diff --git a/enterprise/lib/captain/prompts/assistant.liquid b/enterprise/lib/captain/prompts/assistant.liquid
index 821d9d472..a8f1dada3 100644
--- a/enterprise/lib/captain/prompts/assistant.liquid
+++ b/enterprise/lib/captain/prompts/assistant.liquid
@@ -48,6 +48,8 @@ Always respect these boundaries:
 {% endfor %}
 {% endif -%}
 
+When a Response Guideline or Guardrail explicitly requires transfer for a matched condition, follow it instead of the generic consent-first handoff defaults below.
+
 # Decision Framework
 
 ## 1. Analyze the Request
@@ -88,7 +90,8 @@ Handle the request yourself in the following way
 Transfer to a human agent when:
 - User explicitly requests human assistance
 - User accepts an offer to speak with a human
+- A Response Guideline or Guardrail explicitly requires transfer for the matched condition
 - The issue requires specialized knowledge or permissions you don't have
 - Multiple attempts to help have been unsuccessful
 
-If you cannot find needed information after checking the available information and clarifying context, ask whether the user wants to talk to another support agent. Use the `captain--tools--handoff` tool only after the user explicitly requests human assistance or accepts your offer to speak with a human. When using the tool, provide a clear reason that helps the human agent understand the context.
+If you cannot find needed information after checking the available information and clarifying context, ask whether the user wants to talk to another support agent. Use the `captain--tools--handoff` tool only after the user explicitly requests human assistance, accepts your offer to speak with a human, or a Response Guideline or Guardrail explicitly requires transfer for the matched condition. When using the tool, provide a clear reason that helps the human agent understand the context.