diff --git a/app/controllers/checkout_controller.rb b/app/controllers/checkout_controller.rb
index 13b6654782..547f180a72 100644
--- a/app/controllers/checkout_controller.rb
+++ b/app/controllers/checkout_controller.rb
@@ -37,7 +37,7 @@ class CheckoutController < ::BaseController
     # This is only required because of spree_paypal_express. If we implement
     # a version of paypal that uses this controller, and more specifically
     # the #action_failed method, then we can remove this call
-    OrderCheckoutRestart.new(@order).call
+    reset_order_to_cart
   rescue Spree::Core::GatewayError => e
     rescue_from_spree_gateway_error(e)
   end
@@ -82,7 +82,7 @@ class CheckoutController < ::BaseController
     @order = current_order
 
     redirect_to(main_app.shop_path) && return if redirect_to_shop?
-    redirect_to_cart_path && return unless valid_order_line_items?
+    handle_invalid_stock && return unless valid_order_line_items?
 
     before_address
     setup_for_current_state
@@ -100,7 +100,10 @@ class CheckoutController < ::BaseController
         distributes_order_variants?(@order)
   end
 
-  def redirect_to_cart_path
+  def handle_invalid_stock
+    cancel_incomplete_payments if valid_payment_intent_provided?
+    reset_order_to_cart
+
     respond_to do |format|
       format.html do
         redirect_to main_app.cart_path
@@ -112,6 +115,20 @@ class CheckoutController < ::BaseController
     end
   end
 
+  def cancel_incomplete_payments
+    # The checkout could not complete due to stock running out. We void any pending (incomplete)
+    # Stripe payments here as the order will need to be changed and resubmitted (or abandoned).
+    @order.payments.incomplete.each do |payment|
+      payment.void!
+      payment.adjustment&.update_columns(eligible: false, state: "finalized")
+    end
+    flash[:notice] = I18n.t("checkout.payment_cancelled_due_to_stock")
+  end
+
+  def reset_order_to_cart
+    OrderCheckoutRestart.new(@order).call
+  end
+
   def setup_for_current_state
     method_name = :"before_#{@order.state}"
     __send__(method_name) if respond_to?(method_name, true)
diff --git a/app/models/spree/payment.rb b/app/models/spree/payment.rb
index 3bb4b60858..f33e2eab87 100644
--- a/app/models/spree/payment.rb
+++ b/app/models/spree/payment.rb
@@ -46,9 +46,10 @@ module Spree
     scope :from_credit_card, -> { where(source_type: 'Spree::CreditCard') }
     scope :with_state, ->(s) { where(state: s.to_s) }
     scope :completed, -> { with_state('completed') }
+    scope :incomplete, -> { where(state: %w(checkout pending requires_authorization)) }
     scope :pending, -> { with_state('pending') }
     scope :failed, -> { with_state('failed') }
-    scope :valid, -> { where('state NOT IN (?)', %w(failed invalid)) }
+    scope :valid, -> { where.not(state: %w(failed invalid)) }
     scope :authorization_action_required, -> { where.not(cvv_response_message: nil) }
     scope :requires_authorization, -> { with_state("requires_authorization") }
     scope :with_payment_intent, ->(code) { where(response_code: code) }
@@ -72,7 +73,7 @@ module Spree
         transition from: [:processing, :pending, :checkout, :requires_authorization], to: :completed
       end
       event :void do
-        transition from: [:pending, :completed, :checkout], to: :void
+        transition from: [:pending, :completed, :requires_authorization, :checkout], to: :void
       end
       # when the card brand isnt supported
       event :invalidate do
diff --git a/config/locales/en.yml b/config/locales/en.yml
index 84140e72bc..76943a0815 100644
--- a/config/locales/en.yml
+++ b/config/locales/en.yml
@@ -1315,6 +1315,7 @@ en:
       message_html: "I agree to the seller's %{terms_and_conditions_link} and the platform %{tos_link}."
       terms_and_conditions: "Terms and Conditions"
     failed: "The checkout failed. Please let us know so that we can process your order."
+    payment_cancelled_due_to_stock: "Payment cancelled: the checkout could not be completed due to stock issues."
   shops:
     hubs:
       show_closed_shops: "Show closed shops"
diff --git a/spec/controllers/checkout_controller_spec.rb b/spec/controllers/checkout_controller_spec.rb
index d1813fa16a..e0e00a3ff7 100644
--- a/spec/controllers/checkout_controller_spec.rb
+++ b/spec/controllers/checkout_controller_spec.rb
@@ -49,8 +49,7 @@ describe CheckoutController, type: :controller do
     let(:shipping_method) { distributor.shipping_methods.first }
 
     before do
-      order.line_items << create(:line_item,
-                                 variant: order_cycle.variants_distributed_by(distributor).first)
+      order.contents.add(order_cycle.variants_distributed_by(distributor).first)
 
       allow(controller).to receive(:current_distributor).and_return(distributor)
       allow(controller).to receive(:current_order_cycle).and_return(order_cycle)
@@ -92,19 +91,54 @@ describe CheckoutController, type: :controller do
       allow(OrderCycleDistributedVariants).to receive(:new).and_return(order_cycle_distributed_variants)
     end
 
-    it "redirects when some items are out of stock" do
-      allow(order).to receive_message_chain(:insufficient_stock_lines, :empty?).and_return false
+    context "running out of stock" do
+      it "redirects when some items are out of stock" do
+        allow(order).to receive_message_chain(:insufficient_stock_lines, :empty?).and_return false
 
-      get :edit
-      expect(response).to redirect_to cart_path
-    end
+        get :edit
+        expect(response).to redirect_to cart_path
+      end
 
-    it "redirects when some items are not available" do
-      allow(order).to receive_message_chain(:insufficient_stock_lines, :empty?).and_return true
-      expect(order_cycle_distributed_variants).to receive(:distributes_order_variants?).with(order).and_return(false)
+      it "redirects when some items are not available" do
+        allow(order).to receive_message_chain(:insufficient_stock_lines, :empty?).and_return true
+        expect(order_cycle_distributed_variants).to receive(:distributes_order_variants?).with(order).and_return(false)
 
-      get :edit
-      expect(response).to redirect_to cart_path
+        get :edit
+        expect(response).to redirect_to cart_path
+      end
+
+      context "after redirecting back from Stripe" do
+        let(:order) { create(:order_with_totals_and_distribution) }
+        let!(:payment) { create(:payment, state: "pending", amount: order.total, order: order) }
+        let!(:transaction_fee) {
+          create(:adjustment, state: "open", amount: 10, order: order, adjustable: payment)
+        }
+
+        before do
+          allow(order).to receive_message_chain(:insufficient_stock_lines, :empty?).and_return(false)
+          allow(order_cycle_distributed_variants).to receive(:distributes_order_variants?).
+            with(order).and_return(true)
+          allow(controller).to receive(:valid_payment_intent_provided?) { true }
+          order.save
+          allow(order).to receive_message_chain(:payments, :completed) { [] }
+          allow(order).to receive_message_chain(:payments, :incomplete) { [payment] }
+          allow(payment).to receive(:adjustment) { transaction_fee }
+        end
+
+        it "cancels the payment and resets the order to cart" do
+          expect(payment).to receive(:void!).and_call_original
+
+          spree_post :edit
+
+          expect(response).to redirect_to cart_path
+          expect(flash[:notice]).to eq I18n.t('checkout.payment_cancelled_due_to_stock')
+
+          expect(order.state).to eq "cart"
+          expect(payment.state).to eq "void"
+          expect(transaction_fee.reload.eligible).to eq false
+          expect(transaction_fee.state).to eq "finalized"
+        end
+      end
     end
 
     describe "when items are available and in stock" do