diff --git a/app/Actions/Fortify/CreateNewUser.php b/app/Actions/Fortify/CreateNewUser.php
index 9f97dd0d4c..a2962c4ce5 100644
--- a/app/Actions/Fortify/CreateNewUser.php
+++ b/app/Actions/Fortify/CreateNewUser.php
@@ -2,6 +2,7 @@
 
 namespace App\Actions\Fortify;
 
+use App\Jobs\SyncMailcheepContactJob;
 use App\Models\User;
 use Illuminate\Support\Facades\Hash;
 use Illuminate\Support\Facades\Validator;
@@ -58,6 +59,14 @@ class CreateNewUser implements CreatesNewUsers
             $team = $user->teams()->first();
             if (isCloud()) {
                 $user->sendVerificationEmail();
+                if (config('subscription.mailcheep_api_key')) {
+                    SyncMailcheepContactJob::dispatch(
+                        action: 'create_or_update',
+                        email: $user->email,
+                        name: $user->name,
+                        customFields: ['team_id' => (string) $team->id],
+                    );
+                }
             } else {
                 $user->markEmailAsVerified();
             }
diff --git a/app/Console/Commands/SyncMailcheep.php b/app/Console/Commands/SyncMailcheep.php
new file mode 100644
index 0000000000..97509fac0d
--- /dev/null
+++ b/app/Console/Commands/SyncMailcheep.php
@@ -0,0 +1,76 @@
+<?php
+
+namespace App\Console\Commands;
+
+use App\Jobs\SyncMailcheepContactJob;
+use App\Models\Team;
+use Illuminate\Console\Command;
+
+class SyncMailcheep extends Command
+{
+    protected $signature = 'sync:mailcheep {--dry-run}';
+
+    protected $description = 'Backfill all team owners to Mailcheep contact lists';
+
+    public function handle(): int
+    {
+        if (! isCloud()) {
+            $this->error('This command can only be run on the cloud instance.');
+
+            return self::FAILURE;
+        }
+
+        if (! config('subscription.mailcheep_api_key')) {
+            $this->error('MAILCHEEP_API_KEY is not configured.');
+
+            return self::FAILURE;
+        }
+
+        $dryRun = $this->option('dry-run');
+        $stats = ['subscribed' => 0, 'churned' => 0, 'no_subscription' => 0];
+
+        Team::with(['subscription', 'members'])->chunk(100, function ($teams) use ($dryRun, &$stats) {
+            foreach ($teams as $team) {
+                $owner = $team->members->firstWhere('pivot.role', 'owner');
+
+                if (! $owner) {
+                    continue;
+                }
+
+                $subscription = $team->subscription;
+
+                if ($subscription && $subscription->stripe_invoice_paid && $subscription->stripe_subscription_id) {
+                    $action = 'create_or_update';
+                    $extraFields = [
+                        'team_id' => (string) $team->id,
+                        'plan' => $subscription->billingInterval(),
+                    ];
+                    $stats['subscribed']++;
+                } elseif ($subscription && (! $subscription->stripe_invoice_paid || ! $subscription->stripe_subscription_id)) {
+                    $action = 'add_to_churned';
+                    $extraFields = [];
+                    $stats['churned']++;
+                } else {
+                    $action = 'create_or_update';
+                    $extraFields = ['team_id' => (string) $team->id];
+                    $stats['no_subscription']++;
+                }
+
+                if ($dryRun) {
+                    $this->line("[DRY RUN] {$action}: {$owner->email} (Team #{$team->id})");
+                } else {
+                    SyncMailcheepContactJob::dispatch(
+                        action: $action,
+                        email: $owner->email,
+                        name: $owner->name,
+                        customFields: $extraFields,
+                    );
+                }
+            }
+        });
+
+        $this->info("Subscribed: {$stats['subscribed']}, Churned: {$stats['churned']}, No subscription: {$stats['no_subscription']}");
+
+        return self::SUCCESS;
+    }
+}
diff --git a/app/Jobs/StripeProcessJob.php b/app/Jobs/StripeProcessJob.php
index 3485ffe32c..cd34da0ab7 100644
--- a/app/Jobs/StripeProcessJob.php
+++ b/app/Jobs/StripeProcessJob.php
@@ -299,6 +299,7 @@ class StripeProcessJob implements ShouldBeEncrypted, ShouldQueue
                         $team = data_get($subscription, 'team');
                         if ($team) {
                             $team->subscriptionEnded();
+                            SyncMailcheepContactJob::dispatchForTeam($team, 'add_to_churned');
                         } else {
                             // send_internal_notification('Subscription unpaid but no team found in Coolify for customer: '.$customerId);
                             throw new \RuntimeException("No team found in Coolify for customer: {$customerId}");
@@ -311,6 +312,13 @@ class StripeProcessJob implements ShouldBeEncrypted, ShouldQueue
                                 'stripe_invoice_paid' => true,
                             ]);
                         }
+                        $team = data_get($subscription, 'team');
+                        if ($team) {
+                            SyncMailcheepContactJob::dispatchForTeam($team, 'create_or_update', [
+                                'team_id' => (string) $team->id,
+                                'plan' => $subscription->billingInterval(),
+                            ]);
+                        }
                     }
                     if ($feedback) {
                         $reason = "Cancellation feedback for {$customerId}: '".$feedback."'";
@@ -328,6 +336,7 @@ class StripeProcessJob implements ShouldBeEncrypted, ShouldQueue
                         $team = data_get($subscription, 'team');
                         if ($team) {
                             $team->subscriptionEnded();
+                            SyncMailcheepContactJob::dispatchForTeam($team, 'add_to_churned');
                         } else {
                             // send_internal_notification('Subscription deleted but no team found in Coolify for customer: '.$customerId);
                             throw new \RuntimeException("No team found in Coolify for customer: {$customerId}");
diff --git a/app/Jobs/SyncMailcheepContactJob.php b/app/Jobs/SyncMailcheepContactJob.php
new file mode 100644
index 0000000000..ac418e4d27
--- /dev/null
+++ b/app/Jobs/SyncMailcheepContactJob.php
@@ -0,0 +1,67 @@
+<?php
+
+namespace App\Jobs;
+
+use App\Models\Team;
+use App\Services\MailcheepService;
+use Illuminate\Contracts\Queue\ShouldBeEncrypted;
+use Illuminate\Contracts\Queue\ShouldQueue;
+use Illuminate\Foundation\Queue\Queueable;
+
+class SyncMailcheepContactJob implements ShouldBeEncrypted, ShouldQueue
+{
+    use Queueable;
+
+    public int $tries = 3;
+
+    public int $backoff = 10;
+
+    /**
+     * @param  array<string, string>  $customFields
+     */
+    public function __construct(
+        public string $action,
+        public string $email,
+        public string $name,
+        public array $customFields = [],
+    ) {
+        $this->onQueue('high');
+    }
+
+    public function handle(MailcheepService $mailcheep): void
+    {
+        match ($this->action) {
+            'create_or_update' => $mailcheep->createOrUpdateContact(
+                $this->email,
+                $this->name,
+                config('subscription.mailcheep_list_subscribed'),
+                $this->customFields,
+            ),
+            'add_to_churned' => $mailcheep->addToChurnedList($this->email),
+            default => null,
+        };
+    }
+
+    /**
+     * @param  array<string, string>  $extraFields
+     */
+    public static function dispatchForTeam(Team $team, string $action, array $extraFields = []): void
+    {
+        if (! config('subscription.mailcheep_api_key')) {
+            return;
+        }
+
+        $owner = $team->members->firstWhere('pivot.role', 'owner');
+
+        if (! $owner) {
+            return;
+        }
+
+        static::dispatch(
+            action: $action,
+            email: $owner->email,
+            name: $owner->name,
+            customFields: $extraFields,
+        );
+    }
+}
diff --git a/app/Services/MailcheepService.php b/app/Services/MailcheepService.php
new file mode 100644
index 0000000000..c3ac60c502
--- /dev/null
+++ b/app/Services/MailcheepService.php
@@ -0,0 +1,138 @@
+<?php
+
+namespace App\Services;
+
+use Illuminate\Support\Facades\Http;
+use Illuminate\Support\Facades\Log;
+
+class MailcheepService
+{
+    private string $apiKey;
+
+    private string $baseUrl = 'https://api.mailcheep.cloud/v1';
+
+    public function __construct()
+    {
+        $this->apiKey = config('subscription.mailcheep_api_key');
+    }
+
+    /**
+     * @return array<string, mixed>|null
+     */
+    public function findContactByEmail(string $email): ?array
+    {
+        try {
+            $response = $this->client()->get("{$this->baseUrl}/contacts", [
+                'search' => $email,
+            ]);
+
+            if ($response->successful()) {
+                $contacts = $response->json('data', []);
+                foreach ($contacts as $contact) {
+                    if (data_get($contact, 'email') === $email) {
+                        return $contact;
+                    }
+                }
+            }
+
+            return null;
+        } catch (\Exception $e) {
+            Log::error('Mailcheep: failed to find contact', ['email' => $email, 'error' => $e->getMessage()]);
+
+            return null;
+        }
+    }
+
+    /**
+     * @param  array<string, string>  $customFields
+     * @return array<string, mixed>|null
+     */
+    public function createContact(string $email, string $name, string $listId, array $customFields = []): ?array
+    {
+        try {
+            $response = $this->client()->post("{$this->baseUrl}/contacts", [
+                'email' => $email,
+                'name' => $name,
+                'list_id' => $listId,
+                'custom_fields' => $customFields,
+            ]);
+
+            if ($response->successful()) {
+                return $response->json('data');
+            }
+
+            Log::warning('Mailcheep: failed to create contact', ['email' => $email, 'status' => $response->status()]);
+
+            return null;
+        } catch (\Exception $e) {
+            Log::error('Mailcheep: failed to create contact', ['email' => $email, 'error' => $e->getMessage()]);
+
+            return null;
+        }
+    }
+
+    /**
+     * @param  array<string, mixed>  $data
+     * @return array<string, mixed>|null
+     */
+    public function updateContact(string $id, array $data): ?array
+    {
+        try {
+            $response = $this->client()->put("{$this->baseUrl}/contacts/{$id}", $data);
+
+            if ($response->successful()) {
+                return $response->json('data');
+            }
+
+            Log::warning('Mailcheep: failed to update contact', ['id' => $id, 'status' => $response->status()]);
+
+            return null;
+        } catch (\Exception $e) {
+            Log::error('Mailcheep: failed to update contact', ['id' => $id, 'error' => $e->getMessage()]);
+
+            return null;
+        }
+    }
+
+    /**
+     * @param  array<string, string>  $customFields
+     * @return array<string, mixed>|null
+     */
+    public function createOrUpdateContact(string $email, string $name, string $listId, array $customFields = []): ?array
+    {
+        $existing = $this->findContactByEmail($email);
+
+        if ($existing) {
+            return $this->updateContact(data_get($existing, 'id'), [
+                'name' => $name,
+                'list_id' => $listId,
+                'custom_fields' => $customFields,
+            ]);
+        }
+
+        return $this->createContact($email, $name, $listId, $customFields);
+    }
+
+    /**
+     * @return array<string, mixed>|null
+     */
+    public function addToChurnedList(string $email): ?array
+    {
+        $existing = $this->findContactByEmail($email);
+
+        if ($existing) {
+            return $this->updateContact(data_get($existing, 'id'), [
+                'list_id' => config('subscription.mailcheep_list_churned'),
+            ]);
+        }
+
+        return null;
+    }
+
+    private function client(): \Illuminate\Http\Client\PendingRequest
+    {
+        return Http::withHeaders([
+            'X-API-Key' => $this->apiKey,
+        ])->timeout(15)->retry(2, 100);
+    }
+}
diff --git a/config/subscription.php b/config/subscription.php
index a033862d26..5f55afe74e 100644
--- a/config/subscription.php
+++ b/config/subscription.php
@@ -9,4 +9,9 @@ return [
     'stripe_excluded_plans' => env('STRIPE_EXCLUDED_PLANS', null),
     'stripe_price_id_dynamic_monthly' => env('STRIPE_PRICE_ID_DYNAMIC_MONTHLY', null),
     'stripe_price_id_dynamic_yearly' => env('STRIPE_PRICE_ID_DYNAMIC_YEARLY', null),
+
+    // Mailcheep
+    'mailcheep_api_key' => env('MAILCHEEP_API_KEY'),
+    'mailcheep_list_subscribed' => env('MAILCHEEP_LIST_SUBSCRIBED'),
+    'mailcheep_list_churned' => env('MAILCHEEP_LIST_CHURNED'),
 ];
diff --git a/tests/Feature/MailcheepIntegrationTest.php b/tests/Feature/MailcheepIntegrationTest.php
new file mode 100644
index 0000000000..7e4b69bf2b
--- /dev/null
+++ b/tests/Feature/MailcheepIntegrationTest.php
@@ -0,0 +1,207 @@
+<?php
+
+use App\Jobs\SyncMailcheepContactJob;
+use App\Models\Team;
+use App\Models\User;
+use App\Services\MailcheepService;
+use Illuminate\Support\Facades\Bus;
+use Illuminate\Support\Facades\Http;
+
+beforeEach(function () {
+    config()->set('subscription.mailcheep_api_key', 'test-api-key');
+    config()->set('subscription.mailcheep_list_subscribed', 'list-subscribed-id');
+    config()->set('subscription.mailcheep_list_churned', 'list-churned-id');
+});
+
+describe('MailcheepService', function () {
+    it('finds a contact by email', function () {
+        Http::fake([
+            'api.mailcheep.cloud/v1/contacts*' => Http::response([
+                'data' => [
+                    ['id' => 'contact-1', 'email' => 'test@example.com', 'name' => 'Test User'],
+                ],
+            ]),
+        ]);
+
+        $service = new MailcheepService;
+        $result = $service->findContactByEmail('test@example.com');
+
+        expect($result)->not->toBeNull()
+            ->and($result['email'])->toBe('test@example.com');
+
+        Http::assertSent(function ($request) {
+            return str_contains($request->url(), '/contacts') && $request->data()['search'] === 'test@example.com';
+        });
+    });
+
+    it('returns null when contact is not found', function () {
+        Http::fake([
+            'api.mailcheep.cloud/v1/contacts*' => Http::response(['data' => []]),
+        ]);
+
+        $service = new MailcheepService;
+        $result = $service->findContactByEmail('missing@example.com');
+
+        expect($result)->toBeNull();
+    });
+
+    it('creates a contact', function () {
+        Http::fake([
+            'api.mailcheep.cloud/v1/contacts' => Http::response([
+                'data' => ['id' => 'contact-new', 'email' => 'new@example.com'],
+            ]),
+        ]);
+
+        $service = new MailcheepService;
+        $result = $service->createContact('new@example.com', 'New User', 'list-id', ['team_id' => '1']);
+
+        expect($result)->not->toBeNull()
+            ->and($result['email'])->toBe('new@example.com');
+
+        Http::assertSent(function ($request) {
+            return $request->method() === 'POST'
+                && $request['email'] === 'new@example.com'
+                && $request['list_id'] === 'list-id';
+        });
+    });
+
+    it('updates a contact', function () {
+        Http::fake([
+            'api.mailcheep.cloud/v1/contacts/contact-1' => Http::response([
+                'data' => ['id' => 'contact-1', 'list_id' => 'new-list'],
+            ]),
+        ]);
+
+        $service = new MailcheepService;
+        $result = $service->updateContact('contact-1', ['list_id' => 'new-list']);
+
+        expect($result)->not->toBeNull();
+
+        Http::assertSent(function ($request) {
+            return $request->method() === 'PUT' && $request['list_id'] === 'new-list';
+        });
+    });
+
+    it('creates or updates a contact when existing', function () {
+        Http::fake([
+            'api.mailcheep.cloud/v1/contacts?search=*' => Http::response([
+                'data' => [['id' => 'contact-1', 'email' => 'existing@example.com']],
+            ]),
+            'api.mailcheep.cloud/v1/contacts/contact-1' => Http::response([
+                'data' => ['id' => 'contact-1', 'name' => 'Updated'],
+            ]),
+        ]);
+
+        $service = new MailcheepService;
+        $result = $service->createOrUpdateContact('existing@example.com', 'Updated', 'list-id');
+
+        expect($result)->not->toBeNull();
+    });
+
+    it('returns null on API failure without throwing', function () {
+        Http::fake([
+            'api.mailcheep.cloud/v1/contacts*' => Http::response('Server Error', 500),
+        ]);
+
+        $service = new MailcheepService;
+        $result = $service->findContactByEmail('fail@example.com');
+
+        expect($result)->toBeNull();
+    });
+
+    it('sends X-API-Key header', function () {
+        Http::fake([
+            'api.mailcheep.cloud/v1/contacts*' => Http::response(['data' => []]),
+        ]);
+
+        $service = new MailcheepService;
+        $service->findContactByEmail('test@example.com');
+
+        Http::assertSent(function ($request) {
+            return $request->hasHeader('X-API-Key', 'test-api-key');
+        });
+    });
+});
+
+describe('SyncMailcheepContactJob', function () {
+    it('calls create_or_update on the service', function () {
+        Http::fake([
+            'api.mailcheep.cloud/v1/contacts?search=*' => Http::response(['data' => []]),
+            'api.mailcheep.cloud/v1/contacts' => Http::response([
+                'data' => ['id' => 'new', 'email' => 'job@example.com'],
+            ]),
+        ]);
+
+        $job = new SyncMailcheepContactJob(
+            action: 'create_or_update',
+            email: 'job@example.com',
+            name: 'Job User',
+            customFields: ['team_id' => '1'],
+        );
+
+        $job->handle(app(MailcheepService::class));
+
+        Http::assertSent(function ($request) {
+            return $request->method() === 'POST' && $request['email'] === 'job@example.com';
+        });
+    });
+
+    it('calls add_to_churned on the service', function () {
+        Http::fake([
+            'api.mailcheep.cloud/v1/contacts?search=*' => Http::response([
+                'data' => [['id' => 'contact-1', 'email' => 'churn@example.com']],
+            ]),
+            'api.mailcheep.cloud/v1/contacts/contact-1' => Http::response([
+                'data' => ['id' => 'contact-1'],
+            ]),
+        ]);
+
+        $job = new SyncMailcheepContactJob(
+            action: 'add_to_churned',
+            email: 'churn@example.com',
+            name: 'Churn User',
+        );
+
+        $job->handle(app(MailcheepService::class));
+
+        Http::assertSent(function ($request) {
+            return $request->method() === 'PUT' && $request['list_id'] === 'list-churned-id';
+        });
+    });
+
+    it('dispatchForTeam skips when no API key configured', function () {
+        config()->set('subscription.mailcheep_api_key', null);
+        Bus::fake();
+
+        $team = Team::factory()->create();
+
+        SyncMailcheepContactJob::dispatchForTeam($team, 'create_or_update');
+
+        Bus::assertNothingDispatched();
+    });
+
+    it('dispatchForTeam dispatches job for team owner', function () {
+        Bus::fake();
+
+        $user = User::factory()->create();
+        $team = Team::factory()->create();
+        $team->members()->attach($user->id, ['role' => 'owner']);
+        $team->load('members');
+
+        SyncMailcheepContactJob::dispatchForTeam($team, 'create_or_update', ['team_id' => (string) $team->id]);
+
+        Bus::assertDispatched(SyncMailcheepContactJob::class, function ($job) use ($user) {
+            return $job->action === 'create_or_update'
+                && $job->email === $user->email
+                && $job->name === $user->name;
+        });
+    });
+});
+
+describe('SyncMailcheep command', function () {
+    it('fails when not on cloud', function () {
+        // isCloud() returns false by default in tests
+        $this->artisan('sync:mailcheep')
+            ->assertFailed();
+    });
+});