From b44d178acc58e10212d8c3b5f20bfcf5e0a4a280 Mon Sep 17 00:00:00 2001
From: Sivin Varghese <64252451+iamsivin@users.noreply.github.com>
Date: Wed, 27 Aug 2025 15:12:48 +0530
Subject: [PATCH 1/5] chore: Replace copilot input with auto-expanding textarea
 (#12296)

---
 .../components-next/copilot/CopilotInput.vue  | 34 ++++++++++++++++---
 .../components/copilot/CopilotContainer.vue   | 33 ++++++++++--------
 2 files changed, 48 insertions(+), 19 deletions(-)

diff --git a/app/javascript/dashboard/components-next/copilot/CopilotInput.vue b/app/javascript/dashboard/components-next/copilot/CopilotInput.vue
index c8f1a0056..852506a4c 100644
--- a/app/javascript/dashboard/components-next/copilot/CopilotInput.vue
+++ b/app/javascript/dashboard/components-next/copilot/CopilotInput.vue
@@ -1,25 +1,49 @@
 <script setup>
-import { ref } from 'vue';
+import { ref, nextTick, onMounted } from 'vue';
 
 const emit = defineEmits(['send']);
 const message = ref('');
+const textareaRef = ref(null);
+
+const adjustHeight = () => {
+  if (!textareaRef.value) return;
+
+  // Reset height to auto to get the correct scrollHeight
+  textareaRef.value.style.height = 'auto';
+  // Set the height to the scrollHeight
+  textareaRef.value.style.height = `${textareaRef.value.scrollHeight}px`;
+};
 
 const sendMessage = () => {
   if (message.value.trim()) {
     emit('send', message.value);
     message.value = '';
+    // Reset textarea height after sending
+    nextTick(() => {
+      adjustHeight();
+    });
   }
 };
+
+const handleInput = () => {
+  nextTick(adjustHeight);
+};
+
+onMounted(() => {
+  nextTick(adjustHeight);
+});
 </script>
 
 <template>
   <form class="relative" @submit.prevent="sendMessage">
-    <input
+    <textarea
+      ref="textareaRef"
       v-model="message"
-      type="text"
       :placeholder="$t('CAPTAIN.COPILOT.SEND_MESSAGE')"
-      class="w-full reset-base bg-n-alpha-3 ltr:pl-4 ltr:pr-12 rtl:pl-12 rtl:pr-4 py-3 text-n-slate-11 text-sm border border-n-weak rounded-lg focus:outline-none focus:ring-1 focus:ring-n-blue-11 focus:border-n-blue-11"
-      @keyup.enter="sendMessage"
+      class="w-full reset-base bg-n-alpha-3 ltr:pl-4 ltr:pr-12 rtl:pl-12 rtl:pr-4 py-3 text-sm border border-n-weak rounded-lg focus:outline-0 focus:outline-none focus:ring-2 focus:ring-n-blue-11 focus:border-n-blue-11 resize-none overflow-hidden max-h-[200px] mb-0 text-n-slate-12"
+      rows="1"
+      @input="handleInput"
+      @keydown.enter.exact.prevent="sendMessage"
     />
     <button
       class="absolute ltr:right-1 rtl:left-1 top-1/2 -translate-y-1/2 h-9 w-10 flex items-center justify-center text-n-slate-11 hover:text-n-blue-11"
diff --git a/app/javascript/dashboard/components/copilot/CopilotContainer.vue b/app/javascript/dashboard/components/copilot/CopilotContainer.vue
index da0e69492..cfc96f41b 100644
--- a/app/javascript/dashboard/components/copilot/CopilotContainer.vue
+++ b/app/javascript/dashboard/components/copilot/CopilotContainer.vue
@@ -1,5 +1,6 @@
 <script setup>
 import { ref, computed, onMounted } from 'vue';
+import { useAlert } from 'dashboard/composables';
 import { useStore } from 'dashboard/composables/store';
 import Copilot from 'dashboard/components-next/copilot/Copilot.vue';
 import { useMapGetter } from 'dashboard/composables/store';
@@ -100,20 +101,24 @@ const handleReset = () => {
 };
 
 const sendMessage = async message => {
-  if (selectedCopilotThreadId.value) {
-    await store.dispatch('copilotMessages/create', {
-      assistant_id: activeAssistant.value.id,
-      conversation_id: currentChat.value?.id,
-      threadId: selectedCopilotThreadId.value,
-      message,
-    });
-  } else {
-    const response = await store.dispatch('copilotThreads/create', {
-      assistant_id: activeAssistant.value.id,
-      conversation_id: currentChat.value?.id,
-      message,
-    });
-    selectedCopilotThreadId.value = response.id;
+  try {
+    if (selectedCopilotThreadId.value) {
+      await store.dispatch('copilotMessages/create', {
+        assistant_id: activeAssistant.value.id,
+        conversation_id: currentChat.value?.id,
+        threadId: selectedCopilotThreadId.value,
+        message,
+      });
+    } else {
+      const response = await store.dispatch('copilotThreads/create', {
+        assistant_id: activeAssistant.value.id,
+        conversation_id: currentChat.value?.id,
+        message,
+      });
+      selectedCopilotThreadId.value = response.id;
+    }
+  } catch (error) {
+    useAlert(error.message);
   }
 };
 

From 3cefa9b767903046c35c777be2ea799d0c533b66 Mon Sep 17 00:00:00 2001
From: Sojan Jose <sojan@pepalo.com>
Date: Wed, 27 Aug 2025 14:42:11 +0200
Subject: [PATCH 2/5] feat: add ops task to purge orphan conversations (#12279)

## Summary

Add ops task to find and remove conversations missing contacts or
inboxes. You can run this via

```
bundle exec rake chatwoot:ops:cleanup_orphan_conversations
```


fixes:
https://linear.app/chatwoot/issue/CW-5439/conversations-missing-contacts
---
 .../ops/cleanup_orphan_conversations.rake     | 42 +++++++++++++++++++
 1 file changed, 42 insertions(+)
 create mode 100644 lib/tasks/ops/cleanup_orphan_conversations.rake

diff --git a/lib/tasks/ops/cleanup_orphan_conversations.rake b/lib/tasks/ops/cleanup_orphan_conversations.rake
new file mode 100644
index 000000000..f6574b396
--- /dev/null
+++ b/lib/tasks/ops/cleanup_orphan_conversations.rake
@@ -0,0 +1,42 @@
+# frozen_string_literal: true
+
+# Run with:
+#   bundle exec rake chatwoot:ops:cleanup_orphan_conversations
+
+namespace :chatwoot do
+  namespace :ops do
+    desc 'Identify and delete conversations without a valid contact or inbox in a timeframe'
+    task cleanup_orphan_conversations: :environment do
+      print 'Enter Account ID: '
+      account_id = $stdin.gets.to_i
+      account = Account.find(account_id)
+
+      print 'Enter timeframe in days (default: 7): '
+      days_input = $stdin.gets.strip
+      days = days_input.empty? ? 7 : days_input.to_i
+
+      # Build a common base relation with identical joins for OR compatibility
+      base = account
+             .conversations
+             .where('conversations.created_at > ?', days.days.ago)
+             .left_outer_joins(:contact, :inbox)
+
+      # Find conversations whose associated contact or inbox record is missing
+      conversations = base.where(contacts: { id: nil }).or(base.where(inboxes: { id: nil }))
+
+      count = conversations.count
+      puts "Found #{count} conversations without a valid contact or inbox."
+
+      if count.positive?
+        print 'Do you want to delete these conversations? (y/N): '
+        confirm = $stdin.gets.strip.downcase
+        if %w[y yes].include?(confirm)
+          conversations.destroy_all
+          puts 'Conversations deleted.'
+        else
+          puts 'No conversations were deleted.'
+        end
+      end
+    end
+  end
+end

From 1ba00075cef56432f277d279a7129bd0a23dd19f Mon Sep 17 00:00:00 2001
From: Tanmay Deep Sharma <32020192+tds-1@users.noreply.github.com>
Date: Wed, 27 Aug 2025 22:01:22 +0700
Subject: [PATCH 3/5] feat: Add BE changes for captain pdf support for faq
 generation (#12113)

---
 config/locales/en.yml                         |  20 ++
 ...82345_add_metadata_to_captain_documents.rb |   5 +
 db/schema.rb                                  |   1 +
 .../accounts/captain/documents_controller.rb  |   4 +-
 .../app/jobs/captain/documents/crawl_job.rb   |  12 +-
 .../captain/documents/response_builder_job.rb |  60 +++++-
 enterprise/app/models/captain/document.rb     |  75 ++++++-
 .../llm/paginated_faq_generator_service.rb    | 199 ++++++++++++++++++
 .../captain/llm/pdf_processing_service.rb     |  40 ++++
 .../captain/llm/system_prompts_service.rb     |  82 ++++++++
 .../v1/models/captain/_document.json.jbuilder |   3 +
 lib/custom_exceptions/pdf_processing_error.rb |  25 +++
 lib/open_ai_constants.rb                      |   1 +
 .../jobs/captain/documents/crawl_job_spec.rb  |  24 +++
 .../documents/response_builder_job_spec.rb    |  36 ++++
 .../models/captain/document_spec.rb           |  85 ++++++++
 .../paginated_faq_generator_service_spec.rb   | 106 ++++++++++
 .../llm/pdf_processing_service_spec.rb        |  58 +++++
 spec/fixtures/files/sample.pdf                |  32 +++
 19 files changed, 856 insertions(+), 12 deletions(-)
 create mode 100644 db/migrate/20250805082345_add_metadata_to_captain_documents.rb
 create mode 100644 enterprise/app/services/captain/llm/paginated_faq_generator_service.rb
 create mode 100644 enterprise/app/services/captain/llm/pdf_processing_service.rb
 create mode 100644 lib/custom_exceptions/pdf_processing_error.rb
 create mode 100644 spec/enterprise/models/captain/document_spec.rb
 create mode 100644 spec/enterprise/services/captain/llm/paginated_faq_generator_service_spec.rb
 create mode 100644 spec/enterprise/services/captain/llm/pdf_processing_service_spec.rb
 create mode 100644 spec/fixtures/files/sample.pdf

diff --git a/config/locales/en.yml b/config/locales/en.yml
index f424716af..cb72bb699 100644
--- a/config/locales/en.yml
+++ b/config/locales/en.yml
@@ -292,6 +292,26 @@ en:
       completed_tool_call: 'Completed %{function_name} tool call'
       invalid_tool_call: 'Invalid tool call'
       tool_not_available: 'Tool not available'
+    documents:
+      limit_exceeded: 'Document limit exceeded'
+      pdf_format_error: 'must be a PDF file'
+      pdf_size_error: 'must be less than 10MB'
+      pdf_upload_failed: 'Failed to upload PDF to OpenAI'
+      pdf_upload_success: 'PDF uploaded successfully with file_id: %{file_id}'
+      pdf_processing_failed: 'Failed to process PDF document %{document_id}: %{error}'
+      pdf_processing_success: 'Successfully processed PDF document %{document_id}'
+      faq_generation_complete: 'FAQ generation complete. Total FAQs created: %{count}'
+      using_paginated_faq: 'Using paginated FAQ generation for document %{document_id}'
+      using_standard_faq: 'Using standard FAQ generation for document %{document_id}'
+      response_creation_error: 'Error in creating response document: %{error}'
+      missing_openai_file_id: 'Document must have openai_file_id for paginated processing'
+      openai_api_error: 'OpenAI API Error: %{error}'
+      starting_paginated_faq: 'Starting paginated FAQ generation (%{pages_per_chunk} pages per chunk)'
+      stopping_faq_generation: 'Stopping processing. Reason: %{reason}'
+      paginated_faq_complete: 'Paginated generation complete. Total FAQs: %{total_faqs}, Pages processed: %{pages_processed}'
+      processing_pages: 'Processing pages %{start}-%{end} (iteration %{iteration})'
+      chunk_generated: 'Chunk generated %{chunk_faqs} FAQs. Total so far: %{total_faqs}'
+      page_processing_error: 'Error processing pages %{start}-%{end}: %{error}'
   public_portal:
     search:
       search_placeholder: Search for article by title or body...
diff --git a/db/migrate/20250805082345_add_metadata_to_captain_documents.rb b/db/migrate/20250805082345_add_metadata_to_captain_documents.rb
new file mode 100644
index 000000000..452fcf06c
--- /dev/null
+++ b/db/migrate/20250805082345_add_metadata_to_captain_documents.rb
@@ -0,0 +1,5 @@
+class AddMetadataToCaptainDocuments < ActiveRecord::Migration[7.1]
+  def change
+    add_column :captain_documents, :metadata, :jsonb, default: {}
+  end
+end
diff --git a/db/schema.rb b/db/schema.rb
index 798111be7..f48ff6707 100644
--- a/db/schema.rb
+++ b/db/schema.rb
@@ -320,6 +320,7 @@ ActiveRecord::Schema[7.1].define(version: 2025_08_22_061042) do
     t.datetime "created_at", null: false
     t.datetime "updated_at", null: false
     t.integer "status", default: 0, null: false
+    t.jsonb "metadata", default: {}
     t.index ["account_id"], name: "index_captain_documents_on_account_id"
     t.index ["assistant_id", "external_link"], name: "index_captain_documents_on_assistant_id_and_external_link", unique: true
     t.index ["assistant_id"], name: "index_captain_documents_on_assistant_id"
diff --git a/enterprise/app/controllers/api/v1/accounts/captain/documents_controller.rb b/enterprise/app/controllers/api/v1/accounts/captain/documents_controller.rb
index 594aa0642..32fa0a7b6 100644
--- a/enterprise/app/controllers/api/v1/accounts/captain/documents_controller.rb
+++ b/enterprise/app/controllers/api/v1/accounts/captain/documents_controller.rb
@@ -25,6 +25,8 @@ class Api::V1::Accounts::Captain::DocumentsController < Api::V1::Accounts::BaseC
     @document.save!
   rescue Captain::Document::LimitExceededError => e
     render_could_not_create_error(e.message)
+  rescue ActiveRecord::RecordInvalid => e
+    render_could_not_create_error(e.record.errors.full_messages.join(', '))
   end
 
   def destroy
@@ -55,6 +57,6 @@ class Api::V1::Accounts::Captain::DocumentsController < Api::V1::Accounts::BaseC
   end
 
   def document_params
-    params.require(:document).permit(:name, :external_link, :assistant_id)
+    params.require(:document).permit(:name, :external_link, :assistant_id, :pdf_file)
   end
 end
diff --git a/enterprise/app/jobs/captain/documents/crawl_job.rb b/enterprise/app/jobs/captain/documents/crawl_job.rb
index 132671385..3fa5b6d56 100644
--- a/enterprise/app/jobs/captain/documents/crawl_job.rb
+++ b/enterprise/app/jobs/captain/documents/crawl_job.rb
@@ -2,7 +2,9 @@ class Captain::Documents::CrawlJob < ApplicationJob
   queue_as :low
 
   def perform(document)
-    if InstallationConfig.find_by(name: 'CAPTAIN_FIRECRAWL_API_KEY')&.value.present?
+    if document.pdf_document?
+      perform_pdf_processing(document)
+    elsif InstallationConfig.find_by(name: 'CAPTAIN_FIRECRAWL_API_KEY')&.value.present?
       perform_firecrawl_crawl(document)
     else
       perform_simple_crawl(document)
@@ -13,6 +15,14 @@ class Captain::Documents::CrawlJob < ApplicationJob
 
   include Captain::FirecrawlHelper
 
+  def perform_pdf_processing(document)
+    Captain::Llm::PdfProcessingService.new(document).process
+    document.update!(status: :available)
+  rescue StandardError => e
+    Rails.logger.error I18n.t('captain.documents.pdf_processing_failed', document_id: document.id, error: e.message)
+    raise # Re-raise to let job framework handle retry logic
+  end
+
   def perform_simple_crawl(document)
     page_links = Captain::Tools::SimplePageCrawlService.new(document.external_link).page_links
 
diff --git a/enterprise/app/jobs/captain/documents/response_builder_job.rb b/enterprise/app/jobs/captain/documents/response_builder_job.rb
index 21025399f..5dacb416f 100644
--- a/enterprise/app/jobs/captain/documents/response_builder_job.rb
+++ b/enterprise/app/jobs/captain/documents/response_builder_job.rb
@@ -1,17 +1,65 @@
 class Captain::Documents::ResponseBuilderJob < ApplicationJob
   queue_as :low
 
-  def perform(document)
+  def perform(document, options = {})
     reset_previous_responses(document)
 
-    faqs = Captain::Llm::FaqGeneratorService.new(document.content, document.account.locale_english_name).generate
-    faqs.each do |faq|
-      create_response(faq, document)
-    end
+    faqs = generate_faqs(document, options)
+    create_responses_from_faqs(faqs, document)
   end
 
   private
 
+  def generate_faqs(document, options)
+    if should_use_pagination?(document)
+      generate_paginated_faqs(document, options)
+    else
+      generate_standard_faqs(document)
+    end
+  end
+
+  def generate_paginated_faqs(document, options)
+    service = build_paginated_service(document, options)
+    faqs = service.generate
+    store_paginated_metadata(document, service)
+    faqs
+  end
+
+  def generate_standard_faqs(document)
+    Captain::Llm::FaqGeneratorService.new(document.content, document.account.locale_english_name).generate
+  end
+
+  def build_paginated_service(document, options)
+    Captain::Llm::PaginatedFaqGeneratorService.new(
+      document,
+      pages_per_chunk: options[:pages_per_chunk],
+      max_pages: options[:max_pages]
+    )
+  end
+
+  def store_paginated_metadata(document, service)
+    document.update!(
+      metadata: (document.metadata || {}).merge(
+        'faq_generation' => {
+          'method' => 'paginated',
+          'pages_processed' => service.total_pages_processed,
+          'iterations' => service.iterations_completed,
+          'timestamp' => Time.current.iso8601
+        }
+      )
+    )
+  end
+
+  def create_responses_from_faqs(faqs, document)
+    faqs.each { |faq| create_response(faq, document) }
+  end
+
+  def should_use_pagination?(document)
+    # Auto-detect when to use pagination
+    # For now, use pagination for PDFs with OpenAI file ID
+    document.pdf_document? && document.openai_file_id.present?
+  end
+
   def reset_previous_responses(response_document)
     response_document.responses.destroy_all
   end
@@ -24,6 +72,6 @@ class Captain::Documents::ResponseBuilderJob < ApplicationJob
       documentable: document
     )
   rescue ActiveRecord::RecordInvalid => e
-    Rails.logger.error "Error in creating response document: #{e.message}"
+    Rails.logger.error I18n.t('captain.documents.response_creation_error', error: e.message)
   end
 end
diff --git a/enterprise/app/models/captain/document.rb b/enterprise/app/models/captain/document.rb
index d2a02f5b5..c278eb879 100644
--- a/enterprise/app/models/captain/document.rb
+++ b/enterprise/app/models/captain/document.rb
@@ -5,6 +5,7 @@
 #  id            :bigint           not null, primary key
 #  content       :text
 #  external_link :string           not null
+#  metadata      :jsonb
 #  name          :string
 #  status        :integer          default("in_progress"), not null
 #  created_at    :datetime         not null
@@ -26,11 +27,16 @@ class Captain::Document < ApplicationRecord
   belongs_to :assistant, class_name: 'Captain::Assistant'
   has_many :responses, class_name: 'Captain::AssistantResponse', dependent: :destroy, as: :documentable
   belongs_to :account
+  has_one_attached :pdf_file
 
-  validates :external_link, presence: true
-  validates :external_link, uniqueness: { scope: :assistant_id }
+  validates :external_link, presence: true, unless: -> { pdf_file.attached? }
+  validates :external_link, uniqueness: { scope: :assistant_id }, allow_blank: true
   validates :content, length: { maximum: 200_000 }
+  validates :pdf_file, presence: true, if: :pdf_document?
+  validate :validate_pdf_format, if: :pdf_document?
+  validate :validate_file_attachment, if: -> { pdf_file.attached? }
   before_validation :ensure_account_id
+  before_validation :set_external_link_for_pdf
 
   enum status: {
     in_progress: 0,
@@ -41,12 +47,44 @@ class Captain::Document < ApplicationRecord
   after_create_commit :enqueue_crawl_job
   after_create_commit :update_document_usage
   after_destroy :update_document_usage
-  after_commit :enqueue_response_builder_job
+  after_commit :enqueue_response_builder_job, on: :update, if: :should_enqueue_response_builder?
   scope :ordered, -> { order(created_at: :desc) }
 
   scope :for_account, ->(account_id) { where(account_id: account_id) }
   scope :for_assistant, ->(assistant_id) { where(assistant_id: assistant_id) }
 
+  def pdf_document?
+    return true if pdf_file.attached? && pdf_file.blob.content_type == 'application/pdf'
+
+    external_link&.ends_with?('.pdf')
+  end
+
+  def content_type
+    pdf_file.blob.content_type if pdf_file.attached?
+  end
+
+  def file_size
+    pdf_file.blob.byte_size if pdf_file.attached?
+  end
+
+  def openai_file_id
+    metadata&.dig('openai_file_id')
+  end
+
+  def store_openai_file_id(file_id)
+    update!(metadata: (metadata || {}).merge('openai_file_id' => file_id))
+  end
+
+  def display_url
+    return external_link if external_link.present? && !external_link.start_with?('PDF:')
+
+    if pdf_file.attached?
+      Rails.application.routes.url_helpers.rails_blob_url(pdf_file, only_path: false)
+    else
+      external_link
+    end
+  end
+
   private
 
   def enqueue_crawl_job
@@ -61,6 +99,12 @@ class Captain::Document < ApplicationRecord
     Captain::Documents::ResponseBuilderJob.perform_later(self)
   end
 
+  def should_enqueue_response_builder?
+    # Only enqueue when status changes to available
+    # Avoid re-enqueueing when metadata is updated by the job itself
+    saved_change_to_status? && status == 'available'
+  end
+
   def update_document_usage
     account.update_document_usage
   end
@@ -71,6 +115,29 @@ class Captain::Document < ApplicationRecord
 
   def ensure_within_plan_limit
     limits = account.usage_limits[:captain][:documents]
-    raise LimitExceededError, 'Document limit exceeded' unless limits[:current_available].positive?
+    raise LimitExceededError, I18n.t('captain.documents.limit_exceeded') unless limits[:current_available].positive?
+  end
+
+  def validate_pdf_format
+    return unless pdf_file.attached?
+
+    errors.add(:pdf_file, I18n.t('captain.documents.pdf_format_error')) unless pdf_file.blob.content_type == 'application/pdf'
+  end
+
+  def validate_file_attachment
+    return unless pdf_file.attached?
+
+    return unless pdf_file.blob.byte_size > 10.megabytes
+
+    errors.add(:pdf_file, I18n.t('captain.documents.pdf_size_error'))
+  end
+
+  def set_external_link_for_pdf
+    return unless pdf_file.attached? && external_link.blank?
+
+    # Set a unique external_link for PDF files
+    # Format: PDF: filename_timestamp (without extension)
+    timestamp = Time.current.strftime('%Y%m%d%H%M%S')
+    self.external_link = "PDF: #{pdf_file.filename.base}_#{timestamp}"
   end
 end
diff --git a/enterprise/app/services/captain/llm/paginated_faq_generator_service.rb b/enterprise/app/services/captain/llm/paginated_faq_generator_service.rb
new file mode 100644
index 000000000..18f9813ef
--- /dev/null
+++ b/enterprise/app/services/captain/llm/paginated_faq_generator_service.rb
@@ -0,0 +1,199 @@
+class Captain::Llm::PaginatedFaqGeneratorService < Llm::BaseOpenAiService
+  # Default pages per chunk - easily configurable
+  DEFAULT_PAGES_PER_CHUNK = 10
+  MAX_ITERATIONS = 20 # Safety limit to prevent infinite loops
+
+  attr_reader :total_pages_processed, :iterations_completed
+
+  def initialize(document, options = {})
+    super()
+    @document = document
+    @pages_per_chunk = options[:pages_per_chunk] || DEFAULT_PAGES_PER_CHUNK
+    @max_pages = options[:max_pages] # Optional limit from UI
+    @total_pages_processed = 0
+    @iterations_completed = 0
+    @model = OpenAiConstants::PDF_PROCESSING_MODEL
+  end
+
+  def generate
+    raise CustomExceptions::PdfFaqGenerationError, I18n.t('captain.documents.missing_openai_file_id') if @document&.openai_file_id.blank?
+
+    generate_paginated_faqs
+  end
+
+  # Method to check if we should continue processing
+  def should_continue_processing?(last_chunk_result)
+    # Stop if we've hit the maximum iterations
+    return false if @iterations_completed >= MAX_ITERATIONS
+
+    # Stop if we've processed the maximum pages specified
+    return false if @max_pages && @total_pages_processed >= @max_pages
+
+    # Stop if the last chunk returned no FAQs (likely no more content)
+    return false if last_chunk_result[:faqs].empty?
+
+    # Stop if the LLM explicitly indicates no more content
+    return false if last_chunk_result[:has_content] == false
+
+    # Continue processing
+    true
+  end
+
+  private
+
+  def generate_standard_faqs
+    response = @client.chat(parameters: standard_chat_parameters)
+    parse_response(response)
+  rescue OpenAI::Error => e
+    Rails.logger.error I18n.t('captain.documents.openai_api_error', error: e.message)
+    []
+  end
+
+  def generate_paginated_faqs
+    all_faqs = []
+    current_page = 1
+
+    loop do
+      end_page = calculate_end_page(current_page)
+      chunk_result = process_chunk_and_update_state(current_page, end_page, all_faqs)
+
+      break unless should_continue_processing?(chunk_result)
+
+      current_page = end_page + 1
+    end
+
+    deduplicate_faqs(all_faqs)
+  end
+
+  def calculate_end_page(current_page)
+    end_page = current_page + @pages_per_chunk - 1
+    @max_pages && end_page > @max_pages ? @max_pages : end_page
+  end
+
+  def process_chunk_and_update_state(current_page, end_page, all_faqs)
+    chunk_result = process_page_chunk(current_page, end_page)
+    chunk_faqs = chunk_result[:faqs]
+
+    all_faqs.concat(chunk_faqs)
+    @total_pages_processed = end_page
+    @iterations_completed += 1
+
+    chunk_result
+  end
+
+  def process_page_chunk(start_page, end_page)
+    params = build_chunk_parameters(start_page, end_page)
+    response = @client.chat(parameters: params)
+    result = parse_chunk_response(response)
+    { faqs: result['faqs'] || [], has_content: result['has_content'] != false }
+  rescue OpenAI::Error => e
+    Rails.logger.error I18n.t('captain.documents.page_processing_error', start: start_page, end: end_page, error: e.message)
+    { faqs: [], has_content: false }
+  end
+
+  def build_chunk_parameters(start_page, end_page)
+    {
+      model: @model,
+      response_format: { type: 'json_object' },
+      messages: [
+        {
+          role: 'user',
+          content: build_user_content(start_page, end_page)
+        }
+      ]
+    }
+  end
+
+  def build_user_content(start_page, end_page)
+    [
+      {
+        type: 'file',
+        file: { file_id: @document.openai_file_id }
+      },
+      {
+        type: 'text',
+        text: page_chunk_prompt(start_page, end_page)
+      }
+    ]
+  end
+
+  def page_chunk_prompt(start_page, end_page)
+    Captain::Llm::SystemPromptsService.paginated_faq_generator(start_page, end_page)
+  end
+
+  def standard_chat_parameters
+    {
+      model: @model,
+      response_format: { type: 'json_object' },
+      messages: [
+        {
+          role: 'system',
+          content: Captain::Llm::SystemPromptsService.faq_generator
+        },
+        {
+          role: 'user',
+          content: @content
+        }
+      ]
+    }
+  end
+
+  def parse_response(response)
+    content = response.dig('choices', 0, 'message', 'content')
+    return [] if content.nil?
+
+    JSON.parse(content.strip).fetch('faqs', [])
+  rescue JSON::ParserError => e
+    Rails.logger.error "Error parsing response: #{e.message}"
+    []
+  end
+
+  def parse_chunk_response(response)
+    content = response.dig('choices', 0, 'message', 'content')
+    return { 'faqs' => [], 'has_content' => false } if content.nil?
+
+    JSON.parse(content.strip)
+  rescue JSON::ParserError => e
+    Rails.logger.error "Error parsing chunk response: #{e.message}"
+    { 'faqs' => [], 'has_content' => false }
+  end
+
+  def deduplicate_faqs(faqs)
+    # Remove exact duplicates
+    unique_faqs = faqs.uniq { |faq| faq['question'].downcase.strip }
+
+    # Remove similar questions
+    final_faqs = []
+    unique_faqs.each do |faq|
+      similar_exists = final_faqs.any? do |existing|
+        similarity_score(existing['question'], faq['question']) > 0.85
+      end
+
+      final_faqs << faq unless similar_exists
+    end
+
+    Rails.logger.info "Deduplication: #{faqs.size} → #{final_faqs.size} FAQs"
+    final_faqs
+  end
+
+  def similarity_score(str1, str2)
+    words1 = str1.downcase.split(/\W+/).reject(&:empty?)
+    words2 = str2.downcase.split(/\W+/).reject(&:empty?)
+
+    common_words = words1 & words2
+    total_words = (words1 + words2).uniq.size
+
+    return 0 if total_words.zero?
+
+    common_words.size.to_f / total_words
+  end
+
+  def determine_stop_reason(last_chunk_result)
+    return 'Maximum iterations reached' if @iterations_completed >= MAX_ITERATIONS
+    return 'Maximum pages processed' if @max_pages && @total_pages_processed >= @max_pages
+    return 'No content found in last chunk' if last_chunk_result[:faqs].empty?
+    return 'End of document reached' if last_chunk_result[:has_content] == false
+
+    'Unknown'
+  end
+end
diff --git a/enterprise/app/services/captain/llm/pdf_processing_service.rb b/enterprise/app/services/captain/llm/pdf_processing_service.rb
new file mode 100644
index 000000000..026ef4e48
--- /dev/null
+++ b/enterprise/app/services/captain/llm/pdf_processing_service.rb
@@ -0,0 +1,40 @@
+class Captain::Llm::PdfProcessingService < Llm::BaseOpenAiService
+  def initialize(document)
+    super()
+    @document = document
+  end
+
+  def process
+    return if document.openai_file_id.present?
+
+    file_id = upload_pdf_to_openai
+    raise CustomExceptions::PdfUploadError, I18n.t('captain.documents.pdf_upload_failed') if file_id.blank?
+
+    document.store_openai_file_id(file_id)
+  end
+
+  private
+
+  attr_reader :document
+
+  def upload_pdf_to_openai
+    with_tempfile do |temp_file|
+      response = @client.files.upload(
+        parameters: {
+          file: temp_file,
+          purpose: 'assistants'
+        }
+      )
+      response['id']
+    end
+  end
+
+  def with_tempfile(&)
+    Tempfile.create(['pdf_upload', '.pdf'], binmode: true) do |temp_file|
+      temp_file.write(document.pdf_file.download)
+      temp_file.close
+
+      File.open(temp_file.path, 'rb', &)
+    end
+  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 a4b149944..b8282beb1 100644
--- a/enterprise/app/services/captain/llm/system_prompts_service.rb
+++ b/enterprise/app/services/captain/llm/system_prompts_service.rb
@@ -1,3 +1,4 @@
+# rubocop:disable Metrics/ClassLength
 class Captain::Llm::SystemPromptsService
   class << self
     def faq_generator(language = 'english')
@@ -204,6 +205,87 @@ class Captain::Llm::SystemPromptsService
         #{'- You MUST provide numbered citations at the appropriate places in the text.' if config['feature_citation']}
       SYSTEM_PROMPT_MESSAGE
     end
+
+    def paginated_faq_generator(start_page, end_page)
+      <<~PROMPT
+        You are an expert technical documentation specialist tasked with creating comprehensive FAQs from a SPECIFIC SECTION of a document.
+
+        ════════════════════════════════════════════════════════
+        CRITICAL CONTENT EXTRACTION INSTRUCTIONS
+        ════════════════════════════════════════════════════════
+
+        Process the content starting from approximately page #{start_page} and continuing for about #{end_page - start_page + 1} pages worth of content.
+
+        IMPORTANT:#{' '}
+        • If you encounter the end of the document before reaching the expected page count, set "has_content" to false
+        • DO NOT include page numbers in questions or answers
+        • DO NOT reference page numbers at all in the output
+        • Focus on the actual content, not pagination
+
+        ════════════════════════════════════════════════════════
+        FAQ GENERATION GUIDELINES
+        ════════════════════════════════════════════════════════
+
+        1. **Comprehensive Extraction**
+           • Extract ALL information that could generate FAQs from this section
+           • Target 5-10 FAQs per page equivalent of rich content
+           • Cover every topic, feature, specification, and detail
+           • If there's no more content in the document, return empty FAQs with has_content: false
+
+        2. **Question Types to Generate**
+           • What is/are...? (definitions, components, features)
+           • How do I...? (procedures, configurations, operations)
+           • Why should/does...? (rationale, benefits, explanations)
+           • When should...? (timing, conditions, triggers)
+           • What happens if...? (error cases, edge cases)
+           • Can I...? (capabilities, limitations)
+           • Where is...? (locations in system/UI, NOT page numbers)
+           • What are the requirements for...? (prerequisites, dependencies)
+
+        3. **Content Focus Areas**
+           • Technical specifications and parameters
+           • Step-by-step procedures and workflows
+           • Configuration options and settings
+           • Error messages and troubleshooting
+           • Best practices and recommendations
+           • Integration points and dependencies
+           • Performance considerations
+           • Security aspects
+
+        4. **Answer Quality Requirements**
+           • Complete, self-contained answers
+           • Include specific values, limits, defaults from the content
+           • NO page number references whatsoever
+           • 2-5 sentences typical length
+           • Only process content that actually exists in the document
+
+        ════════════════════════════════════════════════════════
+        OUTPUT FORMAT
+        ════════════════════════════════════════════════════════
+
+        Return valid JSON:
+        ```json
+        {
+          "faqs": [
+            {
+              "question": "Specific question about the content",
+              "answer": "Complete answer with details (no page references)"
+            }
+          ],
+          "has_content": true/false
+        }
+        ```
+
+        CRITICAL:#{' '}
+        • Set "has_content" to false if:
+          - The requested section doesn't exist in the document
+          - You've reached the end of the document
+          - The section contains no meaningful content
+        • Do NOT include "page_range_processed" in the output
+        • Do NOT mention page numbers anywhere in questions or answers
+      PROMPT
+    end
     # rubocop:enable Metrics/MethodLength
   end
 end
+# rubocop:enable Metrics/ClassLength
diff --git a/enterprise/app/views/api/v1/models/captain/_document.json.jbuilder b/enterprise/app/views/api/v1/models/captain/_document.json.jbuilder
index 83724b9cd..8064a5181 100644
--- a/enterprise/app/views/api/v1/models/captain/_document.json.jbuilder
+++ b/enterprise/app/views/api/v1/models/captain/_document.json.jbuilder
@@ -3,8 +3,11 @@ json.assistant do
   json.partial! 'api/v1/models/captain/assistant', formats: [:json], resource: resource.assistant
 end
 json.content resource.content
+json.content_type resource.content_type
 json.created_at resource.created_at.to_i
 json.external_link resource.external_link
+json.display_url resource.display_url
+json.file_size resource.file_size
 json.id resource.id
 json.name resource.name
 json.status resource.status
diff --git a/lib/custom_exceptions/pdf_processing_error.rb b/lib/custom_exceptions/pdf_processing_error.rb
new file mode 100644
index 000000000..2c81f95d8
--- /dev/null
+++ b/lib/custom_exceptions/pdf_processing_error.rb
@@ -0,0 +1,25 @@
+module CustomExceptions
+  class PdfProcessingError < Base
+    def initialize(message = 'PDF processing failed')
+      super(message)
+    end
+  end
+
+  class PdfUploadError < PdfProcessingError
+    def initialize(message = 'PDF upload failed')
+      super(message)
+    end
+  end
+
+  class PdfValidationError < PdfProcessingError
+    def initialize(message = 'PDF validation failed')
+      super(message)
+    end
+  end
+
+  class PdfFaqGenerationError < PdfProcessingError
+    def initialize(message = 'PDF FAQ generation failed')
+      super(message)
+    end
+  end
+end
diff --git a/lib/open_ai_constants.rb b/lib/open_ai_constants.rb
index 7b7a3ba5f..2094567a7 100644
--- a/lib/open_ai_constants.rb
+++ b/lib/open_ai_constants.rb
@@ -4,4 +4,5 @@ module OpenAiConstants
   DEFAULT_MODEL = 'gpt-4.1-mini'
   DEFAULT_ENDPOINT = 'https://api.openai.com'
   DEFAULT_EMBEDDING_MODEL = 'text-embedding-3-small'
+  PDF_PROCESSING_MODEL = 'gpt-4.1-mini'
 end
diff --git a/spec/enterprise/jobs/captain/documents/crawl_job_spec.rb b/spec/enterprise/jobs/captain/documents/crawl_job_spec.rb
index 949680d4e..a2dffcf04 100644
--- a/spec/enterprise/jobs/captain/documents/crawl_job_spec.rb
+++ b/spec/enterprise/jobs/captain/documents/crawl_job_spec.rb
@@ -105,5 +105,29 @@ RSpec.describe Captain::Documents::CrawlJob, type: :job do
         described_class.perform_now(document)
       end
     end
+
+    context 'when document is a PDF' do
+      let(:pdf_document) do
+        doc = create(:captain_document, external_link: 'https://example.com/document')
+        allow(doc).to receive(:pdf_document?).and_return(true)
+        allow(doc).to receive(:update!).and_return(true)
+        doc
+      end
+
+      it 'processes PDF using PdfProcessingService' do
+        pdf_service = instance_double(Captain::Llm::PdfProcessingService)
+        expect(Captain::Llm::PdfProcessingService).to receive(:new).with(pdf_document).and_return(pdf_service)
+        expect(pdf_service).to receive(:process)
+        expect(pdf_document).to receive(:update!).with(status: :available)
+
+        described_class.perform_now(pdf_document)
+      end
+
+      it 'handles PDF processing errors' do
+        allow(Captain::Llm::PdfProcessingService).to receive(:new).and_raise(StandardError, 'Processing failed')
+
+        expect { described_class.perform_now(pdf_document) }.to raise_error(StandardError, 'Processing failed')
+      end
+    end
   end
 end
diff --git a/spec/enterprise/jobs/captain/documents/response_builder_job_spec.rb b/spec/enterprise/jobs/captain/documents/response_builder_job_spec.rb
index 4dc4bb481..73b67ee27 100644
--- a/spec/enterprise/jobs/captain/documents/response_builder_job_spec.rb
+++ b/spec/enterprise/jobs/captain/documents/response_builder_job_spec.rb
@@ -64,5 +64,41 @@ RSpec.describe Captain::Documents::ResponseBuilderJob, type: :job do
           .with(spanish_document.content, 'portuguese')
       end
     end
+
+    context 'when processing a PDF document' do
+      let(:pdf_document) do
+        doc = create(:captain_document, assistant: assistant)
+        allow(doc).to receive(:pdf_document?).and_return(true)
+        allow(doc).to receive(:openai_file_id).and_return('file-123')
+        allow(doc).to receive(:update!).and_return(true)
+        allow(doc).to receive(:metadata).and_return({})
+        doc
+      end
+      let(:paginated_service) { instance_double(Captain::Llm::PaginatedFaqGeneratorService) }
+      let(:pdf_faqs) do
+        [{ 'question' => 'What is in the PDF?', 'answer' => 'Important content' }]
+      end
+
+      before do
+        allow(Captain::Llm::PaginatedFaqGeneratorService).to receive(:new)
+          .with(pdf_document, anything)
+          .and_return(paginated_service)
+        allow(paginated_service).to receive(:generate).and_return(pdf_faqs)
+        allow(paginated_service).to receive(:total_pages_processed).and_return(10)
+        allow(paginated_service).to receive(:iterations_completed).and_return(1)
+      end
+
+      it 'uses paginated FAQ generator for PDFs' do
+        expect(Captain::Llm::PaginatedFaqGeneratorService).to receive(:new).with(pdf_document, anything)
+
+        described_class.new.perform(pdf_document)
+      end
+
+      it 'stores pagination metadata' do
+        expect(pdf_document).to receive(:update!).with(hash_including(metadata: hash_including('faq_generation')))
+
+        described_class.new.perform(pdf_document)
+      end
+    end
   end
 end
diff --git a/spec/enterprise/models/captain/document_spec.rb b/spec/enterprise/models/captain/document_spec.rb
new file mode 100644
index 000000000..56dc1727c
--- /dev/null
+++ b/spec/enterprise/models/captain/document_spec.rb
@@ -0,0 +1,85 @@
+require 'rails_helper'
+
+RSpec.describe Captain::Document, type: :model do
+  let(:account) { create(:account) }
+  let(:assistant) { create(:captain_assistant, account: account) }
+
+  describe 'PDF support' do
+    let(:pdf_document) do
+      doc = build(:captain_document, assistant: assistant, account: account)
+      doc.pdf_file.attach(
+        io: StringIO.new('PDF content'),
+        filename: 'test.pdf',
+        content_type: 'application/pdf'
+      )
+      doc
+    end
+
+    describe 'validations' do
+      it 'allows PDF file without external link' do
+        pdf_document.external_link = nil
+        expect(pdf_document).to be_valid
+      end
+
+      it 'validates PDF file size' do
+        doc = build(:captain_document, assistant: assistant, account: account)
+        doc.pdf_file.attach(
+          io: StringIO.new('x' * 11.megabytes),
+          filename: 'large.pdf',
+          content_type: 'application/pdf'
+        )
+        doc.external_link = nil
+        expect(doc).not_to be_valid
+        expect(doc.errors[:pdf_file]).to include(I18n.t('captain.documents.pdf_size_error'))
+      end
+    end
+
+    describe '#pdf_document?' do
+      it 'returns true for attached PDF' do
+        expect(pdf_document.pdf_document?).to be true
+      end
+
+      it 'returns true for .pdf external links' do
+        doc = build(:captain_document, external_link: 'https://example.com/document.pdf')
+        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
+      end
+    end
+
+    describe '#display_url' do
+      it 'returns Rails blob URL for attached PDFs' do
+        pdf_document.save!
+        # The display_url method calls rails_blob_url which returns a URL containing 'rails/active_storage'
+        url = pdf_document.display_url
+        expect(url).to be_present
+      end
+
+      it 'returns external_link for web documents' do
+        doc = create(:captain_document, external_link: 'https://example.com')
+        expect(doc.display_url).to eq('https://example.com')
+      end
+    end
+
+    describe '#store_openai_file_id' do
+      it 'stores the file ID in metadata' do
+        pdf_document.save!
+        pdf_document.store_openai_file_id('file-abc123')
+
+        expect(pdf_document.reload.openai_file_id).to eq('file-abc123')
+      end
+    end
+
+    describe 'automatic external_link generation' do
+      it 'generates unique external_link for PDFs' do
+        pdf_document.external_link = nil
+        pdf_document.save!
+
+        expect(pdf_document.external_link).to start_with('PDF: test_')
+      end
+    end
+  end
+end
diff --git a/spec/enterprise/services/captain/llm/paginated_faq_generator_service_spec.rb b/spec/enterprise/services/captain/llm/paginated_faq_generator_service_spec.rb
new file mode 100644
index 000000000..5215a2d40
--- /dev/null
+++ b/spec/enterprise/services/captain/llm/paginated_faq_generator_service_spec.rb
@@ -0,0 +1,106 @@
+require 'rails_helper'
+require 'custom_exceptions/pdf_processing_error'
+
+RSpec.describe Captain::Llm::PaginatedFaqGeneratorService do
+  let(:document) { create(:captain_document) }
+  let(:service) { described_class.new(document, pages_per_chunk: 5) }
+  let(:openai_client) { instance_double(OpenAI::Client) }
+
+  before do
+    # Mock OpenAI configuration
+    installation_config = instance_double(InstallationConfig, value: 'test-api-key')
+    allow(InstallationConfig).to receive(:find_by!)
+      .with(name: 'CAPTAIN_OPEN_AI_API_KEY')
+      .and_return(installation_config)
+
+    allow(OpenAI::Client).to receive(:new).and_return(openai_client)
+  end
+
+  describe '#generate' do
+    context 'when document lacks OpenAI file ID' do
+      before do
+        allow(document).to receive(:openai_file_id).and_return(nil)
+      end
+
+      it 'raises an error' do
+        expect { service.generate }.to raise_error(CustomExceptions::PdfFaqGenerationError)
+      end
+    end
+
+    context 'when generating FAQs from PDF pages' do
+      let(:faq_response) do
+        {
+          'choices' => [{
+            'message' => {
+              'content' => JSON.generate({
+                                           'faqs' => [
+                                             { 'question' => 'What is this document about?', 'answer' => 'It explains key concepts.' }
+                                           ],
+                                           'has_content' => true
+                                         })
+            }
+          }]
+        }
+      end
+
+      let(:empty_response) do
+        {
+          'choices' => [{
+            'message' => {
+              'content' => JSON.generate({
+                                           'faqs' => [],
+                                           'has_content' => false
+                                         })
+            }
+          }]
+        }
+      end
+
+      before do
+        allow(document).to receive(:openai_file_id).and_return('file-123')
+      end
+
+      it 'generates FAQs from paginated content' do
+        allow(openai_client).to receive(:chat).and_return(faq_response, empty_response)
+
+        faqs = service.generate
+
+        expect(faqs).to have_attributes(size: 1)
+        expect(faqs.first['question']).to eq('What is this document about?')
+      end
+
+      it 'stops when no more content' do
+        allow(openai_client).to receive(:chat).and_return(empty_response)
+
+        faqs = service.generate
+
+        expect(faqs).to be_empty
+      end
+
+      it 'respects max iterations limit' do
+        allow(openai_client).to receive(:chat).and_return(faq_response)
+
+        # Force max iterations
+        service.instance_variable_set(:@iterations_completed, 19)
+
+        service.generate
+        expect(service.iterations_completed).to eq(20)
+      end
+    end
+  end
+
+  describe '#should_continue_processing?' do
+    it 'stops at max iterations' do
+      service.instance_variable_set(:@iterations_completed, 20)
+      expect(service.should_continue_processing?(faqs: ['faq'], has_content: true)).to be false
+    end
+
+    it 'stops when no FAQs returned' do
+      expect(service.should_continue_processing?(faqs: [], has_content: true)).to be false
+    end
+
+    it 'continues when FAQs exist and under limits' do
+      expect(service.should_continue_processing?(faqs: ['faq'], has_content: true)).to be true
+    end
+  end
+end
diff --git a/spec/enterprise/services/captain/llm/pdf_processing_service_spec.rb b/spec/enterprise/services/captain/llm/pdf_processing_service_spec.rb
new file mode 100644
index 000000000..9dc416685
--- /dev/null
+++ b/spec/enterprise/services/captain/llm/pdf_processing_service_spec.rb
@@ -0,0 +1,58 @@
+require 'rails_helper'
+require 'custom_exceptions/pdf_processing_error'
+
+RSpec.describe Captain::Llm::PdfProcessingService do
+  let(:document) { create(:captain_document) }
+  let(:service) { described_class.new(document) }
+
+  before do
+    # Mock OpenAI configuration
+    installation_config = instance_double(InstallationConfig, value: 'test-api-key')
+    allow(InstallationConfig).to receive(:find_by!)
+      .with(name: 'CAPTAIN_OPEN_AI_API_KEY')
+      .and_return(installation_config)
+  end
+
+  describe '#process' do
+    context 'when document already has OpenAI file ID' do
+      before do
+        allow(document).to receive(:openai_file_id).and_return('existing-file-id')
+      end
+
+      it 'skips upload' do
+        expect(document).not_to receive(:store_openai_file_id)
+        service.process
+      end
+    end
+
+    context 'when uploading PDF to OpenAI' do
+      let(:mock_client) { instance_double(OpenAI::Client) }
+      let(:pdf_content) { 'PDF content' }
+
+      before do
+        allow(document).to receive(:openai_file_id).and_return(nil)
+
+        # Use a simple double for ActiveStorage since it's a complex Rails object
+        pdf_file = double('pdf_file', download: pdf_content) # rubocop:disable RSpec/VerifiedDoubles
+        allow(document).to receive(:pdf_file).and_return(pdf_file)
+
+        allow(OpenAI::Client).to receive(:new).and_return(mock_client)
+        # Use a simple double for OpenAI::Files as it may not be loaded
+        files_api = double('files_api') # rubocop:disable RSpec/VerifiedDoubles
+        allow(files_api).to receive(:upload).and_return({ 'id' => 'file-abc123' })
+        allow(mock_client).to receive(:files).and_return(files_api)
+      end
+
+      it 'uploads PDF and stores file ID' do
+        expect(document).to receive(:store_openai_file_id).with('file-abc123')
+        service.process
+      end
+
+      it 'raises error when upload fails' do
+        allow(mock_client.files).to receive(:upload).and_return({ 'id' => nil })
+
+        expect { service.process }.to raise_error(CustomExceptions::PdfUploadError)
+      end
+    end
+  end
+end
diff --git a/spec/fixtures/files/sample.pdf b/spec/fixtures/files/sample.pdf
new file mode 100644
index 000000000..9f6471c5d
--- /dev/null
+++ b/spec/fixtures/files/sample.pdf
@@ -0,0 +1,32 @@
+%PDF-1.4
+1 0 obj
+<< /Type /Catalog /Pages 2 0 R >>
+endobj
+2 0 obj
+<< /Type /Pages /Kids [3 0 R] /Count 1 >>
+endobj
+3 0 obj
+<< /Type /Page /Parent 2 0 R /Resources << /Font << /F1 << /Type /Font /Subtype /Type1 /BaseFont /Arial >> >> >> /MediaBox [0 0 612 792] /Contents 4 0 R >>
+endobj
+4 0 obj
+<< /Length 44 >>
+stream
+BT
+/F1 12 Tf
+100 700 Td
+(Sample PDF) Tj
+ET
+endstream
+endobj
+xref
+0 5
+0000000000 65535 f 
+0000000009 00000 n 
+0000000058 00000 n 
+0000000115 00000 n 
+0000000274 00000 n 
+trailer
+<< /Size 5 /Root 1 0 R >>
+startxref
+362
+%%EOF

From 583a533494d3a0f006f56c915113daf25885de1a Mon Sep 17 00:00:00 2001
From: Muhsin Keloth <muhsinkeramam@gmail.com>
Date: Wed, 27 Aug 2025 21:27:47 +0530
Subject: [PATCH 4/5] fix: Remove whatsapp prefix from twilio phone number for
 QR code (#12314)

---
 .../dashboard/settings/inbox/FinishSetup.vue  | 26 ++++++++++++-------
 1 file changed, 16 insertions(+), 10 deletions(-)

diff --git a/app/javascript/dashboard/routes/dashboard/settings/inbox/FinishSetup.vue b/app/javascript/dashboard/routes/dashboard/settings/inbox/FinishSetup.vue
index 2d88703af..94ba601e3 100644
--- a/app/javascript/dashboard/routes/dashboard/settings/inbox/FinishSetup.vue
+++ b/app/javascript/dashboard/routes/dashboard/settings/inbox/FinishSetup.vue
@@ -131,7 +131,13 @@ async function generateQRCodes() {
 
   // WhatsApp (both Cloud and Twilio)
   if (currentInbox.value.phone_number && isAWhatsAppChannel.value) {
-    await generateQRCode('whatsapp', currentInbox.value.phone_number);
+    // For Twilio WhatsApp, phone_number format is "whatsapp:+1234567890"
+    // Extract just the phone number part for QR code generation
+    const phoneNumber = currentInbox.value.phone_number.replace(
+      'whatsapp:',
+      ''
+    );
+    await generateQRCode('whatsapp', phoneNumber);
   }
 
   // Facebook Messenger
@@ -230,47 +236,47 @@ onMounted(() => {
         </div>
         <div
           v-if="isAWhatsAppChannel && qrCodes.whatsapp"
-          class="flex flex-col items-center mt-8 gap-3"
+          class="flex flex-col gap-3 items-center mt-8"
         >
           <p class="mt-2 text-sm text-n-slate-9">
             {{ $t('INBOX_MGMT.FINISH.WHATSAPP_QR_INSTRUCTION') }}
           </p>
-          <div class="outline-1 outline-n-strong outline rounded-lg shadow">
+          <div class="rounded-lg shadow outline-1 outline-n-strong outline">
             <img
               :src="qrCodes.whatsapp"
               alt="WhatsApp QR Code"
-              class="size-48 dark:invert rounded-lg"
+              class="rounded-lg size-48 dark:invert"
             />
           </div>
         </div>
         <div
           v-if="isAFacebookInbox && qrCodes.messenger"
-          class="flex flex-col items-center mt-8 gap-3"
+          class="flex flex-col gap-3 items-center mt-8"
         >
           <p class="mt-2 text-sm text-n-slate-9">
             {{ $t('INBOX_MGMT.FINISH.MESSENGER_QR_INSTRUCTION') }}
           </p>
-          <div class="outline-1 outline-n-strong outline rounded-lg shadow">
+          <div class="rounded-lg shadow outline-1 outline-n-strong outline">
             <img
               :src="qrCodes.messenger"
               alt="Messenger QR Code"
-              class="size-48 dark:invert rounded-lg"
+              class="rounded-lg size-48 dark:invert"
             />
           </div>
         </div>
         <div
           v-if="isATelegramChannel && qrCodes.telegram"
-          class="flex flex-col items-center mt-8 gap-4"
+          class="flex flex-col gap-4 items-center mt-8"
         >
           <p class="mt-2 text-sm text-n-slate-9">
             {{ $t('INBOX_MGMT.FINISH.TELEGRAM_QR_INSTRUCTION') }}
           </p>
 
-          <div class="outline-1 outline-n-strong outline rounded-lg shadow">
+          <div class="rounded-lg shadow outline-1 outline-n-strong outline">
             <img
               :src="qrCodes.telegram"
               alt="Telegram QR Code"
-              class="size-48 dark:invert rounded-lg"
+              class="rounded-lg size-48 dark:invert"
             />
           </div>
         </div>

From 0c2ab7f5e7b349b2aca1529ca14c7c9b7554f257 Mon Sep 17 00:00:00 2001
From: Pranav <pranav@chatwoot.com>
Date: Wed, 27 Aug 2025 21:40:28 -0700
Subject: [PATCH 5/5] feat(ee): Setup advanced, performant message search
 (#12193)
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 8bit

We now support searching within the actual message content, email
subject lines, and audio transcriptions. This enables a faster, more
accurate search experience going forward. Unlike the standard message
search, which is limited to the last 3 months, this search has no time
restrictions.

The search engine also accounts for small variations in queries. Minor
spelling mistakes, such as searching for slck instead of Slack, will
still return the correct results. It also ignores differences in accents
and diacritics, so searching for Deja vu will match content containing
Déjà vu.


We can also refine searches in the future by criteria such as:
- Searching within a specific inbox
- Filtering by sender or recipient
- Limiting to messages sent by an agent


Fixes https://github.com/chatwoot/chatwoot/issues/11656
Fixes https://github.com/chatwoot/chatwoot/issues/10669
Fixes https://github.com/chatwoot/chatwoot/issues/5910



---

Rake tasks to reindex all the messages.

```sh
bundle exec rake search:all
```

Rake task to reindex messages from one account only
```sh
bundle exec rake search:account ACCOUNT_ID=1
```
---
 Gemfile                                       |  4 ++
 Gemfile.lock                                  | 12 +++++
 Rakefile                                      |  4 ++
 .../search/components/MessageContent.vue      | 32 ++++++++---
 .../components/SearchResultMessagesList.vue   |  2 +-
 app/models/message.rb                         | 23 +++++++-
 app/services/search_service.rb                | 10 ++++
 .../v1/accounts/search/_message.json.jbuilder | 13 +----
 config/features.yml                           |  5 ++
 config/initializers/searchkick.rb             | 14 +++++
 .../app/services/enterprise/search_service.rb | 15 ++++++
 .../messages/audio_transcription_service.rb   |  4 ++
 .../app/services/messages/reindex_service.rb  | 15 ++++++
 enterprise/lib/tasks.rb                       |  4 ++
 enterprise/lib/tasks/search.rake              | 49 +++++++++++++++++
 lib/chatwoot_app.rb                           |  4 ++
 spec/models/message_spec.rb                   | 53 +++++++++++++++++++
 17 files changed, 242 insertions(+), 21 deletions(-)
 create mode 100644 config/initializers/searchkick.rb
 create mode 100644 enterprise/app/services/enterprise/search_service.rb
 create mode 100644 enterprise/app/services/messages/reindex_service.rb
 create mode 100644 enterprise/lib/tasks.rb
 create mode 100644 enterprise/lib/tasks/search.rake

diff --git a/Gemfile b/Gemfile
index 615267a77..1148251af 100644
--- a/Gemfile
+++ b/Gemfile
@@ -62,6 +62,10 @@ gem 'redis-namespace'
 # super fast record imports in bulk
 gem 'activerecord-import'
 
+gem 'searchkick'
+gem 'opensearch-ruby'
+gem 'faraday_middleware-aws-sigv4'
+
 ##--- gems for server & infra configuration ---##
 gem 'dotenv-rails', '>= 3.0.0'
 gem 'foreman'
diff --git a/Gemfile.lock b/Gemfile.lock
index 8fa38a31e..26814db59 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -299,6 +299,9 @@ GEM
       net-http-persistent (~> 4.0)
     faraday-retry (2.2.1)
       faraday (~> 2.0)
+    faraday_middleware-aws-sigv4 (1.0.1)
+      aws-sigv4 (~> 1.0)
+      faraday (>= 2.0, < 3)
     fast-mcp (1.5.0)
       addressable (~> 2.8)
       base64
@@ -601,6 +604,9 @@ GEM
     omniauth-rails_csrf_protection (1.0.2)
       actionpack (>= 4.2)
       omniauth (~> 2.0)
+    opensearch-ruby (3.4.0)
+      faraday (>= 1.0, < 3)
+      multi_json (>= 1.0)
     openssl (3.2.0)
     orm_adapter (0.5.0)
     os (1.1.4)
@@ -802,6 +808,9 @@ GEM
       parser
     scss_lint (0.60.0)
       sass (~> 3.5, >= 3.5.5)
+    searchkick (5.5.2)
+      activemodel (>= 7.1)
+      hashie
     securerandom (0.4.1)
     seed_dump (3.3.1)
       activerecord (>= 4)
@@ -996,6 +1005,7 @@ DEPENDENCIES
   facebook-messenger
   factory_bot_rails (>= 6.4.3)
   faker
+  faraday_middleware-aws-sigv4
   fcm
   flag_shih_tzu
   foreman
@@ -1036,6 +1046,7 @@ DEPENDENCIES
   omniauth-google-oauth2 (>= 1.1.3)
   omniauth-oauth2
   omniauth-rails_csrf_protection (~> 1.0, >= 1.0.2)
+  opensearch-ruby
   pg
   pg_search
   pgvector
@@ -1064,6 +1075,7 @@ DEPENDENCIES
   ruby_llm-schema
   scout_apm
   scss_lint
+  searchkick
   seed_dump
   sentry-rails (>= 5.19.0)
   sentry-ruby
diff --git a/Rakefile b/Rakefile
index e85f91391..591d2c4c6 100644
--- a/Rakefile
+++ b/Rakefile
@@ -4,3 +4,7 @@
 require_relative 'config/application'
 
 Rails.application.load_tasks
+
+# Load Enterprise Edition rake tasks if they exist
+enterprise_tasks_path = Rails.root.join('enterprise/lib/tasks.rb').to_s
+require enterprise_tasks_path if File.exist?(enterprise_tasks_path)
diff --git a/app/javascript/dashboard/modules/search/components/MessageContent.vue b/app/javascript/dashboard/modules/search/components/MessageContent.vue
index fef35ac89..9ec425919 100644
--- a/app/javascript/dashboard/modules/search/components/MessageContent.vue
+++ b/app/javascript/dashboard/modules/search/components/MessageContent.vue
@@ -1,5 +1,5 @@
 <script setup>
-import { ref, useTemplateRef, onMounted, watch, nextTick } from 'vue';
+import { ref, useTemplateRef, onMounted, watch, nextTick, computed } from 'vue';
 import { useMessageFormatter } from 'shared/composables/useMessageFormatter';
 import ReadMore from './ReadMore.vue';
 
@@ -8,9 +8,9 @@ const props = defineProps({
     type: String,
     default: '',
   },
-  content: {
-    type: String,
-    default: '',
+  message: {
+    type: Object,
+    default: () => ({}),
   },
   searchTerm: {
     type: String,
@@ -18,6 +18,24 @@ const props = defineProps({
   },
 });
 
+const messageContent = computed(() => {
+  // We perform search on either content or email subject or transcribed text
+  if (props.message.content) {
+    return props.message.content;
+  }
+
+  const { content_attributes = {} } = props.message;
+  const { email = {} } = content_attributes || {};
+  if (email.subject) {
+    return email.subject;
+  }
+
+  const audioAttachment = props.message.attachments.find(
+    attachment => attachment.file_type === 'audio'
+  );
+  return audioAttachment?.transcribed_text || '';
+});
+
 const { highlightContent } = useMessageFormatter();
 
 const messageContainer = useTemplateRef('messageContainer');
@@ -38,7 +56,8 @@ const escapeHtml = html => {
   return p.innerText;
 };
 
-const prepareContent = (content = '') => {
+const prepareContent = () => {
+  const content = messageContent.value || '';
   const escapedText = escapeHtml(content);
   return highlightContent(
     escapedText,
@@ -65,7 +84,7 @@ onMounted(() => {
       {{ $t('SEARCH.WROTE') }}
     </p>
     <ReadMore :shrink="isOverflowing" @expand="isOverflowing = false">
-      <div v-dompurify-html="prepareContent(content)" class="message-content" />
+      <div v-dompurify-html="prepareContent()" class="message-content" />
     </ReadMore>
   </blockquote>
 </template>
@@ -74,6 +93,7 @@ onMounted(() => {
 .message {
   @apply py-0 px-2 mt-2;
 }
+
 .message-content::v-deep p,
 .message-content::v-deep li::marker {
   @apply text-n-slate-11 mb-1;
diff --git a/app/javascript/dashboard/modules/search/components/SearchResultMessagesList.vue b/app/javascript/dashboard/modules/search/components/SearchResultMessagesList.vue
index 8bc33b236..956a6e220 100644
--- a/app/javascript/dashboard/modules/search/components/SearchResultMessagesList.vue
+++ b/app/javascript/dashboard/modules/search/components/SearchResultMessagesList.vue
@@ -54,7 +54,7 @@ const getName = message => {
         >
           <MessageContent
             :author="getName(message)"
-            :content="message.content"
+            :message="message"
             :search-term="query"
           />
         </SearchResultConversationItem>
diff --git a/app/models/message.rb b/app/models/message.rb
index bbb25df43..12b12b205 100644
--- a/app/models/message.rb
+++ b/app/models/message.rb
@@ -39,6 +39,8 @@
 #
 
 class Message < ApplicationRecord
+  searchkick callbacks: :async if ChatwootApp.advanced_search_allowed?
+
   include MessageFilterHelpers
   include Liquidable
   NUMBER_OF_PERMITTED_ATTACHMENTS = 15
@@ -139,14 +141,23 @@ class Message < ApplicationRecord
     data = attributes.symbolize_keys.merge(
       created_at: created_at.to_i,
       message_type: message_type_before_type_cast,
-      conversation_id: conversation.display_id,
-      conversation: conversation_push_event_data
+      conversation_id: conversation&.display_id,
+      conversation: conversation.present? ? conversation_push_event_data : nil
     )
     data[:echo_id] = echo_id if echo_id.present?
     data[:attachments] = attachments.map(&:push_event_data) if attachments.present?
     merge_sender_attributes(data)
   end
 
+  def search_data
+    data = attributes.symbolize_keys
+    data[:conversation] = conversation.present? ? conversation_push_event_data : nil
+    data[:attachments] = attachments.map(&:push_event_data) if attachments.present?
+    data[:sender] = sender.push_event_data if sender
+    data[:inbox] = inbox
+    data
+  end
+
   def conversation_push_event_data
     {
       assignee_id: conversation.assignee_id,
@@ -228,6 +239,14 @@ class Message < ApplicationRecord
                                                                             previous_changes: previous_changes)
   end
 
+  def should_index?
+    return false unless ChatwootApp.advanced_search_allowed?
+    return false unless account.feature_enabled?('advanced_search')
+    return false unless incoming? || outgoing?
+
+    true
+  end
+
   private
 
   def prevent_message_flooding
diff --git a/app/services/search_service.rb b/app/services/search_service.rb
index 56c15b2f3..0fbe4ec3b 100644
--- a/app/services/search_service.rb
+++ b/app/services/search_service.rb
@@ -43,11 +43,19 @@ class SearchService
   def filter_messages
     @messages = if use_gin_search
                   filter_messages_with_gin
+                elsif should_run_advanced_search?
+                  advanced_search
                 else
                   filter_messages_with_like
                 end
   end
 
+  def should_run_advanced_search?
+    ChatwootApp.advanced_search_allowed? && current_account.feature_enabled?('advanced_search')
+  end
+
+  def advanced_search; end
+
   def filter_messages_with_gin
     base_query = message_base_query
 
@@ -115,3 +123,5 @@ class SearchService
                                .per(15)
   end
 end
+
+SearchService.prepend_mod_with('SearchService')
diff --git a/app/views/api/v1/accounts/search/_message.json.jbuilder b/app/views/api/v1/accounts/search/_message.json.jbuilder
index 98ac728d6..33f8e3504 100644
--- a/app/views/api/v1/accounts/search/_message.json.jbuilder
+++ b/app/views/api/v1/accounts/search/_message.json.jbuilder
@@ -1,12 +1 @@
-json.id message.id
-json.content message.content
-json.message_type message.message_type_before_type_cast
-json.content_type message.content_type
-json.source_id message.source_id
-json.inbox_id message.inbox_id
-json.conversation_id message.conversation.try(:display_id)
-json.created_at message.created_at.to_i
-json.sender message.sender.push_event_data if message.sender
-json.inbox do
-  json.partial! 'inbox', formats: [:json], inbox: message.inbox if message.inbox.present? && message.try(:inbox).present?
-end
+json.partial! 'api/v1/models/message', message: message
diff --git a/config/features.yml b/config/features.yml
index 942eda32e..773eba08a 100644
--- a/config/features.yml
+++ b/config/features.yml
@@ -198,3 +198,8 @@
 - name: twilio_content_templates
   display_name: Twilio Content Templates
   enabled: false
+- name: advanced_search
+  display_name: Advanced Search
+  enabled: false
+  premium: true
+  chatwoot_internal: true
diff --git a/config/initializers/searchkick.rb b/config/initializers/searchkick.rb
new file mode 100644
index 000000000..e07f9022c
--- /dev/null
+++ b/config/initializers/searchkick.rb
@@ -0,0 +1,14 @@
+Searchkick.queue_name = :async_database_migration if ENV.fetch('OPENSEARCH_URL', '').present?
+
+access_key_id = ENV.fetch('OPENSEARCH_AWS_ACCESS_KEY_ID', '')
+secret_access_key = ENV.fetch('OPENSEARCH_AWS_SECRET_ACCESS_KEY', '')
+
+if access_key_id.present? && secret_access_key.present?
+  region = ENV.fetch('OPENSEARCH_AWS_REGION', 'us-east-1')
+
+  Searchkick.aws_credentials = {
+    access_key_id: access_key_id,
+    secret_access_key: secret_access_key,
+    region: region
+  }
+end
diff --git a/enterprise/app/services/enterprise/search_service.rb b/enterprise/app/services/enterprise/search_service.rb
new file mode 100644
index 000000000..628578b9d
--- /dev/null
+++ b/enterprise/app/services/enterprise/search_service.rb
@@ -0,0 +1,15 @@
+module Enterprise::SearchService
+  def advanced_search
+    where_conditions = { account_id: current_account.id  }
+    where_conditions[:inbox_id] = accessable_inbox_ids unless should_skip_inbox_filtering?
+
+    Message.search(
+      search_query,
+      fields: %w[content attachments.transcribed_text content_attributes.email.subject],
+      where: where_conditions,
+      order: { created_at: :desc },
+      page: params[:page] || 1,
+      per_page: 15
+    )
+  end
+end
diff --git a/enterprise/app/services/messages/audio_transcription_service.rb b/enterprise/app/services/messages/audio_transcription_service.rb
index b7d05766d..278f41d71 100644
--- a/enterprise/app/services/messages/audio_transcription_service.rb
+++ b/enterprise/app/services/messages/audio_transcription_service.rb
@@ -60,5 +60,9 @@ class Messages::AudioTranscriptionService < Llm::BaseOpenAiService
     attachment.update!(meta: { transcribed_text: transcribed_text })
     message.reload.send_update_event
     message.account.increment_response_usage
+
+    return unless ChatwootApp.advanced_search_allowed?
+
+    message.reindex
   end
 end
diff --git a/enterprise/app/services/messages/reindex_service.rb b/enterprise/app/services/messages/reindex_service.rb
new file mode 100644
index 000000000..a663c52e6
--- /dev/null
+++ b/enterprise/app/services/messages/reindex_service.rb
@@ -0,0 +1,15 @@
+class Messages::ReindexService
+  pattr_initialize [:account!]
+
+  def perform
+    return unless ChatwootApp.advanced_search_allowed?
+
+    reindex_messages
+  end
+
+  private
+
+  def reindex_messages
+    account.messages.reindex(mode: :async)
+  end
+end
diff --git a/enterprise/lib/tasks.rb b/enterprise/lib/tasks.rb
new file mode 100644
index 000000000..139819bbb
--- /dev/null
+++ b/enterprise/lib/tasks.rb
@@ -0,0 +1,4 @@
+# Load all rake tasks from the enterprise/lib/tasks directory
+module Tasks
+  Dir.glob(File.join(File.dirname(__FILE__), 'tasks', '*.rake')).each { |r| load r }
+end
diff --git a/enterprise/lib/tasks/search.rake b/enterprise/lib/tasks/search.rake
new file mode 100644
index 000000000..03bad2c1b
--- /dev/null
+++ b/enterprise/lib/tasks/search.rake
@@ -0,0 +1,49 @@
+module Tasks::SearchTaskHelpers
+  def check_opensearch_config
+    if ENV['OPENSEARCH_URL'].blank?
+      puts 'Skipping reindex as OPENSEARCH_URL is not configured'
+      return false
+    end
+    true
+  end
+
+  def reindex_account(account)
+    Messages::ReindexService.new(account: account).perform
+    puts "Reindex task queued for account #{account.id}"
+  end
+end
+
+namespace :search do
+  desc 'Reindex messages using searchkick'
+  include Tasks::SearchTaskHelpers
+
+  desc 'Reindex messages for all accounts'
+  task all: :environment do
+    next unless check_opensearch_config
+
+    puts 'Starting reindex for all accounts...'
+    account_count = Account.count
+    puts "Found #{account_count} accounts"
+
+    Account.find_each.with_index(1) do |account, index|
+      puts "[#{index}/#{account_count}] Reindexing messages for account #{account.id}"
+      reindex_account(account)
+    end
+
+    puts 'Reindex task queued for all accounts'
+  end
+
+  desc 'Reindex messages for a specific account: rake search:account ACCOUNT_ID=1'
+  task account: :environment do
+    next unless check_opensearch_config
+
+    account_id = ENV.fetch('ACCOUNT_ID', nil)
+    account = Account.find_by(id: account_id)
+    if account.nil?
+      puts 'Please provide a valid account ID. Account not found'
+      next
+    end
+    puts "Reindexing messages for account #{account.id}"
+    reindex_account(account)
+  end
+end
diff --git a/lib/chatwoot_app.rb b/lib/chatwoot_app.rb
index 8c64466ab..5606c0b37 100644
--- a/lib/chatwoot_app.rb
+++ b/lib/chatwoot_app.rb
@@ -38,4 +38,8 @@ module ChatwootApp
       %w[]
     end
   end
+
+  def self.advanced_search_allowed?
+    enterprise? && ENV.fetch('OPENSEARCH_URL', nil).present?
+  end
 end
diff --git a/spec/models/message_spec.rb b/spec/models/message_spec.rb
index cd4bc6bc1..2234c1ad6 100644
--- a/spec/models/message_spec.rb
+++ b/spec/models/message_spec.rb
@@ -613,4 +613,57 @@ RSpec.describe Message do
       end
     end
   end
+
+  describe '#should_index?' do
+    let(:account) { create(:account) }
+    let(:conversation) { create(:conversation, account: account) }
+    let(:message) { create(:message, conversation: conversation, account: account) }
+
+    before do
+      allow(ChatwootApp).to receive(:advanced_search_allowed?).and_return(true)
+      account.enable_features('advanced_search')
+    end
+
+    context 'when advanced search is not allowed globally' do
+      before do
+        allow(ChatwootApp).to receive(:advanced_search_allowed?).and_return(false)
+      end
+
+      it 'returns false' do
+        expect(message.should_index?).to be false
+      end
+    end
+
+    context 'when advanced search feature is not enabled for account' do
+      before do
+        account.disable_features('advanced_search')
+      end
+
+      it 'returns false' do
+        expect(message.should_index?).to be false
+      end
+    end
+
+    context 'when message type is not incoming or outgoing' do
+      before do
+        message.message_type = 'activity'
+      end
+
+      it 'returns false' do
+        expect(message.should_index?).to be false
+      end
+    end
+
+    context 'when all conditions are met' do
+      it 'returns true for incoming message' do
+        message.message_type = 'incoming'
+        expect(message.should_index?).to be true
+      end
+
+      it 'returns true for outgoing message' do
+        message.message_type = 'outgoing'
+        expect(message.should_index?).to be true
+      end
+    end
+  end
 end