diff --git a/app/Listeners/CheckoutableListener.php b/app/Listeners/CheckoutableListener.php
index 7d8b5c1c9..cf9464a78 100644
--- a/app/Listeners/CheckoutableListener.php
+++ b/app/Listeners/CheckoutableListener.php
@@ -73,14 +73,17 @@ class CheckoutableListener
              * 2. The item has a EULA
              * 3. The item should send an email at check-in/check-out
              */
-            if ($notifiable instanceof User && $notifiable->email != '') {
+            if ($notifiable instanceof User) {
                 if ($event->checkoutable->requireAcceptance() || $event->checkoutable->getEula() ||
                     (method_exists($event->checkoutable, 'checkin_email') && $event->checkoutable->checkin_email())) {
-                Mail::to($notifiable)->cc($ccEmails)->send($mailable);
+                    if (!empty($notifiable->email)) {
+                        Mail::to($notifiable)->cc($ccEmails)->send($mailable);
+                    } else {
+                        Mail::cc($ccEmails)->send($mailable);
+                    }
                 Log::info('Sending email, Locale: ' . ($event->checkedOutTo->locale ?? 'default'));
             }
         }
-
 //                 Send Webhook notification
                 if ($this->shouldSendWebhookNotification()) {
                     Notification::route(Setting::getSettings()->webhook_selected, Setting::getSettings()->webhook_endpoint)
diff --git a/routes/web.php b/routes/web.php
index e54f4f706..e0e623e8d 100644
--- a/routes/web.php
+++ b/routes/web.php
@@ -25,7 +25,9 @@ use App\Http\Controllers\Auth\ForgotPasswordController;
 use App\Http\Controllers\Auth\ResetPasswordController;
 use App\Livewire\Importer;
 use App\Models\Asset;
+use App\Models\Setting;
 use App\Models\User;
+use Illuminate\Support\Facades\Mail;
 use Illuminate\Support\Facades\Route;
 use Illuminate\Support\Facades\Auth;
 
@@ -552,21 +554,32 @@ Route::middleware(['auth'])->get(
     [DashboardController::class, 'index']
 )->name('home');
 Route::get('/test-email', function() {
-    $item = Asset::find(1); // Load some test data
-    $admin = User::find(1);
-    $target = User::find(2);
+    $item = \App\Models\LicenseSeat::find(1); // Load some test data
+    $admin = User::find(2);
+    $target = User::find(1);
     $acceptance = null; // Simulate acceptance data
     $note = 'Test note';
+    $settings = Setting::getSettings();
+    $adminCcEmailsArray = [];
 
-    $fields = [];
-    if (($item->model) && ($item->model->fieldset)) {
-        $fields = $item->model->fieldset->fields;
+    if($settings->admin_cc_email !== '') {
+        $adminCcEmail = $settings->admin_cc_email;
+        $adminCcEmailsArray = array_map('trim', explode(',', $adminCcEmail));
+    }
+    $ccEmails = array_filter($adminCcEmailsArray);
+    if (!empty($target->email)) {
+        Mail::to($target)->cc($ccEmails)->send( new \App\Mail\CheckoutLicenseMail(
+            $item,
+            $admin,
+            $target,
+            $acceptance,
+            $note));
+    } else {
+        Mail::cc($ccEmails)->send(new \App\Mail\CheckoutLicenseMail(
+            $item,
+            $admin,
+            $target,
+            $acceptance,
+            $note));
     }
-
-    return new \App\Mail\CheckoutAssetMail(
-        $item,
-        $admin,
-        $target,
-        $acceptance,
-        $note);
 });
\ No newline at end of file