diff --git a/app/Listeners/CheckoutableListener.php b/app/Listeners/CheckoutableListener.php
index f8c6c8baa..8fa96acb6 100644
--- a/app/Listeners/CheckoutableListener.php
+++ b/app/Listeners/CheckoutableListener.php
@@ -16,6 +16,7 @@ use App\Models\CheckoutAcceptance;
 use App\Models\Component;
 use App\Models\Consumable;
 use App\Models\LicenseSeat;
+use App\Models\Location;
 use App\Models\Setting;
 use App\Models\User;
 use App\Notifications\CheckinAccessoryNotification;
@@ -60,14 +61,14 @@ class CheckoutableListener
             $adminCcEmailsArray = array_map('trim', explode(',', $adminCcEmail));
         }
         $ccEmails = array_filter($adminCcEmailsArray);
-        $notifiable = $event->checkedOutTo;
         $mailable = $this->getCheckoutMailType($event, $acceptance);
+        $notifiable = $this->getNotifiables($event);
+
+        if  (!$event->checkedOutTo->locale){
+            $mailable->locale($event->checkedOutTo->locale);
+        }
         // Send email notifications
         try {
-                if  (!$event->checkedOutTo->locale){
-                    $mailable->locale($event->checkedOutTo->locale);
-                }
-
             /**
              * Send an email if any of the following conditions are met:
              * 1. The asset requires acceptance
@@ -77,15 +78,20 @@ class CheckoutableListener
 
                 if ($event->checkoutable->requireAcceptance() || $event->checkoutable->getEula() ||
                     (method_exists($event->checkoutable, 'checkin_email') && $event->checkoutable->checkin_email())) {
-                    if (!empty($notifiable->email)) {
+                    if (!empty($notifiable)) {
                         Mail::to($notifiable)->cc($ccEmails)->send($mailable);
-                    } else {
+                    } elseif (!empty($ccEmails)) {
                         Mail::cc($ccEmails)->send($mailable);
                     }
-                Log::info('Sending email, Locale: ' . ($event->checkedOutTo->locale ?? 'default'));
-            }
-
+                    Log::info('Sending email, Locale: ' . ($event->checkedOutTo->locale ?? 'default'));
+                }
+        } catch (ClientException $e) {
+            Log::debug("Exception caught during checkout email: " . $e->getMessage());
+        } catch (Exception $e) {
+            Log::debug("Exception caught during checkout email: " . $e->getMessage());
+        }
 //                 Send Webhook notification
+        try{
                 if ($this->shouldSendWebhookNotification()) {
                     if (Setting::getSettings()->webhook_selected === 'microsoft') {
                         $message = $this->getCheckoutNotification($event)->toMicrosoftTeams();
@@ -137,38 +143,43 @@ class CheckoutableListener
             $adminCcEmailsArray = array_map('trim', explode(',', $adminCcEmail));
         }
         $ccEmails = array_filter($adminCcEmailsArray);
-        $notifiable = $event->checkedOutTo;
         $mailable =  $this->getCheckinMailType($event);
+        $notifiable = $this->getNotifiables($event);
 
+        if  (!$event->checkedOutTo->locale){
+            $mailable->locale($event->checkedOutTo->locale);
+        }
         // Send email notifications
         try {
-            if  (!$event->checkedOutTo->locale){
-                $mailable->locale($event->checkedOutTo->locale);
-            }
             /**
              * Send an email if any of the following conditions are met:
              * 1. The asset requires acceptance
              * 2. The item has a EULA
              * 3. The item should send an email at check-in/check-out
              */
-
                 if ($event->checkoutable->requireAcceptance() || $event->checkoutable->getEula() ||
                     (method_exists($event->checkoutable, 'checkin_email') && $event->checkoutable->checkin_email())) {
-                    if (!empty($notifiable->email)) {
+                    if (!empty($notifiable)) {
                         Mail::to($notifiable)->cc($ccEmails)->send($mailable);
-                    } else {
+                    } elseif (!empty($ccEmails)){
                         Mail::cc($ccEmails)->send($mailable);
                     }
                     Log::info('Sending email, Locale: ' . $event->checkedOutTo->locale);
                 }
+        } catch (ClientException $e) {
+            Log::debug("Exception caught during checkin email: " . $e->getMessage());
+        } catch (Exception $e) {
+            Log::debug("Exception caught during checkin email: " . $e->getMessage());
+        }
 
-            // Send Webhook notification
+        // Send Webhook notification
+        try {
             if ($this->shouldSendWebhookNotification()) {
                     Notification::route(Setting::getSettings()->webhook_selected, Setting::getSettings()->webhook_endpoint)
                         ->notify($this->getCheckinNotification($event));
                 }
         } catch (ClientException $e) {
-            Log::warning("Exception caught during checkout notification: " . $e->getMessage());
+            Log::warning("Exception caught during checkin notification: " . $e->getMessage());
         } catch (Exception $e) {
             Log::warning("Exception caught during checkin notification: " . $e->getMessage());
         }
@@ -278,6 +289,19 @@ class CheckoutableListener
         return new $mailable($event->checkoutable, $event->checkedOutTo, $event->checkedInBy, $event->note);
 
     }
+    private function getNotifiables($event){
+
+        if($event->checkedOutTo instanceof Asset){
+            $event->checkedOutTo->load('assignedTo');
+            return $event->checkedOutTo->assignedto?->email ?? '';
+        }
+        else if($event->checkedOutTo instanceof Location) {
+            return $event->checkedOutTo->manager?->email ?? '';
+        }
+        else{
+            return $event->checkedOutTo->email;
+        }
+    }
 
     /**
      * Register the listeners for the subscriber.
diff --git a/app/Mail/CheckinLicenseMail.php b/app/Mail/CheckinLicenseMail.php
index 97ce4dd3c..8957f367e 100644
--- a/app/Mail/CheckinLicenseMail.php
+++ b/app/Mail/CheckinLicenseMail.php
@@ -23,7 +23,7 @@ class CheckinLicenseMail extends Mailable
     public function __construct(LicenseSeat $licenseSeat, $checkedOutTo, User $checkedInBy, $note)
     {
         $this->target = $checkedOutTo;
-        $this->item = $licenseSeat->license;
+        $this->item = $licenseSeat;
         $this->admin = $checkedInBy;
         $this->note = $note;
         $this->settings = Setting::getSettings();
@@ -50,7 +50,8 @@ class CheckinLicenseMail extends Mailable
         return new Content(
             markdown: 'mail.markdown.checkin-license',
             with:   [
-                'item'          => $this->item,
+                'license_seat'  => $this->item,
+                'license'       => $this->item->license,
                 'admin'         => $this->admin,
                 'note'          => $this->note,
                 'target'        => $this->target,
diff --git a/app/Mail/CheckoutLicenseMail.php b/app/Mail/CheckoutLicenseMail.php
index ecd0d7390..7377ad340 100644
--- a/app/Mail/CheckoutLicenseMail.php
+++ b/app/Mail/CheckoutLicenseMail.php
@@ -22,7 +22,7 @@ class CheckoutLicenseMail extends Mailable
      */
     public function __construct(LicenseSeat $licenseSeat, $checkedOutTo, User $checkedOutBy, $acceptance, $note)
     {
-        $this->item = $licenseSeat->license;
+        $this->item = $licenseSeat;
         $this->admin = $checkedOutBy;
         $this->note = $note;
         $this->target = $checkedOutTo;
@@ -53,11 +53,11 @@ class CheckoutLicenseMail extends Mailable
         $req_accept = method_exists($this->item, 'requireAcceptance') ? $this->item->requireAcceptance() : 0;
 
         $accept_url = is_null($this->acceptance) ? null : route('account.accept.item', $this->acceptance);
-
         return new Content(
             markdown: 'mail.markdown.checkout-license',
             with:   [
-                'item'          => $this->item,
+                'license_seat'  => $this->item,
+                'license'       => $this->item->license,
                 'admin'         => $this->admin,
                 'note'          => $this->note,
                 'target'        => $this->target,
diff --git a/app/Notifications/CheckinAssetNotification.php b/app/Notifications/CheckinAssetNotification.php
index 75077aeb4..fa4780c1f 100644
--- a/app/Notifications/CheckinAssetNotification.php
+++ b/app/Notifications/CheckinAssetNotification.php
@@ -7,6 +7,7 @@ use App\Models\Asset;
 use App\Models\Setting;
 use App\Models\User;
 use Illuminate\Bus\Queueable;
+use Illuminate\Notifications\Channels\SlackWebhookChannel;
 use Illuminate\Notifications\Messages\MailMessage;
 use Illuminate\Notifications\Messages\SlackMessage;
 use Illuminate\Notifications\Notification;
@@ -62,7 +63,7 @@ class CheckinAssetNotification extends Notification
         }
         if (Setting::getSettings()->webhook_selected == 'slack' || Setting::getSettings()->webhook_selected == 'general' ) {
             Log::debug('use webhook');
-            $notifyBy[] = 'slack';
+            $notifyBy[] = SlackWebhookChannel::class;
         }
 
         return $notifyBy;
diff --git a/resources/views/mail/markdown/checkin-license.blade.php b/resources/views/mail/markdown/checkin-license.blade.php
index 0f14c4bfd..d6e146a96 100644
--- a/resources/views/mail/markdown/checkin-license.blade.php
+++ b/resources/views/mail/markdown/checkin-license.blade.php
@@ -6,15 +6,15 @@
 @component('mail::table')
 |        |          |
 | ------------- | ------------- |
-| **{{ trans('mail.asset_name') }}** | {{ $item->name }} |
-@if (isset($item->manufacturer))
-| **{{ trans('general.manufacturer') }}** | {{ $item->manufacturer->name }} |
+| **{{ trans('mail.asset_name') }}** | {{ $license->name }} |
+@if (isset($license->manufacturer))
+| **{{ trans('general.manufacturer') }}** | {{ $license->manufacturer->name }} |
 @endif
-@if ($target->can('update', $item))
-| **Key** | {{ $item->serial }} |
+@if (($target instanceof \App\Models\User && $target->can('view', $license)) ||($target instanceof \App\Models\Asset && $license_seat->user->can('view', $license)))
+| **Key** | {{ $license->serial }} |
 @endif
 @if (isset($item->category))
-| **{{ trans('general.category') }}** | {{ $item->category->name }} |
+| **{{ trans('general.category') }}** | {{ $license->category->name }} |
 @endif
 @if ($admin)
 | **{{ trans('general.administrator') }}** | {{ $admin->present()->fullName() }} |
diff --git a/resources/views/mail/markdown/checkout-license.blade.php b/resources/views/mail/markdown/checkout-license.blade.php
index 08e1e5c76..2c4cd39cc 100644
--- a/resources/views/mail/markdown/checkout-license.blade.php
+++ b/resources/views/mail/markdown/checkout-license.blade.php
@@ -9,15 +9,15 @@
 @if (isset($checkout_date))
 | **{{ trans('mail.checkout_date') }}** | {{ $checkout_date }} |
 @endif
-| **{{ trans('general.license') }}** | {{ $item->name }} |
-@if (isset($item->manufacturer))
-| **{{ trans('general.manufacturer') }}** | {{ $item->manufacturer->name }} |
+| **{{ trans('general.license') }}** | {{ $license->name}} |
+@if (isset($license->manufacturer))
+| **{{ trans('general.manufacturer') }}** | {{ $license->manufacturer->name }} |
 @endif
-@if (isset($item->category))
-| **{{ trans('general.category') }}** | {{ $item->category->name }} |
+@if (isset($license->category))
+| **{{ trans('general.category') }}** | {{ $license->category->name }} |
 @endif
-@if ($target->can('view', $item))
-| **Key** | {{ $item->serial }} |
+@if (($target instanceof \App\Models\User && $target->can('view', $license)) || ($target instanceof \App\Models\Asset && $license_seat->user->can('view', $license)))
+| **Key** | {{ $license->serial }} |
 @endif
 @if ($note)
 | **{{ trans('mail.additional_notes') }}** | {{ $note }} |