diff --git a/app/Http/Controllers/Assets/BulkAssetsController.php b/app/Http/Controllers/Assets/BulkAssetsController.php
index 6c75ae06db05..4b9ccb675373 100644
--- a/app/Http/Controllers/Assets/BulkAssetsController.php
+++ b/app/Http/Controllers/Assets/BulkAssetsController.php
@@ -647,6 +647,15 @@ public function storeCheckout(AssetCheckoutRequest $request) : RedirectResponse
 
             $assets = Asset::findOrFail($asset_ids);
 
+            // Prevent checking out assets that are already checked out
+            if ($assets->pluck('assigned_to')->unique()->filter()->isNotEmpty()) {
+                // re-add the asset ids so the assets select is re-populated
+                $request->session()->flashInput(['selected_assets' => $asset_ids]);
+
+                return redirect(route('hardware.bulkcheckout.show'))
+                    ->with('error', trans('general.error_assets_already_checked_out'));
+            }
+
             if (request('checkout_to_type') == 'asset') {
                 foreach ($asset_ids as $asset_id) {
                     if ($target->id == $asset_id) {
diff --git a/resources/lang/en-US/general.php b/resources/lang/en-US/general.php
index 61b7c9f809f5..42751c5cf924 100644
--- a/resources/lang/en-US/general.php
+++ b/resources/lang/en-US/general.php
@@ -520,6 +520,7 @@
     'item_name_var' => ':item Name',
     'error_user_company' => 'Checkout target company and asset company do not match',
     'error_user_company_accept_view' => 'An Asset assigned to you belongs to a different company so you can\'t accept nor deny it, please check with your manager',
+    'error_assets_already_checked_out' => 'One or more of the assets are already checked out',
     'importer' => [
         'checked_out_to_fullname' => 'Checked Out to: Full Name',
         'checked_out_to_first_name' => 'Checked Out to: First Name',
diff --git a/tests/Feature/Checkouts/Ui/BulkAssetCheckoutTest.php b/tests/Feature/Checkouts/Ui/BulkAssetCheckoutTest.php
index f05c4389e6c1..2f325ba68a0e 100644
--- a/tests/Feature/Checkouts/Ui/BulkAssetCheckoutTest.php
+++ b/tests/Feature/Checkouts/Ui/BulkAssetCheckoutTest.php
@@ -4,8 +4,10 @@
 
 use App\Mail\CheckoutAssetMail;
 use App\Models\Asset;
+use App\Models\Location;
 use App\Models\User;
 use Illuminate\Support\Facades\Mail;
+use PHPUnit\Framework\Attributes\DataProvider;
 use PHPUnit\Framework\ExpectationFailedException;
 use Tests\TestCase;
 
@@ -89,4 +91,63 @@ public function testHandleMissingModelBeingIncluded()
             $this->fail('Asset checkout email was sent when the entire checkout failed.');
         }
     }
+
+    public static function checkoutTargets()
+    {
+        yield 'Checkout to user' => [
+            function () {
+                return [
+                    'type' => 'user',
+                    'target' => User::factory()->forCompany()->create(),
+                ];
+            }
+        ];
+
+        yield 'Checkout to asset' => [
+            function () {
+                return [
+                    'type' => 'asset',
+                    'target' => Asset::factory()->forCompany()->create(),
+                ];
+            }
+        ];
+
+        yield 'Checkout to location' => [
+            function () {
+                return [
+                    'type' => 'location',
+                    'target' => Location::factory()->forCompany()->create(),
+                ];
+            }
+        ];
+    }
+
+    #[DataProvider('checkoutTargets')]
+    public function test_prevents_checkouts_of_checked_out_items($data)
+    {
+        ['type' => $type, 'target' => $target] = $data();
+
+        $asset = Asset::factory()->create();
+        $checkedOutAsset = Asset::factory()->assignedToUser()->create();
+        $existingUserId = $checkedOutAsset->assigned_to;
+
+        $response = $this->actingAs(User::factory()->superuser()->create())
+            ->post(route('hardware.bulkcheckout.store'), [
+                'selected_assets' => [
+                    $asset->id,
+                    $checkedOutAsset->id,
+                ],
+                'checkout_to_type' => $type,
+                "assigned_$type" => $target->id,
+            ]);
+
+        $this->assertEquals(
+            $existingUserId,
+            $checkedOutAsset->fresh()->assigned_to,
+            'Asset was checked out when it should have been prevented.'
+        );
+
+        // ensure redirected back
+        $response->assertRedirectToRoute('hardware.bulkcheckout.show');
+    }
 }