diff --git a/app/Actions/Stripe/CreateCheckoutSession.php b/app/Actions/Stripe/CreateCheckoutSession.php
index 42d14c0f25..dc0c9f72ba 100644
--- a/app/Actions/Stripe/CreateCheckoutSession.php
+++ b/app/Actions/Stripe/CreateCheckoutSession.php
@@ -157,6 +157,12 @@ class CreateCheckoutSession
             'payment_method_collection' => 'if_required',
             'mode' => 'subscription',
             'expires_at' => now()->addMinutes(35)->timestamp,
+            'after_expiration' => [
+                'recovery' => [
+                    'enabled' => true,
+                    'allow_promotion_codes' => false,
+                ],
+            ],
             'success_url' => route('dashboard', ['success' => true]),
             'cancel_url' => route('subscription.index', ['cancelled' => true]),
         ]);
diff --git a/app/Jobs/StripeProcessJob.php b/app/Jobs/StripeProcessJob.php
index 9e4e9f300b..d0d11cee65 100644
--- a/app/Jobs/StripeProcessJob.php
+++ b/app/Jobs/StripeProcessJob.php
@@ -96,6 +96,38 @@ class StripeProcessJob implements ShouldBeEncrypted, ShouldQueue
                         'stripe_subscription_id' => $subscription->stripe_subscription_id,
                     ]);
                     break;
+                case 'checkout.session.expired':
+                    $clientReferenceId = data_get($data, 'client_reference_id');
+                    if (! isCloud() || data_get($data, 'mode') !== 'subscription' || ! is_string($clientReferenceId)) {
+                        break;
+                    }
+                    $userId = Str::before($clientReferenceId, ':');
+                    $teamId = Str::after($clientReferenceId, ':');
+                    $team = Team::find($teamId);
+                    $user = $team?->members->where('id', $userId)->first();
+                    if (! $user?->isAdmin()) {
+                        break;
+                    }
+                    // Atomic claim: one reminder per team per 7 days, also when Stripe delivers several expired sessions at once.
+                    $claimed = Subscription::query()
+                        ->where('team_id', $team->id)
+                        ->where('stripe_invoice_paid', false)
+                        ->where(fn ($query) => $query->whereNull('stripe_checkout_reminder_sent_at')
+                            ->orWhere('stripe_checkout_reminder_sent_at', '<', now()->subDays(7)))
+                        ->update(['stripe_checkout_reminder_sent_at' => now()]);
+                    if ($claimed === 0) {
+                        break;
+                    }
+                    $recoveryUrl = data_get($data, 'after_expiration.recovery.url');
+                    SubscriptionCheckoutReminderJob::dispatch(
+                        $user,
+                        is_string($recoveryUrl) && $recoveryUrl !== '' ? $recoveryUrl : route('subscription.index'),
+                    );
+                    logger()->info('Stripe subscription checkout reminder queued.', [
+                        'team_id' => $team->id,
+                        'stripe_checkout_session_id' => data_get($data, 'id'),
+                    ]);
+                    break;
                 case 'invoice.paid':
                     $customerId = data_get($data, 'customer');
                     $invoiceAmount = data_get($data, 'amount_paid', 0);
diff --git a/app/Jobs/SubscriptionCheckoutReminderJob.php b/app/Jobs/SubscriptionCheckoutReminderJob.php
new file mode 100644
index 0000000000..38ebe45d34
--- /dev/null
+++ b/app/Jobs/SubscriptionCheckoutReminderJob.php
@@ -0,0 +1,32 @@
+<?php
+
+namespace App\Jobs;
+
+use App\Models\User;
+use Illuminate\Bus\Queueable;
+use Illuminate\Contracts\Queue\ShouldBeEncrypted;
+use Illuminate\Contracts\Queue\ShouldQueue;
+use Illuminate\Foundation\Bus\Dispatchable;
+use Illuminate\Notifications\Messages\MailMessage;
+use Illuminate\Queue\InteractsWithQueue;
+use Illuminate\Queue\SerializesModels;
+
+class SubscriptionCheckoutReminderJob implements ShouldBeEncrypted, ShouldQueue
+{
+    use Dispatchable, InteractsWithQueue, Queueable, SerializesModels;
+
+    public function __construct(public User $user, public string $checkoutUrl)
+    {
+        $this->onQueue('high');
+    }
+
+    public function handle(): void
+    {
+        $mail = new MailMessage;
+        $mail->view('emails.subscription-checkout-reminder', [
+            'checkoutUrl' => $this->checkoutUrl,
+        ]);
+        $mail->subject('Coolify: Finish subscribing to Coolify Cloud');
+        send_user_an_email($mail, $this->user->email);
+    }
+}
diff --git a/app/Models/Subscription.php b/app/Models/Subscription.php
index 35df71858e..7fc19356b9 100644
--- a/app/Models/Subscription.php
+++ b/app/Models/Subscription.php
@@ -28,6 +28,7 @@ class Subscription extends Model
         return [
             'stripe_refunded_at' => 'datetime',
             'ended_at' => 'datetime',
+            'stripe_checkout_reminder_sent_at' => 'datetime',
         ];
     }
 
diff --git a/database/migrations/2026_10_29_221743_add_checkout_reminder_sent_at_to_subscriptions_table.php b/database/migrations/2026_10_29_221743_add_checkout_reminder_sent_at_to_subscriptions_table.php
new file mode 100644
index 0000000000..fe794607b7
--- /dev/null
+++ b/database/migrations/2026_10_29_221743_add_checkout_reminder_sent_at_to_subscriptions_table.php
@@ -0,0 +1,22 @@
+<?php
+
+use Illuminate\Database\Migrations\Migration;
+use Illuminate\Database\Schema\Blueprint;
+use Illuminate\Support\Facades\Schema;
+
+return new class extends Migration
+{
+    public function up(): void
+    {
+        Schema::table('subscriptions', function (Blueprint $table) {
+            $table->timestamp('stripe_checkout_reminder_sent_at')->nullable();
+        });
+    }
+
+    public function down(): void
+    {
+        Schema::table('subscriptions', function (Blueprint $table) {
+            $table->dropColumn('stripe_checkout_reminder_sent_at');
+        });
+    }
+};
diff --git a/resources/views/emails/subscription-checkout-reminder.blade.php b/resources/views/emails/subscription-checkout-reminder.blade.php
new file mode 100644
index 0000000000..dd4fb20e2c
--- /dev/null
+++ b/resources/views/emails/subscription-checkout-reminder.blade.php
@@ -0,0 +1,7 @@
+<x-emails.layout>
+You started subscribing to Coolify Cloud but didn't finish.
+
+Pick up where you left off: [Finish subscribing]({{ $checkoutUrl }})
+
+This is a one-off reminder about this checkout. If you do not want to subscribe, you can ignore this email.
+</x-emails.layout>
diff --git a/tests/Feature/Subscription/CreateCheckoutSessionTest.php b/tests/Feature/Subscription/CreateCheckoutSessionTest.php
index 6cb4e712b4..157d754e9c 100644
--- a/tests/Feature/Subscription/CreateCheckoutSessionTest.php
+++ b/tests/Feature/Subscription/CreateCheckoutSessionTest.php
@@ -77,7 +77,8 @@ test('checkout session expiration includes a buffer above Stripe\'s 30-minute mi
     $this->checkoutSessions->shouldReceive('create')->once()
         ->withArgs(function (array $payload): bool {
             expect($payload['expires_at'])->toBeGreaterThanOrEqual(now()->addMinutes(35)->timestamp)
-                ->and($payload['expires_at'])->toBeLessThanOrEqual(now()->addHours(24)->timestamp);
+                ->and($payload['expires_at'])->toBeLessThanOrEqual(now()->addHours(24)->timestamp)
+                ->and($payload['after_expiration'])->toBe(['recovery' => ['enabled' => true, 'allow_promotion_codes' => false]]);
 
             return $payload['customer'] === 'cus_existing';
         })
diff --git a/tests/Feature/Subscription/StripeProcessJobTest.php b/tests/Feature/Subscription/StripeProcessJobTest.php
index c950a4592b..02c12439dc 100644
--- a/tests/Feature/Subscription/StripeProcessJobTest.php
+++ b/tests/Feature/Subscription/StripeProcessJobTest.php
@@ -2,6 +2,7 @@
 
 use App\Jobs\ServerLimitCheckJob;
 use App\Jobs\StripeProcessJob;
+use App\Jobs\SubscriptionCheckoutReminderJob;
 use App\Jobs\SubscriptionInvoiceFailedJob;
 use App\Jobs\VerifyStripeSubscriptionStatusJob;
 use App\Models\Server;
@@ -13,6 +14,7 @@ use Illuminate\Foundation\Testing\RefreshDatabase;
 use Illuminate\Support\Facades\Notification;
 use Illuminate\Support\Facades\Queue;
 use Stripe\Customer;
+use Stripe\Event;
 use Stripe\PaymentIntent;
 use Stripe\Service\CustomerService;
 use Stripe\Service\PaymentIntentService;
@@ -493,3 +495,85 @@ test('an early fraud warning refunds and cancels every subscription of the email
         ->and($endedRow->fresh()->stripe_subscription_id)->toBeNull()
         ->and($server->settings()->first()->is_usable)->toBeFalsy();
 });
+
+describe('checkout.session.expired', function () {
+    beforeEach(function () {
+        Queue::fake([SubscriptionCheckoutReminderJob::class]);
+        Subscription::create([
+            'team_id' => $this->team->id,
+            'stripe_customer_id' => 'cus_TestExpiredCheckout',
+            'stripe_invoice_paid' => false,
+        ]);
+    });
+
+    function expiredCheckoutEvent(string $clientReferenceId, ?string $recoveryUrl = 'https://buy.stripe.com/r/test_recoveryabc123'): Event
+    {
+        $payload = json_decode(file_get_contents(base_path('tests/Fixtures/stripe/checkout.session.expired.json')), true);
+        $payload['data']['object']['client_reference_id'] = $clientReferenceId;
+        if ($recoveryUrl === null) {
+            $payload['data']['object']['after_expiration'] = null;
+        }
+
+        return Event::constructFrom($payload);
+    }
+
+    test('queues one reminder with the recovery url to the user who started checkout', function () {
+        (new StripeProcessJob(expiredCheckoutEvent("{$this->user->id}:{$this->team->id}")))->handle();
+
+        Queue::assertPushed(SubscriptionCheckoutReminderJob::class, 1);
+        Queue::assertPushed(SubscriptionCheckoutReminderJob::class, fn ($job) => $job->user->is($this->user)
+            && $job->checkoutUrl === 'https://buy.stripe.com/r/test_recoveryabc123');
+        expect($this->team->subscription()->first()->stripe_checkout_reminder_sent_at)->not->toBeNull();
+    });
+
+    test('falls back to the subscription page without a recovery url', function () {
+        (new StripeProcessJob(expiredCheckoutEvent("{$this->user->id}:{$this->team->id}", null)))->handle();
+
+        Queue::assertPushed(SubscriptionCheckoutReminderJob::class, fn ($job) => $job->checkoutUrl === route('subscription.index'));
+    });
+
+    test('does not remind a team that is already subscribed', function () {
+        $this->team->subscription()->update(['stripe_invoice_paid' => true]);
+
+        (new StripeProcessJob(expiredCheckoutEvent("{$this->user->id}:{$this->team->id}")))->handle();
+
+        Queue::assertNotPushed(SubscriptionCheckoutReminderJob::class);
+    });
+
+    test('sends at most one reminder per team in 7 days', function () {
+        $event = expiredCheckoutEvent("{$this->user->id}:{$this->team->id}");
+
+        (new StripeProcessJob($event))->handle();
+        $this->travel(6)->days();
+        (new StripeProcessJob($event))->handle();
+        Queue::assertPushed(SubscriptionCheckoutReminderJob::class, 1);
+
+        $this->travel(2)->days();
+        (new StripeProcessJob($event))->handle();
+        Queue::assertPushed(SubscriptionCheckoutReminderJob::class, 2);
+    });
+
+    test('ignores unknown or unauthorized client reference ids', function (string $clientReferenceId) {
+        (new StripeProcessJob(expiredCheckoutEvent($clientReferenceId)))->handle();
+
+        Queue::assertNotPushed(SubscriptionCheckoutReminderJob::class);
+    })->with([
+        'unknown team' => fn () => "{$this->user->id}:999999",
+        'user not in team' => fn () => "999999:{$this->team->id}",
+        'member role' => function () {
+            $member = User::factory()->create();
+            $this->team->members()->attach($member->id, ['role' => 'member']);
+
+            return "{$member->id}:{$this->team->id}";
+        },
+    ]);
+
+    test('does nothing on self-hosted instances', function () {
+        config()->set('constants.coolify.self_hosted', true);
+
+        (new StripeProcessJob(expiredCheckoutEvent("{$this->user->id}:{$this->team->id}")))->handle();
+
+        Queue::assertNotPushed(SubscriptionCheckoutReminderJob::class);
+        expect($this->team->subscription()->first()->stripe_checkout_reminder_sent_at)->toBeNull();
+    });
+});
diff --git a/tests/Fixtures/stripe/checkout.session.expired.json b/tests/Fixtures/stripe/checkout.session.expired.json
new file mode 100644
index 0000000000..d80711d408
--- /dev/null
+++ b/tests/Fixtures/stripe/checkout.session.expired.json
@@ -0,0 +1,109 @@
+{
+  "id": "evt_1QxExpiredCheckout0000001",
+  "object": "event",
+  "api_version": "2025-02-24.acacia",
+  "created": 1761779100,
+  "data": {
+    "object": {
+      "id": "cs_test_b1ExpiredSubscriptionCheckout000000000000000000000000001",
+      "object": "checkout.session",
+      "adaptive_pricing": null,
+      "after_expiration": {
+        "recovery": {
+          "allow_promotion_codes": false,
+          "enabled": true,
+          "expires_at": 1764371100,
+          "url": "https://buy.stripe.com/r/test_recoveryabc123"
+        }
+      },
+      "allow_promotion_codes": true,
+      "amount_subtotal": 1000,
+      "amount_total": 1000,
+      "automatic_tax": {
+        "enabled": true,
+        "liability": {
+          "type": "self"
+        },
+        "provider": "stripe",
+        "status": "requires_location_inputs"
+      },
+      "billing_address_collection": "required",
+      "cancel_url": "https://app.coolify.io/subscription/new?cancelled=1",
+      "client_reference_id": "{{client_reference_id}}",
+      "client_secret": null,
+      "collected_information": null,
+      "consent": null,
+      "consent_collection": null,
+      "created": 1761777000,
+      "currency": "usd",
+      "currency_conversion": null,
+      "custom_fields": [],
+      "custom_text": {
+        "after_submit": null,
+        "shipping_address": null,
+        "submit": null,
+        "terms_of_service_acceptance": null
+      },
+      "customer": "cus_TestExpiredCheckout",
+      "customer_creation": null,
+      "customer_details": null,
+      "customer_email": null,
+      "discounts": [],
+      "expires_at": 1761779100,
+      "invoice": null,
+      "invoice_creation": null,
+      "livemode": false,
+      "locale": null,
+      "metadata": {},
+      "mode": "subscription",
+      "payment_intent": null,
+      "payment_link": null,
+      "payment_method_collection": "if_required",
+      "payment_method_configuration_details": null,
+      "payment_method_options": {},
+      "payment_method_types": [
+        "card"
+      ],
+      "payment_status": "unpaid",
+      "permissions": null,
+      "phone_number_collection": {
+        "enabled": false
+      },
+      "recovered_from": null,
+      "saved_payment_method_options": {
+        "allow_redisplay_filters": [
+          "always"
+        ],
+        "payment_method_remove": null,
+        "payment_method_save": null
+      },
+      "setup_intent": null,
+      "shipping_address_collection": null,
+      "shipping_cost": null,
+      "shipping_details": null,
+      "shipping_options": [],
+      "status": "expired",
+      "submit_type": null,
+      "subscription": null,
+      "success_url": "https://app.coolify.io/?success=1",
+      "tax_id_collection": {
+        "enabled": true,
+        "required": "never"
+      },
+      "total_details": {
+        "amount_discount": 0,
+        "amount_shipping": 0,
+        "amount_tax": 0
+      },
+      "ui_mode": "hosted",
+      "url": null
+    }
+  },
+  "livemode": false,
+  "pending_webhooks": 1,
+  "request": {
+    "id": null,
+    "idempotency_key": null
+  },
+  "type": "checkout.session.expired"
+}