diff --git a/app/jobs/landing_hosts/promotion_sync_scheduler_job.rb b/app/jobs/landing_hosts/promotion_sync_scheduler_job.rb
new file mode 100644
index 000000000..5b72d1ad9
--- /dev/null
+++ b/app/jobs/landing_hosts/promotion_sync_scheduler_job.rb
@@ -0,0 +1,7 @@
+class LandingHosts::PromotionSyncSchedulerJob < ApplicationJob
+  queue_as :scheduled_jobs
+
+  def perform
+    LandingHost.find_each(&:sync_promotion_to_faq)
+  end
+end
diff --git a/app/models/concerns/landing_host_ai_syncable.rb b/app/models/concerns/landing_host_ai_syncable.rb
index 65330a77b..3f364030a 100644
--- a/app/models/concerns/landing_host_ai_syncable.rb
+++ b/app/models/concerns/landing_host_ai_syncable.rb
@@ -1,7 +1,9 @@
 # frozen_string_literal: true
+require 'digest'
 
 module LandingHostAiSyncable
   extend ActiveSupport::Concern
+  SYNC_METADATA_KEY = 'landing_promotion_sync'.freeze
 
   included do
     after_save :sync_promotion_to_faq
@@ -9,72 +11,173 @@ module LandingHostAiSyncable
 
   def sync_promotion_to_faq
     return unless custom_config.is_a?(Hash)
+    return cleanup_all_synced_knowledge unless can_sync_to_portal?
 
-    promotions = custom_config['promotions']
+    active_entries = extract_promotions.each_with_index.filter_map do |promotion, index|
+      next unless promotion_active?(promotion)
 
-    # Fallback to legacy format if array is empty but object exists
-    promotions = [custom_config['promotion']] if promotions.blank? && custom_config['promotion'].is_a?(Hash)
-
-    active_promos = Array(promotions).select { |p| p.is_a?(Hash) && p['active'] }
-
-    if active_promos.any?
-      create_or_update_faq_article(active_promos)
-    else
-      archive_faq_article
+      {
+        promotion: promotion,
+        signature: promotion_signature(promotion, index)
+      }
     end
+
+    sync_active_promotions(active_entries)
+    cleanup_stale_synced_knowledge(active_entries.map { |entry| entry[:signature] })
+    cleanup_legacy_aggregated_sync
   end
 
   private
 
-  def create_or_update_faq_article(promos)
-    return unless can_sync_to_portal?
-
-    article = find_or_initialize_faq_article
-    article.title = faq_article_title
-    article.content = generate_promotions_text(promos)
-    article.description = "FAQ Gerado automaticamente pela Landing Page: #{hostname}"
-    # Setting the author as the portal's account first user (just as a fallback) or we can use a system user
-    article.author ||= default_article_author
-    article.status = :published
-
-    article.save!
+  def extract_promotions
+    promotions = custom_config['promotions']
+    promotions = [custom_config['promotion']] if promotions.blank? && custom_config['promotion'].is_a?(Hash)
+    Array(promotions).select { |promotion| promotion.is_a?(Hash) }
   end
 
-  def generate_promotions_text(promos)
-    text = %(INSTRUÇÃO PARA A IA (PROMOÇÕES ATIVAS DO LINK #{hostname}):\n\n)
-    text += %(Existem promoções ativas para os leads que chegam pela landing page '#{hostname}'.\n)
+  def sync_active_promotions(active_entries)
+    active_entries.each do |entry|
+      article = create_or_update_promotion_article(entry)
+      sync_captain_document(article, entry)
+    end
+  end
+
+  def create_or_update_promotion_article(entry)
+    article = find_synced_article(entry[:signature]) || portal.articles.new(account_id: inbox.account_id)
+    article.title = promotion_article_title(entry[:promotion], entry[:signature])
+    article.content = generate_promotion_text(entry[:promotion])
+    article.description = "FAQ Gerado automaticamente pela Landing Page: #{hostname}"
+    article.meta = (article.meta || {}).merge(sync_metadata_for(signature: entry[:signature]))
+    article.author ||= default_article_author
+    article.status = :published
+    article.save!
+    article
+  end
+
+  def generate_promotion_text(promo)
+    text = %(INSTRUÇÃO PARA A IA (PROMOÇÃO ATIVA DO LINK #{hostname}):\n\n)
+    text += %(Existe uma promoção ativa para os leads que chegam pela landing page '#{hostname}'.\n)
     text += %(Ofereça a promoção correspondente ao Canal/Origem pelo qual o cliente chegou.\n\n)
 
-    promos.each do |promo|
-      channel = promo['channel'].presence || 'Geral'
-      text += "--- CANAL / ORIGEM: #{channel} ---\n"
-      text += "Título da Promoção: #{promo['title']}\n" if promo['title'].present?
-      text += "Condições / Descrição: #{promo['description']}\n" if promo['description'].present?
-      text += "Cupom: #{promo['coupon_code']}\n" if promo['coupon_code'].present?
-      text += "Válida até: #{promo['valid_until']}\n" if promo['valid_until'].present?
-      text += "\n"
-    end
-
+    channel = promo['channel'].presence || 'Geral'
+    text += "--- CANAL / ORIGEM: #{channel} ---\n"
+    text += "Título da Promoção: #{promo['title']}\n" if promo['title'].present?
+    text += "Condições / Descrição: #{promo['description']}\n" if promo['description'].present?
+    text += "Cupom: #{promo['coupon_code']}\n" if promo['coupon_code'].present?
+    text += "Válida até: #{promo['valid_until']}\n" if promo['valid_until'].present?
     text
   end
 
-  def archive_faq_article
-    return unless can_sync_to_portal?
+  def cleanup_stale_synced_knowledge(active_signatures)
+    synced_articles.find_each do |article|
+      signature = article.meta&.dig(SYNC_METADATA_KEY, 'promotion_signature')
+      next if signature.present? && active_signatures.include?(signature)
 
-    article = find_faq_article
-    article&.update!(status: :archived)
+      delete_synced_captain_document(article)
+      article.destroy!
+    end
+
+    return unless captain_assistant.present? && defined?(Captain::Document)
+
+    synced_documents.find_each do |document|
+      signature = document.metadata&.dig(SYNC_METADATA_KEY, 'promotion_signature')
+      next if signature.present? && active_signatures.include?(signature)
+
+      document.destroy!
+    end
   end
 
-  def find_or_initialize_faq_article
-    find_faq_article || portal.articles.new(account_id: inbox.account_id)
+  def cleanup_legacy_aggregated_sync
+    legacy_article = portal.articles.find_by(
+      "meta -> '#{SYNC_METADATA_KEY}' ->> 'landing_host_id' = ? AND (meta -> '#{SYNC_METADATA_KEY}' ->> 'promotion_signature') IS NULL",
+      id.to_s
+    )
+
+    return if legacy_article.blank?
+
+    delete_synced_captain_document(legacy_article)
+    legacy_article.destroy!
   end
 
-  def find_faq_article
-    portal.articles.find_by(title: faq_article_title)
+  def cleanup_all_synced_knowledge
+    cleanup_stale_synced_knowledge([])
+    cleanup_legacy_aggregated_sync
   end
 
-  def faq_article_title
-    "Promoção Automática - #{hostname.upcase}"
+  def find_synced_article(signature)
+    portal.articles.find_by(
+      "meta -> '#{SYNC_METADATA_KEY}' ->> 'landing_host_id' = ? AND meta -> '#{SYNC_METADATA_KEY}' ->> 'promotion_signature' = ?",
+      id.to_s,
+      signature
+    )
+  end
+
+  def synced_articles
+    portal.articles.where("meta -> '#{SYNC_METADATA_KEY}' ->> 'landing_host_id' = ?", id.to_s)
+  end
+
+  def sync_captain_document(article, entry)
+    return unless captain_assistant.present? && defined?(Captain::Document)
+
+    publication_url = article_public_url(article)
+    document = find_synced_document(entry[:signature], article)
+    document ||= captain_assistant.documents.new(external_link: article_public_url(article))
+
+    document.external_link = publication_url
+    document.name = article.title
+    document.content = article.content
+    document.status = :available
+    document.metadata = (document.metadata || {})
+                      .merge(sync_metadata_for(signature: entry[:signature]))
+                      .merge('article_id' => article.id)
+    document.save!
+  end
+
+  def find_synced_document(signature, article)
+    by_article = captain_assistant.documents.find_by("metadata ->> 'article_id' = ?", article.id.to_s)
+    return by_article if by_article.present?
+
+    captain_assistant.documents.find_by(external_link: article_public_url(article))
+  end
+
+  def delete_synced_captain_document(article)
+    return unless captain_assistant.present? && defined?(Captain::Document)
+
+    signature = article.meta&.dig(SYNC_METADATA_KEY, 'promotion_signature')
+
+    document = captain_assistant.documents.find_by("metadata ->> 'article_id' = ?", article.id.to_s)
+    document ||= captain_assistant.documents.find_by(
+      "metadata -> '#{SYNC_METADATA_KEY}' ->> 'landing_host_id' = ? AND metadata -> '#{SYNC_METADATA_KEY}' ->> 'promotion_signature' = ?",
+      id.to_s,
+      signature
+    ) if signature.present?
+    document ||= captain_assistant.documents.find_by(external_link: article_public_url(article))
+    document&.destroy!
+  end
+
+  def synced_documents
+    return Captain::Document.none unless captain_assistant.present? && defined?(Captain::Document)
+
+    captain_assistant.documents.where("metadata -> '#{SYNC_METADATA_KEY}' ->> 'landing_host_id' = ?", id.to_s)
+  end
+
+  def promotion_article_title(promo, signature)
+    promo_title = promo['title'].to_s.strip
+    promo_title = "Promoção #{signature[0, 8].upcase}" if promo_title.blank?
+    "Promoção Automática - #{hostname.upcase} | #{promo_title}".truncate(220)
+  end
+
+  def promotion_signature(promotion, index)
+    payload = {
+      channel: promotion['channel'].to_s.strip,
+      title: promotion['title'].to_s.strip,
+      description: promotion['description'].to_s.strip,
+      coupon_code: promotion['coupon_code'].to_s.strip,
+      valid_until: promotion['valid_until'].to_s.strip,
+      position: index
+    }
+
+    Digest::SHA256.hexdigest(payload.to_json)
   end
 
   def portal
@@ -85,6 +188,68 @@ module LandingHostAiSyncable
     inbox.present? && inbox.portal_id.present?
   end
 
+  def promotion_active?(promotion)
+    return false unless promotion.is_a?(Hash)
+    return false unless promotion['active']
+    return false if promotion_expired?(promotion['valid_until'])
+
+    true
+  end
+
+  def promotion_expired?(raw_date)
+    parsed_date = parse_valid_until(raw_date)
+    parsed_date.present? && parsed_date < Time.zone.today
+  end
+
+  def parse_valid_until(raw_date)
+    return if raw_date.blank?
+
+    value = raw_date.to_s.strip
+
+    Date.strptime(value, '%d/%m/%Y')
+  rescue ArgumentError
+    Date.iso8601(value)
+  rescue ArgumentError
+    Date.parse(value)
+  rescue ArgumentError
+    nil
+  end
+
+  def captain_assistant
+    return unless inbox.respond_to?(:captain_assistant)
+
+    inbox.captain_assistant
+  end
+
+  def sync_metadata_for(signature:)
+    {
+      SYNC_METADATA_KEY => {
+        'source' => 'landing_host_promotions',
+        'landing_host_id' => id,
+        'inbox_id' => inbox_id,
+        'hostname' => hostname,
+        'promotion_signature' => signature
+      }
+    }
+  end
+
+  def article_public_url(article)
+    base_url = portal.custom_domain.present? ? custom_domain_url_base : frontend_url_base
+    "#{base_url}/hc/#{portal.slug}/articles/#{article.slug}"
+  end
+
+  def custom_domain_url_base
+    frontend_uri = URI.parse(ENV.fetch('FRONTEND_URL', 'https://app.chatwoot.com'))
+    "#{frontend_uri.scheme}://#{portal.custom_domain}"
+  rescue URI::InvalidURIError
+    "https://#{portal.custom_domain}"
+  end
+
+  def frontend_url_base
+    base = ENV.fetch('HELPCENTER_URL', '').presence || ENV.fetch('FRONTEND_URL', '')
+    base.delete_suffix('/')
+  end
+
   def default_article_author
     # Assumes that the account has at least one user (owner/admin) to author the article
     inbox.account.users.order(id: :asc).first
diff --git a/config/schedule.yml b/config/schedule.yml
index 0818a761e..689a48d82 100644
--- a/config/schedule.yml
+++ b/config/schedule.yml
@@ -94,3 +94,10 @@ captain_notification_scanner_job:
   cron: '*/5 * * * *'
   class: 'Captain::Notifications::NotificationScannerJob'
   queue: scheduled_jobs
+
+# executed every hour
+# keeps landing page promotions and Captain knowledge in sync (including expired promotions cleanup)
+landing_hosts_promotion_sync_scheduler_job:
+  cron: '0 * * * *'
+  class: 'LandingHosts::PromotionSyncSchedulerJob'
+  queue: scheduled_jobs
diff --git a/spec/jobs/landing_hosts/promotion_sync_scheduler_job_spec.rb b/spec/jobs/landing_hosts/promotion_sync_scheduler_job_spec.rb
new file mode 100644
index 000000000..a435ba9f5
--- /dev/null
+++ b/spec/jobs/landing_hosts/promotion_sync_scheduler_job_spec.rb
@@ -0,0 +1,22 @@
+require 'rails_helper'
+
+RSpec.describe LandingHosts::PromotionSyncSchedulerJob do
+  it 'enqueues the job' do
+    expect { described_class.perform_later }.to have_enqueued_job(described_class).on_queue('scheduled_jobs')
+  end
+
+  it 'triggers sync on all landing hosts' do
+    landing_host_one = build_stubbed(:landing_host, hostname: 'promo-1.example.com')
+    landing_host_two = build_stubbed(:landing_host, hostname: 'promo-2.example.com')
+
+    allow(landing_host_one).to receive(:sync_promotion_to_faq)
+    allow(landing_host_two).to receive(:sync_promotion_to_faq)
+
+    allow(LandingHost).to receive(:find_each).and_yield(landing_host_one).and_yield(landing_host_two)
+
+    described_class.perform_now
+
+    expect(landing_host_one).to have_received(:sync_promotion_to_faq)
+    expect(landing_host_two).to have_received(:sync_promotion_to_faq)
+  end
+end
diff --git a/spec/models/landing_host_spec.rb b/spec/models/landing_host_spec.rb
index c45ef2a6a..4f8be9798 100644
--- a/spec/models/landing_host_spec.rb
+++ b/spec/models/landing_host_spec.rb
@@ -4,6 +4,14 @@ RSpec.describe LandingHost, type: :model do
   let(:account) { create(:account) }
   let(:portal) { create(:portal, account: account) }
   let(:inbox) { create(:inbox, account: account, portal: portal) }
+  let(:assistant) { create(:captain_assistant, account: account) }
+
+  before do
+    create(:captain_inbox, captain_assistant: assistant, inbox: inbox)
+    allow(ENV).to receive(:fetch).and_call_original
+    allow(ENV).to receive(:fetch).with('FRONTEND_URL', '').and_return('https://app.example.com')
+    allow(ENV).to receive(:fetch).with('FRONTEND_URL', 'https://app.chatwoot.com').and_return('https://app.example.com')
+  end
 
   describe 'LandingHostAiSyncable' do
     let(:landing_host) do
@@ -18,38 +26,65 @@ RSpec.describe LandingHost, type: :model do
                   title: 'Black Friday 50% Off',
                   description: 'Valid for all suites.',
                   coupon_code: 'BLACK50',
-                  valid_until: '2024-11-30'
+                  valid_until: '2099-11-30'
+                },
+                {
+                  active: true,
+                  channel: 'Facebook',
+                  title: 'Pernoite 79,90',
+                  description: 'Somente esta semana.',
+                  coupon_code: 'FACE79',
+                  valid_until: '2099-12-31'
                 }
               ]
             })
     end
 
-    it 'creates a new FAQ article when promotion is active' do
+    it 'creates one article and one document per active promotion' do
       expect do
         landing_host.save!
-      end.to change(Article, :count).by(1)
+      end.to change(Article, :count).by(2)
+        .and change(Captain::Document, :count).by(2)
 
-      title = "Promoção Automática - #{landing_host.hostname.upcase}"
-      article = portal.articles.find_by(title: title)
-      expect(article).to be_present
-      expect(article.title).to include("Promoção Automática - #{landing_host.hostname.upcase}")
-      expect(article.content).to include('Black Friday 50% Off')
-      expect(article.content).to include('BLACK50')
-      expect(article.content).to include('Instagram')
-      expect(article.status).to eq('published')
+      synced_articles = portal.articles.where("meta -> 'landing_promotion_sync' ->> 'landing_host_id' = ?", landing_host.id.to_s)
+      expect(synced_articles.count).to eq(2)
+      expect(synced_articles.pluck(:title).join(' | ')).to include('Black Friday 50% Off')
+      expect(synced_articles.pluck(:title).join(' | ')).to include('Pernoite 79,90')
+
+      synced_documents = assistant.documents.where("metadata -> 'landing_promotion_sync' ->> 'landing_host_id' = ?", landing_host.id.to_s)
+      expect(synced_documents.count).to eq(2)
+      expect(synced_documents.map(&:content).join(' ')).to include('Black Friday 50% Off')
+      expect(synced_documents.map(&:content).join(' ')).to include('Pernoite 79,90')
+      expect(synced_documents).to all(be_available)
     end
 
-    it 'archives an existing FAQ article when promotion is deactivated' do
-      landing_host.save! # Automatically creates the article
-      title = "Promoção Automática - #{landing_host.hostname.upcase}"
-      article = portal.articles.find_by(title: title)
-      expect(article.status).to eq('published')
-
-      # Deactivate promotion
-      landing_host.custom_config['promotions'].first['active'] = false
+    it 'removes article, document and FAQs for a promotion removed from config' do
       landing_host.save!
 
-      expect(article.reload.status).to eq('archived')
+      synced_documents = assistant.documents.where("metadata -> 'landing_promotion_sync' ->> 'landing_host_id' = ?", landing_host.id.to_s)
+      synced_documents.each do |document|
+        create(:captain_assistant_response, assistant: assistant, account: account, documentable: document)
+      end
+
+      # keep only one promotion active
+      landing_host.custom_config['promotions'] = [landing_host.custom_config['promotions'].first]
+
+      expect do
+        landing_host.save!
+      end.to change(Article, :count).by(-1)
+        .and change(Captain::Document, :count).by(-1)
+        .and change(Captain::AssistantResponse, :count).by(-1)
+    end
+
+    it 'treats expired promotions as inactive and cleans synced knowledge' do
+      landing_host.save!
+      landing_host.custom_config['promotions'].first['valid_until'] = 1.day.ago.strftime('%d/%m/%Y')
+      landing_host.custom_config['promotions'].second['valid_until'] = 1.day.ago.strftime('%d/%m/%Y')
+
+      expect do
+        landing_host.save!
+      end.to change(Article, :count).by(-2)
+        .and change(Captain::Document, :count).by(-2)
     end
   end
 end