diff --git a/src/Billing/Constants/HandledStripeWebhook.cs b/src/Billing/Constants/HandledStripeWebhook.cs
new file mode 100644
index 000000000..a26bfede0
--- /dev/null
+++ b/src/Billing/Constants/HandledStripeWebhook.cs
@@ -0,0 +1,14 @@
+namespace Bit.Billing.Constants
+{
+    public static class HandledStripeWebhook
+    {
+        public static string SubscriptionDeleted => "customer.subscription.deleted";
+        public static string SubscriptionUpdated => "customer.subscriptions.updated";
+        public static string UpcomingInvoice => "invoice.upcoming";
+        public static string ChargeSucceeded => "charge.succeeded";
+        public static string ChargeRefunded => "charge.refunded";
+        public static string PaymentSucceeded => "invoice.payment_succeeded";
+        public static string PaymentFailed => "invoice.payment_failed";
+        public static string InvoiceCreated => "invoice.created";
+    }
+}
diff --git a/src/Billing/Controllers/AppleController.cs b/src/Billing/Controllers/AppleController.cs
index c3b9bf5fa..0a45f6a32 100644
--- a/src/Billing/Controllers/AppleController.cs
+++ b/src/Billing/Controllers/AppleController.cs
@@ -54,7 +54,7 @@ namespace Bit.Billing.Controllers
             try
             {
                 var json = JsonSerializer.Serialize(JsonSerializer.Deserialize<JsonDocument>(body), JsonHelpers.Indented);
-                _logger.LogInformation(Constants.BypassFiltersEventId, "Apple IAP Notification:\n\n{0}", json);
+                _logger.LogInformation(Bit.Core.Constants.BypassFiltersEventId, "Apple IAP Notification:\n\n{0}", json);
                 return new OkResult();
             }
             catch (Exception e)
diff --git a/src/Billing/Controllers/StripeController.cs b/src/Billing/Controllers/StripeController.cs
index ac5dce95a..15742a39d 100644
--- a/src/Billing/Controllers/StripeController.cs
+++ b/src/Billing/Controllers/StripeController.cs
@@ -4,6 +4,7 @@ using System.Data.SqlClient;
 using System.IO;
 using System.Linq;
 using System.Threading.Tasks;
+using Bit.Billing.Constants;
 using Bit.Core.Entities;
 using Bit.Core.Enums;
 using Bit.Core.Models.Business;
@@ -113,8 +114,8 @@ namespace Bit.Billing.Controllers
                 return new BadRequestResult();
             }
 
-            var subDeleted = parsedEvent.Type.Equals("customer.subscription.deleted");
-            var subUpdated = parsedEvent.Type.Equals("customer.subscription.updated");
+            var subDeleted = parsedEvent.Type.Equals(HandledStripeWebhook.SubscriptionDeleted);
+            var subUpdated = parsedEvent.Type.Equals(HandledStripeWebhook.SubscriptionUpdated);
 
             if (subDeleted || subUpdated)
             {
@@ -159,7 +160,7 @@ namespace Bit.Billing.Controllers
                     }
                 }
             }
-            else if (parsedEvent.Type.Equals("invoice.upcoming"))
+            else if (parsedEvent.Type.Equals(HandledStripeWebhook.UpcomingInvoice))
             {
                 var invoice = await GetInvoiceAsync(parsedEvent);
                 var subscriptionService = new SubscriptionService();
@@ -205,7 +206,7 @@ namespace Bit.Billing.Controllers
                         invoice.NextPaymentAttempt.Value, items, true);
                 }
             }
-            else if (parsedEvent.Type.Equals("charge.succeeded"))
+            else if (parsedEvent.Type.Equals(HandledStripeWebhook.ChargeSucceeded))
             {
                 var charge = await GetChargeAsync(parsedEvent);
                 var chargeTransaction = await _transactionRepository.GetByGatewayIdAsync(
@@ -332,7 +333,7 @@ namespace Bit.Billing.Controllers
                 // Catch foreign key violations because user/org could have been deleted.
                 catch (SqlException e) when (e.Number == 547) { }
             }
-            else if (parsedEvent.Type.Equals("charge.refunded"))
+            else if (parsedEvent.Type.Equals(HandledStripeWebhook.ChargeRefunded))
             {
                 var charge = await GetChargeAsync(parsedEvent);
                 var chargeTransaction = await _transactionRepository.GetByGatewayIdAsync(
@@ -382,7 +383,7 @@ namespace Bit.Billing.Controllers
                     _logger.LogWarning("Charge refund amount doesn't seem correct. " + charge.Id);
                 }
             }
-            else if (parsedEvent.Type.Equals("invoice.payment_succeeded"))
+            else if (parsedEvent.Type.Equals(HandledStripeWebhook.PaymentSucceeded))
             {
                 var invoice = await GetInvoiceAsync(parsedEvent, true);
                 if (invoice.Paid && invoice.BillingReason == "subscription_create")
@@ -434,15 +435,11 @@ namespace Bit.Billing.Controllers
                     }
                 }
             }
-            else if (parsedEvent.Type.Equals("invoice.payment_failed"))
+            else if (parsedEvent.Type.Equals(HandledStripeWebhook.PaymentFailed))
             {
-                var invoice = await GetInvoiceAsync(parsedEvent, true);
-                if (!invoice.Paid && invoice.AttemptCount > 1 && UnpaidAutoChargeInvoiceForSubscriptionCycle(invoice))
-                {
-                    await AttemptToPayInvoiceAsync(invoice);
-                }
+                await HandlePaymentFailed(await GetInvoiceAsync(parsedEvent, true));
             }
-            else if (parsedEvent.Type.Equals("invoice.created"))
+            else if (parsedEvent.Type.Equals(HandledStripeWebhook.InvoiceCreated))
             {
                 var invoice = await GetInvoiceAsync(parsedEvent, true);
                 if (!invoice.Paid && UnpaidAutoChargeInvoiceForSubscriptionCycle(invoice))
@@ -804,5 +801,42 @@ namespace Bit.Billing.Controllers
 
         private static bool IsSponsoredSubscription(Subscription subscription) =>
             StaticStore.SponsoredPlans.Any(p => p.StripePlanId == subscription.Id);
+
+        private async Task HandlePaymentFailed(Invoice invoice)
+        {
+            if (!invoice.Paid && invoice.AttemptCount > 1 && UnpaidAutoChargeInvoiceForSubscriptionCycle(invoice))
+            {
+                // attempt count 4 = 11 days after initial failure
+                if (invoice.AttemptCount > 3)
+                {
+                    await CancelSubscription(invoice.SubscriptionId);
+                    await VoidOpenInvoices(invoice.SubscriptionId);
+                }
+                else
+                {
+                    await AttemptToPayInvoiceAsync(invoice);
+                }
+            }
+        }
+
+        private async Task CancelSubscription(string subscriptionId)
+        {
+            await new SubscriptionService().CancelAsync(subscriptionId, new SubscriptionCancelOptions());
+        }
+
+        private async Task VoidOpenInvoices(string subscriptionId)
+        {
+            var invoiceService = new InvoiceService();
+            var options = new InvoiceListOptions
+            {
+                Status = "open",
+                Subscription = subscriptionId
+            };
+            var invoices = invoiceService.List(options);
+            foreach (var invoice in invoices)
+            {
+                await invoiceService.VoidInvoiceAsync(invoice.Id);
+            }
+        }
     }
 }