diff --git a/app/services/orders/handle_fees_service.rb b/app/services/orders/handle_fees_service.rb
index ab46d95d16..48dacc13f4 100644
--- a/app/services/orders/handle_fees_service.rb
+++ b/app/services/orders/handle_fees_service.rb
@@ -92,8 +92,13 @@ module Orders
     def update_removed_fees!(line_item)
       order_cycle_fees = fee_applicators(line_item.variant).map(&:enterprise_fee)
       removed_fees = line_item.enterprise_fee_adjustments.where.not(originator: order_cycle_fees)
+
       removed_fees.each do |removed_fee|
-        removed_fee.update_adjustment!(line_item, force: true)
+        if removed_fee.originator.nil? || removed_fee.originator.deleted?
+          removed_fee.destroy
+        else
+          removed_fee.update_adjustment!(line_item, force: true)
+        end
       end
     end
 
diff --git a/spec/services/orders/handle_fees_service_spec.rb b/spec/services/orders/handle_fees_service_spec.rb
index 2121c77314..d75bd09fdf 100644
--- a/spec/services/orders/handle_fees_service_spec.rb
+++ b/spec/services/orders/handle_fees_service_spec.rb
@@ -107,6 +107,35 @@ RSpec.describe Orders::HandleFeesService do
         end
       end
 
+      context "when an enterprise fee is deleted" do
+        before do
+          fee.create_adjustment('foo', line_item, true)
+          allow(calculator).to receive(
+            :order_cycle_per_item_enterprise_fee_applicators_for
+          ).and_return([])
+        end
+
+        context "soft delete" do
+          it "deletes the line item fee" do
+            fee.destroy
+
+            expect do
+              service.create_or_update_line_item_fees!
+            end.to change { line_item.adjustments.enterprise_fee.count }.by(-1)
+          end
+        end
+
+        context "hard delete" do
+          it "deletes the line item fee" do
+            fee.really_destroy!
+
+            expect do
+              service.create_or_update_line_item_fees!
+            end.to change { line_item.adjustments.enterprise_fee.count }.by(-1)
+          end
+        end
+      end
+
       context "with a new enterprise fee added to the order cylce" do
         let(:new_fee) { create(:enterprise_fee, enterprise: fee.enterprise) }
         let(:fee_applicator2) {