diff --git a/lib/activerecord-bitemporal/bitemporal.rb b/lib/activerecord-bitemporal/bitemporal.rb
index 35778ff..d9e48b3 100644
--- a/lib/activerecord-bitemporal/bitemporal.rb
+++ b/lib/activerecord-bitemporal/bitemporal.rb
@@ -344,16 +344,17 @@ def _update_row(attribute_names, attempted_action = 'update')
         end || false
       end
 
-      def destroy(force_delete: false, operated_at: Time.current)
+      def destroy(force_delete: false, operated_at: nil)
         return super() if force_delete
 
-        target_datetime = valid_datetime || operated_at
-
-        duplicated_instance = self.class.find_at_time(target_datetime, self.id).dup
-
         ActiveRecord::Base.transaction(requires_new: true, joinable: false) do
           @destroyed = false
           _run_destroy_callbacks {
+            operated_at ||= Time.current
+            target_datetime = valid_datetime || operated_at
+
+            duplicated_instance = self.class.find_at_time(target_datetime, self.id).dup
+
             @destroyed = update_transaction_to(operated_at)
             @previously_force_updated = force_update?
 
diff --git a/spec/activerecord-bitemporal/bitemporal_spec.rb b/spec/activerecord-bitemporal/bitemporal_spec.rb
index ed9661c..68b9e5c 100644
--- a/spec/activerecord-bitemporal/bitemporal_spec.rb
+++ b/spec/activerecord-bitemporal/bitemporal_spec.rb
@@ -1065,26 +1065,53 @@ class EmployeeWithUniquness < Employee
       )
     end
 
-    it "create state-destroy record before _run_destroy_callbacks" do
+    it "create state-destroy record around _run_destroy_callbacks" do
       before_count = Employee.ignore_valid_datetime.count
       before_count_within_deleted = Employee.ignore_valid_datetime.within_deleted.count
 
       self_ = self
+
+      before_destroy_called = false
       employee.define_singleton_method(:on_before_destroy) do
+        before_destroy_called = true
+        # Should not be deleted in before_destroy callbacks
         self_.instance_exec { expect(Employee.ignore_valid_datetime.count).to eq before_count }
         self_.instance_exec { expect(Employee.ignore_valid_datetime.within_deleted.count).to eq before_count_within_deleted }
-      rescue => e
-        self_.instance_exec { expect(e).to eq true }
       end
 
+      after_destroy_called = false
       employee.define_singleton_method(:on_after_destroy) do
+        after_destroy_called = true
+        # Should be deleted in after_destroy callbacks
         self_.instance_exec { expect(Employee.ignore_valid_datetime.count).to eq before_count }
         self_.instance_exec { expect(Employee.ignore_valid_datetime.within_deleted.count).to eq before_count_within_deleted + 1 }
-      rescue => e
-        self_.instance_exec { expect(e).to eq true }
       end
 
       subject
+
+      expect(before_destroy_called).to be true
+      expect(after_destroy_called).to be true
+    end
+
+    context "with associations" do
+      let!(:employee) { Timecop.freeze(created_time) { Employee.create!(name: "Jone", address: Address.new(city: "Tokyo")) } }
+
+      # NOTE: Do not freeze time to record each deleted time
+      subject { employee.destroy }
+
+      it 'deletes address earlier than employee' do
+        expect {
+          subject
+        }.to change(Employee, :count).by(-1)
+        .and change(employee, :valid_to)
+        .and change(employee, :transaction_from)
+        .and change(Address, :count).by(-1)
+        .and change(employee.address, :valid_to)
+        .and change(employee.address, :transaction_from)
+
+        expect(employee.address.valid_to).to be < employee.valid_to
+        expect(employee.address.transaction_from).to be < employee.transaction_from
+      end
     end
 
     context "when raise exception" do
diff --git a/spec/schema.rb b/spec/schema.rb
index 1eae904..5c23f79 100644
--- a/spec/schema.rb
+++ b/spec/schema.rb
@@ -116,8 +116,8 @@ class Employee < ActiveRecord::Base
 
   belongs_to :company, foreign_key: :company_id
 
-  has_one  :address,   foreign_key: :employee_id
-  has_one  :address_without_bitemporal,  foreign_key: :employee_id
+  has_one  :address,   foreign_key: :employee_id, dependent: :destroy
+  has_one  :address_without_bitemporal,  foreign_key: :employee_id, dependent: :destroy
 
   class <<self
     attr_accessor :call_after_save_count
@@ -147,8 +147,8 @@ def on_after_destroy
 class EmployeeWithoutBitemporal < ActiveRecord::Base
   belongs_to :company, foreign_key: :company_id
 
-  has_one  :address,   foreign_key: :employee_id
-  has_one  :address_without_bitemporal,  foreign_key: :employee_id
+  has_one  :address,   foreign_key: :employee_id, dependent: :destroy
+  has_one  :address_without_bitemporal,  foreign_key: :employee_id, dependent: :destroy
 end