diff --git a/enterprise/app/models/captain/reservation.rb b/enterprise/app/models/captain/reservation.rb
index c84bf9fea..fcbe37cf3 100644
--- a/enterprise/app/models/captain/reservation.rb
+++ b/enterprise/app/models/captain/reservation.rb
@@ -88,6 +88,7 @@ class Captain::Reservation < ApplicationRecord
 
   before_validation :set_captain_unit_id, on: :create
   after_commit :sync_conversation_marker_snapshot
+  after_create_commit :update_contact_reservation_metadata
 
   def ui_status
     Captain::Reservations::MarkerBuilder.ui_status(status)
@@ -125,4 +126,23 @@ class Captain::Reservation < ApplicationRecord
   rescue StandardError => e
     Rails.logger.error("[Captain::Reservation] failed to sync conversation marker: #{e.class} - #{e.message}")
   end
+
+  # Atualiza campos visiveis no painel lateral do Chatwoot (custom_attributes)
+  # pra que a recepcionista veja num relance:
+  #   ultima_suite, ultima_permanencia, ultima_reserva_em, total_reservas
+  def update_contact_reservation_metadata # rubocop:disable Metrics/AbcSize
+    return if contact.blank?
+
+    meta = metadata.to_h
+    current = contact.custom_attributes.to_h
+
+    current['ultima_suite'] = meta['category'].presence || suite_identifier.to_s.split('·').first.to_s.strip
+    current['ultima_permanencia'] = meta['stay_type'].presence || suite_identifier.to_s.split('·').last.to_s.strip
+    current['ultima_reserva_em'] = created_at.iso8601
+    current['total_reservas'] = (current['total_reservas'].to_i + 1)
+
+    contact.update_columns(custom_attributes: current) # rubocop:disable Rails/SkipsModelValidations
+  rescue StandardError => e
+    Rails.logger.warn("[Captain::Reservation] failed to update contact metadata: #{e.class} - #{e.message}")
+  end
 end
diff --git a/enterprise/app/services/captain/tools/generate_pix_tool.rb b/enterprise/app/services/captain/tools/generate_pix_tool.rb
index 4808b9415..2912538b8 100644
--- a/enterprise/app/services/captain/tools/generate_pix_tool.rb
+++ b/enterprise/app/services/captain/tools/generate_pix_tool.rb
@@ -2,6 +2,7 @@ class Captain::Tools::GeneratePixTool < Captain::Tools::BaseTool
   CPF_WITH_LABEL_REGEX = /cpf[^\d]*(\d{3}\.?\d{3}\.?\d{3}-?\d{2}|\d{11})/i
   CPF_FALLBACK_REGEX = /\b\d{11}\b/
   NAME_WITH_LABEL_REGEX = /nome\s*[:\-]\s*([^\n\r,;]+)/i
+  EMAIL_REGEX = /\b[A-Za-z0-9._%+\-]+@[A-Za-z0-9.\-]+\.[A-Za-z]{2,}\b/
   SUITE_REGEX = /su[ií]te\s+([^\n\r,.!?]+)/i
   DDMMYYYY_REGEX = %r{\b(\d{1,2}/\d{1,2}/\d{2,4})\b}
   CURRENCY_REGEX = /r\$\s*([\d.,]+)/i
@@ -116,6 +117,8 @@ class Captain::Tools::GeneratePixTool < Captain::Tools::BaseTool
 
     updates[:name] = extracted[:name] if valid_contact_name?(contact.name).blank? && extracted[:name].present?
 
+    updates[:email] = extracted[:email] if contact.email.blank? && extracted[:email].present?
+
     return if updates.blank?
 
     contact.update!(updates)
@@ -132,6 +135,7 @@ class Captain::Tools::GeneratePixTool < Captain::Tools::BaseTool
 
     cpf = nil
     name = nil
+    email = nil
 
     recent_messages.each do |message|
       content = normalize_text(message.content)
@@ -139,15 +143,23 @@ class Captain::Tools::GeneratePixTool < Captain::Tools::BaseTool
 
       cpf ||= extract_cpf_from_text(content)
       name ||= extract_name_from_text(content)
-      break if cpf.present? && name.present?
+      email ||= extract_email_from_text(content)
+      break if cpf.present? && name.present? && email.present?
     end
 
     {
       cpf: cpf,
-      name: name
+      name: name,
+      email: email
     }.compact
   end
 
+  def extract_email_from_text(text)
+    text = normalize_text(text)
+    candidate = text[EMAIL_REGEX]
+    candidate.to_s.strip.downcase.presence
+  end
+
   def extract_cpf_from_text(text)
     text = normalize_text(text)
     candidate = text[CPF_WITH_LABEL_REGEX, 1]
@@ -317,6 +329,18 @@ class Captain::Tools::GeneratePixTool < Captain::Tools::BaseTool
     normalize_payload({ formatted_message: msg, success: true })
   end
 
+  def dispatch_direct_link_message(link, label)
+    return if @conversation.blank? || link.to_s.strip.empty?
+
+    content = "#{label}\n#{link}".strip
+    Messages::MessageBuilder.new(@assistant, @conversation, {
+                                   content: content,
+                                   message_type: 'outgoing'
+                                 }).perform
+  rescue StandardError => e
+    Rails.logger.warn("[GeneratePixTool] failed to dispatch direct link: #{e.class} - #{e.message}")
+  end
+
   def current_pix_charge_for(reservation)
     return nil unless reservation
 
@@ -333,7 +357,13 @@ class Captain::Tools::GeneratePixTool < Captain::Tools::BaseTool
     Rails.logger.info "[GeneratePixTool] Reserva #{reservation.id} → pending_payment"
 
     final_prefix = prefix || 'Cobrança Pix gerada com sucesso.'
-    build_pix_response(charge, reservation, amount: charge_amount, prefix: final_prefix)
+    response = build_pix_response(charge, reservation, amount: charge_amount, prefix: final_prefix)
+
+    # Envia o link como mensagem direta pro cliente. Isso garante que o URL chegue
+    # no WhatsApp mesmo que a LLM parafraseie com placeholder tipo "[Link do Pix]".
+    dispatch_direct_link_message(response[:payment_link], 'Link do Pix:')
+
+    response
   rescue StandardError => e
     safe_error_message = normalize_text(e.message)
     Rails.logger.error("[GeneratePixTool] Falha ao gerar Pix: #{e.class} - #{safe_error_message}")
diff --git a/enterprise/app/services/captain/tools/generate_reservation_link_tool.rb b/enterprise/app/services/captain/tools/generate_reservation_link_tool.rb
index c1a8c0dfb..8df1ecea4 100644
--- a/enterprise/app/services/captain/tools/generate_reservation_link_tool.rb
+++ b/enterprise/app/services/captain/tools/generate_reservation_link_tool.rb
@@ -81,6 +81,10 @@ class Captain::Tools::GenerateReservationLinkTool < Captain::Tools::BaseTool
     query = build_query(enriched_params)
     url = "#{base}/?#{query}"
 
+    # Envia o link como mensagem direta pra garantir que chegue no WhatsApp
+    # mesmo que a LLM parafraseie com placeholder [Link da reserva] etc.
+    dispatch_direct_link_message(conversation, url)
+
     {
       formatted_message: url,
       raw_payload: url,
@@ -117,6 +121,18 @@ class Captain::Tools::GenerateReservationLinkTool < Captain::Tools::BaseTool
     }.compact
   end
 
+  def dispatch_direct_link_message(conversation, url)
+    return if conversation.blank? || url.to_s.strip.empty?
+
+    content = "Link da sua reserva (tudo ja preenchido):\n#{url}"
+    Messages::MessageBuilder.new(@assistant, conversation, {
+                                   content: content,
+                                   message_type: 'outgoing'
+                                 }).perform
+  rescue StandardError => e
+    Rails.logger.warn("[GenerateReservationLinkTool] failed to dispatch link: #{e.class} - #{e.message}")
+  end
+
   def build_query(actual_params)
     mapping = {
       marca: actual_params[:marca],