diff --git a/Gemfile b/Gemfile
index b4752c745..53ba9f783 100644
--- a/Gemfile
+++ b/Gemfile
@@ -177,6 +177,7 @@ gem 'reverse_markdown'
 
 gem 'iso-639'
 gem 'ruby-openai'
+gem 'ai-agents', '>= 0.2.1'
 
 gem 'shopify_api'
 
diff --git a/Gemfile.lock b/Gemfile.lock
index 8315a5374..d55cfa0a9 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -126,6 +126,8 @@ GEM
       jbuilder (~> 2)
       rails (>= 4.2, < 7.2)
       selectize-rails (~> 0.6)
+    ai-agents (0.2.1)
+      ruby_llm (~> 1.3)
     annotate (3.2.0)
       activerecord (>= 3.2, < 8.0)
       rake (>= 10.4, < 14.0)
@@ -717,6 +719,15 @@ GEM
     ruby2ruby (2.5.0)
       ruby_parser (~> 3.1)
       sexp_processor (~> 4.6)
+    ruby_llm (1.3.1)
+      base64
+      event_stream_parser (~> 1)
+      faraday (>= 1.10.0)
+      faraday-multipart (>= 1)
+      faraday-net_http (>= 1)
+      faraday-retry (>= 1)
+      marcel (~> 1.0)
+      zeitwerk (~> 2)
     ruby_parser (3.20.0)
       sexp_processor (~> 4.16)
     sass (3.7.4)
@@ -895,6 +906,7 @@ DEPENDENCIES
   administrate (>= 0.20.1)
   administrate-field-active_storage (>= 1.0.3)
   administrate-field-belongs_to_search (>= 0.9.0)
+  ai-agents (>= 0.2.1)
   annotate
   attr_extras
   audited (~> 5.4, >= 5.4.1)
diff --git a/config/agents/tools.yml b/config/agents/tools.yml
new file mode 100644
index 000000000..b994e93d3
--- /dev/null
+++ b/config/agents/tools.yml
@@ -0,0 +1,26 @@
+######  Captain Agent Tools Configuration #######
+# id: Tool identifier used to resolve the class (Captain::Tools::{PascalCase(id)}Tool)
+# title: Human-readable tool name for frontend display
+# description: Brief description of what the tool does
+# icon: Icon name for frontend display (frontend icon system)
+#######################################################
+
+- id: add_contact_note
+  title: 'Add Contact Note'
+  description: 'Add a note to a contact profile'
+  icon: 'note-add'
+
+- id: add_private_note
+  title: 'Add Private Note'
+  description: 'Add a private note to a conversation (internal only)'
+  icon: 'eye-off'
+
+- id: update_priority
+  title: 'Update Priority'
+  description: 'Update conversation priority level'
+  icon: 'exclamation-triangle'
+
+- id: add_label_to_conversation
+  title: 'Add Label to Conversation'
+  description: 'Add a label to a conversation'
+  icon: 'tag'
diff --git a/config/routes.rb b/config/routes.rb
index f262febdf..681c21e44 100644
--- a/config/routes.rb
+++ b/config/routes.rb
@@ -56,6 +56,9 @@ Rails.application.routes.draw do
               member do
                 post :playground
               end
+              collection do
+                get :tools
+              end
               resources :inboxes, only: [:index, :create, :destroy], param: :inbox_id
               resources :scenarios
             end
diff --git a/enterprise/app/controllers/api/v1/accounts/captain/assistants_controller.rb b/enterprise/app/controllers/api/v1/accounts/captain/assistants_controller.rb
index 1bd928271..aaf81677a 100644
--- a/enterprise/app/controllers/api/v1/accounts/captain/assistants_controller.rb
+++ b/enterprise/app/controllers/api/v1/accounts/captain/assistants_controller.rb
@@ -32,6 +32,10 @@ class Api::V1::Accounts::Captain::AssistantsController < Api::V1::Accounts::Base
     render json: response
   end
 
+  def tools
+    @tools = Captain::Assistant.available_agent_tools
+  end
+
   private
 
   def set_assistant
diff --git a/enterprise/app/models/captain/assistant.rb b/enterprise/app/models/captain/assistant.rb
index 4ce4c4afd..cdf2b53f3 100644
--- a/enterprise/app/models/captain/assistant.rb
+++ b/enterprise/app/models/captain/assistant.rb
@@ -18,6 +18,7 @@
 #
 class Captain::Assistant < ApplicationRecord
   include Avatarable
+  include Concerns::CaptainToolsHelpers
 
   self.table_name = 'captain_assistants'
 
diff --git a/enterprise/app/models/captain/scenario.rb b/enterprise/app/models/captain/scenario.rb
index ff8e63c64..ecfba396f 100644
--- a/enterprise/app/models/captain/scenario.rb
+++ b/enterprise/app/models/captain/scenario.rb
@@ -21,6 +21,8 @@
 #  index_captain_scenarios_on_enabled                   (enabled)
 #
 class Captain::Scenario < ApplicationRecord
+  include Concerns::CaptainToolsHelpers
+
   self.table_name = 'captain_scenarios'
 
   belongs_to :assistant, class_name: 'Captain::Assistant'
@@ -31,14 +33,60 @@ class Captain::Scenario < ApplicationRecord
   validates :instruction, presence: true
   validates :assistant_id, presence: true
   validates :account_id, presence: true
+  validate :validate_instruction_tools
 
   scope :enabled, -> { where(enabled: true) }
 
-  before_save :populate_tools
+  before_save :resolve_tool_references
 
   private
 
-  def populate_tools
-    # TODO: Implement tools population logic
+  # Validates that all tool references in the instruction are valid.
+  # Parses the instruction for tool references and checks if they exist
+  # in the available tools configuration.
+  #
+  # @return [void]
+  # @api private
+  # @example Valid instruction
+  #   scenario.instruction = "Use [Add Contact Note](tool://add_contact_note) to document"
+  #   scenario.valid? # => true
+  #
+  # @example Invalid instruction
+  #   scenario.instruction = "Use [Invalid Tool](tool://invalid_tool) to process"
+  #   scenario.valid? # => false
+  #   scenario.errors[:instruction] # => ["contains invalid tools: invalid_tool"]
+  def validate_instruction_tools
+    return if instruction.blank?
+
+    tool_ids = extract_tool_ids_from_text(instruction)
+    return if tool_ids.empty?
+
+    available_tool_ids = self.class.available_tool_ids
+    invalid_tools = tool_ids - available_tool_ids
+
+    return unless invalid_tools.any?
+
+    errors.add(:instruction, "contains invalid tools: #{invalid_tools.join(', ')}")
+  end
+
+  # Resolves tool references from the instruction text into the tools field.
+  # Parses the instruction for tool references and materializes them as
+  # tool IDs stored in the tools JSONB field.
+  #
+  # @return [void]
+  # @api private
+  # @example
+  #   scenario.instruction = "First [@Add Private Note](tool://add_private_note) then [@Update Priority](tool://update_priority)"
+  #   scenario.save!
+  #   scenario.tools # => ["add_private_note", "update_priority"]
+  #
+  #   scenario.instruction = "No tools mentioned here"
+  #   scenario.save!
+  #   scenario.tools # => nil
+  def resolve_tool_references
+    return if instruction.blank?
+
+    tool_ids = extract_tool_ids_from_text(instruction)
+    self.tools = tool_ids.presence
   end
 end
diff --git a/enterprise/app/models/concerns/captain_tools_helpers.rb b/enterprise/app/models/concerns/captain_tools_helpers.rb
new file mode 100644
index 000000000..5a660310c
--- /dev/null
+++ b/enterprise/app/models/concerns/captain_tools_helpers.rb
@@ -0,0 +1,76 @@
+# Provides helper methods for working with Captain agent tools including
+# tool resolution, text parsing, and metadata retrieval.
+module Concerns::CaptainToolsHelpers
+  extend ActiveSupport::Concern
+
+  # Regular expression pattern for matching tool references in text.
+  # Matches patterns like [Tool name](tool://tool_id) following markdown link syntax.
+  TOOL_REFERENCE_REGEX = %r{\[[^\]]+\]\(tool://([^/)]+)\)}
+
+  class_methods do
+    # Returns all available agent tools with their metadata.
+    # Only includes tools that have corresponding class files and can be resolved.
+    #
+    # @return [Array<Hash>] Array of tool hashes with :id, :title, :description, :icon
+    def available_agent_tools
+      @available_agent_tools ||= load_agent_tools
+    end
+
+    # Resolves a tool class from a tool ID.
+    # Converts snake_case tool IDs to PascalCase class names and constantizes them.
+    #
+    # @param tool_id [String] The snake_case tool identifier
+    # @return [Class, nil] The tool class if found, nil if not resolvable
+    def resolve_tool_class(tool_id)
+      class_name = "Captain::Tools::#{tool_id.classify}Tool"
+      class_name.safe_constantize
+    end
+
+    # Returns an array of all available tool IDs.
+    # Convenience method that extracts just the IDs from available_agent_tools.
+    #
+    # @return [Array<String>] Array of available tool IDs
+    def available_tool_ids
+      @available_tool_ids ||= available_agent_tools.map { |tool| tool[:id] }
+    end
+
+    private
+
+    # Loads agent tools from the YAML configuration file.
+    # Filters out tools that cannot be resolved to actual classes.
+    #
+    # @return [Array<Hash>] Array of resolvable tools with metadata
+    # @api private
+    def load_agent_tools
+      tools_config = YAML.load_file(Rails.root.join('config/agents/tools.yml'))
+
+      tools_config.filter_map do |tool_config|
+        tool_class = resolve_tool_class(tool_config['id'])
+
+        if tool_class
+          {
+            id: tool_config['id'],
+            title: tool_config['title'],
+            description: tool_config['description'],
+            icon: tool_config['icon']
+          }
+        else
+          Rails.logger.warn "Tool class not found for ID: #{tool_config['id']}"
+          nil
+        end
+      end
+    end
+  end
+
+  # Extracts tool IDs from text containing tool references.
+  # Parses text for (tool://tool_id) patterns and returns unique tool IDs.
+  #
+  # @param text [String] Text to parse for tool references
+  # @return [Array<String>] Array of unique tool IDs found in the text
+  def extract_tool_ids_from_text(text)
+    return [] if text.blank?
+
+    tool_matches = text.scan(TOOL_REFERENCE_REGEX)
+    tool_matches.flatten.uniq
+  end
+end
diff --git a/enterprise/app/policies/captain/assistant_policy.rb b/enterprise/app/policies/captain/assistant_policy.rb
index 2a03fc0ea..7fbb47aa9 100644
--- a/enterprise/app/policies/captain/assistant_policy.rb
+++ b/enterprise/app/policies/captain/assistant_policy.rb
@@ -7,6 +7,10 @@ class Captain::AssistantPolicy < ApplicationPolicy
     true
   end
 
+  def tools?
+    @account_user.administrator?
+  end
+
   def create?
     @account_user.administrator?
   end
diff --git a/enterprise/app/views/api/v1/accounts/captain/assistants/tools.json.jbuilder b/enterprise/app/views/api/v1/accounts/captain/assistants/tools.json.jbuilder
new file mode 100644
index 000000000..3a993caeb
--- /dev/null
+++ b/enterprise/app/views/api/v1/accounts/captain/assistants/tools.json.jbuilder
@@ -0,0 +1,6 @@
+json.array! @tools do |tool|
+  json.id tool[:id]
+  json.title tool[:title]
+  json.description tool[:description]
+  json.icon tool[:icon]
+end
diff --git a/enterprise/lib/captain/tools/add_contact_note_tool.rb b/enterprise/lib/captain/tools/add_contact_note_tool.rb
new file mode 100644
index 000000000..e1475abf0
--- /dev/null
+++ b/enterprise/lib/captain/tools/add_contact_note_tool.rb
@@ -0,0 +1,26 @@
+class Captain::Tools::AddContactNoteTool < Captain::Tools::BasePublicTool
+  description 'Add a note to a contact profile'
+  param :note, type: 'string', desc: 'The note content to add to the contact'
+
+  def perform(tool_context, note:)
+    contact = find_contact(tool_context.state)
+    return 'Contact not found' unless contact
+
+    return 'Note content is required' if note.blank?
+
+    log_tool_usage('add_contact_note', { contact_id: contact.id, note_length: note.length })
+
+    create_contact_note(contact, note)
+    "Note added successfully to contact #{contact.name} (ID: #{contact.id})"
+  end
+
+  private
+
+  def create_contact_note(contact, note)
+    contact.notes.create!(content: note)
+  end
+
+  def permissions
+    %w[contact_manage]
+  end
+end
diff --git a/enterprise/lib/captain/tools/add_label_to_conversation_tool.rb b/enterprise/lib/captain/tools/add_label_to_conversation_tool.rb
new file mode 100644
index 000000000..429f33b7b
--- /dev/null
+++ b/enterprise/lib/captain/tools/add_label_to_conversation_tool.rb
@@ -0,0 +1,34 @@
+class Captain::Tools::AddLabelToConversationTool < Captain::Tools::BasePublicTool
+  description 'Add a label to a conversation'
+  param :label_name, type: 'string', desc: 'The name of the label to add'
+
+  def perform(tool_context, label_name:)
+    conversation = find_conversation(tool_context.state)
+    return 'Conversation not found' unless conversation
+
+    label_name = label_name&.strip&.downcase
+    return 'Label name is required' if label_name.blank?
+
+    label = find_label(label_name)
+    return 'Label not found' unless label
+
+    add_label_to_conversation(conversation, label_name)
+
+    log_tool_usage('added_label', conversation_id: conversation.id, label: label_name)
+
+    "Label '#{label_name}' added to conversation ##{conversation.display_id}"
+  end
+
+  private
+
+  def find_label(label_name)
+    account_scoped(Label).find_by(title: label_name)
+  end
+
+  def add_label_to_conversation(conversation, label_name)
+    conversation.add_labels(label_name)
+  rescue StandardError => e
+    Rails.logger.error "Failed to add label to conversation: #{e.message}"
+    raise
+  end
+end
diff --git a/enterprise/lib/captain/tools/add_private_note_tool.rb b/enterprise/lib/captain/tools/add_private_note_tool.rb
new file mode 100644
index 000000000..36e1ef977
--- /dev/null
+++ b/enterprise/lib/captain/tools/add_private_note_tool.rb
@@ -0,0 +1,33 @@
+class Captain::Tools::AddPrivateNoteTool < Captain::Tools::BasePublicTool
+  description 'Add a private note to a conversation'
+  param :note, type: 'string', desc: 'The private note content'
+
+  def perform(tool_context, note:)
+    conversation = find_conversation(tool_context.state)
+    return 'Conversation not found' unless conversation
+
+    return 'Note content is required' if note.blank?
+
+    log_tool_usage('add_private_note', { conversation_id: conversation.id, note_length: note.length })
+    create_private_note(conversation, note)
+
+    'Private note added successfully'
+  end
+
+  private
+
+  def create_private_note(conversation, note)
+    conversation.messages.create!(
+      account: @assistant.account,
+      inbox: conversation.inbox,
+      sender: @assistant,
+      message_type: :outgoing,
+      content: note,
+      private: true
+    )
+  end
+
+  def permissions
+    %w[conversation_manage conversation_unassigned_manage conversation_participating_manage]
+  end
+end
diff --git a/enterprise/lib/captain/tools/base_public_tool.rb b/enterprise/lib/captain/tools/base_public_tool.rb
new file mode 100644
index 000000000..e1f779b36
--- /dev/null
+++ b/enterprise/lib/captain/tools/base_public_tool.rb
@@ -0,0 +1,45 @@
+require 'agents'
+
+class Captain::Tools::BasePublicTool < Agents::Tool
+  def initialize(assistant)
+    @assistant = assistant
+    super()
+  end
+
+  def active?
+    # Public tools are always active
+    true
+  end
+
+  def permissions
+    # Override in subclasses to specify required permissions
+    # Returns empty array for public tools (no permissions required)
+    []
+  end
+
+  private
+
+  def account_scoped(model_class)
+    model_class.where(account_id: @assistant.account_id)
+  end
+
+  def find_conversation(state)
+    conversation_id = state&.dig(:conversation, :id)
+    return nil unless conversation_id
+
+    account_scoped(::Conversation).find_by(id: conversation_id)
+  end
+
+  def find_contact(state)
+    contact_id = state&.dig(:contact, :id)
+    return nil unless contact_id
+
+    account_scoped(::Contact).find_by(id: contact_id)
+  end
+
+  def log_tool_usage(action, details = {})
+    Rails.logger.info do
+      "#{self.class.name}: #{action} for assistant #{@assistant&.id} - #{details.inspect}"
+    end
+  end
+end
diff --git a/enterprise/lib/captain/tools/update_priority_tool.rb b/enterprise/lib/captain/tools/update_priority_tool.rb
new file mode 100644
index 000000000..8fc75f601
--- /dev/null
+++ b/enterprise/lib/captain/tools/update_priority_tool.rb
@@ -0,0 +1,48 @@
+class Captain::Tools::UpdatePriorityTool < Captain::Tools::BasePublicTool
+  description 'Update the priority of a conversation'
+  param :priority, type: 'string', desc: 'The priority level: low, medium, high, urgent, or nil to remove priority'
+
+  def perform(tool_context, priority:)
+    @conversation = find_conversation(tool_context.state)
+    return 'Conversation not found' unless @conversation
+
+    @normalized_priority = normalize_priority(priority)
+    return "Invalid priority. Valid options: #{valid_priority_options}" unless valid_priority?(@normalized_priority)
+
+    log_tool_usage('update_priority', { conversation_id: @conversation.id, priority: priority })
+
+    execute_priority_update
+  end
+
+  private
+
+  def execute_priority_update
+    update_conversation_priority(@conversation, @normalized_priority)
+    priority_text = @normalized_priority || 'none'
+    "Priority updated to '#{priority_text}' for conversation ##{@conversation.display_id}"
+  end
+
+  def normalize_priority(priority)
+    priority == 'nil' || priority.blank? ? nil : priority
+  end
+
+  def valid_priority?(priority)
+    valid_priorities.include?(priority)
+  end
+
+  def valid_priorities
+    @valid_priorities ||= [nil] + Conversation.priorities.keys
+  end
+
+  def valid_priority_options
+    (valid_priorities.compact + ['nil']).join(', ')
+  end
+
+  def update_conversation_priority(conversation, priority)
+    conversation.update!(priority: priority)
+  end
+
+  def permissions
+    %w[conversation_manage conversation_unassigned_manage conversation_participating_manage]
+  end
+end
diff --git a/spec/enterprise/lib/captain/tools/add_contact_note_tool_spec.rb b/spec/enterprise/lib/captain/tools/add_contact_note_tool_spec.rb
new file mode 100644
index 000000000..c087242dc
--- /dev/null
+++ b/spec/enterprise/lib/captain/tools/add_contact_note_tool_spec.rb
@@ -0,0 +1,116 @@
+require 'rails_helper'
+
+RSpec.describe Captain::Tools::AddContactNoteTool, type: :model do
+  let(:account) { create(:account) }
+  let(:assistant) { create(:captain_assistant, account: account) }
+  let(:tool) { described_class.new(assistant) }
+  let(:user) { create(:user, account: account) }
+  let(:inbox) { create(:inbox, account: account) }
+  let(:contact) { create(:contact, account: account) }
+  let(:conversation) { create(:conversation, account: account, inbox: inbox, contact: contact) }
+  let(:tool_context) { Struct.new(:state).new({ contact: { id: contact.id } }) }
+
+  describe '#description' do
+    it 'returns the correct description' do
+      expect(tool.description).to eq('Add a note to a contact profile')
+    end
+  end
+
+  describe '#parameters' do
+    it 'returns the correct parameters' do
+      expect(tool.parameters).to have_key(:note)
+      expect(tool.parameters[:note].name).to eq(:note)
+      expect(tool.parameters[:note].type).to eq('string')
+      expect(tool.parameters[:note].description).to eq('The note content to add to the contact')
+    end
+  end
+
+  describe '#perform' do
+    context 'when contact exists' do
+      context 'with valid note content' do
+        it 'creates a contact note and returns success message' do
+          note_content = 'This is a contact note'
+
+          expect do
+            result = tool.perform(tool_context, note: note_content)
+            expect(result).to eq("Note added successfully to contact #{contact.name} (ID: #{contact.id})")
+          end.to change(Note, :count).by(1)
+
+          created_note = Note.last
+          expect(created_note.content).to eq(note_content)
+          expect(created_note.account).to eq(account)
+          expect(created_note.contact).to eq(contact)
+          expect(created_note.user).to eq(assistant.account.users.first)
+        end
+
+        it 'logs tool usage' do
+          expect(tool).to receive(:log_tool_usage).with(
+            'add_contact_note',
+            { contact_id: contact.id, note_length: 19 }
+          )
+
+          tool.perform(tool_context, note: 'This is a test note')
+        end
+      end
+
+      context 'with blank note content' do
+        it 'returns error message' do
+          result = tool.perform(tool_context, note: '')
+          expect(result).to eq('Note content is required')
+        end
+
+        it 'does not create a note' do
+          expect do
+            tool.perform(tool_context, note: '')
+          end.not_to change(Note, :count)
+        end
+      end
+
+      context 'with nil note content' do
+        it 'returns error message' do
+          result = tool.perform(tool_context, note: nil)
+          expect(result).to eq('Note content is required')
+        end
+      end
+    end
+
+    context 'when contact does not exist' do
+      let(:tool_context) { Struct.new(:state).new({ contact: { id: 999_999 } }) }
+
+      it 'returns error message' do
+        result = tool.perform(tool_context, note: 'Some note')
+        expect(result).to eq('Contact not found')
+      end
+
+      it 'does not create a note' do
+        expect do
+          tool.perform(tool_context, note: 'Some note')
+        end.not_to change(Note, :count)
+      end
+    end
+
+    context 'when contact state is missing' do
+      let(:tool_context) { Struct.new(:state).new({}) }
+
+      it 'returns error message' do
+        result = tool.perform(tool_context, note: 'Some note')
+        expect(result).to eq('Contact not found')
+      end
+    end
+
+    context 'when contact id is nil' do
+      let(:tool_context) { Struct.new(:state).new({ contact: { id: nil } }) }
+
+      it 'returns error message' do
+        result = tool.perform(tool_context, note: 'Some note')
+        expect(result).to eq('Contact not found')
+      end
+    end
+  end
+
+  describe '#active?' do
+    it 'returns true for public tools' do
+      expect(tool.active?).to be true
+    end
+  end
+end
diff --git a/spec/enterprise/lib/captain/tools/add_label_to_conversation_tool_spec.rb b/spec/enterprise/lib/captain/tools/add_label_to_conversation_tool_spec.rb
new file mode 100644
index 000000000..38e4dc7c6
--- /dev/null
+++ b/spec/enterprise/lib/captain/tools/add_label_to_conversation_tool_spec.rb
@@ -0,0 +1,125 @@
+require 'rails_helper'
+
+RSpec.describe Captain::Tools::AddLabelToConversationTool, type: :model do
+  let(:account) { create(:account) }
+  let(:assistant) { create(:captain_assistant, account: account) }
+  let(:tool) { described_class.new(assistant) }
+  let(:user) { create(:user, account: account) }
+  let(:inbox) { create(:inbox, account: account) }
+  let(:contact) { create(:contact, account: account) }
+  let(:conversation) { create(:conversation, account: account, inbox: inbox, contact: contact) }
+  let(:label) { create(:label, account: account, title: 'urgent') }
+  let(:tool_context) { Struct.new(:state).new({ conversation: { id: conversation.id } }) }
+
+  describe '#description' do
+    it 'returns the correct description' do
+      expect(tool.description).to eq('Add a label to a conversation')
+    end
+  end
+
+  describe '#parameters' do
+    it 'returns the correct parameters' do
+      expect(tool.parameters).to have_key(:label_name)
+      expect(tool.parameters[:label_name].name).to eq(:label_name)
+      expect(tool.parameters[:label_name].type).to eq('string')
+      expect(tool.parameters[:label_name].description).to eq('The name of the label to add')
+    end
+  end
+
+  describe '#perform' do
+    context 'when conversation exists' do
+      context 'with valid label that exists' do
+        before { label }
+
+        it 'adds label to conversation and returns success message' do
+          result = tool.perform(tool_context, label_name: 'urgent')
+          expect(result).to eq("Label 'urgent' added to conversation ##{conversation.display_id}")
+
+          expect(conversation.reload.label_list).to include('urgent')
+        end
+
+        it 'logs tool usage' do
+          expect(tool).to receive(:log_tool_usage).with(
+            'added_label',
+            { conversation_id: conversation.id, label: 'urgent' }
+          )
+
+          tool.perform(tool_context, label_name: 'urgent')
+        end
+
+        it 'handles case insensitive label names' do
+          result = tool.perform(tool_context, label_name: 'URGENT')
+          expect(result).to eq("Label 'urgent' added to conversation ##{conversation.display_id}")
+        end
+
+        it 'strips whitespace from label names' do
+          result = tool.perform(tool_context, label_name: '  urgent  ')
+          expect(result).to eq("Label 'urgent' added to conversation ##{conversation.display_id}")
+        end
+      end
+
+      context 'with label that does not exist' do
+        it 'returns error message' do
+          result = tool.perform(tool_context, label_name: 'nonexistent')
+          expect(result).to eq('Label not found')
+        end
+
+        it 'does not add any labels to conversation' do
+          expect do
+            tool.perform(tool_context, label_name: 'nonexistent')
+          end.not_to(change { conversation.reload.labels.count })
+        end
+      end
+
+      context 'with blank label name' do
+        it 'returns error message for empty string' do
+          result = tool.perform(tool_context, label_name: '')
+          expect(result).to eq('Label name is required')
+        end
+
+        it 'returns error message for nil' do
+          result = tool.perform(tool_context, label_name: nil)
+          expect(result).to eq('Label name is required')
+        end
+
+        it 'returns error message for whitespace only' do
+          result = tool.perform(tool_context, label_name: '   ')
+          expect(result).to eq('Label name is required')
+        end
+      end
+    end
+
+    context 'when conversation does not exist' do
+      let(:tool_context) { Struct.new(:state).new({ conversation: { id: 999_999 } }) }
+
+      it 'returns error message' do
+        result = tool.perform(tool_context, label_name: 'urgent')
+        expect(result).to eq('Conversation not found')
+      end
+    end
+
+    context 'when conversation state is missing' do
+      let(:tool_context) { Struct.new(:state).new({}) }
+
+      it 'returns error message' do
+        result = tool.perform(tool_context, label_name: 'urgent')
+        expect(result).to eq('Conversation not found')
+      end
+    end
+
+    context 'when conversation id is nil' do
+      let(:tool_context) { Struct.new(:state).new({ conversation: { id: nil } }) }
+
+      it 'returns error message' do
+        result = tool.perform(tool_context, label_name: 'urgent')
+        expect(result).to eq('Conversation not found')
+      end
+    end
+  end
+
+  describe '#active?' do
+    it 'returns true for public tools' do
+      expect(tool.active?).to be true
+    end
+  end
+end
diff --git a/spec/enterprise/lib/captain/tools/add_private_note_tool_spec.rb b/spec/enterprise/lib/captain/tools/add_private_note_tool_spec.rb
new file mode 100644
index 000000000..cfce1a7d1
--- /dev/null
+++ b/spec/enterprise/lib/captain/tools/add_private_note_tool_spec.rb
@@ -0,0 +1,124 @@
+require 'rails_helper'
+
+RSpec.describe Captain::Tools::AddPrivateNoteTool, type: :model do
+  let(:account) { create(:account) }
+  let(:assistant) { create(:captain_assistant, account: account) }
+  let(:tool) { described_class.new(assistant) }
+  let(:user) { create(:user, account: account) }
+  let(:inbox) { create(:inbox, account: account) }
+  let(:contact) { create(:contact, account: account) }
+  let(:conversation) { create(:conversation, account: account, inbox: inbox, contact: contact) }
+  let(:tool_context) { Struct.new(:state).new({ conversation: { id: conversation.id } }) }
+
+  describe '#description' do
+    it 'returns the correct description' do
+      expect(tool.description).to eq('Add a private note to a conversation')
+    end
+  end
+
+  describe '#parameters' do
+    it 'returns the correct parameters' do
+      expect(tool.parameters).to have_key(:note)
+      expect(tool.parameters[:note].name).to eq(:note)
+      expect(tool.parameters[:note].type).to eq('string')
+      expect(tool.parameters[:note].description).to eq('The private note content')
+    end
+  end
+
+  describe '#perform' do
+    context 'when conversation exists' do
+      context 'with valid note content' do
+        it 'creates a private note and returns success message' do
+          note_content = 'This is a private note'
+
+          expect do
+            result = tool.perform(tool_context, note: note_content)
+            expect(result).to eq('Private note added successfully')
+          end.to change(Message, :count).by(1)
+        end
+
+        it 'creates a private note with correct attributes' do
+          note_content = 'This is a private note'
+
+          tool.perform(tool_context, note: note_content)
+
+          created_message = Message.last
+          expect(created_message.content).to eq(note_content)
+          expect(created_message.message_type).to eq('outgoing')
+          expect(created_message.private).to be true
+          expect(created_message.account).to eq(account)
+          expect(created_message.inbox).to eq(inbox)
+          expect(created_message.conversation).to eq(conversation)
+        end
+
+        it 'logs tool usage' do
+          expect(tool).to receive(:log_tool_usage).with(
+            'add_private_note',
+            { conversation_id: conversation.id, note_length: 19 }
+          )
+
+          tool.perform(tool_context, note: 'This is a test note')
+        end
+      end
+
+      context 'with blank note content' do
+        it 'returns error message' do
+          result = tool.perform(tool_context, note: '')
+          expect(result).to eq('Note content is required')
+        end
+
+        it 'does not create a message' do
+          expect do
+            tool.perform(tool_context, note: '')
+          end.not_to change(Message, :count)
+        end
+      end
+
+      context 'with nil note content' do
+        it 'returns error message' do
+          result = tool.perform(tool_context, note: nil)
+          expect(result).to eq('Note content is required')
+        end
+      end
+    end
+
+    context 'when conversation does not exist' do
+      let(:tool_context) { Struct.new(:state).new({ conversation: { id: 999_999 } }) }
+
+      it 'returns error message' do
+        result = tool.perform(tool_context, note: 'Some note')
+        expect(result).to eq('Conversation not found')
+      end
+
+      it 'does not create a message' do
+        expect do
+          tool.perform(tool_context, note: 'Some note')
+        end.not_to change(Message, :count)
+      end
+    end
+
+    context 'when conversation state is missing' do
+      let(:tool_context) { Struct.new(:state).new({}) }
+
+      it 'returns error message' do
+        result = tool.perform(tool_context, note: 'Some note')
+        expect(result).to eq('Conversation not found')
+      end
+    end
+
+    context 'when conversation id is nil' do
+      let(:tool_context) { Struct.new(:state).new({ conversation: { id: nil } }) }
+
+      it 'returns error message' do
+        result = tool.perform(tool_context, note: 'Some note')
+        expect(result).to eq('Conversation not found')
+      end
+    end
+  end
+
+  describe '#active?' do
+    it 'returns true for public tools' do
+      expect(tool.active?).to be true
+    end
+  end
+end
diff --git a/spec/enterprise/lib/captain/tools/update_priority_tool_spec.rb b/spec/enterprise/lib/captain/tools/update_priority_tool_spec.rb
new file mode 100644
index 000000000..9aa858593
--- /dev/null
+++ b/spec/enterprise/lib/captain/tools/update_priority_tool_spec.rb
@@ -0,0 +1,117 @@
+require 'rails_helper'
+
+RSpec.describe Captain::Tools::UpdatePriorityTool, type: :model do
+  let(:account) { create(:account) }
+  let(:assistant) { create(:captain_assistant, account: account) }
+  let(:tool) { described_class.new(assistant) }
+  let(:user) { create(:user, account: account) }
+  let(:inbox) { create(:inbox, account: account) }
+  let(:contact) { create(:contact, account: account) }
+  let(:conversation) { create(:conversation, account: account, inbox: inbox, contact: contact) }
+  let(:tool_context) { Struct.new(:state).new({ conversation: { id: conversation.id } }) }
+
+  describe '#description' do
+    it 'returns the correct description' do
+      expect(tool.description).to eq('Update the priority of a conversation')
+    end
+  end
+
+  describe '#parameters' do
+    it 'returns the correct parameters' do
+      expect(tool.parameters).to have_key(:priority)
+      expect(tool.parameters[:priority].name).to eq(:priority)
+      expect(tool.parameters[:priority].type).to eq('string')
+      expect(tool.parameters[:priority].description).to eq('The priority level: low, medium, high, urgent, or nil to remove priority')
+    end
+  end
+
+  describe '#perform' do
+    context 'when conversation exists' do
+      context 'with valid priority levels' do
+        %w[low medium high urgent].each do |priority|
+          it "updates conversation priority to #{priority}" do
+            result = tool.perform(tool_context, priority: priority)
+            expect(result).to eq("Priority updated to '#{priority}' for conversation ##{conversation.display_id}")
+
+            expect(conversation.reload.priority).to eq(priority)
+          end
+        end
+
+        it 'removes priority when set to nil' do
+          conversation.update!(priority: 'high')
+
+          result = tool.perform(tool_context, priority: 'nil')
+          expect(result).to eq("Priority updated to 'none' for conversation ##{conversation.display_id}")
+
+          expect(conversation.reload.priority).to be_nil
+        end
+
+        it 'removes priority when set to empty string' do
+          conversation.update!(priority: 'high')
+
+          result = tool.perform(tool_context, priority: '')
+          expect(result).to eq("Priority updated to 'none' for conversation ##{conversation.display_id}")
+
+          expect(conversation.reload.priority).to be_nil
+        end
+
+        it 'logs tool usage' do
+          expect(tool).to receive(:log_tool_usage).with(
+            'update_priority',
+            { conversation_id: conversation.id, priority: 'high' }
+          )
+
+          tool.perform(tool_context, priority: 'high')
+        end
+      end
+
+      context 'with invalid priority levels' do
+        it 'returns error message for invalid priority' do
+          result = tool.perform(tool_context, priority: 'invalid')
+          expect(result).to eq('Invalid priority. Valid options: low, medium, high, urgent, nil')
+        end
+
+        it 'does not update conversation priority' do
+          original_priority = conversation.priority
+
+          tool.perform(tool_context, priority: 'invalid')
+
+          expect(conversation.reload.priority).to eq(original_priority)
+        end
+      end
+    end
+
+    context 'when conversation does not exist' do
+      let(:tool_context) { Struct.new(:state).new({ conversation: { id: 999_999 } }) }
+
+      it 'returns error message' do
+        result = tool.perform(tool_context, priority: 'high')
+        expect(result).to eq('Conversation not found')
+      end
+    end
+
+    context 'when conversation state is missing' do
+      let(:tool_context) { Struct.new(:state).new({}) }
+
+      it 'returns error message' do
+        result = tool.perform(tool_context, priority: 'high')
+        expect(result).to eq('Conversation not found')
+      end
+    end
+
+    context 'when conversation id is nil' do
+      let(:tool_context) { Struct.new(:state).new({ conversation: { id: nil } }) }
+
+      it 'returns error message' do
+        result = tool.perform(tool_context, priority: 'high')
+        expect(result).to eq('Conversation not found')
+      end
+    end
+  end
+
+  describe '#active?' do
+    it 'returns true for public tools' do
+      expect(tool.active?).to be true
+    end
+  end
+end
diff --git a/spec/enterprise/models/captain/scenario_spec.rb b/spec/enterprise/models/captain/scenario_spec.rb
index 1f13a362b..7a39559c3 100644
--- a/spec/enterprise/models/captain/scenario_spec.rb
+++ b/spec/enterprise/models/captain/scenario_spec.rb
@@ -33,15 +33,119 @@ RSpec.describe Captain::Scenario, type: :model do
     let(:account) { create(:account) }
     let(:assistant) { create(:captain_assistant, account: account) }
 
-    describe 'before_save :populate_tools' do
-      it 'calls populate_tools before saving' do
+    describe 'before_save :resolve_tool_references' do
+      it 'calls resolve_tool_references before saving' do
         scenario = build(:captain_scenario, assistant: assistant, account: account)
-        expect(scenario).to receive(:populate_tools)
+        expect(scenario).to receive(:resolve_tool_references)
         scenario.save
       end
     end
   end
 
+  describe 'tool validation and population' do
+    let(:account) { create(:account) }
+    let(:assistant) { create(:captain_assistant, account: account) }
+
+    before do
+      # Mock available tools
+      allow(described_class).to receive(:available_tool_ids).and_return(%w[
+                                                                          add_contact_note add_private_note update_priority
+                                                                        ])
+    end
+
+    describe 'validate_instruction_tools' do
+      it 'is valid with valid tool references' do
+        scenario = build(:captain_scenario,
+                         assistant: assistant,
+                         account: account,
+                         instruction: 'Use [@Add Contact Note](tool://add_contact_note) to document')
+
+        expect(scenario).to be_valid
+      end
+
+      it 'is invalid with invalid tool references' do
+        scenario = build(:captain_scenario,
+                         assistant: assistant,
+                         account: account,
+                         instruction: 'Use [@Invalid Tool](tool://invalid_tool) to process')
+
+        expect(scenario).not_to be_valid
+        expect(scenario.errors[:instruction]).to include('contains invalid tools: invalid_tool')
+      end
+
+      it 'is invalid with multiple invalid tools' do
+        scenario = build(:captain_scenario,
+                         assistant: assistant,
+                         account: account,
+                         instruction: 'Use [@Invalid Tool](tool://invalid_tool) and [@Another Invalid](tool://another_invalid)')
+
+        expect(scenario).not_to be_valid
+        expect(scenario.errors[:instruction]).to include('contains invalid tools: invalid_tool, another_invalid')
+      end
+
+      it 'is valid with no tool references' do
+        scenario = build(:captain_scenario,
+                         assistant: assistant,
+                         account: account,
+                         instruction: 'Just respond politely to the customer')
+
+        expect(scenario).to be_valid
+      end
+
+      it 'is valid with blank instruction' do
+        scenario = build(:captain_scenario,
+                         assistant: assistant,
+                         account: account,
+                         instruction: '')
+
+        # Will be invalid due to presence validation, not tool validation
+        expect(scenario).not_to be_valid
+        expect(scenario.errors[:instruction]).not_to include(/contains invalid tools/)
+      end
+    end
+
+    describe 'resolve_tool_references' do
+      it 'populates tools array with referenced tool IDs' do
+        scenario = create(:captain_scenario,
+                          assistant: assistant,
+                          account: account,
+                          instruction: 'First [@Add Contact Note](tool://add_contact_note) then [@Update Priority](tool://update_priority)')
+
+        expect(scenario.tools).to eq(%w[add_contact_note update_priority])
+      end
+
+      it 'sets tools to nil when no tools are referenced' do
+        scenario = create(:captain_scenario,
+                          assistant: assistant,
+                          account: account,
+                          instruction: 'Just respond politely to the customer')
+
+        expect(scenario.tools).to be_nil
+      end
+
+      it 'handles duplicate tool references' do
+        scenario = create(:captain_scenario,
+                          assistant: assistant,
+                          account: account,
+                          instruction: 'Use [@Add Contact Note](tool://add_contact_note) and [@Add Contact Note](tool://add_contact_note) again')
+
+        expect(scenario.tools).to eq(['add_contact_note'])
+      end
+
+      it 'updates tools when instruction changes' do
+        scenario = create(:captain_scenario,
+                          assistant: assistant,
+                          account: account,
+                          instruction: 'Use [@Add Contact Note](tool://add_contact_note)')
+
+        expect(scenario.tools).to eq(['add_contact_note'])
+
+        scenario.update!(instruction: 'Use [@Update Priority](tool://update_priority) instead')
+        expect(scenario.tools).to eq(['update_priority'])
+      end
+    end
+  end
+
   describe 'factory' do
     it 'creates a valid scenario with associations' do
       account = create(:account)
diff --git a/spec/enterprise/models/concerns/captain_tools_helpers_spec.rb b/spec/enterprise/models/concerns/captain_tools_helpers_spec.rb
new file mode 100644
index 000000000..afe482385
--- /dev/null
+++ b/spec/enterprise/models/concerns/captain_tools_helpers_spec.rb
@@ -0,0 +1,180 @@
+require 'rails_helper'
+
+RSpec.describe Concerns::CaptainToolsHelpers, type: :concern do
+  # Create a test class that includes the concern
+  let(:test_class) do
+    Class.new do
+      include Concerns::CaptainToolsHelpers
+
+      def self.name
+        'TestClass'
+      end
+    end
+  end
+
+  let(:test_instance) { test_class.new }
+
+  describe 'TOOL_REFERENCE_REGEX' do
+    it 'matches tool references in text' do
+      text = 'Use [@Add Contact Note](tool://add_contact_note) and [Update Priority](tool://update_priority)'
+      matches = text.scan(Concerns::CaptainToolsHelpers::TOOL_REFERENCE_REGEX)
+
+      expect(matches.flatten).to eq(%w[add_contact_note update_priority])
+    end
+
+    it 'does not match invalid formats' do
+      invalid_formats = [
+        '<tool://invalid>',
+        'tool://invalid',
+        '(tool:invalid)',
+        '(tool://)',
+        '(tool://with/slash)',
+        '(tool://add_contact_note)',
+        '[@Tool](tool://)',
+        '[Tool](tool://with/slash)',
+        '[](tool://valid)'
+      ]
+
+      invalid_formats.each do |format|
+        matches = format.scan(Concerns::CaptainToolsHelpers::TOOL_REFERENCE_REGEX)
+        expect(matches).to be_empty, "Should not match: #{format}"
+      end
+    end
+  end
+
+  describe '.available_agent_tools' do
+    before do
+      # Mock the YAML file loading
+      allow(YAML).to receive(:load_file).and_return([
+                                                      {
+                                                        'id' => 'add_contact_note',
+                                                        'title' => 'Add Contact Note',
+                                                        'description' => 'Add a note to a contact',
+                                                        'icon' => 'note-add'
+                                                      },
+                                                      {
+                                                        'id' => 'invalid_tool',
+                                                        'title' => 'Invalid Tool',
+                                                        'description' => 'This tool does not exist',
+                                                        'icon' => 'invalid'
+                                                      }
+                                                    ])
+
+      # Mock class resolution - only add_contact_note exists
+      allow(test_class).to receive(:resolve_tool_class) do |tool_id|
+        case tool_id
+        when 'add_contact_note'
+          Captain::Tools::AddContactNoteTool
+        end
+      end
+    end
+
+    it 'returns only resolvable tools' do
+      tools = test_class.available_agent_tools
+
+      expect(tools.length).to eq(1)
+      expect(tools.first).to eq({
+                                  id: 'add_contact_note',
+                                  title: 'Add Contact Note',
+                                  description: 'Add a note to a contact',
+                                  icon: 'note-add'
+                                })
+    end
+
+    it 'logs warnings for unresolvable tools' do
+      expect(Rails.logger).to receive(:warn).with('Tool class not found for ID: invalid_tool')
+
+      test_class.available_agent_tools
+    end
+
+    it 'memoizes the result' do
+      expect(YAML).to receive(:load_file).once.and_return([])
+
+      2.times { test_class.available_agent_tools }
+    end
+  end
+
+  describe '.resolve_tool_class' do
+    it 'resolves valid tool classes' do
+      # Mock the constantize to return a class
+      stub_const('Captain::Tools::AddContactNoteTool', Class.new)
+
+      result = test_class.resolve_tool_class('add_contact_note')
+      expect(result).to eq(Captain::Tools::AddContactNoteTool)
+    end
+
+    it 'returns nil for invalid tool classes' do
+      result = test_class.resolve_tool_class('invalid_tool')
+      expect(result).to be_nil
+    end
+
+    it 'converts snake_case to PascalCase' do
+      stub_const('Captain::Tools::AddPrivateNoteTool', Class.new)
+
+      result = test_class.resolve_tool_class('add_private_note')
+      expect(result).to eq(Captain::Tools::AddPrivateNoteTool)
+    end
+  end
+
+  describe '.available_tool_ids' do
+    before do
+      allow(test_class).to receive(:available_agent_tools).and_return([
+                                                                        { id: 'add_contact_note', title: 'Add Contact Note', description: '...',
+                                                                          icon: 'note' },
+                                                                        { id: 'update_priority', title: 'Update Priority', description: '...',
+                                                                          icon: 'priority' }
+                                                                      ])
+    end
+
+    it 'returns array of tool IDs' do
+      ids = test_class.available_tool_ids
+      expect(ids).to eq(%w[add_contact_note update_priority])
+    end
+
+    it 'memoizes the result' do
+      expect(test_class).to receive(:available_agent_tools).once.and_return([])
+
+      2.times { test_class.available_tool_ids }
+    end
+  end
+
+  describe '#extract_tool_ids_from_text' do
+    it 'extracts tool IDs from text' do
+      text = 'First [@Add Contact Note](tool://add_contact_note) then [@Update Priority](tool://update_priority)'
+      result = test_instance.extract_tool_ids_from_text(text)
+
+      expect(result).to eq(%w[add_contact_note update_priority])
+    end
+
+    it 'returns unique tool IDs' do
+      text = 'Use [@Add Contact Note](tool://add_contact_note) and [@Contact Note](tool://add_contact_note) again'
+      result = test_instance.extract_tool_ids_from_text(text)
+
+      expect(result).to eq(['add_contact_note'])
+    end
+
+    it 'returns empty array for blank text' do
+      expect(test_instance.extract_tool_ids_from_text('')).to eq([])
+      expect(test_instance.extract_tool_ids_from_text(nil)).to eq([])
+      expect(test_instance.extract_tool_ids_from_text('   ')).to eq([])
+    end
+
+    it 'returns empty array when no tools found' do
+      text = 'This text has no tool references'
+      result = test_instance.extract_tool_ids_from_text(text)
+
+      expect(result).to eq([])
+    end
+
+    it 'handles complex text with multiple tools' do
+      text = <<~TEXT
+        Start with [@Add Contact Note](tool://add_contact_note) to document.
+        Then use [@Update Priority](tool://update_priority) if needed.
+        Finally [@Add Private Note](tool://add_private_note) for internal notes.
+      TEXT
+
+      result = test_instance.extract_tool_ids_from_text(text)
+      expect(result).to eq(%w[add_contact_note update_priority add_private_note])
+    end
+  end
+end