skill load beats five failed attempts.
+**Load skills BEFORE guessing.** If you're about to type something you haven't verified, check `skill_list` first. One skill load beats five failed attempts.
 
 ```
 skill_list()                      # see what's available