diff --git a/app/Models/User.php b/app/Models/User.php
index 1cb00cece5..e9a1a28728 100644
--- a/app/Models/User.php
+++ b/app/Models/User.php
@@ -183,6 +183,17 @@ class User extends SnipeModel implements AuthenticatableContract, AuthorizableCo
         );
     }
 
+    protected static function booted(): void
+    {
+        static::forceDeleted(function (User $user) {
+            CheckoutRequest::where(['user_id' => $user->id])->forceDelete();
+        });
+
+        static::softDeleted(function (User $user) {
+            CheckoutRequest::where(['user_id' => $user->id])->delete();
+        });
+    }
+
 
     public function isAvatarExternal()
     {
diff --git a/tests/Unit/Models/CheckoutRequestTest.php b/tests/Unit/Models/CheckoutRequestTest.php
index 71e1215b3a..4b06ef38c6 100644
--- a/tests/Unit/Models/CheckoutRequestTest.php
+++ b/tests/Unit/Models/CheckoutRequestTest.php
@@ -36,11 +36,9 @@ class CheckoutRequestTest extends TestCase
 
     public function test_checkout_request_soft_deleted_when_requesting_user_soft_deleted()
     {
-        $this->markTestIncomplete();
-
         $checkoutRequest = CheckoutRequest::factory()->create();
 
-        $requestingUser = $checkoutRequest->requestingUser;
+        $requestingUser = $checkoutRequest->user;
 
         $requestingUser->delete();
 
@@ -53,7 +51,7 @@ class CheckoutRequestTest extends TestCase
 
         $checkoutRequest = CheckoutRequest::factory()->create();
 
-        $requestingUser = $checkoutRequest->requestingUser;
+        $requestingUser = $checkoutRequest->user;
 
         $requestingUser->forceDelete();