diff --git a/app/models/order_cycle.rb b/app/models/order_cycle.rb
index e880083316..c6e2d4a0aa 100644
--- a/app/models/order_cycle.rb
+++ b/app/models/order_cycle.rb
@@ -280,7 +280,7 @@ class OrderCycle < ApplicationRecord
   end
 
   def was_closed?
-    orders_close_at_previously_was && Time.zone.now > orders_close_at_previously_was
+    orders_close_at_previously_was.blank? || Time.zone.now > orders_close_at_previously_was
   end
 
   def sync_subscriptions
diff --git a/spec/models/order_cycle_spec.rb b/spec/models/order_cycle_spec.rb
index 652eecafdd..4ebb79a9a1 100644
--- a/spec/models/order_cycle_spec.rb
+++ b/spec/models/order_cycle_spec.rb
@@ -572,6 +572,18 @@ describe OrderCycle do
         oc.update(orders_open_at: 1.day.from_now, orders_close_at: 1.week.from_now)
       }.to change{ ProxyOrder.count }
     end
+
+    context "when the current dates are nil" do
+      before { oc.update(orders_open_at: nil, orders_close_at: nil) }
+
+      it "syncs subscriptions when transitioning from closed to open" do
+        expect(OrderManagement::Subscriptions::ProxyOrderSyncer).to receive(:new).and_call_original
+
+        expect{
+          oc.update(orders_open_at: 1.day.ago, orders_close_at: 1.week.from_now)
+        }.to change{ ProxyOrder.count }
+      end
+    end
   end
 
   describe "processed_at " do