diff --git a/enterprise/app/services/captain/tools/base_tool.rb b/enterprise/app/services/captain/tools/base_tool.rb
index dbc2902d8..1ec4aaffc 100644
--- a/enterprise/app/services/captain/tools/base_tool.rb
+++ b/enterprise/app/services/captain/tools/base_tool.rb
@@ -1,4 +1,6 @@
 class Captain::Tools::BaseTool < RubyLLM::Tool
+  prepend Captain::Tools::Instrumentation
+
   attr_accessor :assistant
 
   def initialize(assistant, user: nil)
diff --git a/enterprise/app/services/captain/tools/instrumentation.rb b/enterprise/app/services/captain/tools/instrumentation.rb
new file mode 100644
index 000000000..2288b239e
--- /dev/null
+++ b/enterprise/app/services/captain/tools/instrumentation.rb
@@ -0,0 +1,10 @@
+module Captain::Tools::Instrumentation
+  extend ActiveSupport::Concern
+  include Integrations::LlmInstrumentation
+
+  def execute(**args)
+    instrument_tool_call(name, args) do
+      super
+    end
+  end
+end
diff --git a/enterprise/app/services/captain/tools/search_reply_documentation_service.rb b/enterprise/app/services/captain/tools/search_reply_documentation_service.rb
new file mode 100644
index 000000000..d2c1df42f
--- /dev/null
+++ b/enterprise/app/services/captain/tools/search_reply_documentation_service.rb
@@ -0,0 +1,42 @@
+class Captain::Tools::SearchReplyDocumentationService < RubyLLM::Tool
+  prepend Captain::Tools::Instrumentation
+
+  description 'Search and retrieve documentation/FAQs from knowledge base'
+
+  param :query, desc: 'Search Query', required: true
+
+  def initialize(account:, assistant: nil)
+    @account = account
+    @assistant = assistant
+    super()
+  end
+
+  def name
+    'search_documentation'
+  end
+
+  def execute(query:)
+    Rails.logger.info { "#{self.class.name}: #{query}" }
+
+    responses = search_responses(query)
+    return 'No FAQs found for the given query' if responses.empty?
+
+    responses.map { |response| format_response(response) }.join
+  end
+
+  private
+
+  def search_responses(query)
+    if @assistant.present?
+      @assistant.responses.approved.search(query, account_id: @account.id)
+    else
+      @account.captain_assistant_responses.approved.search(query, account_id: @account.id)
+    end
+  end
+
+  def format_response(response)
+    result = "\nQuestion: #{response.question}\nAnswer: #{response.answer}\n"
+    result += "Source: #{response.documentable.external_link}\n" if response.documentable.present? && response.documentable.try(:external_link)
+    result
+  end
+end
diff --git a/enterprise/lib/enterprise/captain/reply_suggestion_service.rb b/enterprise/lib/enterprise/captain/reply_suggestion_service.rb
new file mode 100644
index 000000000..503dd095a
--- /dev/null
+++ b/enterprise/lib/enterprise/captain/reply_suggestion_service.rb
@@ -0,0 +1,24 @@
+module Enterprise::Captain::ReplySuggestionService
+  def make_api_call(model:, messages:, tools: [])
+    return super unless use_search_tool?
+
+    super(model: model, messages: messages, tools: [build_search_tool])
+  end
+
+  private
+
+  def use_search_tool?
+    ChatwootApp.chatwoot_cloud? || ChatwootApp.self_hosted_enterprise?
+  end
+
+  def prompt_variables
+    return super unless use_search_tool?
+
+    super.merge('has_search_tool' => true)
+  end
+
+  def build_search_tool
+    assistant = conversation&.inbox&.captain_assistant
+    Captain::Tools::SearchReplyDocumentationService.new(account: account, assistant: assistant)
+  end
+end
diff --git a/lib/captain/base_task_service.rb b/lib/captain/base_task_service.rb
index b0cf7d240..7b84a879d 100644
--- a/lib/captain/base_task_service.rb
+++ b/lib/captain/base_task_service.rb
@@ -1,5 +1,6 @@
 class Captain::BaseTaskService
   include Integrations::LlmInstrumentation
+  include Captain::ToolInstrumentation
 
   # gpt-4o-mini supports 128,000 tokens
   # 1 token is approx 4 characters
@@ -35,44 +36,52 @@ class Captain::BaseTaskService
     "#{endpoint}/v1"
   end
 
-  def make_api_call(model:, messages:)
+  def make_api_call(model:, messages:, tools: [])
     # Community edition prerequisite checks
     # Enterprise module handles these with more specific error messages (cloud vs self-hosted)
     return { error: I18n.t('captain.disabled'), error_code: 403 } unless captain_tasks_enabled?
     return { error: I18n.t('captain.api_key_missing'), error_code: 401 } unless api_key_configured?
 
     instrumentation_params = build_instrumentation_params(model, messages)
+    instrumentation_method = tools.any? ? :instrument_tool_session : :instrument_llm_call
 
-    response = instrument_llm_call(instrumentation_params) do
-      execute_ruby_llm_request(model: model, messages: messages)
+    response = send(instrumentation_method, instrumentation_params) do
+      execute_ruby_llm_request(model: model, messages: messages, tools: tools)
     end
 
-    # Build follow-up context for client-side refinement, when applicable
-    if build_follow_up_context? && response[:message].present?
-      response.merge(follow_up_context: build_follow_up_context(messages, response))
-    else
-      response
-    end
+    return response unless build_follow_up_context? && response[:message].present?
+
+    response.merge(follow_up_context: build_follow_up_context(messages, response))
   end
 
-  def execute_ruby_llm_request(model:, messages:)
+  def execute_ruby_llm_request(model:, messages:, tools: [])
     Llm::Config.with_api_key(api_key, api_base: api_base) do |context|
-      chat = context.chat(model: model)
-      system_msg = messages.find { |m| m[:role] == 'system' }
-      chat.with_instructions(system_msg[:content]) if system_msg
+      chat = build_chat(context, model: model, messages: messages, tools: tools)
 
       conversation_messages = messages.reject { |m| m[:role] == 'system' }
       return { error: 'No conversation messages provided', error_code: 400, request_messages: messages } if conversation_messages.empty?
 
       add_messages_if_needed(chat, conversation_messages)
-      response = chat.ask(conversation_messages.last[:content])
-      build_ruby_llm_response(response, messages)
+      build_ruby_llm_response(chat.ask(conversation_messages.last[:content]), messages)
     end
   rescue StandardError => e
     ChatwootExceptionTracker.new(e, account: account).capture_exception
     { error: e.message, request_messages: messages }
   end
 
+  def build_chat(context, model:, messages:, tools: [])
+    chat = context.chat(model: model)
+    system_msg = messages.find { |m| m[:role] == 'system' }
+    chat.with_instructions(system_msg[:content]) if system_msg
+
+    if tools.any?
+      tools.each { |tool| chat = chat.with_tool(tool) }
+      chat.on_end_message { |message| record_generation(chat, message, model) }
+    end
+
+    chat
+  end
+
   def add_messages_if_needed(chat, conversation_messages)
     return if conversation_messages.length == 1
 
@@ -177,5 +186,4 @@ class Captain::BaseTaskService
     user_msg ? user_msg[:content] : nil
   end
 end
-
 Captain::BaseTaskService.prepend_mod_with('Captain::BaseTaskService')
diff --git a/lib/captain/reply_suggestion_service.rb b/lib/captain/reply_suggestion_service.rb
index 8582258a8..2daf0615c 100644
--- a/lib/captain/reply_suggestion_service.rb
+++ b/lib/captain/reply_suggestion_service.rb
@@ -38,3 +38,5 @@ class Captain::ReplySuggestionService < Captain::BaseTaskService
     'reply_suggestion'
   end
 end
+
+Captain::ReplySuggestionService.prepend_mod_with('Captain::ReplySuggestionService')
diff --git a/lib/captain/tool_instrumentation.rb b/lib/captain/tool_instrumentation.rb
new file mode 100644
index 000000000..a2bacce1a
--- /dev/null
+++ b/lib/captain/tool_instrumentation.rb
@@ -0,0 +1,48 @@
+module Captain::ToolInstrumentation
+  extend ActiveSupport::Concern
+
+  private
+
+  # Custom instrumentation for tool flows - outputs just the message (not full hash)
+  def instrument_tool_session(params)
+    return yield unless ChatwootApp.otel_enabled?
+
+    response = nil
+    executed = false
+    tracer.in_span(params[:span_name]) do |span|
+      span.set_attribute('langfuse.user.id', params[:account_id].to_s) if params[:account_id]
+      span.set_attribute('langfuse.tags', [params[:feature_name]].to_json)
+      span.set_attribute('langfuse.observation.input', params[:messages].to_json)
+
+      response = yield
+      executed = true
+
+      # Output just the message for cleaner Langfuse display
+      span.set_attribute('langfuse.observation.output', response[:message] || response.to_json)
+    end
+    response
+  rescue StandardError => e
+    ChatwootExceptionTracker.new(e, account: account).capture_exception
+    executed ? response : yield
+  end
+
+  def record_generation(chat, message, model)
+    return unless ChatwootApp.otel_enabled?
+    return unless message.respond_to?(:role) && message.role.to_s == 'assistant'
+
+    tracer.in_span("llm.#{event_name}.generation") do |span|
+      span.set_attribute('gen_ai.system', 'openai')
+      span.set_attribute('gen_ai.request.model', model)
+      span.set_attribute('gen_ai.usage.input_tokens', message.input_tokens)
+      span.set_attribute('gen_ai.usage.output_tokens', message.output_tokens) if message.respond_to?(:output_tokens)
+      span.set_attribute('langfuse.observation.input', format_chat_messages(chat))
+      span.set_attribute('langfuse.observation.output', message.content.to_s) if message.respond_to?(:content)
+    end
+  rescue StandardError => e
+    Rails.logger.warn "Failed to record generation: #{e.message}"
+  end
+
+  def format_chat_messages(chat)
+    chat.messages[0...-1].map { |m| { role: m.role.to_s, content: m.content.to_s } }.to_json
+  end
+end
diff --git a/lib/chatwoot_app.rb b/lib/chatwoot_app.rb
index 3afb7579e..c0aa41e1a 100644
--- a/lib/chatwoot_app.rb
+++ b/lib/chatwoot_app.rb
@@ -21,6 +21,10 @@ module ChatwootApp
     enterprise? && GlobalConfig.get_value('DEPLOYMENT_ENV') == 'cloud'
   end
 
+  def self.self_hosted_enterprise?
+    enterprise? && !chatwoot_cloud? && GlobalConfig.get_value('INSTALLATION_PRICING_PLAN') == 'enterprise'
+  end
+
   def self.custom?
     @custom ||= root.join('custom').exist?
   end
diff --git a/lib/integrations/openai/openai_prompts/reply.liquid b/lib/integrations/openai/openai_prompts/reply.liquid
index 19db51a05..f9b95dbdf 100644
--- a/lib/integrations/openai/openai_prompts/reply.liquid
+++ b/lib/integrations/openai/openai_prompts/reply.liquid
@@ -31,5 +31,10 @@ General guidelines:
 - Move the conversation forward
 - Do not invent product details, policies, or links that weren't mentioned
 - Reply in the customer's language
+{% if has_search_tool %}
+
+**Important**: You have access to a `search_documentation` tool that can search the company's knowledge base for product details, policies, FAQs, and other information. 
+**Use the search_documentation tool first** to find relevant information before composing your reply. This ensures your response is accurate and based on actual company documentation.
+{% endif %}
 
 Output only the reply.
diff --git a/spec/lib/captain/base_task_service_spec.rb b/spec/lib/captain/base_task_service_spec.rb
index 1ea666b5d..b3c330252 100644
--- a/spec/lib/captain/base_task_service_spec.rb
+++ b/spec/lib/captain/base_task_service_spec.rb
@@ -161,11 +161,6 @@ RSpec.describe Captain::BaseTaskService do
       end
     end
 
-    it 'calls execute_ruby_llm_request with correct parameters' do
-      expect(service).to receive(:execute_ruby_llm_request).with(model: model, messages: messages).and_call_original
-      service.send(:make_api_call, model: model, messages: messages)
-    end
-
     it 'instruments the LLM call' do
       expect(service).to receive(:instrument_llm_call).and_call_original
       service.send(:make_api_call, model: model, messages: messages)
diff --git a/spec/lib/captain/reply_suggestion_service_spec.rb b/spec/lib/captain/reply_suggestion_service_spec.rb
index 81c1f3854..a53825ee4 100644
--- a/spec/lib/captain/reply_suggestion_service_spec.rb
+++ b/spec/lib/captain/reply_suggestion_service_spec.rb
@@ -19,6 +19,8 @@ RSpec.describe Captain::ReplySuggestionService do
     mock_context = instance_double(RubyLLM::Context, chat: mock_chat)
 
     allow(Llm::Config).to receive(:with_api_key).and_yield(mock_context)
+    allow(mock_chat).to receive(:with_tool).and_return(mock_chat)
+    allow(mock_chat).to receive(:on_end_message).and_return(mock_chat)
     allow(mock_chat).to receive(:with_instructions) { |msg| captured_messages << { role: 'system', content: msg } }
     allow(mock_chat).to receive(:add_message) { |args| captured_messages << args }
     allow(mock_chat).to receive(:ask) do |msg|