diff --git a/app/Console/Commands/CleanOldCheckoutRequests.php b/app/Console/Commands/CleanOldCheckoutRequests.php
new file mode 100644
index 0000000000..a96a58a349
--- /dev/null
+++ b/app/Console/Commands/CleanOldCheckoutRequests.php
@@ -0,0 +1,74 @@
+<?php
+
+namespace App\Console\Commands;
+
+use App\Models\CheckoutRequest;
+use Illuminate\Console\Command;
+
+class CleanOldCheckoutRequests extends Command
+{
+    private int $deletions = 0;
+    private int $skips = 0;
+
+    /**
+     * The name and signature of the console command.
+     *
+     * @var string
+     */
+    protected $signature = 'snipeit:clean-old-checkout-requests';
+
+    /**
+     * The console command description.
+     *
+     * @var string
+     */
+    protected $description = 'Removes checkout requests that reference deleted assets or users.';
+
+    /**
+     * Execute the console command.
+     */
+    public function handle()
+    {
+        $requests = CheckoutRequest::with([
+            'user' => function ($query) {
+                $query->withTrashed();
+            },
+            'requestedItem' => function ($query) {
+                $query->withTrashed();
+            },
+        ])->get();
+
+        $this->info("Processing {$requests->count()} checkout requests");
+
+        $this->withProgressBar($requests, function ($request) {
+            if ($this->shouldForceDelete($request)) {
+                $request->forceDelete();
+                $this->deletions++;
+                return;
+            }
+
+            if ($this->shouldSoftDelete($request)) {
+                $request->delete();
+                $this->deletions++;
+                return;
+            }
+
+            $this->skips++;
+        });
+
+        $this->info("Final deletion count: $this->deletions, and skip count: $this->skips");
+
+        return 0;
+    }
+
+    private function shouldForceDelete(CheckoutRequest $request)
+    {
+        // check if the requestable or user relationship is null
+        return !$request->requestable || !$request->user;
+    }
+
+    private function shouldSoftDelete(CheckoutRequest $request)
+    {
+        return $request->requestable->trashed() || $request->user->trashed();
+    }
+}
diff --git a/app/Models/Asset.php b/app/Models/Asset.php
index a977ec3816..72bef375f6 100644
--- a/app/Models/Asset.php
+++ b/app/Models/Asset.php
@@ -206,6 +206,17 @@ class Asset extends Depreciable
         'model.manufacturer' => ['name'],
     ];
 
+    protected static function booted(): void
+    {
+        static::forceDeleted(function (Asset $asset) {
+            $asset->requests()->forceDelete();
+        });
+
+        static::softDeleted(function (Asset $asset) {
+            $asset->requests()->delete();
+        });
+    }
+
     // To properly set the expected checkin as Y-m-d
     public function setExpectedCheckinAttribute($value)
     {
diff --git a/app/Models/AssetModel.php b/app/Models/AssetModel.php
index bdb87d4f75..c73e4492ac 100755
--- a/app/Models/AssetModel.php
+++ b/app/Models/AssetModel.php
@@ -98,8 +98,16 @@ class AssetModel extends SnipeModel
         'manufacturer' => ['name'],
     ];
 
+    protected static function booted(): void
+    {
+        static::forceDeleted(function (AssetModel $assetModel) {
+            $assetModel->requests()->forceDelete();
+        });
 
-
+        static::softDeleted(function (AssetModel $assetModel) {
+            $assetModel->requests()->delete();
+        });
+    }
 
     /**
      * Establishes the model -> assets relationship
diff --git a/app/Models/CheckoutRequest.php b/app/Models/CheckoutRequest.php
index d6a85f2972..42512d8fda 100644
--- a/app/Models/CheckoutRequest.php
+++ b/app/Models/CheckoutRequest.php
@@ -2,11 +2,13 @@
 
 namespace App\Models;
 
+use Illuminate\Database\Eloquent\Factories\HasFactory;
 use Illuminate\Database\Eloquent\Model;
 use Illuminate\Database\Eloquent\SoftDeletes;
 
 class CheckoutRequest extends Model
 {
+    use HasFactory;
     use SoftDeletes;
     protected $fillable = ['user_id'];
     protected $table = 'checkout_requests';
diff --git a/app/Models/User.php b/app/Models/User.php
index b673761b3b..6bd44380eb 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/database/factories/CheckoutRequestFactory.php b/database/factories/CheckoutRequestFactory.php
new file mode 100644
index 0000000000..5363b5e281
--- /dev/null
+++ b/database/factories/CheckoutRequestFactory.php
@@ -0,0 +1,44 @@
+<?php
+
+namespace Database\Factories;
+
+use App\Models\Asset;
+use App\Models\AssetModel;
+use App\Models\CheckoutRequest;
+use App\Models\User;
+use Illuminate\Database\Eloquent\Factories\Factory;
+
+class CheckoutRequestFactory extends Factory
+{
+    protected $model = CheckoutRequest::class;
+
+    public function definition(): array
+    {
+        return [
+            'requestable_id' => Asset::factory(),
+            'requestable_type' => Asset::class,
+            'quantity' => 1,
+            'user_id' => User::factory(),
+        ];
+    }
+
+    public function forAsset()
+    {
+        return $this->state(function (array $attributes) {
+            return [
+                'requestable_id' => Asset::factory(),
+                'requestable_type' => Asset::class,
+            ];
+        });
+    }
+
+    public function forAssetModel()
+    {
+        return $this->state(function (array $attributes) {
+            return [
+                'requestable_id' => AssetModel::factory(),
+                'requestable_type' => AssetModel::class,
+            ];
+        });
+    }
+}
diff --git a/tests/Feature/Console/CleanOldCheckoutRequestsTest.php b/tests/Feature/Console/CleanOldCheckoutRequestsTest.php
new file mode 100644
index 0000000000..b1bdf8e603
--- /dev/null
+++ b/tests/Feature/Console/CleanOldCheckoutRequestsTest.php
@@ -0,0 +1,82 @@
+<?php
+
+namespace Tests\Feature\Console;
+
+use App\Models\CheckoutRequest;
+use Illuminate\Database\Eloquent\Model;
+use Tests\TestCase;
+
+class CleanOldCheckoutRequestsTest extends TestCase
+{
+    private CheckoutRequest $validRequest;
+
+    protected function setUp(): void
+    {
+        parent::setUp();
+
+        $this->validRequest = CheckoutRequest::factory()->forAsset()->create();
+    }
+
+    public function test_clean_old_checkout_requests_command_for_soft_deleted_asset()
+    {
+        $requestForSoftDeletedAsset = CheckoutRequest::factory()->forAsset()->create();
+        Model::withoutEvents(fn() => $requestForSoftDeletedAsset->requestedItem->delete());
+
+        $this->artisan('snipeit:clean-old-checkout-requests')->assertExitCode(0);
+
+        $this->assertNotSoftDeleted($this->validRequest);
+        $this->assertSoftDeleted($requestForSoftDeletedAsset->fresh());
+    }
+
+    public function test_clean_old_checkout_requests_command_for_missing_asset()
+    {
+        $requestForMissingAsset = CheckoutRequest::factory()->forAsset()->create(['requestable_id' => 99999999]);
+
+        $this->artisan('snipeit:clean-old-checkout-requests')->assertExitCode(0);
+
+        $this->assertNotSoftDeleted($this->validRequest);
+        $this->assertDatabaseMissing('checkout_requests', ['requestable_id' => $requestForMissingAsset->requestable_id]);
+    }
+
+    public function test_clean_old_checkout_requests_command_for_soft_deleted_model()
+    {
+        $requestForSoftDeletedAssetModel = CheckoutRequest::factory()->forAssetModel()->create();
+        Model::withoutEvents(fn() => $requestForSoftDeletedAssetModel->requestedItem->delete());
+
+        $this->artisan('snipeit:clean-old-checkout-requests')->assertExitCode(0);
+
+        $this->assertNotSoftDeleted($this->validRequest);
+        $this->assertSoftDeleted($requestForSoftDeletedAssetModel->fresh());
+    }
+
+    public function test_clean_old_checkout_requests_command_for_missing_model()
+    {
+        $requestForMissingModel = CheckoutRequest::factory()->forAssetModel()->create(['requestable_id' => 99999999]);
+
+        $this->artisan('snipeit:clean-old-checkout-requests')->assertExitCode(0);
+
+        $this->assertNotSoftDeleted($this->validRequest);
+        $this->assertDatabaseMissing('checkout_requests', ['requestable_id' => $requestForMissingModel->requestable_id]);
+    }
+
+    public function test_clean_old_checkout_requests_command_for_soft_deleted_user()
+    {
+        $requestForSoftDeletedUser = CheckoutRequest::factory()->forAsset()->create();
+        Model::withoutEvents(fn() => $requestForSoftDeletedUser->user->delete());
+
+        $this->artisan('snipeit:clean-old-checkout-requests')->assertExitCode(0);
+
+        $this->assertNotSoftDeleted($this->validRequest);
+        $this->assertSoftDeleted($requestForSoftDeletedUser->fresh());
+    }
+
+    public function test_clean_old_checkout_requests_command_for_missing_user()
+    {
+        $requestForMissingUser = CheckoutRequest::factory()->forAsset()->create(['user_id' => 99999999]);
+
+        $this->artisan('snipeit:clean-old-checkout-requests')->assertExitCode(0);
+
+        $this->assertNotSoftDeleted($this->validRequest);
+        $this->assertDatabaseMissing('checkout_requests', ['user_id' => $requestForMissingUser->user_id]);
+    }
+}
diff --git a/tests/Feature/Requests/Ui/AssetRequestIndexTest.php b/tests/Feature/Requests/Ui/AssetRequestIndexTest.php
new file mode 100644
index 0000000000..474b1c5c26
--- /dev/null
+++ b/tests/Feature/Requests/Ui/AssetRequestIndexTest.php
@@ -0,0 +1,28 @@
+<?php
+
+namespace Tests\Feature\Requests\Ui;
+
+use App\Models\CheckoutRequest;
+use App\Models\User;
+use Tests\TestCase;
+
+class AssetRequestIndexTest extends TestCase
+{
+    public function test_requires_permission_to_view_asset_request_index()
+    {
+        $this->actingAs(User::factory()->create())
+            ->get(route('assets.requested'))
+            ->assertForbidden();
+    }
+
+    public function test_can_view_request_asset_request_index()
+    {
+        $checkoutRequest = CheckoutRequest::factory()->create();
+
+        $this->actingAs(User::factory()->viewAssets()->create())
+            ->get(route('assets.requested'))
+            ->assertOk()
+            ->assertViewHas('requestedItems')
+            ->assertSeeText($checkoutRequest->requestedItem->asset_tag);
+    }
+}
diff --git a/tests/Unit/Models/CheckoutRequestTest.php b/tests/Unit/Models/CheckoutRequestTest.php
new file mode 100644
index 0000000000..7eceafadfd
--- /dev/null
+++ b/tests/Unit/Models/CheckoutRequestTest.php
@@ -0,0 +1,75 @@
+<?php
+
+namespace Tests\Unit\Models;
+
+use App\Models\CheckoutRequest;
+use Tests\TestCase;
+
+class CheckoutRequestTest extends TestCase
+{
+    public function test_checkout_request_soft_deleted_when_requested_asset_soft_deleted()
+    {
+        $checkoutRequest = CheckoutRequest::factory()->forAsset()->create();
+
+        $requestedAsset = $checkoutRequest->requestedItem;
+
+        $requestedAsset->delete();
+
+        $this->assertSoftDeleted($checkoutRequest->fresh());
+    }
+
+    public function test_checkout_request_deleted_when_requested_asset_force_deleted()
+    {
+        $checkoutRequest = CheckoutRequest::factory()->forAsset()->create();
+
+        $requestedAsset = $checkoutRequest->requestedItem;
+
+        $requestedAsset->forceDelete();
+
+        $this->assertDatabaseMissing('checkout_requests', ['id' => $checkoutRequest->id]);
+    }
+
+    public function test_checkout_request_soft_deleted_when_requested_model_soft_deleted()
+    {
+        $checkoutRequest = CheckoutRequest::factory()->forAssetModel()->create();
+
+        $requestedAssetModel = $checkoutRequest->requestedItem;
+
+        $requestedAssetModel->delete();
+
+        $this->assertSoftDeleted($checkoutRequest->fresh());
+    }
+
+    public function test_checkout_request_deleted_when_requested_model_force_deleted()
+    {
+        $checkoutRequest = CheckoutRequest::factory()->forAssetModel()->create();
+
+        $requestedAsset = $checkoutRequest->requestedItem;
+
+        $requestedAsset->forceDelete();
+
+        $this->assertDatabaseMissing('checkout_requests', ['id' => $checkoutRequest->id]);
+    }
+
+    public function test_checkout_request_soft_deleted_when_requesting_user_soft_deleted()
+    {
+        $checkoutRequest = CheckoutRequest::factory()->forAsset()->create();
+
+        $requestingUser = $checkoutRequest->user;
+
+        $requestingUser->delete();
+
+        $this->assertSoftDeleted($checkoutRequest->fresh());
+    }
+
+    public function test_checkout_request_deleted_when_requesting_user_force_deleted()
+    {
+        $checkoutRequest = CheckoutRequest::factory()->forAsset()->create();
+
+        $requestingUser = $checkoutRequest->user;
+
+        $requestingUser->forceDelete();
+
+        $this->assertDatabaseMissing('checkout_requests', ['id' => $checkoutRequest->id]);
+    }
+}