diff --git a/Gemfile b/Gemfile
index b4752c745..78fe3016f 100644
--- a/Gemfile
+++ b/Gemfile
@@ -31,6 +31,14 @@ gem 'haikunator'
 gem 'liquid'
 # Parse Markdown to HTML
 gem 'commonmarker'
+# Convert PDF pages to images for content extraction
+gem 'pdftoimage'
+# Google Vision API for text extraction from images
+gem 'google-cloud-vision'
+# Tesseract OCR fallback when Vision API not available
+gem 'rtesseract'
+# Image manipulation for PDF page batching
+gem 'mini_magick'
 # Validate Data against JSON Schema
 gem 'json_schemer'
 # used in swagger build
diff --git a/enterprise/app/jobs/captain/documents/pdf_processing_job.rb b/enterprise/app/jobs/captain/documents/pdf_processing_job.rb
new file mode 100644
index 000000000..2bc300ce5
--- /dev/null
+++ b/enterprise/app/jobs/captain/documents/pdf_processing_job.rb
@@ -0,0 +1,30 @@
+class Captain::Documents::PdfProcessingJob < ApplicationJob
+  queue_as :low
+
+  def perform(document)
+    return unless document.pdf_document?
+
+    Rails.logger.info "Starting PDF processing for document #{document.id}"
+    
+    begin
+      service = Captain::Tools::PdfProcessingService.new(document)
+      extracted_content = service.process
+      
+      Rails.logger.info "Successfully processed PDF document #{document.id}, extracted #{extracted_content.length} characters"
+      
+    rescue Captain::Tools::PdfProcessingService::PdfProcessingError => e
+      Rails.logger.error "PDF processing failed for document #{document.id}: #{e.message}"
+      
+      # Mark document as failed (you may want to add a 'failed' status to the enum)
+      document.update!(status: :in_progress) # Keep as in_progress for potential retry
+      
+      # Optionally, you could add a retry mechanism or notification
+      raise e
+      
+    rescue StandardError => e
+      Rails.logger.error "Unexpected error processing PDF document #{document.id}: #{e.message}"
+      document.update!(status: :in_progress)
+      raise e
+    end
+  end
+end
\ No newline at end of file
diff --git a/enterprise/app/models/captain/document.rb b/enterprise/app/models/captain/document.rb
index d2a02f5b5..6ed8d6e8a 100644
--- a/enterprise/app/models/captain/document.rb
+++ b/enterprise/app/models/captain/document.rb
@@ -37,7 +37,13 @@ class Captain::Document < ApplicationRecord
     available: 1
   }
 
+  enum document_type: {
+    url: 0,
+    pdf: 1
+  }
+
   before_create :ensure_within_plan_limit
+  before_create :detect_document_type
   after_create_commit :enqueue_crawl_job
   after_create_commit :update_document_usage
   after_destroy :update_document_usage
@@ -52,7 +58,33 @@ class Captain::Document < ApplicationRecord
   def enqueue_crawl_job
     return if status != 'in_progress'
 
-    Captain::Documents::CrawlJob.perform_later(self)
+    if pdf_document?
+      Captain::Documents::PdfProcessingJob.perform_later(self)
+    else
+      Captain::Documents::CrawlJob.perform_later(self)
+    end
+  end
+
+  def url_document?
+    document_type == 'url'
+  end
+
+  def pdf_document?
+    document_type == 'pdf'
+  end
+
+  def detect_document_type
+    return unless external_link.present?
+    
+    # Check if URL points to a PDF file
+    uri = URI.parse(external_link)
+    if uri.path.downcase.end_with?('.pdf') || external_link.downcase.include?('.pdf')
+      self.document_type = :pdf
+    else
+      self.document_type = :url
+    end
+  rescue URI::InvalidURIError
+    self.document_type = :url
   end
 
   def enqueue_response_builder_job
diff --git a/enterprise/app/services/captain/tools/pdf_page_batcher_service.rb b/enterprise/app/services/captain/tools/pdf_page_batcher_service.rb
new file mode 100644
index 000000000..7e0374b20
--- /dev/null
+++ b/enterprise/app/services/captain/tools/pdf_page_batcher_service.rb
@@ -0,0 +1,57 @@
+require 'mini_magick'
+
+class Captain::Tools::PdfPageBatcherService
+  PAGES_PER_BATCH = 3
+  
+  def initialize(temp_files_tracker)
+    @temp_files = temp_files_tracker
+  end
+
+  def batch_pages(image_files)
+    return image_files if image_files.length <= PAGES_PER_BATCH
+    
+    batched_images = []
+    
+    image_files.each_slice(PAGES_PER_BATCH) do |batch|
+      if batch.length == 1
+        # Single page, use as-is
+        batched_images << batch.first
+      else
+        # Multiple pages, combine them
+        combined_image = combine_images(batch)
+        batched_images << combined_image
+      end
+    end
+    
+    batched_images
+  end
+
+  private
+
+  def combine_images(image_paths)
+    # Create a vertical montage of the images
+    output_path = create_temp_file_path('.png')
+    
+    MiniMagick::Tool::Montage.new do |montage|
+      image_paths.each { |path| montage << path }
+      montage.tile('1x')  # Arrange in single column (vertically)
+      montage.geometry('+0+10')  # Add 10px spacing between images
+      montage.background('white')
+      montage << output_path
+    end
+    
+    @temp_files << output_path
+    output_path
+  rescue StandardError => e
+    Rails.logger.error "Failed to combine images: #{e.message}"
+    # Fallback to first image if combining fails
+    image_paths.first
+  end
+
+  def create_temp_file_path(extension)
+    temp_file = Tempfile.new(['combined_pages', extension])
+    temp_file.close
+    @temp_files << temp_file
+    temp_file.path
+  end
+end
\ No newline at end of file
diff --git a/enterprise/app/services/captain/tools/pdf_processing_service.rb b/enterprise/app/services/captain/tools/pdf_processing_service.rb
new file mode 100644
index 000000000..fbe36bfb2
--- /dev/null
+++ b/enterprise/app/services/captain/tools/pdf_processing_service.rb
@@ -0,0 +1,75 @@
+class Captain::Tools::PdfProcessingService
+  def initialize(document)
+    @document = document
+    @temp_files = []
+  end
+
+  def process
+    return unless @document.pdf_document?
+
+    content = extract_text_content
+    
+    # Follow the same pattern as SimplePageCrawlParserJob
+    @document.update!(
+      content: content[0..14_999], # Same limit as crawler
+      status: :available
+    )
+    
+    content
+  rescue StandardError => e
+    Rails.logger.error "PDF processing failed for document #{@document.id}: #{e.message}"
+    @document.update!(content: "Error processing PDF: #{e.message}", status: :available)
+    raise e
+  ensure
+    cleanup_temp_files
+  end
+
+  private
+
+  def extract_text_content
+    require 'down'
+    
+    pdf_file = Down.download(@document.external_link)
+    @temp_files << pdf_file
+    
+    output_dir = Dir.mktmpdir
+    @temp_files << output_dir
+    
+    # Convert PDF to images
+    system("pdftoimage", "-png", "-r", "150", pdf_file.path, "#{output_dir}/page")
+    
+    image_files = Dir.glob("#{output_dir}/page-*.png").sort
+    return fallback_content if image_files.empty?
+    
+    # Batch pages for efficient processing
+    batcher = Captain::Tools::PdfPageBatcherService.new(@temp_files)
+    batched_images = batcher.batch_pages(image_files)
+    
+    # Extract text using Google Vision
+    vision_extractor = Captain::Tools::VisionTextExtractorService.new
+    extracted_text = vision_extractor.extract_text_from_multiple_images(batched_images)
+    
+    extracted_text.present? ? extracted_text : fallback_content
+  end
+
+  def fallback_content
+    "PDF Document: #{@document.name || 'Untitled'}\nSource: #{@document.external_link}"
+  end
+
+  def cleanup_temp_files
+    @temp_files.each do |file_or_dir|
+      case file_or_dir
+      when String # directory path
+        FileUtils.rm_rf(file_or_dir)
+      when Tempfile
+        file_or_dir.close
+        file_or_dir.unlink
+      else # Down::ChunkedIO or similar
+        file_or_dir.close if file_or_dir.respond_to?(:close)
+        file_or_dir.unlink if file_or_dir.respond_to?(:unlink)
+      end
+    rescue StandardError => e
+      Rails.logger.warn "Failed to cleanup temp file: #{e.message}"
+    end
+  end
+end
\ No newline at end of file
diff --git a/enterprise/app/services/captain/tools/vision_text_extractor_service.rb b/enterprise/app/services/captain/tools/vision_text_extractor_service.rb
new file mode 100644
index 000000000..547503986
--- /dev/null
+++ b/enterprise/app/services/captain/tools/vision_text_extractor_service.rb
@@ -0,0 +1,68 @@
+class Captain::Tools::VisionTextExtractorService
+  class TextExtractionError < StandardError; end
+
+  def initialize
+    @use_vision = vision_available?
+    @vision = Google::Cloud::Vision.image_annotator if @use_vision
+  end
+
+  def extract_text_from_image(image_path)
+    if @use_vision
+      extract_with_vision(image_path)
+    else
+      extract_with_tesseract(image_path)
+    end
+  end
+
+  def extract_text_from_multiple_images(image_paths)
+    Rails.logger.info "Using #{@use_vision ? 'Google Vision' : 'Tesseract'} for text extraction"
+    
+    extracted_texts = []
+    
+    image_paths.each_with_index do |image_path, index|
+      Rails.logger.info "Extracting text from image #{index + 1}/#{image_paths.length}"
+      
+      text = extract_text_from_image(image_path)
+      extracted_texts << text if text.present?
+    end
+    
+    extracted_texts.join("\n\n")
+  end
+
+  private
+
+  def vision_available?
+    require 'google/cloud/vision'
+    Google::Cloud::Vision.image_annotator
+    true
+  rescue StandardError => e
+    Rails.logger.info "Google Vision not available, falling back to Tesseract: #{e.message}"
+    false
+  end
+
+  def extract_with_vision(image_path)
+    image = Google::Cloud::Vision::Image.new(image_path)
+    response = @vision.text_detection(image: image)
+    
+    if response.error
+      raise TextExtractionError, "Vision API error: #{response.error.message}"
+    end
+    
+    text_annotation = response.full_text_annotation
+    return "" unless text_annotation
+    
+    text_annotation.text
+  rescue Google::Cloud::Error => e
+    Rails.logger.error "Google Vision API error: #{e.message}"
+    raise TextExtractionError, "Failed to extract text: #{e.message}"
+  end
+
+  def extract_with_tesseract(image_path)
+    require 'rtesseract'
+    
+    RTesseract.new(image_path).to_s.strip
+  rescue StandardError => e
+    Rails.logger.error "Tesseract extraction error: #{e.message}"
+    raise TextExtractionError, "Failed to extract text with Tesseract: #{e.message}"
+  end
+end
\ No newline at end of file
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..cce21fe6d 100644
--- a/enterprise/app/views/api/v1/models/captain/_document.json.jbuilder
+++ b/enterprise/app/views/api/v1/models/captain/_document.json.jbuilder
@@ -4,6 +4,7 @@ json.assistant do
 end
 json.content resource.content
 json.created_at resource.created_at.to_i
+json.document_type resource.document_type
 json.external_link resource.external_link
 json.id resource.id
 json.name resource.name
diff --git a/enterprise/db/migrate/20250623_add_document_type_and_file_to_captain_documents.rb b/enterprise/db/migrate/20250623_add_document_type_and_file_to_captain_documents.rb
new file mode 100644
index 000000000..989596674
--- /dev/null
+++ b/enterprise/db/migrate/20250623_add_document_type_and_file_to_captain_documents.rb
@@ -0,0 +1,6 @@
+class AddDocumentTypeToCaptainDocuments < ActiveRecord::Migration[7.0]
+  def change
+    add_column :captain_documents, :document_type, :integer, default: 0, null: false
+    add_index :captain_documents, :document_type
+  end
+end
\ No newline at end of file
diff --git a/spec/enterprise/models/captain/document_spec.rb b/spec/enterprise/models/captain/document_spec.rb
new file mode 100644
index 000000000..fc5e52130
--- /dev/null
+++ b/spec/enterprise/models/captain/document_spec.rb
@@ -0,0 +1,69 @@
+require 'rails_helper'
+
+RSpec.describe Captain::Document, type: :model do
+  let(:account) { create(:account) }
+  let(:assistant) { create(:captain_assistant, account: account) }
+
+  describe 'document_type detection' do
+    it 'detects PDF documents from URL' do
+      document = assistant.documents.build(
+        name: 'Test PDF',
+        external_link: 'https://example.com/document.pdf'
+      )
+      
+      document.save!
+      
+      expect(document.document_type).to eq('pdf')
+      expect(document.pdf_document?).to be true
+      expect(document.url_document?).to be false
+    end
+
+    it 'detects URL documents for non-PDF links' do
+      document = assistant.documents.build(
+        name: 'Test Page',
+        external_link: 'https://example.com/page.html'
+      )
+      
+      document.save!
+      
+      expect(document.document_type).to eq('url')
+      expect(document.url_document?).to be true
+      expect(document.pdf_document?).to be false
+    end
+
+    it 'defaults to URL for invalid URIs' do
+      document = assistant.documents.build(
+        name: 'Invalid URL',
+        external_link: 'not-a-valid-url'
+      )
+      
+      document.save!
+      
+      expect(document.document_type).to eq('url')
+    end
+  end
+
+  describe 'job enqueueing' do
+    it 'enqueues PDF processing job for PDF documents' do
+      document = assistant.documents.build(
+        name: 'Test PDF',
+        external_link: 'https://example.com/document.pdf'
+      )
+      
+      expect(Captain::Documents::PdfProcessingJob).to receive(:perform_later).with(document)
+      
+      document.save!
+    end
+
+    it 'enqueues crawl job for URL documents' do
+      document = assistant.documents.build(
+        name: 'Test Page',
+        external_link: 'https://example.com/page.html'
+      )
+      
+      expect(Captain::Documents::CrawlJob).to receive(:perform_later).with(document)
+      
+      document.save!
+    end
+  end
+end
\ No newline at end of file
diff --git a/spec/enterprise/services/captain/tools/pdf_processing_service_spec.rb b/spec/enterprise/services/captain/tools/pdf_processing_service_spec.rb
new file mode 100644
index 000000000..6e6c4ebbd
--- /dev/null
+++ b/spec/enterprise/services/captain/tools/pdf_processing_service_spec.rb
@@ -0,0 +1,76 @@
+require 'rails_helper'
+
+RSpec.describe Captain::Tools::PdfProcessingService do
+  let(:account) { create(:account) }
+  let(:assistant) { create(:captain_assistant, account: account) }
+  let(:document) do
+    assistant.documents.create!(
+      name: 'Test PDF',
+      external_link: 'https://example.com/test.pdf',
+      document_type: :pdf
+    )
+  end
+
+  subject { described_class.new(document) }
+
+  describe '#process' do
+    context 'when document is not a PDF' do
+      before { allow(document).to receive(:pdf_document?).and_return(false) }
+
+      it 'returns early without processing' do
+        expect(subject.process).to be_nil
+      end
+    end
+
+    context 'when document is a PDF' do
+      let(:mock_file) { double('file', path: '/tmp/test.pdf', close: nil, unlink: nil) }
+      let(:mock_batcher) { double('batcher') }
+      let(:mock_vision) { double('vision') }
+
+      before do
+        allow(Down).to receive(:download).and_return(mock_file)
+        allow(Dir).to receive(:mktmpdir).and_return('/tmp/pdf_images')
+        allow(Dir).to receive(:glob).and_return(['/tmp/image1.png', '/tmp/image2.png'])
+        allow(FileUtils).to receive(:rm_rf)
+        
+        allow(Captain::Tools::PdfPageBatcherService).to receive(:new).and_return(mock_batcher)
+        allow(mock_batcher).to receive(:batch_pages).and_return(['/tmp/batched1.png'])
+        
+        allow(Captain::Tools::VisionTextExtractorService).to receive(:new).and_return(mock_vision)
+        allow(mock_vision).to receive(:extract_text_from_multiple_images).and_return('Extracted text content')
+      end
+
+      it 'processes the PDF and updates document' do
+        expect { subject.process }.to change { document.reload.status }.to('available')
+      end
+
+      it 'sets extracted content on the document' do
+        subject.process
+        expect(document.reload.content).to eq('Extracted text content')
+      end
+
+      it 'uses batching service for page processing' do
+        expect(mock_batcher).to receive(:batch_pages).with(['/tmp/image1.png', '/tmp/image2.png'])
+        subject.process
+      end
+
+      it 'uses Vision API for text extraction' do
+        expect(mock_vision).to receive(:extract_text_from_multiple_images).with(['/tmp/batched1.png'])
+        subject.process
+      end
+    end
+
+    context 'when processing fails' do
+      before do
+        allow(Down).to receive(:download).and_raise(StandardError.new('Download failed'))
+      end
+
+      it 'logs error and updates document with error message' do
+        expect(Rails.logger).to receive(:error).with(/PDF processing failed/)
+        
+        expect { subject.process }.to raise_error(StandardError)
+        expect(document.reload.content).to include('Error processing PDF')
+      end
+    end
+  end
+end
\ No newline at end of file
diff --git a/spec/enterprise/services/captain/tools/vision_text_extractor_service_spec.rb b/spec/enterprise/services/captain/tools/vision_text_extractor_service_spec.rb
new file mode 100644
index 000000000..f224968da
--- /dev/null
+++ b/spec/enterprise/services/captain/tools/vision_text_extractor_service_spec.rb
@@ -0,0 +1,98 @@
+require 'rails_helper'
+
+RSpec.describe Captain::Tools::VisionTextExtractorService do
+  let(:image_path) { '/tmp/test_image.png' }
+
+  describe 'when Google Vision is available' do
+    subject { described_class.new }
+
+    let(:mock_vision) { double('vision_client') }
+    let(:mock_response) { double('response', error: nil) }
+    let(:mock_text_annotation) { double('text_annotation', text: 'Vision extracted text') }
+
+    before do
+      allow(Google::Cloud::Vision).to receive(:image_annotator).and_return(mock_vision)
+      allow(Google::Cloud::Vision::Image).to receive(:new).with(image_path).and_return(double('image'))
+      allow(mock_vision).to receive(:text_detection).and_return(mock_response)
+      allow(mock_response).to receive(:full_text_annotation).and_return(mock_text_annotation)
+    end
+
+    describe '#extract_text_from_image' do
+      it 'uses Vision API for text extraction' do
+        result = subject.extract_text_from_image(image_path)
+        expect(result).to eq('Vision extracted text')
+      end
+
+      context 'when Vision API returns error' do
+        before do
+          allow(mock_response).to receive(:error).and_return(double('error', message: 'API Error'))
+        end
+
+        it 'raises TextExtractionError' do
+          expect { subject.extract_text_from_image(image_path) }.to raise_error(
+            Captain::Tools::VisionTextExtractorService::TextExtractionError,
+            /Vision API error/
+          )
+        end
+      end
+    end
+  end
+
+  describe 'when Google Vision is not available' do
+    subject { described_class.new }
+
+    let(:mock_tesseract) { double('tesseract', to_s: 'Tesseract extracted text') }
+
+    before do
+      allow(Google::Cloud::Vision).to receive(:image_annotator).and_raise(StandardError.new('No credentials'))
+      allow(RTesseract).to receive(:new).with(image_path).and_return(mock_tesseract)
+    end
+
+    describe '#extract_text_from_image' do
+      it 'falls back to Tesseract for text extraction' do
+        result = subject.extract_text_from_image(image_path)
+        expect(result).to eq('Tesseract extracted text')
+      end
+
+      context 'when Tesseract fails' do
+        before do
+          allow(RTesseract).to receive(:new).and_raise(StandardError.new('Tesseract error'))
+        end
+
+        it 'raises TextExtractionError' do
+          expect { subject.extract_text_from_image(image_path) }.to raise_error(
+            Captain::Tools::VisionTextExtractorService::TextExtractionError,
+            /Failed to extract text with Tesseract/
+          )
+        end
+      end
+    end
+  end
+
+  describe '#extract_text_from_multiple_images' do
+    let(:image_paths) { ['/tmp/image1.png', '/tmp/image2.png'] }
+    
+    before do
+      allow(Google::Cloud::Vision).to receive(:image_annotator).and_return(double('vision'))
+      allow(subject).to receive(:extract_text_from_image).with('/tmp/image1.png').and_return('Text from page 1')
+      allow(subject).to receive(:extract_text_from_image).with('/tmp/image2.png').and_return('Text from page 2')
+    end
+
+    it 'extracts text from multiple images and joins them' do
+      result = subject.extract_text_from_multiple_images(image_paths)
+      expect(result).to eq("Text from page 1\n\nText from page 2")
+    end
+
+    it 'skips empty results' do
+      allow(subject).to receive(:extract_text_from_image).with('/tmp/image2.png').and_return('')
+      
+      result = subject.extract_text_from_multiple_images(image_paths)
+      expect(result).to eq('Text from page 1')
+    end
+
+    it 'logs which extraction method is being used' do
+      expect(Rails.logger).to receive(:info).with(/Using (Google Vision|Tesseract) for text extraction/)
+      subject.extract_text_from_multiple_images(image_paths)
+    end
+  end
+end
\ No newline at end of file