diff --git a/app/Listeners/CheckoutableListener.php b/app/Listeners/CheckoutableListener.php
index 9d6cd942bd..5a39b5f513 100644
--- a/app/Listeners/CheckoutableListener.php
+++ b/app/Listeners/CheckoutableListener.php
@@ -32,11 +32,26 @@ class CheckoutableListener
     public function onCheckedOut($event)
     {
 
+        // @todo: update docblock
 
         /**
          * When the item wasn't checked out to a user, we can't send notifications
          */
+        // @todo: update comment
         if (! $event->checkedOutTo instanceof User) {
+
+            // @todo: comment
+            if (Setting::getSettings() && Setting::getSettings()->slack_endpoint) {
+                Notification::route('slack', Setting::getSettings()->slack_endpoint)
+                    ->notify(new CheckoutAssetNotification(
+                            $event->checkoutable,
+                            $event->checkedOutTo,
+                            $event->checkedOutBy,
+                            null,
+                            $event->note)
+                    );
+            }
+
             return;
         }
 
diff --git a/tests/Feature/Notifications/AssetCheckoutSlackNotificationTest.php b/tests/Feature/Notifications/AssetCheckoutSlackNotificationTest.php
index 75df4a1626..468d81678a 100644
--- a/tests/Feature/Notifications/AssetCheckoutSlackNotificationTest.php
+++ b/tests/Feature/Notifications/AssetCheckoutSlackNotificationTest.php
@@ -9,16 +9,27 @@ use App\Models\Location;
 use App\Models\Setting;
 use App\Models\User;
 use App\Notifications\CheckoutAssetNotification;
+use Illuminate\Notifications\AnonymousNotifiable;
 use Illuminate\Support\Facades\Notification;
 use Tests\TestCase;
 
 class AssetCheckoutSlackNotificationTest extends TestCase
 {
+    private Category $assetLaptopCategory;
+    private string $slackWebhookUrl = 'https://hooks.slack.com/services/NZ59O2F54K/Q4465WNLM8/672N8MU5JV15RP436WDHRN58';
+
+    protected function setUp(): void
+    {
+        parent::setUp();
+
+        $this->assetLaptopCategory = Category::factory()->assetLaptopCategory();
+    }
+
     public function testNotificationSentToSlackWhenAssetCheckedOutToUserAndSlackNotificationEnabled()
     {
         Notification::fake();
 
-        $this->setSlackWebhook();
+        Setting::factory()->create(['slack_endpoint' => $this->slackWebhookUrl]);
 
         $asset = $this->createAsset();
         $user = User::factory()->create();
@@ -28,70 +39,99 @@ class AssetCheckoutSlackNotificationTest extends TestCase
             User::factory()->superuser()->create()->id
         );
 
-        $this->assetSlackNotificationSentTo($user);
+        Notification::assertSentTo(
+            $user,
+            function (CheckoutAssetNotification $notification, $channels) {
+                // @todo: is this actually accurate?
+                return in_array('slack', $channels);
+            }
+        );
     }
 
     public function testNotificationSentToSlackWhenAssetCheckedOutToAssetAndSlackNotificationEnabled()
     {
-        $this->markTestIncomplete();
-
         Notification::fake();
 
-        $this->setSlackWebhook();
+        Setting::factory()->create(['slack_endpoint' => $this->slackWebhookUrl]);
 
         $assetBeingCheckedOut = $this->createAsset();
-        $targetAsset = $this->createAsset();
-
         $assetBeingCheckedOut->checkOut(
-            $targetAsset,
+            $this->createAsset(),
             User::factory()->superuser()->create()->id
         );
 
-        $this->assetSlackNotificationSentTo($targetAsset);
+        // Since the target is not a user with an email address we have
+        // to check if an AnonymousNotifiable was sent.
+        Notification::assertSentTo(
+            new AnonymousNotifiable,
+            CheckoutAssetNotification::class,
+            function ($notification, $channels, $notifiable) {
+                return $notifiable->routes['slack'] === $this->slackWebhookUrl;
+            }
+        );
+    }
+
+    public function testDoesNotSendNotificationViaSlackIfWebHookEndpointIsNotSetWhenCheckingOutAssetToAsset()
+    {
+        Notification::fake();
+
+        $assetBeingCheckedOut = $this->createAsset();
+        $assetBeingCheckedOut->checkOut(
+            $this->createAsset(),
+            User::factory()->superuser()->create()->id
+        );
+
+        Notification::assertNotSentTo(
+            new AnonymousNotifiable,
+            CheckoutAssetNotification::class,
+        );
     }
 
     public function testNotificationSentToSlackWhenAssetCheckedOutToLocationAndSlackNotificationEnabled()
     {
-        $this->markTestIncomplete();
-
         Notification::fake();
 
-        $this->setSlackWebhook();
+        Setting::factory()->create(['slack_endpoint' => $this->slackWebhookUrl]);
 
         $asset = $this->createAsset();
-        $location = Location::factory()->create();
-
         $asset->checkOut(
-            $location,
+            Location::factory()->create(),
             User::factory()->superuser()->create()->id
         );
 
-        $this->assetSlackNotificationSentTo($location);
+        // Since the target is not a user with an email address we have
+        // to check if an AnonymousNotifiable was sent.
+        Notification::assertSentTo(
+            new AnonymousNotifiable,
+            CheckoutAssetNotification::class,
+            function ($notification, $channels, $notifiable) {
+                return $notifiable->routes['slack'] === $this->slackWebhookUrl;
+            }
+        );
     }
 
-    private function setSlackWebhook()
+    public function testtestDoesNotSendNotificationViaSlackIfWebHookEndpointIsNotSetWhenCheckingOutAssetToLocation()
     {
-        Setting::factory()->create([
-            'slack_endpoint' => 'https://hooks.slack.com/services/NZ59O2F54K/Q4465WNLM8/672N8MU5JV15RP436WDHRN58',
-        ]);
+        Notification::fake();
+
+        $asset = $this->createAsset();
+        $asset->checkOut(
+            Location::factory()->create(),
+            User::factory()->superuser()->create()->id
+        );
+
+        Notification::assertNotSentTo(
+            new AnonymousNotifiable,
+            CheckoutAssetNotification::class,
+        );
     }
 
     private function createAsset()
     {
         return Asset::factory()->create([
             'model_id' => AssetModel::factory()->create([
-                'category_id' => Category::factory()->assetLaptopCategory()->id,
+                'category_id' => $this->assetLaptopCategory->id,
             ])->id,
         ]);
     }
-
-    private function assetSlackNotificationSentTo($target)
-    {
-        Notification::assertSentTo(
-            $target,
-            function (CheckoutAssetNotification $notification, $channels) {
-                return in_array('slack', $channels);
-            }
-        );
-    }
 }