diff --git a/app/javascript/dashboard/components-next/captain/assistant/AssistantPlayground.vue b/app/javascript/dashboard/components-next/captain/assistant/AssistantPlayground.vue
index 69cbb9be5..51aae6477 100644
--- a/app/javascript/dashboard/components-next/captain/assistant/AssistantPlayground.vue
+++ b/app/javascript/dashboard/components-next/captain/assistant/AssistantPlayground.vue
@@ -18,10 +18,18 @@ const newMessage = ref('');
 const isLoading = ref(false);
 
 const formatMessagesForApi = () => {
-  return messages.value.map(message => ({
-    role: message.sender,
-    content: message.content,
-  }));
+  return messages.value.map(message => {
+    const payload = {
+      role: message.sender,
+      content: message.content,
+    };
+
+    if (message.sender === 'assistant' && message.agentName) {
+      payload.agent_name = message.agentName;
+    }
+
+    return payload;
+  });
 };
 
 const resetConversation = () => {
@@ -62,6 +70,7 @@ const sendMessage = async () => {
     messages.value.push({
       content: data.response,
       sender: 'assistant',
+      agentName: data.agent_name,
       timestamp: new Date().toISOString(),
     });
   } catch (error) {
diff --git a/config/features.yml b/config/features.yml
index eed6a9da1..41515ff64 100644
--- a/config/features.yml
+++ b/config/features.yml
@@ -191,7 +191,6 @@
 - name: assignment_v2
   display_name: Assignment V2
   enabled: false
-  chatwoot_internal: true
 - name: twilio_content_templates
   display_name: Twilio Content Templates
   enabled: false
diff --git a/enterprise/app/controllers/api/v1/accounts/captain/assistants_controller.rb b/enterprise/app/controllers/api/v1/accounts/captain/assistants_controller.rb
index ebeaaf67f..c1ac4b98b 100644
--- a/enterprise/app/controllers/api/v1/accounts/captain/assistants_controller.rb
+++ b/enterprise/app/controllers/api/v1/accounts/captain/assistants_controller.rb
@@ -24,10 +24,16 @@ class Api::V1::Accounts::Captain::AssistantsController < Api::V1::Accounts::Base
   end
 
   def playground
-    response = Captain::Llm::AssistantChatService.new(assistant: @assistant).generate_response(
-      additional_message: params[:message_content],
-      message_history: message_history
-    )
+    response = if captain_v2_enabled?
+                 Captain::Assistant::AgentRunnerService.new(assistant: @assistant, source: 'playground').generate_response(
+                   message_history: playground_message_history
+                 )
+               else
+                 Captain::Llm::AssistantChatService.new(assistant: @assistant, source: 'playground').generate_response(
+                   additional_message: playground_params[:message_content],
+                   message_history: message_history
+                 )
+               end
 
     render json: response
   end
@@ -64,10 +70,31 @@ class Api::V1::Accounts::Captain::AssistantsController < Api::V1::Accounts::Base
   end
 
   def playground_params
-    params.require(:assistant).permit(:message_content, message_history: [:role, :content])
+    params.require(:assistant).permit(:message_content, message_history: [:role, :content, :agent_name])
   end
 
   def message_history
-    (playground_params[:message_history] || []).map { |message| { role: message[:role], content: message[:content] } }
+    (playground_params[:message_history] || []).map do |message|
+      {
+        role: message[:role],
+        content: message[:content],
+        agent_name: message[:agent_name]
+      }.compact
+    end
+  end
+
+  def playground_message_history
+    history = message_history
+    current_message = playground_params[:message_content]
+    return history if current_message.blank?
+
+    current_user_message = { role: 'user', content: current_message }
+    return history if history.last == current_user_message
+
+    history + [current_user_message]
+  end
+
+  def captain_v2_enabled?
+    @assistant.account.feature_enabled?('captain_integration_v2')
   end
 end
diff --git a/enterprise/app/helpers/captain/chat_helper.rb b/enterprise/app/helpers/captain/chat_helper.rb
index d5ac6df33..265f54d69 100644
--- a/enterprise/app/helpers/captain/chat_helper.rb
+++ b/enterprise/app/helpers/captain/chat_helper.rb
@@ -5,7 +5,6 @@ module Captain::ChatHelper
 
   def request_chat_completion
     log_chat_completion_request
-
     chat = build_chat
 
     add_messages_to_chat(chat)
@@ -86,7 +85,8 @@ module Captain::ChatHelper
       temperature: temperature,
       metadata: {
         assistant_id: @assistant&.id,
-        channel_type: resolved_channel_type
+        channel_type: resolved_channel_type,
+        source: @source
       }.compact
     }
   end
@@ -130,7 +130,6 @@ module Captain::ChatHelper
   end
 
   def log_chat_completion_request
-    Rails.logger.info("#{self.class.name} Assistant: #{@assistant.id}, Requesting chat completion " \
-                      "for messages #{@messages} with #{@tools&.length || 0} tools")
+    Rails.logger.info("#{self.class.name} Assistant: #{@assistant.id}, requesting completion for #{@messages} with #{@tools&.length || 0} tools")
   end
 end
diff --git a/enterprise/app/models/captain/assistant.rb b/enterprise/app/models/captain/assistant.rb
index 4f039d57a..08bff5ef3 100644
--- a/enterprise/app/models/captain/assistant.rb
+++ b/enterprise/app/models/captain/assistant.rb
@@ -106,7 +106,7 @@ class Captain::Assistant < ApplicationRecord
       scenarios: scenarios.enabled.map do |scenario|
         {
           title: scenario.title,
-          key: scenario.title.parameterize.underscore,
+          key: scenario.handoff_key,
           description: scenario.description
         }
       end,
diff --git a/enterprise/app/models/captain/scenario.rb b/enterprise/app/models/captain/scenario.rb
index c43468804..8a6a3c979 100644
--- a/enterprise/app/models/captain/scenario.rb
+++ b/enterprise/app/models/captain/scenario.rb
@@ -24,6 +24,19 @@ class Captain::Scenario < ApplicationRecord
   include Concerns::CaptainToolsHelpers
   include Concerns::Agentable
 
+  # OpenAI enforces a 64-char limit on function names. The ai-agents gem
+  # prepends "handoff_to_" (11 chars), so we keep a safety margin and cap
+  # the full tool name to MAX_HANDOFF_TOOL_NAME_LENGTH (60 chars).
+  # Format: "scenario_{id}_{slug}_agent" for persisted records (stable + readable),
+  # and "scenario_draft_{slug}_agent" for unsaved records, with slug truncated
+  # based on the available length budget.
+  HANDOFF_TOOL_PREFIX = 'handoff_to_'.freeze
+  HANDOFF_KEY_PREFIX = 'scenario'.freeze
+  HANDOFF_KEY_SUFFIX = 'agent'.freeze
+  MAX_HANDOFF_TOOL_NAME_LENGTH = 60
+  MAX_AGENT_NAME_LENGTH = MAX_HANDOFF_TOOL_NAME_LENGTH - HANDOFF_TOOL_PREFIX.length
+  MAX_HANDOFF_SLUG_LENGTH = 24
+
   self.table_name = 'captain_scenarios'
 
   belongs_to :assistant, class_name: 'Captain::Assistant'
@@ -42,6 +55,10 @@ class Captain::Scenario < ApplicationRecord
 
   before_save :resolve_tool_references
 
+  def handoff_key
+    [handoff_id_key, compact_handoff_slug, HANDOFF_KEY_SUFFIX].compact.join('_')
+  end
+
   def prompt_context
     {
       title: title,
@@ -56,7 +73,28 @@ class Captain::Scenario < ApplicationRecord
   private
 
   def agent_name
-    "#{title} Agent".parameterize(separator: '_')
+    handoff_key
+  end
+
+  def handoff_id_key
+    return "#{HANDOFF_KEY_PREFIX}_#{id}" if id.present?
+
+    "#{HANDOFF_KEY_PREFIX}_draft"
+  end
+
+  def compact_handoff_slug
+    slug = title.to_s.parameterize(separator: '_').presence
+    return nil if slug.blank?
+
+    max_slug_length = [MAX_HANDOFF_SLUG_LENGTH, dynamic_slug_max_length].min
+    return nil if max_slug_length <= 0
+
+    slug.first(max_slug_length).sub(/_+\z/, '').presence
+  end
+
+  def dynamic_slug_max_length
+    # handoff_to_#{scenario_<id>_<slug>_agent}
+    MAX_AGENT_NAME_LENGTH - handoff_id_key.length - HANDOFF_KEY_SUFFIX.length - 2
   end
 
   def agent_tools
diff --git a/enterprise/app/services/captain/assistant/agent_runner_service.rb b/enterprise/app/services/captain/assistant/agent_runner_service.rb
index bdf35e98e..1875a9953 100644
--- a/enterprise/app/services/captain/assistant/agent_runner_service.rb
+++ b/enterprise/app/services/captain/assistant/agent_runner_service.rb
@@ -19,11 +19,11 @@ class Captain::Assistant::AgentRunnerService
   CONTACT_INBOX_STATE_ATTRIBUTES = %i[id hmac_verified].freeze
 
   CAMPAIGN_STATE_ATTRIBUTES = %i[id title message campaign_type description].freeze
-
-  def initialize(assistant:, conversation: nil, callbacks: {})
+  def initialize(assistant:, conversation: nil, callbacks: {}, source: nil)
     @assistant = assistant
     @conversation = conversation
     @callbacks = callbacks
+    @source = source
   end
 
   def generate_response(message_history: [])
@@ -32,8 +32,7 @@ class Captain::Assistant::AgentRunnerService
 
     process_agent_result(result)
   rescue StandardError => e
-    # when running the agent runner service in a rake task, the conversation might not have an account associated
-    # for regular production usage, it will run just fine
+    # In rake/local runs, conversation may not be present, so account is optional here.
     ChatwootExceptionTracker.new(e, account: @conversation&.account).capture_exception
     Rails.logger.error "[Captain V2] AgentRunnerService error: #{e.message}"
     Rails.logger.error e.backtrace.join("\n")
@@ -128,6 +127,7 @@ class Captain::Assistant::AgentRunnerService
       assistant_id: @assistant.id,
       assistant_config: @assistant.config
     }
+    state[:source] = @source if @source.present?
 
     build_conversation_state(state) if @conversation
     state
@@ -140,8 +140,7 @@ class Captain::Assistant::AgentRunnerService
     state[:campaign] = @conversation.campaign.attributes.symbolize_keys.slice(*CAMPAIGN_STATE_ATTRIBUTES) if @conversation.campaign
     return unless @conversation.contact_inbox
 
-    state[:contact_inbox] =
-      @conversation.contact_inbox.attributes.symbolize_keys.slice(*CONTACT_INBOX_STATE_ATTRIBUTES)
+    state[:contact_inbox] = @conversation.contact_inbox.attributes.symbolize_keys.slice(*CONTACT_INBOX_STATE_ATTRIBUTES)
   end
 
   def build_and_wire_agents
@@ -180,6 +179,7 @@ class Captain::Assistant::AgentRunnerService
       format(ATTR_LANGFUSE_METADATA, 'conversation_id') => conversation[:id],
       format(ATTR_LANGFUSE_METADATA, 'conversation_display_id') => conversation[:display_id],
       format(ATTR_LANGFUSE_METADATA, 'channel_type') => state[:channel_type],
+      format(ATTR_LANGFUSE_METADATA, 'source') => state[:source],
       ATTR_LANGFUSE_TRACE_INPUT => trace_input,
       ATTR_LANGFUSE_OBSERVATION_INPUT => trace_input
     }.compact.transform_values(&:to_s)
diff --git a/enterprise/app/services/captain/llm/assistant_chat_service.rb b/enterprise/app/services/captain/llm/assistant_chat_service.rb
index 5a2976e39..c1403ed1a 100644
--- a/enterprise/app/services/captain/llm/assistant_chat_service.rb
+++ b/enterprise/app/services/captain/llm/assistant_chat_service.rb
@@ -1,11 +1,12 @@
 class Captain::Llm::AssistantChatService < Llm::BaseAiService
   include Captain::ChatHelper
 
-  def initialize(assistant: nil, conversation_id: nil)
+  def initialize(assistant: nil, conversation_id: nil, source: nil)
     super()
 
     @assistant = assistant
     @conversation_id = conversation_id
+    @source = source
 
     @messages = [system_message]
     @response = ''
diff --git a/spec/enterprise/controllers/api/v1/accounts/captain/assistants_controller_spec.rb b/spec/enterprise/controllers/api/v1/accounts/captain/assistants_controller_spec.rb
index 24deb98dd..4689defaf 100644
--- a/spec/enterprise/controllers/api/v1/accounts/captain/assistants_controller_spec.rb
+++ b/spec/enterprise/controllers/api/v1/accounts/captain/assistants_controller_spec.rb
@@ -259,10 +259,12 @@ RSpec.describe 'Api::V1::Accounts::Captain::Assistants', type: :request do
         message_content: 'Hello assistant',
         message_history: [
           { role: 'user', content: 'Previous message' },
-          { role: 'assistant', content: 'Previous response' }
+          { role: 'assistant', content: 'Previous response', agent_name: 'billing_scenario' }
         ]
       }
     end
+    let(:chat_service) { instance_double(Captain::Llm::AssistantChatService) }
+    let(:agent_runner_service) { instance_double(Captain::Assistant::AgentRunnerService) }
 
     context 'when it is an un-authenticated user' do
       it 'returns unauthorized' do
@@ -274,11 +276,14 @@ RSpec.describe 'Api::V1::Accounts::Captain::Assistants', type: :request do
       end
     end
 
-    context 'when it is an agent' do
-      it 'generates a response' do
-        chat_service = instance_double(Captain::Llm::AssistantChatService)
-        allow(Captain::Llm::AssistantChatService).to receive(:new).with(assistant: assistant).and_return(chat_service)
+    context 'when captain v2 is disabled' do
+      it 'generates a response with the legacy assistant chat service' do
+        allow(Captain::Llm::AssistantChatService).to receive(:new).with(
+          assistant: assistant,
+          source: 'playground'
+        ).and_return(chat_service)
         allow(chat_service).to receive(:generate_response).and_return({ content: 'Assistant response' })
+        expect(Captain::Assistant::AgentRunnerService).not_to receive(:new)
 
         post "/api/v1/accounts/#{account.id}/captain/assistants/#{assistant.id}/playground",
              params: valid_params,
@@ -292,14 +297,15 @@ RSpec.describe 'Api::V1::Accounts::Captain::Assistants', type: :request do
         )
         expect(json_response[:content]).to eq('Assistant response')
       end
-    end
 
-    context 'when message_history is not provided' do
       it 'uses empty array as default' do
         params_without_history = { message_content: 'Hello assistant' }
-        chat_service = instance_double(Captain::Llm::AssistantChatService)
-        allow(Captain::Llm::AssistantChatService).to receive(:new).with(assistant: assistant).and_return(chat_service)
+        allow(Captain::Llm::AssistantChatService).to receive(:new).with(
+          assistant: assistant,
+          source: 'playground'
+        ).and_return(chat_service)
         allow(chat_service).to receive(:generate_response).and_return({ content: 'Assistant response' })
+        expect(Captain::Assistant::AgentRunnerService).not_to receive(:new)
 
         post "/api/v1/accounts/#{account.id}/captain/assistants/#{assistant.id}/playground",
              params: params_without_history,
@@ -313,5 +319,53 @@ RSpec.describe 'Api::V1::Accounts::Captain::Assistants', type: :request do
         )
       end
     end
+
+    context 'when captain v2 is enabled' do
+      before do
+        account.enable_features('captain_integration_v2')
+      end
+
+      it 'generates a response with the agent runner service' do
+        allow(Captain::Assistant::AgentRunnerService).to receive(:new).with(
+          assistant: assistant,
+          source: 'playground'
+        ).and_return(agent_runner_service)
+        allow(agent_runner_service).to receive(:generate_response).and_return({ response: 'Assistant response' })
+        expect(Captain::Llm::AssistantChatService).not_to receive(:new)
+
+        post "/api/v1/accounts/#{account.id}/captain/assistants/#{assistant.id}/playground",
+             params: valid_params,
+             headers: agent.create_new_auth_token,
+             as: :json
+
+        expect(response).to have_http_status(:success)
+        expect(agent_runner_service).to have_received(:generate_response).with(
+          message_history: valid_params[:message_history] + [{ role: 'user', content: valid_params[:message_content] }]
+        )
+        expect(json_response[:response]).to eq('Assistant response')
+      end
+
+      it 'does not duplicate the latest user message if it is already in history' do
+        params_with_latest_message = {
+          message_content: 'Hello assistant',
+          message_history: [{ role: 'user', content: 'Hello assistant' }]
+        }
+        allow(Captain::Assistant::AgentRunnerService).to receive(:new).with(
+          assistant: assistant,
+          source: 'playground'
+        ).and_return(agent_runner_service)
+        allow(agent_runner_service).to receive(:generate_response).and_return({ response: 'Assistant response' })
+
+        post "/api/v1/accounts/#{account.id}/captain/assistants/#{assistant.id}/playground",
+             params: params_with_latest_message,
+             headers: agent.create_new_auth_token,
+             as: :json
+
+        expect(response).to have_http_status(:success)
+        expect(agent_runner_service).to have_received(:generate_response).with(
+          message_history: params_with_latest_message[:message_history]
+        )
+      end
+    end
   end
 end
diff --git a/spec/enterprise/models/captain/scenario_spec.rb b/spec/enterprise/models/captain/scenario_spec.rb
index 163581f01..94ce5325a 100644
--- a/spec/enterprise/models/captain/scenario_spec.rb
+++ b/spec/enterprise/models/captain/scenario_spec.rb
@@ -42,6 +42,45 @@ RSpec.describe Captain::Scenario, type: :model do
     end
   end
 
+  describe '#handoff_key' do
+    let(:account) { create(:account) }
+    let(:assistant) { create(:captain_assistant, account: account) }
+
+    it 'uses id plus readable slug for persisted scenarios' do
+      scenario = create(:captain_scenario, assistant: assistant, account: account,
+                                           title: 'Handle complex refund requests requiring manager approval steps')
+
+      expect(scenario.handoff_key).to start_with("scenario_#{scenario.id}_")
+      expect(scenario.handoff_key).to end_with('_agent')
+      expect("handoff_to_#{scenario.handoff_key}".length).to be <= 60
+    end
+
+    it 'uses a truncated slug key for unsaved scenarios' do
+      scenario = build(:captain_scenario, assistant: assistant, account: account,
+                                          title: 'Troubleshoot payment gateway errors for recurring subscription charges')
+
+      expect(scenario.handoff_key).to match(/\Ascenario_draft_[a-z0-9_]+_agent\z/)
+      expect("handoff_to_#{scenario.handoff_key}".length).to be <= 60
+    end
+
+    it 'stays within length budget even for large ids' do
+      scenario = build(:captain_scenario, assistant: assistant, account: account,
+                                          title: 'A very long scenario title used only for budget verification')
+      allow(scenario).to receive(:id).and_return(1_234_567_890_123_456_789)
+
+      expect("handoff_to_#{scenario.handoff_key}".length).to be <= 60
+    end
+
+    it 'exposes handoff keys in assistant prompt context' do
+      scenario = create(:captain_scenario, assistant: assistant, account: account)
+
+      prompt_context = assistant.send(:prompt_context)
+      scenario_config = prompt_context[:scenarios].find { |entry| entry[:title] == scenario.title }
+
+      expect(scenario_config[:key]).to eq(scenario.handoff_key)
+    end
+  end
+
   describe 'tool validation and population' do
     let(:account) { create(:account) }
     let(:assistant) { create(:captain_assistant, account: account) }