diff --git a/enterprise/app/jobs/captain/lifecycle/dispatcher_job.rb b/enterprise/app/jobs/captain/lifecycle/dispatcher_job.rb
new file mode 100644
index 000000000..69ebe66d1
--- /dev/null
+++ b/enterprise/app/jobs/captain/lifecycle/dispatcher_job.rb
@@ -0,0 +1,13 @@
+# frozen_string_literal: true
+
+class Captain::Lifecycle::DispatcherJob < ApplicationJob
+  queue_as :default
+
+  def self.perform_at(fire_at, delivery_id)
+    set(wait_until: fire_at).perform_later(delivery_id)
+  end
+
+  def perform(delivery_id)
+    # Stub — full implementation lands in Task 16.
+  end
+end
diff --git a/enterprise/app/services/captain/lifecycle/scheduler.rb b/enterprise/app/services/captain/lifecycle/scheduler.rb
new file mode 100644
index 000000000..18bf23e7b
--- /dev/null
+++ b/enterprise/app/services/captain/lifecycle/scheduler.rb
@@ -0,0 +1,60 @@
+# frozen_string_literal: true
+
+class Captain::Lifecycle::Scheduler
+  CHECKIN_EVENTS = %w[checkin.scheduled_at checkin.detected].freeze
+
+  class << self
+    def schedule_for(reservation)
+      rules = Captain::Lifecycle::Rule
+              .where(account_id: reservation.account_id)
+              .active
+      rules.each { |rule| schedule_one_rule(reservation, rule) }
+    end
+
+    def cancel_pending(reservation)
+      Captain::Lifecycle::Delivery
+        .where(captain_reservation_id: reservation.id, status: 'scheduled')
+        .update_all(status: 'cancelled', updated_at: Time.current) # rubocop:disable Rails/SkipsModelValidations
+    end
+
+    def reschedule_for_checkin_change(reservation)
+      Captain::Lifecycle::Delivery
+        .where(captain_reservation_id: reservation.id, status: 'scheduled')
+        .joins('INNER JOIN captain_lifecycle_rules ON captain_lifecycle_rules.id = captain_lifecycle_deliveries.lifecycle_rule_id')
+        .where(captain_lifecycle_rules: { event: CHECKIN_EVENTS })
+        .update_all(status: 'cancelled', updated_at: Time.current) # rubocop:disable Rails/SkipsModelValidations
+
+      Captain::Lifecycle::Rule
+        .where(account_id: reservation.account_id, event: CHECKIN_EVENTS)
+        .active
+        .each { |rule| schedule_one_rule(reservation, rule) }
+    end
+
+    private
+
+    def schedule_one_rule(reservation, rule)
+      return unless rule.matches_reservation?(reservation)
+
+      fire_at = compute_fire_at(reservation, rule)
+      return if fire_at.nil? || fire_at <= Time.current
+
+      delivery = Captain::Lifecycle::Delivery.create!(
+        account_id: reservation.account_id,
+        lifecycle_rule_id: rule.id,
+        captain_reservation_id: reservation.id,
+        inbox_id: reservation.unit&.concierge_inbox_id,
+        fire_at: fire_at,
+        status: 'scheduled',
+        origin: 'scheduled_lifecycle'
+      )
+      Captain::Lifecycle::DispatcherJob.perform_at(fire_at, delivery.id)
+    end
+
+    def compute_fire_at(reservation, rule)
+      event_time = Captain::Lifecycle::EventResolver.resolve(reservation, rule.event)
+      return nil if event_time.nil?
+
+      event_time + rule.offset_minutes.minutes
+    end
+  end
+end
diff --git a/spec/enterprise/services/captain/lifecycle/scheduler_spec.rb b/spec/enterprise/services/captain/lifecycle/scheduler_spec.rb
new file mode 100644
index 000000000..f3c1ee5b4
--- /dev/null
+++ b/spec/enterprise/services/captain/lifecycle/scheduler_spec.rb
@@ -0,0 +1,103 @@
+# frozen_string_literal: true
+
+require 'rails_helper'
+
+RSpec.describe Captain::Lifecycle::Scheduler do
+  let(:account) { create(:account) }
+  let(:brand) { create(:captain_brand, account: account) }
+  let(:unit) { Captain::Unit.create!(account: account, brand: brand, name: 'Test Unit') }
+  let(:reservation) do
+    create(:captain_reservation,
+           account: account,
+           unit: unit,
+           check_in_at: 2.hours.from_now,
+           check_out_at: 10.hours.from_now)
+  end
+
+  describe '.schedule_for' do
+    let!(:matching_rule) do
+      create(:captain_lifecycle_rule,
+             account: account,
+             event: 'checkin.scheduled_at',
+             offset_minutes: -10)
+    end
+
+    it 'creates a scheduled delivery for each matching enabled rule' do
+      expect { described_class.schedule_for(reservation) }
+        .to change(Captain::Lifecycle::Delivery, :count).by(1)
+    end
+
+    it 'sets fire_at to event_time + offset' do
+      described_class.schedule_for(reservation)
+      delivery = Captain::Lifecycle::Delivery.last
+      expect(delivery.fire_at).to be_within(1.second).of(reservation.check_in_at - 10.minutes)
+    end
+
+    it 'enqueues a Sidekiq job for fire_at' do
+      expect(Captain::Lifecycle::DispatcherJob).to receive(:perform_at)
+        .with(kind_of(Time), kind_of(Integer))
+      described_class.schedule_for(reservation)
+    end
+
+    it 'skips disabled rules' do
+      matching_rule.update!(enabled: false)
+      expect { described_class.schedule_for(reservation) }
+        .not_to change(Captain::Lifecycle::Delivery, :count)
+    end
+
+    it 'skips rules where filter does not match' do
+      matching_rule.update!(filters: { 'categorias' => ['DoesNotExist'] })
+      expect { described_class.schedule_for(reservation) }
+        .not_to change(Captain::Lifecycle::Delivery, :count)
+    end
+  end
+
+  describe '.cancel_pending' do
+    let!(:delivery) do
+      create(:captain_lifecycle_delivery,
+             account: account,
+             captain_reservation: reservation,
+             status: 'scheduled')
+    end
+    let!(:sent) do
+      create(:captain_lifecycle_delivery,
+             account: account,
+             captain_reservation: reservation,
+             status: 'sent')
+    end
+
+    it 'marks scheduled deliveries as cancelled' do
+      described_class.cancel_pending(reservation)
+      expect(delivery.reload.status).to eq('cancelled')
+    end
+
+    it 'does not touch sent deliveries' do
+      described_class.cancel_pending(reservation)
+      expect(sent.reload.status).to eq('sent')
+    end
+  end
+
+  describe '.reschedule_for_checkin_change' do
+    let!(:checkin_rule) do
+      create(:captain_lifecycle_rule,
+             account: account,
+             event: 'checkin.scheduled_at',
+             offset_minutes: -10)
+    end
+
+    before do
+      create(:captain_lifecycle_rule,
+             account: account,
+             event: 'reservation.confirmed',
+             offset_minutes: 0)
+      described_class.schedule_for(reservation)
+    end
+
+    it 'cancels checkin-based scheduled deliveries' do
+      expect { described_class.reschedule_for_checkin_change(reservation) }
+        .to(change do
+          Captain::Lifecycle::Delivery.where(lifecycle_rule_id: checkin_rule.id, status: 'cancelled').count
+        end)
+    end
+  end
+end