diff --git a/Gemfile b/Gemfile
index 1ae6cf0..c20a4d5 100755
--- a/Gemfile
+++ b/Gemfile
@@ -188,6 +188,7 @@ gem 'neighbor'
 gem 'pgvector'
 # Convert Website HTML to Markdown
 gem 'reverse_markdown'
+gem 'pdf-reader'
 
 gem 'iso-639'
 gem 'ruby-openai'
diff --git a/enterprise/app/jobs/captain/conversation/response_builder_job.rb b/enterprise/app/jobs/captain/conversation/response_builder_job.rb
index 7e6b5b1..26facfd 100755
--- a/enterprise/app/jobs/captain/conversation/response_builder_job.rb
+++ b/enterprise/app/jobs/captain/conversation/response_builder_job.rb
@@ -104,6 +104,8 @@ class Captain::Conversation::ResponseBuilderJob < ApplicationJob
       I18n.with_locale(@assistant.account.locale) do
         create_handoff_message
         @conversation.bot_handoff!
+        apply_handoff_side_effects
+        log_handoff_event
         send_out_of_office_message_if_applicable
       end
     end
@@ -121,6 +123,7 @@ class Captain::Conversation::ResponseBuilderJob < ApplicationJob
 
   def create_messages
     response_text = inject_preferred_name(@response['response'])
+    response_text = prevent_fake_handoff(response_text)
     validate_message_content!(response_text)
     create_outgoing_message(response_text, agent_name: @response['agent_name'])
   end
@@ -155,6 +158,41 @@ class Captain::Conversation::ResponseBuilderJob < ApplicationJob
     "#{preferred_name}, #{content}"
   end
 
+  def prevent_fake_handoff(content)
+    return content if content.blank? || handoff_requested?
+
+    handoff_message = @assistant.config['handoff_message'].presence || I18n.t('conversations.captain.handoff')
+    return content unless content.strip == handoff_message.to_s.strip
+
+    fallback_question
+  end
+
+  def fallback_question
+    'Pode me dizer sua duvida de forma mais especifica?'
+  end
+
+  def apply_handoff_side_effects
+    @conversation.add_labels(['handoff_requested'])
+
+    return if @conversation.assignee.present?
+
+    allowed_agent_ids = @conversation.inbox.member_ids_with_assignment_capacity
+    AutoAssignment::AgentAssignmentService.new(conversation: @conversation, allowed_agent_ids: allowed_agent_ids).perform
+  end
+
+  def log_handoff_event
+    Rails.logger.info(
+      "[CAPTAIN][handoff] request_id=#{extract_request_id} conversation_id=#{@conversation.id} assistant_id=#{@assistant.id} " \
+      "assignee_id=#{@conversation.assignee_id} team_id=#{@conversation.team_id}"
+    )
+  end
+
+  def extract_request_id
+    return RequestStore.store[:request_id] if defined?(RequestStore) && RequestStore.store[:request_id].present?
+
+    Thread.current[:request_id] || 'unknown'
+  end
+
   def handle_error(error)
     log_error(error)
     process_action('handoff')
diff --git a/enterprise/app/jobs/captain/llm/update_embedding_job.rb b/enterprise/app/jobs/captain/llm/update_embedding_job.rb
index 72ab540..fdce748 100755
--- a/enterprise/app/jobs/captain/llm/update_embedding_job.rb
+++ b/enterprise/app/jobs/captain/llm/update_embedding_job.rb
@@ -3,7 +3,13 @@ class Captain::Llm::UpdateEmbeddingJob < ApplicationJob
 
   def perform(record, content)
     account_id = record.account_id
+    Rails.logger.info(
+      "[CAPTAIN][embedding] Generating embedding for record_id=#{record.id} account_id=#{account_id} type=#{record.class.name}"
+    )
     embedding = Captain::Llm::EmbeddingService.new(account_id: account_id).get_embedding(content)
     record.update!(embedding: embedding)
+    Rails.logger.info(
+      "[CAPTAIN][embedding] Stored embedding for record_id=#{record.id} vector_size=#{embedding&.length}"
+    )
   end
 end
diff --git a/enterprise/app/services/captain/llm/assistant_chat_service.rb b/enterprise/app/services/captain/llm/assistant_chat_service.rb
index 0462c80..d8cb341 100755
--- a/enterprise/app/services/captain/llm/assistant_chat_service.rb
+++ b/enterprise/app/services/captain/llm/assistant_chat_service.rb
@@ -103,7 +103,7 @@ class Captain::Llm::AssistantChatService < Llm::BaseAiService
   end
 
   def build_tools
-    [Captain::Tools::SearchDocumentationService.new(@assistant, user: nil)]
+    [Captain::Tools::SearchDocumentationService.new(@assistant, user: nil, conversation: @conversation)]
   end
 
   def system_message
diff --git a/enterprise/app/services/captain/llm/pdf_processing_service.rb b/enterprise/app/services/captain/llm/pdf_processing_service.rb
index 98df459..6aac195 100755
--- a/enterprise/app/services/captain/llm/pdf_processing_service.rb
+++ b/enterprise/app/services/captain/llm/pdf_processing_service.rb
@@ -20,6 +20,7 @@ class Captain::Llm::PdfProcessingService < Llm::LegacyBaseOpenAiService
   attr_reader :document
 
   def extract_text_from_pdf
+    ensure_pdf_reader!
     content = ''
     document.pdf_file.open do |file|
       reader = PDF::Reader.new(file)
@@ -27,10 +28,20 @@ class Captain::Llm::PdfProcessingService < Llm::LegacyBaseOpenAiService
     end
 
     if content.present?
+      Rails.logger.info "PDF extracted content for document #{document.id} (chars=#{content.length})"
       # Update content and ensure openai_file_id is nil to force standard FAQ generation
       document.update!(content: content, openai_file_id: nil)
     else
       Rails.logger.warn "PDF extracted content is empty for document #{document.id}"
     end
   end
+
+  def ensure_pdf_reader!
+    return if defined?(PDF::Reader)
+
+    require 'pdf/reader'
+  rescue LoadError => e
+    Rails.logger.error "PDF Processing Error: missing pdf-reader gem (#{e.message})"
+    raise e
+  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 8f45095..7d8e9c9 100755
--- a/enterprise/app/services/captain/llm/system_prompts_service.rb
+++ b/enterprise/app/services/captain/llm/system_prompts_service.rb
@@ -155,10 +155,9 @@ class Captain::Llm::SystemPromptsService
     def assistant_response_generator(assistant_name, product_name, config = {})
       assistant_citation_guidelines = if config['feature_citation']
                                         <<~CITATION_TEXT
-                                          - Always include citations for any information provided, referencing the specific source (document only - skip if it was derived from a conversation).
-                                          - Citations must be numbered sequentially and formatted as `[[n](URL)]` (where n is the sequential number) at the end of each paragraph or sentence where external information is used.
+                                          - When you use information from documentation, include citations that reference the specific source (document only - skip if it was derived from a conversation).
+                                          - Citations must be numbered sequentially and formatted as `[[n](URL)]` at the end of the sentence that uses the source.
                                           - If multiple sentences share the same source, reuse the same citation number.
-                                          - Do not generate citations if the information is derived from a conversation and not an external document.
                                         CITATION_TEXT
                                       else
                                         ''
@@ -182,7 +181,8 @@ class Captain::Llm::SystemPromptsService
         - Sometimes the user might just want to chat. Ask them relevant follow-up questions.
         - Don't ask them if there's anything else they need help with (e.g. don't say things like "How can I assist you further?").
         - Don't use lists, markdown, bullet points, or other formatting that's not typically spoken.
-        - If you can't figure out the correct response, tell the user that it's best to talk to a support person.
+        - If you cannot answer from the provided context, ask one brief, objective follow-up question or return response="conversation_handoff".
+        - Never say you will hand off to a human unless you return response="conversation_handoff".
         - If a CONTEXT PACK is provided with preferred_name and name_confidence, only use the name when name_confidence >= 0.8.
         - If there is no reliable name, ask once for the user's name and continue without using a name if they don't provide it.
         - Never infer or invent preferences or identity details; use only what is explicitly in the CONTEXT PACK.
@@ -196,8 +196,7 @@ class Captain::Llm::SystemPromptsService
         - Provide the user with the steps required to complete the action one by one.
         - Do not return list numbers in the steps, just the plain text is enough.
         - Do not share anything outside of the context provided.
-        - Add the reasoning why you arrived at the answer
-        - Your answers will always be formatted in a valid JSON hash, as shown below. Never respond in non-JSON format.
+        - Your answers must be formatted in a valid JSON hash, as shown below. Never respond in non-JSON format.
         #{config['instructions'] || ''}
 
         [SDR Playbook]
@@ -205,12 +204,10 @@ class Captain::Llm::SystemPromptsService
 
         ```json
         {
-          reasoning: '',
           response: '',
         }
         ```
-        - If the answer is not provided in context sections, Respond to the customer and ask whether they want to talk to another support agent . If they ask to Chat with another agent, return `conversation_handoff' as the response in JSON response
-        #{'- You MUST provide numbered citations at the appropriate places in the text.' if config['feature_citation']}
+        - If the answer is not provided in context sections, ask one objective question or return response="conversation_handoff".
       SYSTEM_PROMPT_MESSAGE
     end
 
diff --git a/enterprise/app/services/captain/tools/search_documentation_service.rb b/enterprise/app/services/captain/tools/search_documentation_service.rb
index fbc8f41..491b1ca 100755
--- a/enterprise/app/services/captain/tools/search_documentation_service.rb
+++ b/enterprise/app/services/captain/tools/search_documentation_service.rb
@@ -1,4 +1,6 @@
 class Captain::Tools::SearchDocumentationService < Captain::Tools::BaseTool
+  LOW_CONFIDENCE_DISTANCE = 0.55
+
   def self.name
     'search_documentation'
   end
@@ -6,18 +8,59 @@ class Captain::Tools::SearchDocumentationService < Captain::Tools::BaseTool
 
   param :query, desc: 'Search Query', required: true
 
+  def initialize(assistant, user: nil, conversation: nil)
+    @conversation = conversation
+    super(assistant, user: user)
+  end
+
   def execute(query:)
     Rails.logger.info { "#{self.class.name}: #{query}" }
 
     responses = assistant.responses.approved.search(query)
 
-    return 'No FAQs found for the given query' if responses.empty?
+    log_results(query, responses)
+
+    return 'No FAQs found for the given query' if responses.empty? || low_confidence?(responses.first)
 
     responses.map { |response| format_response(response) }.join
   end
 
   private
 
+  def log_results(query, responses)
+    request_id = extract_request_id
+    conversation_id = @conversation&.id
+    response_count = responses.length
+    scores = responses.map { |response| result_score_payload(response) }
+    top_response = responses.first
+    top_snippet = top_response&.answer.to_s.strip[0, 200]
+    low_confidence = top_response&.neighbor_distance.to_f > LOW_CONFIDENCE_DISTANCE if top_response
+
+    Rails.logger.info(
+      "[CAPTAIN][search_documentation] request_id=#{request_id} conversation_id=#{conversation_id} query=#{query.inspect} " \
+      "count=#{response_count} results=#{scores} low_confidence=#{low_confidence} top_snippet=#{top_snippet.inspect}"
+    )
+  end
+
+  def low_confidence?(response)
+    return false unless response&.respond_to?(:neighbor_distance)
+
+    response.neighbor_distance.to_f > LOW_CONFIDENCE_DISTANCE
+  end
+
+  def result_score_payload(response)
+    {
+      id: response.id,
+      distance: response.respond_to?(:neighbor_distance) ? response.neighbor_distance : nil
+    }
+  end
+
+  def extract_request_id
+    return RequestStore.store[:request_id] if defined?(RequestStore) && RequestStore.store[:request_id].present?
+
+    Thread.current[:request_id] || 'unknown'
+  end
+
   def format_response(response)
     formatted_response = "
         Question: #{response.question}
diff --git a/progresso/2026-01-05_fix_assets_antigos_volume_public.md b/progresso/2026-01-05_fix_assets_antigos_volume_public.md
new file mode 100644
index 0000000..2e42b27
--- /dev/null
+++ b/progresso/2026-01-05_fix_assets_antigos_volume_public.md
@@ -0,0 +1,30 @@
+# Fix: assets antigos por volume em /app/public
+
+## Sintoma
+- Build da imagem passava, mas o front em producao (arm64) nao mostrava mudancas novas.
+- Dentro do container, o codigo fonte tinha os componentes novos, mas os assets servidos nao tinham as alteracoes.
+
+## Causa
+- O stack montava um volume em `/app/public`, sobrescrevendo os assets gerados na imagem.
+- Resultado: mesmo com imagem nova, o container servia assets antigos do volume.
+
+## Como confirmar
+No container:
+- `grep -R -n "i-lucide-brain" /app/public 2>/dev/null | head -n 5`
+  - Se nao retorna nada, os assets no volume estao desatualizados.
+
+No Portainer (Inspect do container):
+- Ver se existe mount com `Destination: /app/public`.
+
+## Resolucao (Portainer)
+1. Portainer -> Stacks -> `chatwoot-wuzapi` -> **Stop**.
+2. Portainer -> Volumes -> remover `chatwoot-wuzapi_chatwoot_public`.
+3. Portainer -> Stacks -> **Start/Deploy**.
+4. Validar no front se as mudancas apareceram.
+
+## Observacoes
+- `assets:precompile` nao roda no container final (nao tem pnpm/vite). Os assets devem vir prontos da imagem.
+- Se precisar manter volume, e necessario copiar os assets da imagem para o volume na hora do deploy.
+
+## Prevencao
+- Evitar montar volume em `/app/public` em producao, a menos que exista processo explicito para atualizar os assets.