diff --git a/app/jobs/order_cycle_opened_job.rb b/app/jobs/order_cycle_opened_job.rb
index 67904764f2d..e100d216444 100644
--- a/app/jobs/order_cycle_opened_job.rb
+++ b/app/jobs/order_cycle_opened_job.rb
@@ -3,9 +3,13 @@
 # Trigger jobs for any order cycles that recently opened
 class OrderCycleOpenedJob < ApplicationJob
   def perform
-    recently_opened_order_cycles.each do |oc_id|
-      SubscriptionPlacementJob.perform_later(oc_id)
-      OrderCycleWebhookJob.perform_later(oc_id, 'order_cycle.opened')
+    ActiveRecord::Base.transaction do
+      recently_opened_order_cycles.find_each do |order_cycle|
+        SubscriptionPlacementJob.perform_later(order_cycle.id)
+        OrderCycleWebhookJob.perform_later(order_cycle.id, 'order_cycle.opened')
+
+        mark_as_notified(order_cycle)
+      end
     end
   end
 
@@ -13,7 +17,13 @@ def perform
 
   def recently_opened_order_cycles
     OrderCycle
+      .where(opened_notification_at: nil)
       .where(orders_open_at: 1.hour.ago..Time.zone.now)
-      .pluck(:id)
+      .lock.order(:id)
+  end
+
+  def mark_as_notified(order_cycle)
+    now = Time.zone.now
+    order_cycle.update_columns(opened_notification_at: now, updated_at: now)
   end
 end
diff --git a/app/models/order_cycle.rb b/app/models/order_cycle.rb
index ce1846cf540..bdb1d9beb40 100644
--- a/app/models/order_cycle.rb
+++ b/app/models/order_cycle.rb
@@ -34,6 +34,7 @@ class OrderCycle < ApplicationRecord
 
   attr_accessor :incoming_exchanges, :outgoing_exchanges
 
+  before_update :reset_opened_notification_at, if: :will_save_change_to_orders_open_at?
   before_update :reset_processed_at, if: :will_save_change_to_orders_close_at?
   after_save :sync_subscriptions, if: :opening?
 
@@ -333,6 +334,13 @@ def orders_close_at_after_orders_open_at?
     errors.add(:orders_close_at, :after_orders_open_at)
   end
 
+  def reset_opened_notification_at
+    return unless orders_open_at.present? && orders_open_at_was.present?
+    return unless orders_open_at > orders_open_at_was
+
+    self.opened_notification_at = nil
+  end
+
   def reset_processed_at
     return unless orders_close_at.present? && orders_close_at_was.present?
     return unless orders_close_at > orders_close_at_was
diff --git a/db/migrate/20220919063831_add_opened_notification_at_to_order_cycle.rb b/db/migrate/20220919063831_add_opened_notification_at_to_order_cycle.rb
new file mode 100644
index 00000000000..b56e0a87d02
--- /dev/null
+++ b/db/migrate/20220919063831_add_opened_notification_at_to_order_cycle.rb
@@ -0,0 +1,7 @@
+# frozen_string_literal: true
+
+class AddOpenedNotificationAtToOrderCycle < ActiveRecord::Migration[6.1]
+  def change
+    add_column :order_cycles, :opened_notification_at, :timestamp
+  end
+end
diff --git a/db/schema.rb b/db/schema.rb
index ec58ba107fd..a689f5afced 100644
--- a/db/schema.rb
+++ b/db/schema.rb
@@ -310,6 +310,7 @@
     t.datetime "processed_at"
     t.boolean "automatic_notifications", default: false
     t.boolean "mails_sent", default: false
+    t.datetime "opened_notification_at"
   end
 
   create_table "order_cycles_distributor_payment_methods", id: false, force: :cascade do |t|
diff --git a/spec/jobs/order_cycle_opened_job_spec.rb b/spec/jobs/order_cycle_opened_job_spec.rb
index bee76640419..fddb6e3167d 100644
--- a/spec/jobs/order_cycle_opened_job_spec.rb
+++ b/spec/jobs/order_cycle_opened_job_spec.rb
@@ -29,4 +29,38 @@
       .to enqueue_job(SubscriptionPlacementJob).with(oc_opened_now.id)
       .and enqueue_job(OrderCycleWebhookJob).with(oc_opened_now.id, 'order_cycle.opened')
   end
+
+  describe "concurrency", concurrency: true do
+    let(:breakpoint) { Mutex.new }
+
+    it "doesn't place duplicate orders when run concurrently" do
+      oc_opened_now
+
+      # Pause jobs when placing new job:
+      breakpoint.lock
+      allow(OrderCycleWebhookJob).to(
+        receive(:new).and_wrap_original do |method, *args|
+          breakpoint.synchronize {}
+          method.call(*args)
+        end
+      )
+
+      expect {
+        # Start two jobs in parallel:
+        threads = [
+          Thread.new { OrderCycleOpenedJob.perform_now },
+          Thread.new { OrderCycleOpenedJob.perform_now },
+        ]
+
+        # Wait for both to jobs to pause.
+        # This can reveal a race condition.
+        sleep 0.1
+
+        # Resume and complete both jobs:
+        breakpoint.unlock
+        threads.each(&:join)
+      }.to enqueue_job(OrderCycleWebhookJob)
+        .with(oc_opened_now.id, 'order_cycle.opened').once
+    end
+  end
 end
diff --git a/spec/jobs/order_cycle_webhook_job_spec.rb b/spec/jobs/order_cycle_webhook_job_spec.rb
index b3eb548d0a6..3ef3664e2bc 100644
--- a/spec/jobs/order_cycle_webhook_job_spec.rb
+++ b/spec/jobs/order_cycle_webhook_job_spec.rb
@@ -11,7 +11,6 @@
       orders_close_at: "2022-09-19 17:00:00".to_time,
     )
   }
-  let(:endpoint) { order_cycle.webhook_endpoints.create url: "http://url", event_name: "order_cycle.event" }
 
   context "enterprise owner has a webhook endpoint" do
     before do
@@ -54,7 +53,6 @@
       job = OrderCycleWebhookJob.new(order_cycle.id, 'order_cycle.event')
       order_cycle.destroy!
 
-      expect(WebhookDeliveryJob).to_not receive(:perform_later)
       expect(JobLogger.logger).to receive(:info).with(/Couldn't find OrderCycle/)
 
       expect{ job.perform_now }.not_to raise_error # so that job runner doesn't attempt to re-run
@@ -67,6 +65,4 @@
         .not_to enqueue_job(WebhookDeliveryJob)
     end
   end
-
-  pending "doesn't create duplicate webhook jobs"
 end
diff --git a/spec/models/order_cycle_spec.rb b/spec/models/order_cycle_spec.rb
index 818b900e196..3abcff1d9c6 100644
--- a/spec/models/order_cycle_spec.rb
+++ b/spec/models/order_cycle_spec.rb
@@ -551,6 +551,30 @@
     end
   end
 
+  describe "opened_notification_at " do
+    let!(:oc) {
+      create(:simple_order_cycle, orders_open_at: 2.days.ago, orders_close_at: 1.day.ago, opened_notification_at: 1.week.ago)
+    }
+
+    it "reset opened_notification_at if open date change in future" do
+      expect(oc.opened_notification_at).to_not be_nil
+      oc.update!(orders_open_at: 1.week.from_now, orders_close_at: 2.weeks.from_now)
+      expect(oc.opened_notification_at).to be_nil
+    end
+
+    it "it does not reset opened_notification_at if open date is changed to be earlier" do
+      expect(oc.opened_notification_at).to_not be_nil
+      oc.update!(orders_open_at: 3.days.ago)
+      expect(oc.opened_notification_at).to_not be_nil
+    end
+
+    it "it does not reset opened_notification_at if open date does not change" do
+      expect(oc.opened_notification_at).to_not be_nil
+      oc.update!(orders_close_at: 1.day.from_now)
+      expect(oc.opened_notification_at).to_not be_nil
+    end
+  end
+
   describe "processed_at " do
     let!(:oc) {
       create(:simple_order_cycle, orders_open_at: 1.week.ago, orders_close_at: 1.day.ago, processed_at: 1.hour.ago)
@@ -562,13 +586,13 @@
       expect(oc.processed_at).to be_nil
     end
 
-    it "it does not reset processed_at if close date change in the past" do
+    it "it does not reset processed_at if close date is changed to be earlier" do
       expect(oc.processed_at).to_not be_nil
       oc.update!(orders_close_at: 2.days.ago)
       expect(oc.processed_at).to_not be_nil
     end
 
-    it "it does not reset processed_at if close date do not change" do
+    it "it does not reset processed_at if close date does not change" do
       expect(oc.processed_at).to_not be_nil
       oc.update!(orders_open_at: 2.weeks.ago)
       expect(oc.processed_at).to_not be_nil