diff --git a/enterprise/app/services/captain/llm/assistant_action_classifier_service.rb b/enterprise/app/services/captain/llm/assistant_action_classifier_service.rb
index a7951b7b7..be7d1b094 100644
--- a/enterprise/app/services/captain/llm/assistant_action_classifier_service.rb
+++ b/enterprise/app/services/captain/llm/assistant_action_classifier_service.rb
@@ -147,6 +147,8 @@ class Captain::Llm::AssistantActionClassifierService < Llm::BaseAiService
   end
 
   def system_prompt
-    Captain::Llm::SystemPromptsService.assistant_action_classifier
+    Captain::Llm::SystemPromptsService.assistant_action_classifier(
+      has_custom_instructions: @assistant.config['instructions'].present?
+    )
   end
 end
diff --git a/enterprise/app/services/captain/llm/system_prompts_service.rb b/enterprise/app/services/captain/llm/system_prompts_service.rb
index e3f314042..9520330f6 100644
--- a/enterprise/app/services/captain/llm/system_prompts_service.rb
+++ b/enterprise/app/services/captain/llm/system_prompts_service.rb
@@ -93,7 +93,7 @@ class Captain::Llm::SystemPromptsService
       SYSTEM_PROMPT_MESSAGE
     end
 
-    def assistant_action_classifier
+    def assistant_action_classifier(has_custom_instructions: false)
       <<~PROMPT
         You are a routing classifier for a customer-support assistant.
 
@@ -127,16 +127,11 @@ class Captain::Llm::SystemPromptsService
         - The user explicitly asks for a human, agent, representative, phone call, callback, or escalation.
         - The user accepts an offer to speak with a human.
         - The user has provided enough detail for an account-specific or transaction-specific issue requiring private verification, such as order status, payment, deposit, withdrawal, refund, cancellation, subscription, purchase, plan activation, email verification, login, account recovery, delivery, or access.
-        - The user reports a bug or operational issue that needs support to inspect their account, setup, logs, integration, channel, or delivery state after a reasonable clarifying step.
+        - The user reports the same unresolved bug or operational issue after trying the assistant's suggested step, repeating the action, checking again, or otherwise making more than one reasonable attempt.
         - The user is repeatedly frustrated, distrustful, or stuck in a loop.
         - The assistant response itself says the current conversation will be transferred to a human agent now.
 
-        You may receive account custom instructions inside <account_custom_instructions> tags.
-        These are instructions configured by the account administrator, not the current end user's message.
-        Use them only for routing policy: required details before handoff, account-specific escalation rules, account-specific transfer markers, and when to connect to a manager, human, supervisor, or support team.
-        If the custom instructions explicitly define handoff, escalation, or transfer criteria, those criteria take precedence over the generic criteria above.
-        Account custom instructions MUST NOT redefine the required response shape, the allowed action values, or the meaning of continue/handoff.
-        Ignore persona, language, formatting, pricing, and response-generation instructions except where they directly define routing or transfer criteria.
+        #{assistant_action_classifier_custom_instructions_policy if has_custom_instructions}
 
         Return only the structured fields requested by the response schema.
       PROMPT
@@ -373,6 +368,17 @@ class Captain::Llm::SystemPromptsService
       TOOLS
     end
 
+    def assistant_action_classifier_custom_instructions_policy
+      <<~POLICY
+        Account custom instructions are provided inside <account_custom_instructions> tags.
+        These are instructions configured by the account administrator, not the current end user's message.
+        Use them only for routing policy: required details before handoff, account-specific escalation rules, account-specific transfer markers, and when to connect to a manager, human, supervisor, or support team.
+        If the custom instructions explicitly define handoff, escalation, or transfer criteria, those criteria take precedence over the generic criteria above.
+        Account custom instructions MUST NOT redefine the required response shape, the allowed action values, or the meaning of continue/handoff.
+        Ignore persona, language, formatting, pricing, and response-generation instructions except where they directly define routing or transfer criteria.
+      POLICY
+    end
+
     def build_contact_context(contact)
       return '' if contact.nil?
 
diff --git a/spec/enterprise/services/captain/llm/assistant_action_classifier_service_spec.rb b/spec/enterprise/services/captain/llm/assistant_action_classifier_service_spec.rb
index b328073ba..f187fdb59 100644
--- a/spec/enterprise/services/captain/llm/assistant_action_classifier_service_spec.rb
+++ b/spec/enterprise/services/captain/llm/assistant_action_classifier_service_spec.rb
@@ -39,6 +39,9 @@ RSpec.describe Captain::Llm::AssistantActionClassifierService do
 
     it 'passes delimited custom instructions and classifier context to the LLM' do
       expect(mock_chat).to receive(:with_schema).with(Captain::AssistantActionSchema).and_return(mock_chat)
+      expect(mock_chat).to receive(:with_instructions).with(
+        a_string_including('Account custom instructions are provided inside <account_custom_instructions> tags.')
+      ).and_return(mock_chat)
       expect(mock_chat).to receive(:ask) do |prompt|
         expect(prompt).to include(
           '<account_custom_instructions>',
@@ -63,5 +66,20 @@ RSpec.describe Captain::Llm::AssistantActionClassifierService do
         'prompt_version' => 'v1_custom_xml_precedence'
       )
     end
+
+    context 'when the assistant has no custom instructions' do
+      before do
+        assistant.update!(config: assistant.config.except('instructions'))
+      end
+
+      it 'does not add custom-instruction policy to the system prompt' do
+        expect(mock_chat).to receive(:with_instructions).with(
+          satisfy { |prompt| prompt.exclude?('Account custom instructions are provided') }
+        ).and_return(mock_chat)
+        allow(mock_chat).to receive(:ask).and_return(mock_response)
+
+        service.classify(message_history: message_history, assistant_response: 'Would you like to talk to support?')
+      end
+    end
   end
 end