diff --git a/app/javascript/dashboard/components-next/copilot/Copilot.vue b/app/javascript/dashboard/components-next/copilot/Copilot.vue
index 966018e69..d2769d7b7 100644
--- a/app/javascript/dashboard/components-next/copilot/Copilot.vue
+++ b/app/javascript/dashboard/components-next/copilot/Copilot.vue
@@ -159,7 +159,14 @@ watch(
               :conversation-inbox-type="conversationInboxType"
             />
           </template>
-          <CopilotThinkingGroup v-else :messages="item.messages" />
+          <CopilotThinkingGroup
+            v-else
+            :messages="item.messages"
+            :has-assistant-message-after="
+              groupedMessages[groupedMessages.indexOf(item) + 1]?.message
+                ?.role === 'assistant'
+            "
+          />
         </template>
 
         <CopilotLoader v-if="isCaptainTyping" />
diff --git a/app/javascript/dashboard/components-next/copilot/CopilotThinkingGroup.vue b/app/javascript/dashboard/components-next/copilot/CopilotThinkingGroup.vue
index 14fe756d4..3d1a451a4 100644
--- a/app/javascript/dashboard/components-next/copilot/CopilotThinkingGroup.vue
+++ b/app/javascript/dashboard/components-next/copilot/CopilotThinkingGroup.vue
@@ -1,16 +1,28 @@
 <script setup>
-import { ref } from 'vue';
+import { ref, watch } from 'vue';
 import { useI18n } from 'vue-i18n';
 import Icon from '../icon/Icon.vue';
 import CopilotThinkingBlock from 'dashboard/components/copilot/CopilotThinkingBlock.vue';
 
-defineProps({ messages: { type: Array, required: true } });
+const props = defineProps({
+  messages: { type: Array, required: true },
+  hasAssistantMessageAfter: { type: Boolean, default: false },
+});
 const { t } = useI18n();
-const isExpanded = ref(false);
+const isExpanded = ref(!props.hasAssistantMessageAfter);
+
+watch(
+  () => props.hasAssistantMessageAfter,
+  newValue => {
+    if (newValue) {
+      isExpanded.value = false;
+    }
+  }
+);
 </script>
 
 <template>
-  <div class="flex flex-col gap-2">
+  <div class="flex flex-col gap-2 pl-4">
     <button
       class="flex items-center gap-2 text-xs text-n-slate-10 hover:text-n-slate-11"
       @click="isExpanded = !isExpanded"
diff --git a/app/javascript/dashboard/components/copilot/CopilotContainer.vue b/app/javascript/dashboard/components/copilot/CopilotContainer.vue
index 4f4f311c6..0d9935c35 100644
--- a/app/javascript/dashboard/components/copilot/CopilotContainer.vue
+++ b/app/javascript/dashboard/components/copilot/CopilotContainer.vue
@@ -132,7 +132,7 @@ const handleClose = () => {
 <template>
   <div
     v-if="isSidebarOpen"
-    class="border-l border-n-weak w-[18rem] min-w-[18rem]"
+    class="border-l border-n-weak w-[20rem] min-w-[20rem]"
   >
     <Copilot
       :messages="messages"
diff --git a/app/javascript/dashboard/components/copilot/CopilotThinkingBlock.vue b/app/javascript/dashboard/components/copilot/CopilotThinkingBlock.vue
index 9f2308d7d..de902f901 100644
--- a/app/javascript/dashboard/components/copilot/CopilotThinkingBlock.vue
+++ b/app/javascript/dashboard/components/copilot/CopilotThinkingBlock.vue
@@ -12,13 +12,13 @@ defineProps({
 </script>
 
 <template>
-  <div class="flex flex-col gap-2 p-2 rounded bg-n-background">
+  <div class="flex flex-col gap-1 px-2 rounded bg-n-background">
     <div
       v-if="reasoning"
-      class="text-xs text-n-slate-11 border-t border-n-weak pt-2"
+      class="text-xs text-n-slate-11 border-t border-n-weak"
     >
       {{ reasoning }}
     </div>
-    <p class="text-sm text-n-slate-12">{{ content }}</p>
+    <p class="text-sm text-n-slate-11">{{ content }}</p>
   </div>
 </template>
diff --git a/app/javascript/dashboard/components/widgets/conversation/ConversationSidebar.vue b/app/javascript/dashboard/components/widgets/conversation/ConversationSidebar.vue
index 44bcb1e85..783936827 100644
--- a/app/javascript/dashboard/components/widgets/conversation/ConversationSidebar.vue
+++ b/app/javascript/dashboard/components/widgets/conversation/ConversationSidebar.vue
@@ -35,7 +35,7 @@ const closeConversationPanel = () => {
 <template>
   <div
     v-if="showConversationSidebar"
-    class="ltr:border-l rtl:border-r border-n-weak h-full overflow-hidden z-10 w-[18rem] min-w-[18rem] flex flex-col"
+    class="ltr:border-l rtl:border-r border-n-weak h-full overflow-hidden z-10 w-[20rem] min-w-[20rem] flex flex-col"
   >
     <div class="flex flex-1 flex-col overflow-auto">
       <div
diff --git a/enterprise/app/jobs/captain/process_copilot_message_job.rb b/enterprise/app/jobs/captain/process_copilot_message_job.rb
index 19800b998..5675f8953 100644
--- a/enterprise/app/jobs/captain/process_copilot_message_job.rb
+++ b/enterprise/app/jobs/captain/process_copilot_message_job.rb
@@ -2,6 +2,7 @@ class Captain::ProcessCopilotMessageJob < ApplicationJob
   queue_as :default
 
   def perform(assistant_id:, message:, options: {})
+    Rails.logger.info("[Captain::ProcessCopilotMessageJob] Starting job for assistant_id=#{assistant_id}")
     ensure_assistant(assistant_id)
     ensure_user(options[:user_id])
     process_message(message, options)
@@ -10,17 +11,22 @@ class Captain::ProcessCopilotMessageJob < ApplicationJob
   private
 
   def ensure_assistant(assistant_id)
+    Rails.logger.info("[Captain::ProcessCopilotMessageJob] Finding assistant with id=#{assistant_id}")
     @assistant = Captain::Assistant.find(assistant_id)
     @account = @assistant.account
+    Rails.logger.info("[Captain::ProcessCopilotMessageJob] Found assistant for account_id=#{@account.id}")
   end
 
   def ensure_user(user_id)
+    Rails.logger.info("[Captain::ProcessCopilotMessageJob] Finding user with id=#{user_id}")
     @user = @account.users.find(user_id)
+    Rails.logger.info("[Captain::ProcessCopilotMessageJob] Found user #{@user.name}")
   end
 
   def process_message(message, options)
     return unless @assistant
 
+    Rails.logger.info("[Captain::ProcessCopilotMessageJob] Processing message with conversation_id=#{options[:conversation_id]}")
     conversation = find_conversation(options[:conversation_id])
     generate_chat_response(message, conversation, options[:previous_history])
   end
@@ -32,6 +38,7 @@ class Captain::ProcessCopilotMessageJob < ApplicationJob
   end
 
   def generate_chat_response(message, conversation, previous_history)
+    Rails.logger.info("[Captain::ProcessCopilotMessageJob] Generating chat response for conversation_id=#{conversation&.display_id}")
     Captain::Copilot::ChatService.new(
       @assistant,
       previous_messages: previous_history || [],
@@ -45,6 +52,7 @@ class Captain::ProcessCopilotMessageJob < ApplicationJob
   end
 
   def broadcast_response(data)
+    Rails.logger.info("[Captain::ProcessCopilotMessageJob] Broadcasting response to account_id=#{@account.id} user_id=#{@user.id}")
     ActionCable.server.broadcast(
       "copilot_#{@account.id}_#{@user.id}",
       { event: 'copilot.response', data: data }
diff --git a/enterprise/app/services/captain/copilot/chat_service.rb b/enterprise/app/services/captain/copilot/chat_service.rb
index 3d8363a32..6e05f0b62 100644
--- a/enterprise/app/services/captain/copilot/chat_service.rb
+++ b/enterprise/app/services/captain/copilot/chat_service.rb
@@ -28,9 +28,12 @@ class Captain::Copilot::ChatService < Llm::BaseOpenAiService
   end
 
   def build_initial_messages(config)
+    Rails.logger.info("[CAPTAIN][CopilotChatService] Building initial messages for conversation_id=#{@conversation_id}")
     messages = [system_message]
     messages += (config[:previous_messages] || [])
+    Rails.logger.info("[CAPTAIN][CopilotChatService] Added #{config[:previous_messages]&.length || 0} previous messages")
     messages << current_viewing_history if @conversation_id
+    Rails.logger.info("[CAPTAIN][CopilotChatService] Total messages built: #{messages.length}")
     messages
   end
 
@@ -53,6 +56,7 @@ class Captain::Copilot::ChatService < Llm::BaseOpenAiService
   private
 
   def system_message
+    Rails.logger.info("[CAPTAIN][CopilotChatService] Generating system message for product=#{@assistant.config['product_name']} language=#{@language}")
     {
       role: 'system',
       content: Captain::Llm::SystemPromptsService.copilot_response_generator(@assistant.config['product_name'], @language, @assistant.account_id)
@@ -60,6 +64,7 @@ class Captain::Copilot::ChatService < Llm::BaseOpenAiService
   end
 
   def current_viewing_history
+    Rails.logger.info("[CAPTAIN][CopilotChatService] Fetching viewing history for conversation_id=#{@conversation_id}")
     return unless @conversation_id
 
     {
diff --git a/enterprise/app/services/captain/tools/copilot/get_contact_service.rb b/enterprise/app/services/captain/tools/copilot/get_contact_service.rb
index bacea1c0a..6aec470e7 100644
--- a/enterprise/app/services/captain/tools/copilot/get_contact_service.rb
+++ b/enterprise/app/services/captain/tools/copilot/get_contact_service.rb
@@ -12,11 +12,11 @@ class Captain::Tools::Copilot::GetContactService < Captain::Tools::BaseService
       type: 'object',
       properties: {
         contact_id: {
-          type: 'string',
+          type: 'number',
           description: 'The ID of the contact to retrieve'
         },
         account_id: {
-          type: 'string',
+          type: 'number',
           description: 'The ID of the account the contact belongs to'
         }
       },
diff --git a/enterprise/app/services/captain/tools/copilot/get_conversation_service.rb b/enterprise/app/services/captain/tools/copilot/get_conversation_service.rb
index c564f8ced..798d65f56 100644
--- a/enterprise/app/services/captain/tools/copilot/get_conversation_service.rb
+++ b/enterprise/app/services/captain/tools/copilot/get_conversation_service.rb
@@ -12,11 +12,11 @@ class Captain::Tools::Copilot::GetConversationService < Captain::Tools::BaseServ
       type: 'object',
       properties: {
         conversation_id: {
-          type: 'string',
+          type: 'number',
           description: 'The ID of the conversation to retrieve'
         },
         account_id: {
-          type: 'string',
+          type: 'number',
           description: 'The ID of the account the conversation belongs to'
         }
       },
diff --git a/enterprise/app/services/captain/tools/copilot/search_contact_service.rb b/enterprise/app/services/captain/tools/copilot/search_contact_service.rb
index bf57926d0..b5e3de641 100644
--- a/enterprise/app/services/captain/tools/copilot/search_contact_service.rb
+++ b/enterprise/app/services/captain/tools/copilot/search_contact_service.rb
@@ -12,7 +12,7 @@ class Captain::Tools::Copilot::SearchContactService < Captain::Tools::BaseServic
       type: 'object',
       properties: {
         account_id: {
-          type: 'string',
+          type: 'number',
           description: 'The ID of the account to search contacts in'
         },
         email: {
diff --git a/enterprise/app/services/captain/tools/copilot/search_conversation_service.rb b/enterprise/app/services/captain/tools/copilot/search_conversation_service.rb
index 1fb223678..151ec33a9 100644
--- a/enterprise/app/services/captain/tools/copilot/search_conversation_service.rb
+++ b/enterprise/app/services/captain/tools/copilot/search_conversation_service.rb
@@ -12,11 +12,11 @@ class Captain::Tools::Copilot::SearchConversationService < Captain::Tools::BaseS
       type: 'object',
       properties: {
         account_id: {
-          type: 'string',
+          type: 'number',
           description: 'The ID of the account to search conversations in'
         },
         contact_id: {
-          type: 'string',
+          type: 'number',
           description: 'Filter conversations by contact ID'
         },
         status: {