diff --git a/Gemfile b/Gemfile
index e6c5a5250..0636b7b2b 100644
--- a/Gemfile
+++ b/Gemfile
@@ -191,7 +191,7 @@ gem 'reverse_markdown'
 
 gem 'iso-639'
 gem 'ruby-openai'
-gem 'ai-agents'
+gem 'ai-agents', '>= 0.9.1'
 
 # TODO: Move this gem as a dependency of ai-agents
 gem 'ruby_llm', '>= 1.8.2'
diff --git a/Gemfile.lock b/Gemfile.lock
index aad0438cf..7a7316e3c 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -126,7 +126,7 @@ GEM
       jbuilder (~> 2)
       rails (>= 4.2, < 7.2)
       selectize-rails (~> 0.6)
-    ai-agents (0.9.0)
+    ai-agents (0.9.1)
       ruby_llm (~> 1.9.1)
     annotaterb (4.20.0)
       activerecord (>= 6.0.0)
@@ -1024,7 +1024,7 @@ DEPENDENCIES
   administrate (>= 0.20.1)
   administrate-field-active_storage (>= 1.0.3)
   administrate-field-belongs_to_search (>= 0.9.0)
-  ai-agents
+  ai-agents (>= 0.9.1)
   annotaterb
   attr_extras
   audited (~> 5.4, >= 5.4.1)
diff --git a/enterprise/app/services/captain/assistant/agent_runner_service.rb b/enterprise/app/services/captain/assistant/agent_runner_service.rb
index 9aeee605f..72c44024f 100644
--- a/enterprise/app/services/captain/assistant/agent_runner_service.rb
+++ b/enterprise/app/services/captain/assistant/agent_runner_service.rb
@@ -3,6 +3,8 @@ require 'agents/instrumentation'
 
 class Captain::Assistant::AgentRunnerService
   include Integrations::LlmInstrumentationConstants
+  include Captain::Assistant::RunnerCallbacksHelper
+  include Captain::Assistant::TracePayloadHelper
 
   CONVERSATION_STATE_ATTRIBUTES = %i[
     id display_id inbox_id contact_id status priority
@@ -21,13 +23,7 @@ class Captain::Assistant::AgentRunnerService
   end
 
   def generate_response(message_history: [])
-    agents = build_and_wire_agents
-    context = build_context(message_history)
-    message_to_process = extract_last_user_message(message_history)
-    runner = Agents::Runner.with_agents(*agents)
-    runner = add_usage_metadata_callback(runner)
-    runner = add_callbacks_to_runner(runner) if @callbacks.any?
-    install_instrumentation(runner)
+    message_to_process, context = run_payload(message_history)
     result = runner.run(message_to_process, context: context, max_turns: 100)
 
     process_agent_result(result)
@@ -45,7 +41,10 @@ class Captain::Assistant::AgentRunnerService
 
   def build_context(message_history)
     conversation_history = message_history.map do |msg|
-      content = extract_text_from_content(msg[:content])
+      content = msg[:content]
+      # Preserve multimodal arrays (with image_url entries) as-is for the runner to restore with attachments.
+      # Only extract text from non-array formats (hashes from agent structured output, plain strings).
+      content = extract_text_from_content(content) unless content.is_a?(Array)
 
       {
         role: msg[:role].to_sym,
@@ -63,8 +62,22 @@ class Captain::Assistant::AgentRunnerService
 
   def extract_last_user_message(message_history)
     last_user_msg = message_history.reverse.find { |msg| msg[:role] == 'user' }
+    return '' if last_user_msg.blank?
 
-    extract_text_from_content(last_user_msg[:content])
+    content = last_user_msg[:content]
+    return extract_text_from_content(content) unless content.is_a?(Array)
+
+    text, attachments = Captain::OpenAiMessageBuilderService.extract_text_and_attachments(content)
+    return text if attachments.blank?
+
+    RubyLLM::Content.new(text, attachments)
+  end
+
+  def message_history_without_last_user_message(message_history)
+    last_user_index = message_history.rindex { |msg| msg[:role] == 'user' }
+    return message_history if last_user_index.nil?
+
+    message_history.reject.with_index { |_msg, index| index == last_user_index }
   end
 
   def extract_text_from_content(content)
@@ -143,28 +156,25 @@ class Captain::Assistant::AgentRunnerService
       },
       attribute_provider: ->(context_wrapper) { dynamic_trace_attributes(context_wrapper) }
     )
+    register_trace_input_callback(runner)
   end
 
   def dynamic_trace_attributes(context_wrapper)
     state = context_wrapper&.context&.dig(:state) || {}
     conversation = state[:conversation] || {}
+    trace_input = context_wrapper&.context&.dig(:captain_v2_trace_input)
+
     {
       ATTR_LANGFUSE_USER_ID => state[:account_id],
       format(ATTR_LANGFUSE_METADATA, 'assistant_id') => state[:assistant_id],
       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, 'channel_type') => state[:channel_type],
+      ATTR_LANGFUSE_TRACE_INPUT => trace_input,
+      ATTR_LANGFUSE_OBSERVATION_INPUT => trace_input
     }.compact.transform_values(&:to_s)
   end
 
-  def add_callbacks_to_runner(runner)
-    runner = add_agent_thinking_callback(runner) if @callbacks[:on_agent_thinking]
-    runner = add_tool_start_callback(runner) if @callbacks[:on_tool_start]
-    runner = add_tool_complete_callback(runner) if @callbacks[:on_tool_complete]
-    runner = add_agent_handoff_callback(runner) if @callbacks[:on_agent_handoff]
-    runner
-  end
-
   def add_usage_metadata_callback(runner)
     return runner unless ChatwootApp.otel_enabled?
 
@@ -195,35 +205,20 @@ class Captain::Assistant::AgentRunnerService
     root_span.set_attribute(format(ATTR_LANGFUSE_METADATA, 'credit_used'), credit_used.to_s)
   end
 
-  def add_agent_thinking_callback(runner)
-    runner.on_agent_thinking do |*args|
-      @callbacks[:on_agent_thinking].call(*args)
-    rescue StandardError => e
-      Rails.logger.warn "[Captain] Callback error for agent_thinking: #{e.message}"
+  def runner
+    @runner ||= begin
+      configured_runner = Agents::Runner.with_agents(*build_and_wire_agents)
+      configured_runner = add_usage_metadata_callback(configured_runner)
+      configured_runner = add_callbacks_to_runner(configured_runner) if @callbacks.any?
+      install_instrumentation(configured_runner)
+      configured_runner
     end
   end
 
-  def add_tool_start_callback(runner)
-    runner.on_tool_start do |*args|
-      @callbacks[:on_tool_start].call(*args)
-    rescue StandardError => e
-      Rails.logger.warn "[Captain] Callback error for tool_start: #{e.message}"
-    end
-  end
-
-  def add_tool_complete_callback(runner)
-    runner.on_tool_complete do |*args|
-      @callbacks[:on_tool_complete].call(*args)
-    rescue StandardError => e
-      Rails.logger.warn "[Captain] Callback error for tool_complete: #{e.message}"
-    end
-  end
-
-  def add_agent_handoff_callback(runner)
-    runner.on_agent_handoff do |*args|
-      @callbacks[:on_agent_handoff].call(*args)
-    rescue StandardError => e
-      Rails.logger.warn "[Captain] Callback error for agent_handoff: #{e.message}"
-    end
+  def run_payload(message_history)
+    message_to_process = extract_last_user_message(message_history)
+    context = build_context(message_history_without_last_user_message(message_history))
+    enrich_context_with_trace_payload!(context, message_history, message_to_process)
+    [message_to_process, context]
   end
 end
diff --git a/enterprise/app/services/captain/assistant/runner_callbacks_helper.rb b/enterprise/app/services/captain/assistant/runner_callbacks_helper.rb
new file mode 100644
index 000000000..58fa0ca33
--- /dev/null
+++ b/enterprise/app/services/captain/assistant/runner_callbacks_helper.rb
@@ -0,0 +1,53 @@
+module Captain::Assistant::RunnerCallbacksHelper
+  private
+
+  def add_callbacks_to_runner(runner)
+    runner = add_agent_thinking_callback(runner) if @callbacks[:on_agent_thinking]
+    runner = add_tool_start_callback(runner) if @callbacks[:on_tool_start]
+    runner = add_tool_complete_callback(runner) if @callbacks[:on_tool_complete]
+    runner = add_agent_handoff_callback(runner) if @callbacks[:on_agent_handoff]
+    runner
+  end
+
+  def register_trace_input_callback(runner)
+    runner.on_agent_thinking do |_agent_name, _input, context_wrapper|
+      tracing = context_wrapper&.context&.dig(:__otel_tracing)
+      next unless tracing
+
+      trace_input = context_wrapper.context[:captain_v2_trace_current_input]
+      tracing[:pending_llm_input] = trace_input if trace_input.present?
+    end
+  end
+
+  def add_agent_thinking_callback(runner)
+    runner.on_agent_thinking do |*args|
+      @callbacks[:on_agent_thinking].call(*args)
+    rescue StandardError => e
+      Rails.logger.warn "[Captain] Callback error for agent_thinking: #{e.message}"
+    end
+  end
+
+  def add_tool_start_callback(runner)
+    runner.on_tool_start do |*args|
+      @callbacks[:on_tool_start].call(*args)
+    rescue StandardError => e
+      Rails.logger.warn "[Captain] Callback error for tool_start: #{e.message}"
+    end
+  end
+
+  def add_tool_complete_callback(runner)
+    runner.on_tool_complete do |*args|
+      @callbacks[:on_tool_complete].call(*args)
+    rescue StandardError => e
+      Rails.logger.warn "[Captain] Callback error for tool_complete: #{e.message}"
+    end
+  end
+
+  def add_agent_handoff_callback(runner)
+    runner.on_agent_handoff do |*args|
+      @callbacks[:on_agent_handoff].call(*args)
+    rescue StandardError => e
+      Rails.logger.warn "[Captain] Callback error for agent_handoff: #{e.message}"
+    end
+  end
+end
diff --git a/enterprise/app/services/captain/assistant/trace_payload_helper.rb b/enterprise/app/services/captain/assistant/trace_payload_helper.rb
new file mode 100644
index 000000000..3b6546c12
--- /dev/null
+++ b/enterprise/app/services/captain/assistant/trace_payload_helper.rb
@@ -0,0 +1,51 @@
+module Captain::Assistant::TracePayloadHelper
+  private
+
+  def enrich_context_with_trace_payload!(context, message_history, message_to_process)
+    context[:captain_v2_trace_input] = serialize_trace_messages(message_history)
+    context[:captain_v2_trace_current_input] = serialize_trace_content(message_to_process)
+  end
+
+  def serialize_trace_messages(message_history)
+    message_history.map do |message|
+      {
+        role: message[:role].to_s,
+        content: trace_content_payload(message[:content])
+      }
+    end.to_json
+  end
+
+  def serialize_trace_content(content)
+    payload = trace_content_payload(content)
+    return '' if payload.blank?
+
+    payload.is_a?(String) ? payload : payload.to_json
+  end
+
+  def trace_content_payload(content)
+    case content
+    when RubyLLM::Content
+      trace_parts_from_ruby_llm_content(content)
+    when Array, Hash
+      content
+    when NilClass
+      ''
+    else
+      content.to_s
+    end
+  end
+
+  def trace_parts_from_ruby_llm_content(content)
+    parts = []
+    parts << { type: 'text', text: content.text } if content.text.present?
+
+    content.attachments.each do |attachment|
+      parts << { type: 'image_url', image_url: { url: attachment.source.to_s } }
+    end
+
+    return '' if parts.blank?
+    return parts.first[:text] if parts.one? && parts.first[:type] == 'text'
+
+    parts
+  end
+end
diff --git a/spec/enterprise/services/captain/assistant/agent_runner_service_spec.rb b/spec/enterprise/services/captain/assistant/agent_runner_service_spec.rb
index c3019b82c..13e4804ce 100644
--- a/spec/enterprise/services/captain/assistant/agent_runner_service_spec.rb
+++ b/spec/enterprise/services/captain/assistant/agent_runner_service_spec.rb
@@ -74,12 +74,11 @@ RSpec.describe Captain::Assistant::AgentRunnerService do
     end
 
     it 'runs agent with extracted user message and context' do
-      expected_context = {
+      expected_context = hash_including(
         session_id: "#{account.id}_#{conversation.display_id}",
         conversation_history: [
           { role: :user, content: 'Hello there', agent_name: nil },
-          { role: :assistant, content: 'Hi! How can I help you?', agent_name: 'Assistant' },
-          { role: :user, content: 'I need help with my account', agent_name: nil }
+          { role: :assistant, content: 'Hi! How can I help you?', agent_name: 'Assistant' }
         ],
         state: hash_including(
           account_id: account.id,
@@ -87,7 +86,7 @@ RSpec.describe Captain::Assistant::AgentRunnerService do
           conversation: hash_including(id: conversation.id),
           contact: hash_including(id: contact.id)
         )
-      }
+      )
 
       expect(mock_runner).to receive(:run).with(
         'I need help with my account',
@@ -98,6 +97,71 @@ RSpec.describe Captain::Assistant::AgentRunnerService do
       service.generate_response(message_history: message_history)
     end
 
+    context 'when the latest user message is multimodal' do
+      let(:multimodal_message_history) do
+        [
+          { role: 'assistant', content: 'Please share a screenshot' },
+          {
+            role: 'user',
+            content: [
+              { type: 'text', text: 'What does this error mean?' },
+              { type: 'image_url', image_url: { url: 'https://example.com/error.png' } }
+            ]
+          }
+        ]
+      end
+
+      it 'passes image attachments to the runner input' do
+        expect(mock_runner).to receive(:run) do |input, context:, max_turns:|
+          expect(input).to be_a(RubyLLM::Content)
+          expect(input.text).to eq('What does this error mean?')
+          expect(input.attachments.first.source.to_s).to eq('https://example.com/error.png')
+          expect(context[:conversation_history]).to eq([{ role: :assistant, content: 'Please share a screenshot', agent_name: nil }])
+          expect(max_turns).to eq(100)
+        end
+
+        service.generate_response(message_history: multimodal_message_history)
+      end
+
+      it 'preserves multimodal content in earlier history messages' do
+        history_with_prior_image = [
+          {
+            role: 'user',
+            content: [
+              { type: 'text', text: 'Here is my error screenshot' },
+              { type: 'image_url', image_url: { url: 'https://example.com/error.png' } }
+            ]
+          },
+          { role: 'assistant', content: 'I see the error. Try restarting.' },
+          { role: 'user', content: 'It still does not work' }
+        ]
+
+        expect(mock_runner).to receive(:run) do |input, context:, max_turns:|
+          expect(input).to eq('It still does not work')
+          # The earlier user message with the image should preserve the multimodal array
+          first_history_msg = context[:conversation_history].first
+          expect(first_history_msg[:content]).to be_a(Array)
+          expect(first_history_msg[:content]).to include(
+            { type: 'text', text: 'Here is my error screenshot' },
+            { type: 'image_url', image_url: { url: 'https://example.com/error.png' } }
+          )
+          expect(max_turns).to eq(100)
+        end
+
+        service.generate_response(message_history: history_with_prior_image)
+      end
+
+      it 'stores multimodal trace payloads in runner context' do
+        expect(mock_runner).to receive(:run) do |_input, context:, max_turns:|
+          expect(context[:captain_v2_trace_input]).to include('image_url')
+          expect(context[:captain_v2_trace_current_input]).to include('image_url')
+          expect(max_turns).to eq(100)
+        end
+
+        service.generate_response(message_history: multimodal_message_history)
+      end
+    end
+
     it 'processes and formats agent result' do
       result = service.generate_response(message_history: message_history)
 
@@ -197,22 +261,21 @@ RSpec.describe Captain::Assistant::AgentRunnerService do
     end
 
     context 'with multimodal content' do
-      let(:multimodal_message_history) do
+      let(:multimodal_content) do
         [
-          {
-            role: 'user',
-            content: [
-              { type: 'text', text: 'Can you help with this image?' },
-              { type: 'image_url', image_url: { url: 'https://example.com/image.jpg' } }
-            ]
-          }
+          { type: 'text', text: 'Can you help with this image?' },
+          { type: 'image_url', image_url: { url: 'https://example.com/image.jpg' } }
         ]
       end
 
-      it 'extracts text content from multimodal messages' do
+      let(:multimodal_message_history) do
+        [{ role: 'user', content: multimodal_content }]
+      end
+
+      it 'preserves multimodal arrays in conversation history for image context retention' do
         context = service.send(:build_context, multimodal_message_history)
 
-        expect(context[:conversation_history].first[:content]).to eq('Can you help with this image?')
+        expect(context[:conversation_history].first[:content]).to eq(multimodal_content)
       end
     end
   end
@@ -225,6 +288,24 @@ RSpec.describe Captain::Assistant::AgentRunnerService do
 
       expect(result).to eq('I need help with my account')
     end
+
+    it 'returns multimodal content with image attachments for the runner input' do
+      multimodal_message_history = [
+        {
+          role: 'user',
+          content: [
+            { type: 'text', text: 'Can you check this screenshot?' },
+            { type: 'image_url', image_url: { url: 'https://example.com/image.jpg' } }
+          ]
+        }
+      ]
+
+      result = service.send(:extract_last_user_message, multimodal_message_history)
+
+      expect(result).to be_a(RubyLLM::Content)
+      expect(result.text).to eq('Can you check this screenshot?')
+      expect(result.attachments.first.source.to_s).to eq('https://example.com/image.jpg')
+    end
   end
 
   describe '#extract_text_from_content' do
@@ -256,6 +337,28 @@ RSpec.describe Captain::Assistant::AgentRunnerService do
     end
   end
 
+  describe '#dynamic_trace_attributes' do
+    subject(:service) { described_class.new(assistant: assistant, conversation: conversation) }
+
+    it 'adds serialized trace input attributes when present in context' do
+      context = {
+        state: {
+          account_id: account.id,
+          assistant_id: assistant.id,
+          conversation: { id: conversation.id, display_id: conversation.display_id }
+        },
+        captain_v2_trace_input: '[{"role":"user","content":[{"type":"image_url","image_url":{"url":"https://example.com/image.jpg"}}]}]'
+      }
+      context_wrapper = Struct.new(:context).new(context)
+
+      attributes = service.send(:dynamic_trace_attributes, context_wrapper)
+
+      expect(attributes['langfuse.trace.input']).to include('image_url')
+      expect(attributes['langfuse.observation.input']).to include('image_url')
+      expect(attributes['langfuse.user.id']).to eq(account.id.to_s)
+    end
+  end
+
   describe '#build_state' do
     subject(:service) { described_class.new(assistant: assistant, conversation: conversation) }