diff --git a/lib/activerecord-bitemporal/bitemporal.rb b/lib/activerecord-bitemporal/bitemporal.rb
index 52b484ab..175157b7 100644
--- a/lib/activerecord-bitemporal/bitemporal.rb
+++ b/lib/activerecord-bitemporal/bitemporal.rb
@@ -445,14 +445,14 @@ def _update_row(attribute_names, attempted_action = 'update')
 
             # 以前の履歴データは valid_to を詰めて保存
             before_instance.valid_to = target_datetime
-            raise ActiveRecord::Rollback if before_instance.valid_from_cannot_be_greater_equal_than_valid_to
+            raise ActiveRecord::RecordInvalid.new(before_instance) if before_instance.valid_from_cannot_be_greater_equal_than_valid_to
             before_instance.transaction_from = current_time
             before_instance.save!(validate: false)
 
             # 以降の履歴データは valid_from と valid_to を調整して保存する
             after_instance.valid_from = target_datetime
             after_instance.valid_to = current_valid_record.valid_to
-            raise ActiveRecord::Rollback if after_instance.valid_from_cannot_be_greater_equal_than_valid_to
+            raise ActiveRecord::RecordInvalid.new(after_instance) if after_instance.valid_from_cannot_be_greater_equal_than_valid_to
             after_instance.transaction_from = current_time
             after_instance.save!(validate: false)
 
@@ -460,6 +460,10 @@ def _update_row(attribute_names, attempted_action = 'update')
           else
             # 一番近い未来にある Instance を取ってきて、その valid_from を valid_to に入れる
             nearest_instance = self.class.where(bitemporal_id: bitemporal_id).bitemporal_where_bind("valid_from", :gt, target_datetime).ignore_valid_datetime.order(valid_from: :asc).first
+            if nearest_instance.nil?
+              message = "Update failed: Couldn't find #{self.class} with 'bitemporal_id'=#{self.bitemporal_id} and 'valid_from' < #{target_datetime}"
+              raise ActiveRecord::RecordNotFound.new(message, self.class, "bitemporal_id", self.bitemporal_id)
+            end
 
             # valid_from と valid_to を調整して保存する
             after_instance.valid_from = target_datetime
diff --git a/spec/activerecord-bitemporal/bitemporal_spec.rb b/spec/activerecord-bitemporal/bitemporal_spec.rb
index e10d9f9b..9ff83bfa 100644
--- a/spec/activerecord-bitemporal/bitemporal_spec.rb
+++ b/spec/activerecord-bitemporal/bitemporal_spec.rb
@@ -784,13 +784,12 @@ def employee.wrapped_name
     end
 
     context "failure" do
-      let(:company) { Company.create!(valid_from: "2019/2/1") }
-      let(:company_count) { -> { Company.ignore_valid_datetime.bitemporal_for(company.id).count } }
-      let(:company_deleted_at) { -> { Company.ignore_valid_datetime.within_deleted.bitemporal_for(company.id).first.deleted_at } }
-      subject { -> { company.valid_at(valid_datetime) { |c| c.update(name: "Company") } } }
-
       context "`valid_datetime` is `company.valid_from`" do
+        let(:company) { Company.create!(valid_from: "2019/2/1") }
+        let(:company_count) { -> { Company.ignore_valid_datetime.bitemporal_for(company.id).count } }
+        let(:company_deleted_at) { -> { Company.ignore_valid_datetime.within_deleted.bitemporal_for(company.id).first.deleted_at } }
         let(:valid_datetime) { company.valid_from }
+        subject { -> { company.valid_at(valid_datetime) { |c| c.update(name: "Company") } } }
 
         it { expect(subject.call).to be_falsey }
         it { is_expected.not_to change(&company_count) }
@@ -798,9 +797,23 @@ def employee.wrapped_name
 
         context "call `update!`" do
           subject { -> { company.valid_at(valid_datetime) { |c| c.update!(name: "Company") } } }
-          it { is_expected.to raise_error(ActiveRecord::RecordNotSaved) }
+          it { is_expected.to raise_error(ActiveRecord::RecordInvalid) }
+          it { is_expected.to raise_error { |e|
+            expect(e.message).to eq "Validation failed: Valid from can't be greater equal than valid_to"
+          } }
         end
       end
+
+      context "update for deleted record" do
+        let(:datetime) { "2020/01/01".in_time_zone }
+        let(:company) { Company.create!(valid_from: "2019/02/01", valid_to: "2019/04/01") }
+        subject { -> { Timecop.freeze(datetime) { company.update!(name: "Company2") } } }
+        before { company.destroy }
+        it { is_expected.to raise_error(ActiveRecord::RecordNotFound) }
+        it { is_expected.to raise_error { |e|
+          expect(e.message).to eq "Update failed: Couldn't find Company with 'bitemporal_id'=#{company.bitemporal_id} and 'valid_from' < #{datetime}"
+        } }
+      end
     end
   end