diff --git a/app/Jobs/CreateUserFromStripeCustomer.php b/app/Jobs/CreateUserFromStripeCustomer.php
index e383259c..a54a5057 100644
--- a/app/Jobs/CreateUserFromStripeCustomer.php
+++ b/app/Jobs/CreateUserFromStripeCustomer.php
@@ -9,6 +9,7 @@
 use Illuminate\Queue\InteractsWithQueue;
 use Illuminate\Queue\SerializesModels;
 use Illuminate\Support\Facades\Hash;
+use Illuminate\Support\Facades\Log;
 use Illuminate\Support\Str;
 use Laravel\Cashier\Cashier;
 use Stripe\Customer;
@@ -21,14 +22,19 @@ public function __construct(public Customer $customer) {}
 
     public function handle(): void
     {
-        if (Cashier::findBillable($this->customer)) {
-            $this->fail("A user already exists for Stripe customer [{$this->customer->id}].");
+        /** @var User $user */
+        if ($user = Cashier::findBillable($this->customer)) {
+            Log::debug("A user [{$user->id} | {$user->email}] with stripe_id [{$this->customer->id}] already exists.");
 
             return;
         }
 
-        if (User::query()->where('email', $this->customer->email)->exists()) {
-            $this->fail("A user already exists for email [{$this->customer->email}].");
+        if ($user = User::query()->where('email', $this->customer->email)->first()) {
+            // This could occur if a user performs/attempts multiple checkouts with the same email address.
+            // In the event all existing stripe customers for this email address do NOT have an active
+            // subscription, we could theoretically update the stripe_id for the existing user
+            // and continue. However, for now, we will throw an exception.
+            $this->fail("A user with email [{$user->email}] already exists but the current stripe_id [{$user->stripe_id}] does not match the new customer id [{$this->customer->id}].");
 
             return;
         }
diff --git a/app/Listeners/StripeWebhookReceivedListener.php b/app/Listeners/StripeWebhookReceivedListener.php
index 7ccfd1a3..dd0e5855 100644
--- a/app/Listeners/StripeWebhookReceivedListener.php
+++ b/app/Listeners/StripeWebhookReceivedListener.php
@@ -3,7 +3,9 @@
 namespace App\Listeners;
 
 use App\Jobs\CreateUserFromStripeCustomer;
+use Exception;
 use Illuminate\Support\Facades\Log;
+use Laravel\Cashier\Cashier;
 use Laravel\Cashier\Events\WebhookReceived;
 use Stripe\Customer;
 
@@ -19,7 +21,25 @@ public function handle(WebhookReceived $event): void
             'customer.created' => dispatch_sync(new CreateUserFromStripeCustomer(
                 Customer::constructFrom($event->payload['data']['object'])
             )),
+            'customer.subscription.created' => $this->createUserIfNotExists($event->payload['data']['object']['customer']),
             default => null,
         };
     }
+
+    private function createUserIfNotExists(string $stripeCustomerId): void
+    {
+        if (Cashier::findBillable($stripeCustomerId)) {
+            return;
+        }
+
+        $customer = Customer::retrieve($stripeCustomerId);
+
+        if (! $customer) {
+            throw new Exception(
+                'A user needed to be created for customer.subscription.created but was unable to retrieve the customer from Stripe.'
+            );
+        }
+
+        dispatch_sync(new CreateUserFromStripeCustomer($customer));
+    }
 }
diff --git a/app/Providers/AppServiceProvider.php b/app/Providers/AppServiceProvider.php
index f58138ee..66fb3ecf 100644
--- a/app/Providers/AppServiceProvider.php
+++ b/app/Providers/AppServiceProvider.php
@@ -3,8 +3,14 @@
 namespace App\Providers;
 
 use App\Support\GitHub;
+use Illuminate\Queue\Events\JobFailed;
+use Illuminate\Support\Facades\Queue;
 use Illuminate\Support\Facades\View;
 use Illuminate\Support\ServiceProvider;
+use Sentry\State\Scope;
+
+use function Sentry\captureException;
+use function Sentry\configureScope;
 
 class AppServiceProvider extends ServiceProvider
 {
@@ -22,6 +28,8 @@ public function register(): void
     public function boot(): void
     {
         $this->registerSharedViewVariables();
+
+        $this->sendFailingJobsToSentry();
     }
 
     private function registerSharedViewVariables(): void
@@ -35,4 +43,22 @@ private function registerSharedViewVariables(): void
         View::share('openCollectiveLink', 'https://opencollective.com/nativephp');
         View::share('githubLink', 'https://github.com/NativePHP');
     }
+
+    private function sendFailingJobsToSentry(): void
+    {
+        Queue::failing(static function (JobFailed $event) {
+            if (app()->bound('sentry')) {
+                configureScope(function (Scope $scope) use ($event): void {
+                    $scope->setContext('job', [
+                        'connection' => $event->connectionName,
+                        'queue' => $event->job->getQueue(),
+                        'name' => $event->job->resolveName(),
+                        'payload' => $event->job->payload(),
+                    ]);
+                });
+
+                captureException($event->exception);
+            }
+        });
+    }
 }