diff --git a/app/controllers/application_controller.rb b/app/controllers/application_controller.rb
index a3c4433397..af057db34e 100644
--- a/app/controllers/application_controller.rb
+++ b/app/controllers/application_controller.rb
@@ -153,9 +153,11 @@ class ApplicationController < ActionController::Base
 
   def check_order_cycle_expiry
     if current_order_cycle&.closed?
+      Bugsnag.notify("Notice: order cycle closed during checkout completion", order: current_order)
       current_order.empty!
       current_order.set_order_cycle! nil
       flash[:info] = I18n.t('order_cycle_closed')
+
       redirect_to main_app.shop_path
     end
   end
diff --git a/app/controllers/checkout_controller.rb b/app/controllers/checkout_controller.rb
index fe392d5058..49bfb940ab 100644
--- a/app/controllers/checkout_controller.rb
+++ b/app/controllers/checkout_controller.rb
@@ -81,7 +81,11 @@ class CheckoutController < ::BaseController
   def load_order
     @order = current_order
 
-    redirect_to(main_app.shop_path) && return if redirect_to_shop?
+    if order_invalid_for_checkout?
+      Bugsnag.notify("Notice: invalid order loaded during Stripe processing", order: @order) if valid_payment_intent_provided?
+      redirect_to(main_app.shop_path) && return
+    end
+
     handle_invalid_stock && return unless valid_order_line_items?
 
     return if valid_payment_intent_provided?
@@ -90,10 +94,8 @@ class CheckoutController < ::BaseController
     setup_for_current_state
   end
 
-  def redirect_to_shop?
-    !@order ||
-      !@order.checkout_allowed? ||
-      @order.completed?
+  def order_invalid_for_checkout?
+    !@order || @order.completed? || !@order.checkout_allowed?
   end
 
   def valid_order_line_items?
@@ -241,7 +243,7 @@ class CheckoutController < ::BaseController
   end
 
   def checkout_failed(error = RuntimeError.new(order_error))
-    Bugsnag.notify(error)
+    Bugsnag.notify(error, order: @order)
     flash[:error] = order_error if flash.blank?
     Checkout::PostCheckoutActions.new(@order).failure
   end
diff --git a/spec/controllers/base_controller_spec.rb b/spec/controllers/base_controller_spec.rb
index 02b68b3750..98d6183ea4 100644
--- a/spec/controllers/base_controller_spec.rb
+++ b/spec/controllers/base_controller_spec.rb
@@ -102,7 +102,7 @@ describe BaseController, type: :controller do
 
   it "redirects to shopfront with message if order cycle is expired" do
     expect(controller).to receive(:current_order_cycle).and_return(oc)
-    expect(controller).to receive(:current_order).and_return(order).twice
+    expect(controller).to receive(:current_order).and_return(order).at_least(:twice)
     expect(oc).to receive(:closed?).and_return(true)
     expect(order).to receive(:empty!)
     expect(order).to receive(:set_order_cycle!).with(nil)