From b7175169f0f463d1060e67e1132925becd26edc9 Mon Sep 17 00:00:00 2001
From: Ovidiu U <nonreal@gmail.com>
Date: Thu, 23 Apr 2026 10:56:26 +0100
Subject: [PATCH] =?UTF-8?q?feat:=20handle=20invoice.payment=5Ffailed=20?=
 =?UTF-8?q?=E2=80=94=20set=20grace=20period=20and=20queue=20reminders?=
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Co-Authored-By: Claude Opus 4.7 (1M context) <noreply@anthropic.com>
---
 app/Listeners/HandleStripeWebhook.php         | 20 +++++++++
 .../Payments/HandleStripeWebhookTest.php      | 43 +++++++++++++++++++
 2 files changed, 63 insertions(+)

diff --git a/app/Listeners/HandleStripeWebhook.php b/app/Listeners/HandleStripeWebhook.php
index 305775b..23cba12 100644
--- a/app/Listeners/HandleStripeWebhook.php
+++ b/app/Listeners/HandleStripeWebhook.php
@@ -2,8 +2,10 @@
 
 namespace App\Listeners;
 
+use App\Jobs\SendPaymentFailedReminderJob;
 use App\Models\User;
 use App\Models\UserNotificationPreference;
+use Illuminate\Support\Carbon;
 use Illuminate\Support\Facades\Cache;
 use Laravel\Cashier\Events\WebhookReceived;
 
@@ -29,6 +31,7 @@ final class HandleStripeWebhook
             'customer.subscription.updated' => $this->bustPlanCache($user),
             'customer.subscription.deleted' => $this->handleSubscriptionDeleted($user),
             'invoice.payment_succeeded' => $this->handlePaymentSucceeded($user),
+            'invoice.payment_failed' => $this->handlePaymentFailed($user),
             default => null,
         };
     }
@@ -51,6 +54,23 @@ final class HandleStripeWebhook
         $this->bustPlanCache($user);
     }
 
+    private function handlePaymentFailed(User $user): void
+    {
+        // Idempotency: only the first failed-payment event in a grace window
+        // transitions state + dispatches reminders. Stripe may fire this event
+        // multiple times per billing cycle (once per failed retry attempt).
+        if ($user->grace_period_until !== null) {
+            return;
+        }
+
+        $user->forceFill(['grace_period_until' => Carbon::now()->addDays(5)])->save();
+
+        SendPaymentFailedReminderJob::dispatch($user->id, 3)->delay(Carbon::now()->addDays(3));
+        SendPaymentFailedReminderJob::dispatch($user->id, 5)->delay(Carbon::now()->addDays(5));
+
+        $this->bustPlanCache($user);
+    }
+
     private function bustPlanCache(User $user): void
     {
         Cache::tags(['plans'])->forget("plan_for_user_{$user->id}");
diff --git a/tests/Feature/Payments/HandleStripeWebhookTest.php b/tests/Feature/Payments/HandleStripeWebhookTest.php
index d3edee6..86e8a8d 100644
--- a/tests/Feature/Payments/HandleStripeWebhookTest.php
+++ b/tests/Feature/Payments/HandleStripeWebhookTest.php
@@ -1,10 +1,12 @@
 <?php
 
+use App\Jobs\SendPaymentFailedReminderJob;
 use App\Listeners\HandleStripeWebhook;
 use App\Models\User;
 use App\Models\UserNotificationPreference;
 use Illuminate\Foundation\Testing\RefreshDatabase;
 use Illuminate\Support\Facades\Cache;
+use Illuminate\Support\Facades\Queue;
 use Laravel\Cashier\Events\WebhookReceived;
 
 uses(RefreshDatabase::class);
@@ -94,3 +96,44 @@ it('invoice.payment_succeeded is a no-op when grace was never set', function ():
 
     expect($user->fresh()->grace_period_until)->toBeNull();
 });
+
+it('on invoice.payment_failed sets grace_period_until 5 days out and queues both reminders', function (): void {
+    Queue::fake();
+    $user = User::factory()->create(['stripe_id' => 'cus_failed_1', 'grace_period_until' => null]);
+
+    $before = now();
+    (new HandleStripeWebhook)->handle(new WebhookReceived([
+        'type' => 'invoice.payment_failed',
+        'data' => ['object' => ['customer' => 'cus_failed_1']],
+    ]));
+
+    $grace = $user->fresh()->grace_period_until;
+    expect($grace)->not->toBeNull();
+    expect($grace->greaterThanOrEqualTo($before->copy()->addDays(5)->subSecond()))->toBeTrue();
+    expect($grace->lessThanOrEqualTo($before->copy()->addDays(5)->addSeconds(5)))->toBeTrue();
+
+    Queue::assertPushed(SendPaymentFailedReminderJob::class, function ($job) use ($user) {
+        return $job->userId === $user->id && $job->day === 3;
+    });
+    Queue::assertPushed(SendPaymentFailedReminderJob::class, function ($job) use ($user) {
+        return $job->userId === $user->id && $job->day === 5;
+    });
+    Queue::assertPushed(SendPaymentFailedReminderJob::class, 2);
+});
+
+it('repeat invoice.payment_failed within grace does not re-dispatch reminders', function (): void {
+    Queue::fake();
+    $existingGrace = now()->addDays(3)->startOfSecond();
+    $user = User::factory()->create(['stripe_id' => 'cus_failed_2', 'grace_period_until' => $existingGrace]);
+
+    (new HandleStripeWebhook)->handle(new WebhookReceived([
+        'type' => 'invoice.payment_failed',
+        'data' => ['object' => ['customer' => 'cus_failed_2']],
+    ]));
+
+    // grace_period_until unchanged (same value)
+    expect($user->fresh()->grace_period_until->equalTo($existingGrace))->toBeTrue();
+
+    // No new jobs queued
+    Queue::assertNothingPushed();
+});