diff --git a/enterprise/app/services/captain/tools/documentation_search.rb b/enterprise/app/services/captain/tools/documentation_search.rb
new file mode 100644
index 000000000..65fdf3e71
--- /dev/null
+++ b/enterprise/app/services/captain/tools/documentation_search.rb
@@ -0,0 +1,27 @@
+class Captain::Tools::DocumentationSearch < RubyLLM::Tool
+  description 'Search through the documentation to find relevant answers'
+
+  param :search_query,
+        type: :string,
+        desc: 'The search query to find relevant documentation'
+
+  def execute(search_query:)
+    responses = ::Captain::AssistantResponse.approved.search(search_query)
+    format_responses(responses)
+  end
+
+  private
+
+  def format_responses(responses)
+    responses.map do |response|
+      formatted_response = {
+        question: response.question,
+        answer: response.answer
+      }
+
+      formatted_response[:source] = response.documentable.external_link if response.documentable.present? && response.documentable.try(:external_link)
+
+      formatted_response
+    end
+  end
+end
diff --git a/spec/enterprise/services/captain/tools/documentation_search_spec.rb b/spec/enterprise/services/captain/tools/documentation_search_spec.rb
new file mode 100644
index 000000000..2678c322d
--- /dev/null
+++ b/spec/enterprise/services/captain/tools/documentation_search_spec.rb
@@ -0,0 +1,90 @@
+require 'rails_helper'
+
+RSpec.describe Captain::Tools::DocumentationSearch do
+  let(:tool) { described_class.new }
+  let(:search_query) { 'how to configure inbox' }
+  let(:account) { create(:account) }
+  let(:assistant) { create(:captain_assistant, account: account) }
+  let(:embedding) { Array.new(1536) { rand(-1.0..1.0) } }
+  let(:embedding_service) { instance_double(Captain::Llm::EmbeddingService) }
+
+  before do
+    allow(Captain::Llm::UpdateEmbeddingJob).to receive(:perform_later)
+    allow(Captain::Llm::EmbeddingService).to receive(:new).and_return(embedding_service)
+    allow(embedding_service).to receive(:get_embedding).with(search_query).and_return(embedding)
+  end
+
+  describe '#execute' do
+    context 'when matching responses exist' do
+      let!(:response) do
+        create(:captain_assistant_response,
+               assistant: assistant,
+               account: account,
+               question: 'How do I configure my inbox?',
+               answer: 'Follow these steps...',
+               status: :approved,
+               embedding: embedding)
+      end
+
+      let!(:response_with_source) do
+        document = create(:captain_document,
+                          assistant: assistant,
+                          account: account,
+                          external_link: 'https://example.com/docs')
+        create(:captain_assistant_response,
+               assistant: assistant,
+               account: account,
+               question: 'What are inbox settings?',
+               answer: 'Inbox settings include...',
+               documentable: document,
+               status: :approved,
+               embedding: embedding)
+      end
+
+      it 'returns formatted responses' do
+        result = tool.execute(search_query: search_query)
+
+        expect(result).to be_an(Array)
+        expect(result.size).to eq(2)
+
+        # First response without source
+        expect(result[0]).to include(
+          question: response.question,
+          answer: response.answer
+        )
+        expect(result[0]).not_to have_key(:source)
+
+        # Second response with source
+        expect(result[1]).to include(
+          question: response_with_source.question,
+          answer: response_with_source.answer,
+          source: 'https://example.com/docs'
+        )
+      end
+    end
+
+    context 'when no matching responses exist' do
+      it 'returns an empty array' do
+        result = tool.execute(search_query: search_query)
+        expect(result).to eq([])
+      end
+    end
+  end
+
+  describe '.description' do
+    it 'has a description' do
+      expect(described_class.description).to eq('Search through the documentation to find relevant answers')
+    end
+  end
+
+  describe '.parameters' do
+    it 'defines search_query parameter' do
+      param = described_class.parameters[:search_query]
+      expect(param).to be_a(RubyLLM::Parameter)
+      expect(param.name).to eq(:search_query)
+      expect(param.type).to eq(:string)
+      expect(param.description).to eq('The search query to find relevant documentation')
+      expect(param.required).to be true
+    end
+  end
+end