diff --git a/.rubocop.yml b/.rubocop.yml
index e30a71ee9..83e2b1951 100644
--- a/.rubocop.yml
+++ b/.rubocop.yml
@@ -16,6 +16,7 @@ Metrics/ClassLength:
   Exclude:
     - 'app/models/message.rb'
     - 'app/models/conversation.rb'
+    - 'enterprise/app/services/captain/llm/system_prompts_service.rb'
 
 Metrics/MethodLength:
   Max: 19
diff --git a/config/routes.rb b/config/routes.rb
index 7fb348084..6016fdd00 100644
--- a/config/routes.rb
+++ b/config/routes.rb
@@ -67,7 +67,11 @@ Rails.application.routes.draw do
             resources :copilot_threads, only: [:index, :create] do
               resources :copilot_messages, only: [:index, :create]
             end
-            resources :documents, only: [:index, :show, :create, :destroy]
+            resources :documents, only: [:index, :show, :create, :destroy] do
+              collection do
+                post :upload_pdf
+              end
+            end
           end
           resources :agent_bots, only: [:index, :create, :show, :update, :destroy] do
             delete :avatar, on: :member
diff --git a/db/migrate/20250804110000_add_pdf_support_to_captain_documents.rb b/db/migrate/20250804110000_add_pdf_support_to_captain_documents.rb
new file mode 100644
index 000000000..1fdffe34f
--- /dev/null
+++ b/db/migrate/20250804110000_add_pdf_support_to_captain_documents.rb
@@ -0,0 +1,8 @@
+class AddPdfSupportToCaptainDocuments < ActiveRecord::Migration[7.1]
+  def change
+    add_column :captain_documents, :content_type, :string
+    add_column :captain_documents, :file_size, :bigint
+
+    add_index :captain_documents, :content_type
+  end
+end
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 eb7409b8b..b3b53f967 100644
--- a/db/schema.rb
+++ b/db/schema.rb
@@ -10,7 +10,7 @@
 #
 # It's strongly recommended that you check this file into your version control system.
 
-ActiveRecord::Schema[7.1].define(version: 2025_07_22_152516) do
+ActiveRecord::Schema[7.1].define(version: 2025_08_05_082345) do
   # These extensions should be enabled to support this database
   enable_extension "pg_stat_statements"
   enable_extension "pg_trgm"
@@ -292,9 +292,13 @@ ActiveRecord::Schema[7.1].define(version: 2025_07_22_152516) do
     t.datetime "created_at", null: false
     t.datetime "updated_at", null: false
     t.integer "status", default: 0, null: false
+    t.string "content_type"
+    t.bigint "file_size"
+    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"
+    t.index ["content_type"], name: "index_captain_documents_on_content_type"
     t.index ["status"], name: "index_captain_documents_on_status"
   end
 
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..ac9a5e6a7 100644
--- a/enterprise/app/controllers/api/v1/accounts/captain/documents_controller.rb
+++ b/enterprise/app/controllers/api/v1/accounts/captain/documents_controller.rb
@@ -3,9 +3,9 @@ class Api::V1::Accounts::Captain::DocumentsController < Api::V1::Accounts::BaseC
   before_action -> { check_authorization(Captain::Assistant) }
 
   before_action :set_current_page, only: [:index]
-  before_action :set_documents, except: [:create]
+  before_action :set_documents, except: [:create, :upload_pdf]
   before_action :set_document, only: [:show, :destroy]
-  before_action :set_assistant, only: [:create]
+  before_action :set_assistant, only: [:create, :upload_pdf]
   RESULTS_PER_PAGE = 25
 
   def index
@@ -22,9 +22,33 @@ class Api::V1::Accounts::Captain::DocumentsController < Api::V1::Accounts::BaseC
     return render_could_not_create_error('Missing Assistant') if @assistant.nil?
 
     @document = @assistant.documents.build(document_params)
+
+    # Handle PDF file upload if present
+    @document.pdf_file.attach(document_params[:pdf_file]) if document_params[:pdf_file].present?
+
     @document.save!
   rescue Captain::Document::LimitExceededError => e
     render_could_not_create_error(e.message)
+  rescue StandardError => e
+    Rails.logger.error "Document creation error: #{e.message}"
+    render_could_not_create_error('Failed to create document')
+  end
+
+  def upload_pdf
+    pdf_file = params[:pdf_file]
+
+    return render_could_not_create_error('PDF file is required') if pdf_file.blank?
+    return render_could_not_create_error('Invalid file type') unless valid_pdf?(pdf_file)
+    return render_could_not_create_error('File too large (max 512MB)') if pdf_file.size > 512.megabytes
+    return render_could_not_create_error('Missing Assistant') if @assistant.nil?
+
+    create_pdf_document(pdf_file)
+    render :show
+  rescue Captain::Document::LimitExceededError => e
+    render_could_not_create_error(e.message)
+  rescue StandardError => e
+    Rails.logger.error "PDF upload error: #{e.message}"
+    render_could_not_create_error('Failed to upload PDF')
   end
 
   def destroy
@@ -43,7 +67,8 @@ class Api::V1::Accounts::Captain::DocumentsController < Api::V1::Accounts::BaseC
   end
 
   def set_assistant
-    @assistant = Current.account.captain_assistants.find_by(id: document_params[:assistant_id])
+    assistant_id = document_params[:assistant_id] || params[:assistant_id]
+    @assistant = Current.account.captain_assistants.find_by(id: assistant_id)
   end
 
   def set_current_page
@@ -55,6 +80,19 @@ 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
+
+  def valid_pdf?(file)
+    file.content_type == 'application/pdf'
+  end
+
+  def create_pdf_document(pdf_file)
+    @document = @assistant.documents.build(
+      name: pdf_file.original_filename,
+      account: Current.account
+    )
+    @document.pdf_file.attach(pdf_file)
+    @document.save!
   end
 end
diff --git a/enterprise/app/jobs/captain/documents/crawl_job.rb b/enterprise/app/jobs/captain/documents/crawl_job.rb
index 132671385..a4bd67d4f 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 +15,19 @@ class Captain::Documents::CrawlJob < ApplicationJob
 
   include Captain::FirecrawlHelper
 
+  def perform_pdf_processing(document)
+    pdf_processor = Captain::Llm::PdfProcessingService.new(document)
+    pdf_processor.process
+
+    # Mark document as available - content is not needed for paginated processing
+    document.update!(status: :available)
+
+    Rails.logger.info "Successfully processed PDF document #{document.id}"
+  rescue StandardError => e
+    Rails.logger.error "Failed to process PDF document #{document.id}: #{e.message}"
+    document.update!(status: :available)
+  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 27406ebdf..e1b457a0c 100644
--- a/enterprise/app/jobs/captain/documents/response_builder_job.rb
+++ b/enterprise/app/jobs/captain/documents/response_builder_job.rb
@@ -1,17 +1,69 @@
 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).generate
-    faqs.each do |faq|
-      create_response(faq, document)
+    faqs = generate_faqs(document, options)
+    create_responses_from_faqs(faqs, document)
+
+    Rails.logger.info "FAQ generation complete. Total FAQs created: #{faqs.size}"
+  end
+
+  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)
+    Rails.logger.info "Using paginated FAQ generation for document #{document.id}"
+    service = build_paginated_service(document, options)
+    faqs = service.generate
+    store_paginated_metadata(document, service)
+    faqs
+  end
+
+  def generate_standard_faqs(document)
+    Rails.logger.info "Using standard FAQ generation for document #{document.id}"
+    Captain::Llm::FaqGeneratorService.new(document.content).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
+
   private
 
+  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
diff --git a/enterprise/app/jobs/captain/llm/update_embedding_job.rb b/enterprise/app/jobs/captain/llm/update_embedding_job.rb
index 20d10f8f5..e88c5d4f9 100644
--- a/enterprise/app/jobs/captain/llm/update_embedding_job.rb
+++ b/enterprise/app/jobs/captain/llm/update_embedding_job.rb
@@ -2,6 +2,9 @@ class Captain::Llm::UpdateEmbeddingJob < ApplicationJob
   queue_as :low
 
   def perform(record, content)
+    # Early return if record was deleted before job execution
+    return unless record&.persisted?
+
     embedding = Captain::Llm::EmbeddingService.new.get_embedding(content)
     record.update!(embedding: embedding)
   end
diff --git a/enterprise/app/models/captain/document.rb b/enterprise/app/models/captain/document.rb
index d2a02f5b5..89b30e667 100644
--- a/enterprise/app/models/captain/document.rb
+++ b/enterprise/app/models/captain/document.rb
@@ -4,7 +4,10 @@
 #
 #  id            :bigint           not null, primary key
 #  content       :text
+#  content_type  :string
 #  external_link :string           not null
+#  file_size     :bigint
+#  metadata      :jsonb
 #  name          :string
 #  status        :integer          default("in_progress"), not null
 #  created_at    :datetime         not null
@@ -26,11 +29,15 @@ 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?
   before_validation :ensure_account_id
+  before_validation :set_external_link_for_pdf
 
   enum status: {
     in_progress: 0,
@@ -41,12 +48,34 @@ 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?
+    (external_link&.ends_with?('.pdf')) || (pdf_file.attached? && pdf_file.content_type == 'application/pdf')
+  end
+
+  def openai_file_id
+    metadata['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 +90,12 @@ 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
@@ -73,4 +108,23 @@ class Captain::Document < ApplicationRecord
     limits = account.usage_limits[:captain][:documents]
     raise LimitExceededError, 'Document limit exceeded' unless limits[:current_available].positive?
   end
+
+  def validate_pdf_format
+    return unless pdf_file.attached?
+
+    errors.add(:pdf_file, 'must be a PDF file') unless pdf_file.content_type == 'application/pdf'
+
+    return unless pdf_file.byte_size > 512.megabytes
+
+    errors.add(:pdf_file, 'must be less than 512MB')
+  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..272b71636
--- /dev/null
+++ b/enterprise/app/services/captain/llm/paginated_faq_generator_service.rb
@@ -0,0 +1,206 @@
+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
+  end
+
+  def generate
+    raise 'Document must have openai_file_id for paginated processing' if @document&.openai_file_id.blank?
+
+    generate_paginated_faqs
+  end
+
+  # Method to check if we should continue processing
+  def should_continue_processing?(last_chunk_faqs)
+    # 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_faqs.empty?
+
+    # 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 "OpenAI API Error: #{e.message}"
+    []
+  end
+
+  def generate_paginated_faqs
+    Rails.logger.info "Starting paginated FAQ generation (#{@pages_per_chunk} pages per chunk)"
+
+    all_faqs = []
+    current_page = 1
+
+    loop do
+      end_page = calculate_end_page(current_page)
+      chunk_faqs = process_chunk_and_update_state(current_page, end_page, all_faqs)
+
+      unless should_continue_processing?(chunk_faqs)
+        Rails.logger.info "Stopping processing. Reason: #{determine_stop_reason(chunk_faqs)}"
+        break
+      end
+
+      current_page = end_page + 1
+    end
+
+    Rails.logger.info "Paginated generation complete. Total FAQs: #{all_faqs.size}, Pages processed: #{@total_pages_processed}"
+    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)
+    Rails.logger.info "Processing pages #{current_page}-#{end_page} (iteration #{@iterations_completed + 1})"
+
+    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
+
+    Rails.logger.info "Chunk generated #{chunk_faqs.size} FAQs. Total so far: #{all_faqs.size}"
+    chunk_faqs
+  end
+
+  def process_page_chunk(start_page, end_page)
+    response = @client.chat(parameters: build_chunk_parameters(start_page, end_page))
+    result = parse_chunk_response(response)
+    { faqs: result['faqs'] || [], has_content: result['has_content'] != false }
+  rescue OpenAI::Error => e
+    Rails.logger.error "Error processing pages #{start_page}-#{end_page}: #{e.message}"
+    { faqs: [], has_content: false }
+  end
+
+  def build_chunk_parameters(start_page, end_page)
+    {
+      model: @model,
+      response_format: { type: 'json_object' },
+      messages: [
+        {
+          role: 'system',
+          content: page_chunk_prompt(start_page, end_page)
+        },
+        {
+          role: 'user',
+          content: build_user_content
+        }
+      ]
+    }
+  end
+
+  def build_user_content
+    [
+      {
+        type: 'file',
+        file: { file_id: @document.openai_file_id }
+      },
+      {
+        type: 'text',
+        text: 'Process this document according to the system instructions.'
+      }
+    ]
+  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_faqs)
+    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_faqs.empty?
+
+    '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..89e04b8a1
--- /dev/null
+++ b/enterprise/app/services/captain/llm/pdf_processing_service.rb
@@ -0,0 +1,59 @@
+class Captain::Llm::PdfProcessingService < Llm::BaseOpenAiService
+  def initialize(document)
+    @document = document
+    super()
+  end
+
+  def process
+    # We only use paginated processing now - just upload and store file_id
+    process_for_pagination
+  end
+
+  private
+
+  attr_reader :document
+
+  def upload_pdf_to_openai
+    pdf_file = document.pdf_file
+
+    # Create a temporary file from the attached PDF
+    temp_file = Tempfile.new(['pdf_upload', '.pdf'])
+    temp_file.binmode
+    temp_file.write(pdf_file.download)
+    temp_file.close
+
+    begin
+      File.open(temp_file.path, 'rb') do |file|
+        @client.files.upload(
+          parameters: {
+            file: file,
+            purpose: 'assistants'  # Use 'assistants' as it's supported by the API
+          }
+        )
+      end
+    ensure
+      temp_file.unlink
+    end
+  end
+
+  def process_for_pagination
+    # For paginated processing, we only need to upload the PDF and store the file_id
+    # No content extraction is needed as the paginated FAQ generator will access the file directly
+    if @document.openai_file_id.present?
+      Rails.logger.info "PDF already uploaded with file_id: #{@document.openai_file_id}"
+      return 'PDF ready for paginated processing'
+    end
+
+    # Upload PDF to OpenAI
+    openai_response = upload_pdf_to_openai
+    file_id = openai_response['id']
+
+    raise 'Failed to upload PDF to OpenAI' unless file_id
+
+    # Store the file ID for future use
+    document.store_openai_file_id(file_id)
+
+    Rails.logger.info "PDF uploaded successfully with file_id: #{file_id}"
+    "PDF ready for paginated processing (file_id: #{file_id})"
+  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 3a699b445..d0056379c 100644
--- a/enterprise/app/services/captain/llm/system_prompts_service.rb
+++ b/enterprise/app/services/captain/llm/system_prompts_service.rb
@@ -156,5 +156,73 @@ class Captain::Llm::SystemPromptsService
         - You MUST provide numbered citations at the appropriate places in the text.
       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 SPECIFIC PAGES of a document.
+
+        ════════════════════════════════════════════════════════
+        CRITICAL PAGE RANGE INSTRUCTIONS
+        ════════════════════════════════════════════════════════
+
+        You MUST analyze ONLY pages #{start_page} to #{end_page} of the document.
+
+        ════════════════════════════════════════════════════════
+        FAQ GENERATION GUIDELINES
+        ════════════════════════════════════════════════════════
+
+        1. **Comprehensive Extraction**
+           • Extract ALL information that could generate FAQs from pages #{start_page}-#{end_page}
+           • Target 5-10 FAQs per page of rich content
+           • Cover every topic, feature, specification, and detail
+
+        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, references)
+           • 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
+           • Reference page numbers for critical information
+           • 2-5 sentences typical length
+           • No references to content outside pages #{start_page}-#{end_page}
+
+        ════════════════════════════════════════════════════════
+        OUTPUT FORMAT
+        ════════════════════════════════════════════════════════
+
+        Return valid JSON:
+        ```json
+        {
+          "faqs": [
+            {
+              "question": "Specific question from pages #{start_page}-#{end_page}",
+              "answer": "Complete answer with details from these pages only"
+            }
+          ],
+          "has_content": true/false,
+          "page_range_processed": "#{start_page}-#{end_page}"
+        }
+        ```
+
+        IMPORTANT: Set "has_content" to false if the pages don't exist or contain no meaningful content.
+      PROMPT
+    end
   end
 end
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..5f9e76e66 100644
--- a/enterprise/app/views/api/v1/models/captain/_document.json.jbuilder
+++ b/enterprise/app/views/api/v1/models/captain/_document.json.jbuilder
@@ -5,6 +5,7 @@ end
 json.content resource.content
 json.created_at resource.created_at.to_i
 json.external_link resource.external_link
+json.display_url resource.display_url
 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..116bf3ead
--- /dev/null
+++ b/lib/custom_exceptions/pdf_processing_error.rb
@@ -0,0 +1,23 @@
+class PdfProcessingError < CustomExceptions::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