diff --git a/enterprise/app/jobs/captain/documents/perform_sync_job.rb b/enterprise/app/jobs/captain/documents/perform_sync_job.rb
new file mode 100644
index 000000000..baa9c03d2
--- /dev/null
+++ b/enterprise/app/jobs/captain/documents/perform_sync_job.rb
@@ -0,0 +1,97 @@
+class Captain::Documents::PerformSyncJob < MutexApplicationJob
+  queue_as :low
+
+  LOCK_TIMEOUT = 10.minutes
+
+  # Safety net for anything we didn't rescue by name — parser bugs, ActiveRecord blips,
+  # random infra issues. Three attempts lets a real hiccup recover. The exhaustion block
+  # absorbs the final exception so Sidekiq doesn't layer its own retry policy on top, and
+  # is the single place we report to Sentry — handle_unexpected_failure logs but does not
+  # capture, so a deterministic bug emits one Sentry event instead of one per attempt.
+  # Goes first because retry_on handlers dispatch bottom-to-top.
+  retry_on StandardError, wait: 5.seconds, attempts: 3 do |job, error|
+    document = job.arguments.first
+    ChatwootExceptionTracker.new(error, account: document.account).capture_exception
+    job.send(:log_sync_outcome, document, result: :unexpected_retry_exhausted,
+                                          error_code: 'sync_error',
+                                          exception_class: error.class.name)
+  end
+
+  # Permanent errors (404, 403, empty content) — no point retrying, discard immediately.
+  # Document is already marked failed by SyncService before the exception reaches here.
+  discard_on(Captain::Documents::SyncService::PermanentSyncError)
+
+  # TransientSyncError is raised by SyncService when the customer's site is unreachable —
+  # timeouts, TLS errors, 5xx, connection drops. Four attempts with backoff gives the site
+  # a chance to recover before we give up.
+  #
+  # The exhaustion block absorbs the exception so it doesn't propagate to Sentry —
+  # site flakiness isn't an application bug.
+  retry_on(
+    Captain::Documents::SyncService::TransientSyncError,
+    wait: ->(executions) { [30.seconds, 2.minutes, 5.minutes][executions - 1] || 5.minutes },
+    attempts: 4
+  ) do |job, error|
+    document = job.arguments.first
+    job.send(:log_sync_outcome, document, result: :transient_retry_exhausted, error_code: error.message)
+  end
+
+  discard_on ActiveJob::DeserializationError
+  discard_on ActiveRecord::RecordNotFound
+
+  def perform(document)
+    start_time = Time.current
+    return if document.pdf_document?
+
+    with_lock(lock_key(document), LOCK_TIMEOUT) do
+      document.update!(sync_status: :syncing, last_sync_attempted_at: Time.current)
+      result = Captain::Documents::SyncService.new(document.reload).perform
+      log_sync_outcome(document, result: result, duration_ms: duration_ms_since(start_time))
+    end
+  rescue LockAcquisitionError
+    log_sync_outcome(document, result: :already_syncing)
+  rescue Captain::Documents::SyncService::PermanentSyncError => e
+    log_failure_and_raise(document, :permanent_failure, e, start_time)
+  rescue Captain::Documents::SyncService::TransientSyncError => e
+    log_failure_and_raise(document, :transient_failure, e, start_time)
+  rescue StandardError => e
+    handle_unexpected_failure(document, e, start_time)
+  end
+
+  private
+
+  def log_sync_outcome(document, **fields)
+    payload = {
+      document_id: document.id,
+      account_id: document.account_id,
+      assistant_id: document.assistant_id
+    }.merge(fields)
+    Rails.logger.info("[Captain::Documents::PerformSyncJob] #{payload.to_json}")
+  end
+
+  def log_failure_and_raise(document, result, error, start_time)
+    log_sync_outcome(document, result: result, error_code: error.message,
+                               duration_ms: duration_ms_since(start_time))
+    raise error
+  end
+
+  def handle_unexpected_failure(document, error, start_time)
+    document.update!(
+      sync_status: :failed,
+      last_sync_error_code: 'sync_error',
+      last_sync_attempted_at: Time.current
+    )
+    log_sync_outcome(document, result: :unexpected_failure, error_code: 'sync_error',
+                               exception_class: error.class.name,
+                               duration_ms: duration_ms_since(start_time))
+    raise error
+  end
+
+  def lock_key(document)
+    format(::Redis::Alfred::CAPTAIN_DOCUMENT_SYNC_MUTEX, document_id: document.id)
+  end
+
+  def duration_ms_since(start_time)
+    ((Time.current - start_time) * 1000).round
+  end
+end
diff --git a/enterprise/app/jobs/captain/documents/response_builder_job.rb b/enterprise/app/jobs/captain/documents/response_builder_job.rb
index 553cec110..60f1fa2cf 100644
--- a/enterprise/app/jobs/captain/documents/response_builder_job.rb
+++ b/enterprise/app/jobs/captain/documents/response_builder_job.rb
@@ -62,7 +62,7 @@ class Captain::Documents::ResponseBuilderJob < ApplicationJob
   end
 
   def reset_previous_responses(response_document)
-    response_document.responses.destroy_all
+    response_document.responses.where(edited: false).destroy_all
   end
 
   def create_response(faq, document)
diff --git a/enterprise/app/models/captain/document.rb b/enterprise/app/models/captain/document.rb
index d8e07a2d9..2abf18437 100644
--- a/enterprise/app/models/captain/document.rb
+++ b/enterprise/app/models/captain/document.rb
@@ -62,6 +62,7 @@ class Captain::Document < ApplicationRecord
 
   def pdf_document?
     return true if pdf_file.attached? && pdf_file.blob.content_type == 'application/pdf'
+    return true if external_link&.start_with?('PDF:')
 
     external_link&.ends_with?('.pdf')
   end
@@ -90,6 +91,14 @@ class Captain::Document < ApplicationRecord
     self.metadata = (metadata || {}).merge('last_sync_error_code' => value)
   end
 
+  def sync_step
+    metadata&.dig('sync_step')
+  end
+
+  def store_sync_step(step)
+    update!(metadata: (metadata || {}).merge('sync_step' => step))
+  end
+
   def openai_file_id
     metadata&.dig('openai_file_id')
   end
diff --git a/enterprise/app/services/captain/documents/single_page_fetcher.rb b/enterprise/app/services/captain/documents/single_page_fetcher.rb
new file mode 100644
index 000000000..115cd55b0
--- /dev/null
+++ b/enterprise/app/services/captain/documents/single_page_fetcher.rb
@@ -0,0 +1,80 @@
+class Captain::Documents::SinglePageFetcher
+  Result = Struct.new(:success, :title, :content, :error_code, keyword_init: true)
+
+  CONTENT_MAX_LENGTH = 200_000
+  TITLE_MAX_LENGTH = 255 # captain_documents.name is a varchar(255)
+
+  def initialize(url)
+    @url = url
+  end
+
+  def fetch
+    result = firecrawl_configured? ? fetch_with_firecrawl : fetch_with_fallback
+    validate_content(result)
+  rescue Net::ReadTimeout, Net::OpenTimeout, Errno::ETIMEDOUT
+    Result.new(success: false, error_code: 'timeout')
+  rescue SocketError, Errno::ECONNREFUSED, Errno::ECONNRESET, OpenSSL::SSL::SSLError
+    Result.new(success: false, error_code: 'fetch_failed')
+  end
+
+  private
+
+  def firecrawl_configured?
+    InstallationConfig.find_by(name: 'CAPTAIN_FIRECRAWL_API_KEY')&.value.present?
+  end
+
+  def fetch_with_firecrawl
+    response = Captain::Tools::FirecrawlService.new.scrape(@url)
+    handle_firecrawl_response(response)
+  end
+
+  def handle_firecrawl_response(response)
+    return Result.new(success: false, error_code: http_error_code(response.code)) unless response.success?
+
+    data = response.parsed_response&.dig('data')
+    target_error = firecrawl_target_error_code(data)
+    return Result.new(success: false, error_code: target_error) if target_error
+
+    Result.new(
+      success: true,
+      title: data&.dig('metadata', 'title')&.truncate(TITLE_MAX_LENGTH, omission: ''),
+      content: data&.dig('markdown')&.truncate(CONTENT_MAX_LENGTH, omission: '')
+    )
+  end
+
+  # Firecrawl returns API 200 even when the scraped page itself failed —
+  # the target page's real status lives in data.metadata.statusCode.
+  def firecrawl_target_error_code(data)
+    status = data&.dig('metadata', 'statusCode')
+    return nil if status.blank? || (200..299).cover?(status)
+
+    http_error_code(status)
+  end
+
+  def fetch_with_fallback
+    response = HTTParty.get(@url)
+    return Result.new(success: false, error_code: http_error_code(response.code)) unless response.success?
+
+    parser = Captain::Tools::HtmlPageParser.new(response.body)
+    Result.new(
+      success: true,
+      title: parser.title&.truncate(TITLE_MAX_LENGTH, omission: ''),
+      content: parser.body_markdown&.truncate(CONTENT_MAX_LENGTH, omission: '')
+    )
+  end
+
+  def validate_content(result)
+    return result unless result.success && result.content.blank?
+
+    Result.new(success: false, error_code: 'content_empty')
+  end
+
+  def http_error_code(status_code)
+    case status_code
+    when 404 then 'not_found'
+    when 401, 403 then 'access_denied'
+    when 408, 504 then 'timeout'
+    else 'fetch_failed'
+    end
+  end
+end
diff --git a/enterprise/app/services/captain/documents/sync_service.rb b/enterprise/app/services/captain/documents/sync_service.rb
new file mode 100644
index 000000000..5dcb52447
--- /dev/null
+++ b/enterprise/app/services/captain/documents/sync_service.rb
@@ -0,0 +1,76 @@
+class Captain::Documents::SyncService
+  class PermanentSyncError < StandardError
+  end
+
+  class TransientSyncError < StandardError
+  end
+
+  PERMANENT_ERROR_CODES = %w[not_found access_denied content_empty].freeze
+
+  def initialize(document)
+    @document = document
+  end
+
+  def perform
+    @document.store_sync_step('fetching')
+    result = Captain::Documents::SinglePageFetcher.new(@document.external_link).fetch
+
+    unless result.success
+      mark_failed(result.error_code)
+      raise_for_error_code(result.error_code)
+    end
+
+    @document.store_sync_step('comparing')
+    fingerprint = compute_fingerprint(result.content)
+
+    if fingerprint == @document.content_fingerprint
+      mark_synced
+      return :unchanged
+    end
+
+    @document.store_sync_step('updating')
+    update_content(result, fingerprint)
+    :updated
+  end
+
+  private
+
+  def compute_fingerprint(content)
+    Digest::SHA256.hexdigest(content.gsub(/\s+/, ' ').strip)
+  end
+
+  def mark_failed(error_code)
+    @document.update!(
+      sync_status: :failed,
+      last_sync_error_code: error_code,
+      last_sync_attempted_at: Time.current
+    )
+  end
+
+  def mark_synced
+    @document.update!(
+      sync_status: :synced,
+      last_synced_at: Time.current,
+      last_sync_attempted_at: Time.current,
+      last_sync_error_code: nil
+    )
+  end
+
+  def update_content(result, fingerprint)
+    @document.update!(
+      content: result.content,
+      name: result.title.presence || @document.name,
+      content_fingerprint: fingerprint,
+      sync_status: :synced,
+      last_synced_at: Time.current,
+      last_sync_attempted_at: Time.current,
+      last_sync_error_code: nil
+    )
+  end
+
+  def raise_for_error_code(error_code)
+    raise PermanentSyncError, error_code if PERMANENT_ERROR_CODES.include?(error_code)
+
+    raise TransientSyncError, error_code
+  end
+end
diff --git a/enterprise/app/services/captain/tools/firecrawl_service.rb b/enterprise/app/services/captain/tools/firecrawl_service.rb
index 397c3ad63..fc7448593 100644
--- a/enterprise/app/services/captain/tools/firecrawl_service.rb
+++ b/enterprise/app/services/captain/tools/firecrawl_service.rb
@@ -1,4 +1,6 @@
 class Captain::Tools::FirecrawlService
+  BASE_URL = 'https://api.firecrawl.dev/v1'.freeze
+
   def initialize
     @api_key = InstallationConfig.find_by!(name: 'CAPTAIN_FIRECRAWL_API_KEY').value
     raise 'Missing API key' if @api_key.empty?
@@ -6,7 +8,7 @@ class Captain::Tools::FirecrawlService
 
   def perform(url, webhook_url, crawl_limit = 10)
     HTTParty.post(
-      'https://api.firecrawl.dev/v1/crawl',
+      "#{BASE_URL}/crawl",
       body: crawl_payload(url, webhook_url, crawl_limit),
       headers: headers
     )
@@ -14,6 +16,14 @@ class Captain::Tools::FirecrawlService
     raise "Failed to crawl URL: #{e.message}"
   end
 
+  def scrape(url)
+    HTTParty.post(
+      "#{BASE_URL}/scrape",
+      body: scrape_payload(url),
+      headers: headers
+    )
+  end
+
   private
 
   def crawl_payload(url, webhook_url, crawl_limit)
@@ -31,6 +41,10 @@ class Captain::Tools::FirecrawlService
     }.to_json
   end
 
+  def scrape_payload(url)
+    { url: url, formats: ['markdown'], excludeTags: ['iframe'] }.to_json
+  end
+
   def headers
     {
       'Authorization' => "Bearer #{@api_key}",
diff --git a/enterprise/app/services/captain/tools/html_page_parser.rb b/enterprise/app/services/captain/tools/html_page_parser.rb
new file mode 100644
index 000000000..a7afb52cf
--- /dev/null
+++ b/enterprise/app/services/captain/tools/html_page_parser.rb
@@ -0,0 +1,15 @@
+class Captain::Tools::HtmlPageParser
+  attr_reader :doc
+
+  def initialize(html)
+    @doc = Nokogiri::HTML(html)
+  end
+
+  def title
+    @doc.at_xpath('//title')&.text&.strip
+  end
+
+  def body_markdown
+    ReverseMarkdown.convert(@doc.at_xpath('//body'), unknown_tags: :bypass, github_flavored: true)
+  end
+end
diff --git a/enterprise/app/services/captain/tools/simple_page_crawl_service.rb b/enterprise/app/services/captain/tools/simple_page_crawl_service.rb
index 65731ad90..5eaee6e5e 100644
--- a/enterprise/app/services/captain/tools/simple_page_crawl_service.rb
+++ b/enterprise/app/services/captain/tools/simple_page_crawl_service.rb
@@ -3,7 +3,8 @@ class Captain::Tools::SimplePageCrawlService
 
   def initialize(external_link)
     @external_link = external_link
-    @doc = Nokogiri::HTML(HTTParty.get(external_link).body)
+    @parser = Captain::Tools::HtmlPageParser.new(HTTParty.get(external_link).body)
+    @doc = @parser.doc
   end
 
   def page_links
@@ -11,12 +12,11 @@ class Captain::Tools::SimplePageCrawlService
   end
 
   def page_title
-    title_element = @doc.at_xpath('//title')
-    title_element&.text&.strip
+    @parser.title
   end
 
   def body_text_content
-    ReverseMarkdown.convert @doc.at_xpath('//body'), unknown_tags: :bypass, github_flavored: true
+    @parser.body_markdown
   end
 
   def meta_description
diff --git a/lib/redis/redis_keys.rb b/lib/redis/redis_keys.rb
index 59e33036d..893fb50ef 100644
--- a/lib/redis/redis_keys.rb
+++ b/lib/redis/redis_keys.rb
@@ -44,6 +44,7 @@ module Redis::RedisKeys
   SLACK_MESSAGE_MUTEX = 'SLACK_MESSAGE_LOCK::%<conversation_id>s::%<reference_id>s'.freeze
   EMAIL_MESSAGE_MUTEX = 'EMAIL_CHANNEL_LOCK::%<inbox_id>s'.freeze
   CRM_PROCESS_MUTEX = 'CRM_PROCESS_MUTEX::%<hook_id>s'.freeze
+  CAPTAIN_DOCUMENT_SYNC_MUTEX = 'CAPTAIN_DOCUMENT_SYNC_LOCK::%<document_id>s'.freeze
 
   ## Auto Assignment Keys
   # Track conversation assignments to agents for rate limiting
diff --git a/spec/enterprise/models/captain/document_spec.rb b/spec/enterprise/models/captain/document_spec.rb
index e6543e0d7..af6c1cb58 100644
--- a/spec/enterprise/models/captain/document_spec.rb
+++ b/spec/enterprise/models/captain/document_spec.rb
@@ -55,6 +55,11 @@ RSpec.describe Captain::Document, type: :model do
         expect(doc.pdf_document?).to be true
       end
 
+      it 'returns true for PDF:-prefixed external links even when the blob is missing' do
+        doc = build(:captain_document, external_link: 'PDF: report_20250101120000')
+        expect(doc.pdf_document?).to be true
+      end
+
       it 'returns false for non-PDF documents' do
         doc = build(:captain_document, external_link: 'https://example.com')
         expect(doc.pdf_document?).to be false