diff --git a/enterprise/app/models/captain/assistant.rb b/enterprise/app/models/captain/assistant.rb
index 4f039d57a..08bff5ef3 100644
--- a/enterprise/app/models/captain/assistant.rb
+++ b/enterprise/app/models/captain/assistant.rb
@@ -106,7 +106,7 @@ class Captain::Assistant < ApplicationRecord
       scenarios: scenarios.enabled.map do |scenario|
         {
           title: scenario.title,
-          key: scenario.title.parameterize.underscore,
+          key: scenario.handoff_key,
           description: scenario.description
         }
       end,
diff --git a/enterprise/app/models/captain/scenario.rb b/enterprise/app/models/captain/scenario.rb
index c43468804..8a6a3c979 100644
--- a/enterprise/app/models/captain/scenario.rb
+++ b/enterprise/app/models/captain/scenario.rb
@@ -24,6 +24,19 @@ class Captain::Scenario < ApplicationRecord
   include Concerns::CaptainToolsHelpers
   include Concerns::Agentable
 
+  # OpenAI enforces a 64-char limit on function names. The ai-agents gem
+  # prepends "handoff_to_" (11 chars), so we keep a safety margin and cap
+  # the full tool name to MAX_HANDOFF_TOOL_NAME_LENGTH (60 chars).
+  # Format: "scenario_{id}_{slug}_agent" for persisted records (stable + readable),
+  # and "scenario_draft_{slug}_agent" for unsaved records, with slug truncated
+  # based on the available length budget.
+  HANDOFF_TOOL_PREFIX = 'handoff_to_'.freeze
+  HANDOFF_KEY_PREFIX = 'scenario'.freeze
+  HANDOFF_KEY_SUFFIX = 'agent'.freeze
+  MAX_HANDOFF_TOOL_NAME_LENGTH = 60
+  MAX_AGENT_NAME_LENGTH = MAX_HANDOFF_TOOL_NAME_LENGTH - HANDOFF_TOOL_PREFIX.length
+  MAX_HANDOFF_SLUG_LENGTH = 24
+
   self.table_name = 'captain_scenarios'
 
   belongs_to :assistant, class_name: 'Captain::Assistant'
@@ -42,6 +55,10 @@ class Captain::Scenario < ApplicationRecord
 
   before_save :resolve_tool_references
 
+  def handoff_key
+    [handoff_id_key, compact_handoff_slug, HANDOFF_KEY_SUFFIX].compact.join('_')
+  end
+
   def prompt_context
     {
       title: title,
@@ -56,7 +73,28 @@ class Captain::Scenario < ApplicationRecord
   private
 
   def agent_name
-    "#{title} Agent".parameterize(separator: '_')
+    handoff_key
+  end
+
+  def handoff_id_key
+    return "#{HANDOFF_KEY_PREFIX}_#{id}" if id.present?
+
+    "#{HANDOFF_KEY_PREFIX}_draft"
+  end
+
+  def compact_handoff_slug
+    slug = title.to_s.parameterize(separator: '_').presence
+    return nil if slug.blank?
+
+    max_slug_length = [MAX_HANDOFF_SLUG_LENGTH, dynamic_slug_max_length].min
+    return nil if max_slug_length <= 0
+
+    slug.first(max_slug_length).sub(/_+\z/, '').presence
+  end
+
+  def dynamic_slug_max_length
+    # handoff_to_#{scenario_<id>_<slug>_agent}
+    MAX_AGENT_NAME_LENGTH - handoff_id_key.length - HANDOFF_KEY_SUFFIX.length - 2
   end
 
   def agent_tools
diff --git a/spec/enterprise/models/captain/scenario_spec.rb b/spec/enterprise/models/captain/scenario_spec.rb
index 163581f01..94ce5325a 100644
--- a/spec/enterprise/models/captain/scenario_spec.rb
+++ b/spec/enterprise/models/captain/scenario_spec.rb
@@ -42,6 +42,45 @@ RSpec.describe Captain::Scenario, type: :model do
     end
   end
 
+  describe '#handoff_key' do
+    let(:account) { create(:account) }
+    let(:assistant) { create(:captain_assistant, account: account) }
+
+    it 'uses id plus readable slug for persisted scenarios' do
+      scenario = create(:captain_scenario, assistant: assistant, account: account,
+                                           title: 'Handle complex refund requests requiring manager approval steps')
+
+      expect(scenario.handoff_key).to start_with("scenario_#{scenario.id}_")
+      expect(scenario.handoff_key).to end_with('_agent')
+      expect("handoff_to_#{scenario.handoff_key}".length).to be <= 60
+    end
+
+    it 'uses a truncated slug key for unsaved scenarios' do
+      scenario = build(:captain_scenario, assistant: assistant, account: account,
+                                          title: 'Troubleshoot payment gateway errors for recurring subscription charges')
+
+      expect(scenario.handoff_key).to match(/\Ascenario_draft_[a-z0-9_]+_agent\z/)
+      expect("handoff_to_#{scenario.handoff_key}".length).to be <= 60
+    end
+
+    it 'stays within length budget even for large ids' do
+      scenario = build(:captain_scenario, assistant: assistant, account: account,
+                                          title: 'A very long scenario title used only for budget verification')
+      allow(scenario).to receive(:id).and_return(1_234_567_890_123_456_789)
+
+      expect("handoff_to_#{scenario.handoff_key}".length).to be <= 60
+    end
+
+    it 'exposes handoff keys in assistant prompt context' do
+      scenario = create(:captain_scenario, assistant: assistant, account: account)
+
+      prompt_context = assistant.send(:prompt_context)
+      scenario_config = prompt_context[:scenarios].find { |entry| entry[:title] == scenario.title }
+
+      expect(scenario_config[:key]).to eq(scenario.handoff_key)
+    end
+  end
+
   describe 'tool validation and population' do
     let(:account) { create(:account) }
     let(:assistant) { create(:captain_assistant, account: account) }