diff --git a/app/Events/CheckoutablesCheckedOutInBulk.php b/app/Events/CheckoutablesCheckedOutInBulk.php
new file mode 100644
index 000000000000..4b75b32145b5
--- /dev/null
+++ b/app/Events/CheckoutablesCheckedOutInBulk.php
@@ -0,0 +1,24 @@
+<?php
+
+namespace App\Events;
+
+use App\Models\User;
+use Illuminate\Database\Eloquent\Model;
+use Illuminate\Foundation\Events\Dispatchable;
+use Illuminate\Queue\SerializesModels;
+use Illuminate\Support\Collection;
+
+class CheckoutablesCheckedOutInBulk
+{
+    use Dispatchable, SerializesModels;
+
+    public function __construct(
+        public Collection $assets,
+        public Model $target,
+        public User $admin,
+        public string $checkout_at,
+        public string $expected_checkin,
+        public string $note,
+    ) {
+    }
+}
diff --git a/app/Http/Controllers/Assets/BulkAssetsController.php b/app/Http/Controllers/Assets/BulkAssetsController.php
index cb4fa5fa5b32..f6f9dca44ccd 100644
--- a/app/Http/Controllers/Assets/BulkAssetsController.php
+++ b/app/Http/Controllers/Assets/BulkAssetsController.php
@@ -2,6 +2,7 @@
 
 namespace App\Http\Controllers\Assets;
 
+use App\Events\CheckoutablesCheckedOutInBulk;
 use App\Helpers\Helper;
 use App\Http\Controllers\CheckInOutRequest;
 use App\Http\Controllers\Controller;
@@ -12,6 +13,7 @@
 use App\View\Label;
 use Carbon\Carbon;
 use Illuminate\Http\Request;
+use Illuminate\Support\Facades\Context;
 use Illuminate\Support\Facades\Crypt;
 use Illuminate\Support\Facades\DB;
 use Illuminate\Support\Facades\Gate;
@@ -631,6 +633,8 @@ public function showCheckout() : View
      */
     public function storeCheckout(AssetCheckoutRequest $request) : RedirectResponse | ModelNotFoundException
     {
+        Context::add('action', 'bulk_asset_checkout');
+
         $this->authorize('checkout', Asset::class);
 
         try {
@@ -717,6 +721,15 @@ public function storeCheckout(AssetCheckoutRequest $request) : RedirectResponse
             });
 
             if (! $errors) {
+                CheckoutablesCheckedOutInBulk::dispatch(
+                    $assets,
+                    $target,
+                    $admin,
+                    $checkout_at,
+                    $expected_checkin,
+                    e($request->get('note')),
+                );
+
                 // Redirect to the new asset page
                 return redirect()->to('hardware')->with('success', trans_choice('admin/hardware/message.multi-checkout.success', $asset_ids));
             }
diff --git a/app/Listeners/CheckoutableListener.php b/app/Listeners/CheckoutableListener.php
index 908dd58dfded..ee6902bcc5f0 100644
--- a/app/Listeners/CheckoutableListener.php
+++ b/app/Listeners/CheckoutableListener.php
@@ -33,6 +33,7 @@
 use App\Notifications\CheckoutLicenseSeatNotification;
 use GuzzleHttp\Exception\ClientException;
 use Illuminate\Database\Eloquent\Model;
+use Illuminate\Support\Facades\Context;
 use Illuminate\Support\Facades\Mail;
 use Illuminate\Support\Facades\Notification;
 use Exception;
@@ -427,13 +428,20 @@ private function newMicrosoftTeamsWebhookEnabled(): bool
 
     private function shouldSendCheckoutEmailToUser(Model $checkoutable): bool
     {
+        // @todo: update comment
         /**
-         * Send an email if any of the following conditions are met:
+         * Send an email if we didn't get here from a bulk checkout
+         * and 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 (Context::get('action') === 'bulk_asset_checkout') {
+            // @todo: maybe we should see if there is only one asset being checked out and allow this to proceed if it is?
+            return false;
+        }
+
         if ($checkoutable->requireAcceptance()) {
             return true;
         }
@@ -451,6 +459,10 @@ private function shouldSendCheckoutEmailToUser(Model $checkoutable): bool
 
     private function shouldSendEmailToAlertAddress($acceptance = null): bool
     {
+        if (Context::get('action') === 'bulk_asset_checkout') {
+            return false;
+        }
+
         $setting = Setting::getSettings();
 
         if (!$setting) {
diff --git a/app/Listeners/CheckoutablesCheckedOutInBulkListener.php b/app/Listeners/CheckoutablesCheckedOutInBulkListener.php
new file mode 100644
index 000000000000..e081d767eeec
--- /dev/null
+++ b/app/Listeners/CheckoutablesCheckedOutInBulkListener.php
@@ -0,0 +1,149 @@
+<?php
+
+namespace App\Listeners;
+
+use App\Events\CheckoutablesCheckedOutInBulk;
+use App\Mail\BulkAssetCheckoutMail;
+use App\Models\Asset;
+use App\Models\Location;
+use App\Models\Setting;
+use App\Models\User;
+use Exception;
+use Illuminate\Support\Collection;
+use Illuminate\Support\Facades\Log;
+use Illuminate\Support\Facades\Mail;
+
+class CheckoutablesCheckedOutInBulkListener
+{
+
+    public function subscribe($events)
+    {
+        $events->listen(
+            CheckoutablesCheckedOutInBulk::class,
+            CheckoutablesCheckedOutInBulkListener::class
+        );
+    }
+
+    public function handle(CheckoutablesCheckedOutInBulk $event): void
+    {
+        $notifiableUser = $this->getNotifiableUser($event);
+
+        $shouldSendEmailToUser = $this->shouldSendCheckoutEmailToUser($notifiableUser, $event->assets);
+        $shouldSendEmailToAlertAddress = $this->shouldSendEmailToAlertAddress($event->assets);
+
+        if ($shouldSendEmailToUser && $notifiableUser) {
+            try {
+                Mail::to($notifiableUser)->send(new BulkAssetCheckoutMail(
+                    $event->assets,
+                    $event->target,
+                    $event->admin,
+                    $event->checkout_at,
+                    $event->expected_checkin,
+                    $event->note,
+                ));
+
+                Log::info('BulkAssetCheckoutMail sent to checkout target');
+            } catch (Exception $e) {
+                Log::debug("Exception caught during BulkAssetCheckoutMail to target: " . $e->getMessage());
+            }
+        }
+
+        if ($shouldSendEmailToAlertAddress && Setting::getSettings()->admin_cc_email) {
+            try {
+                Mail::to(Setting::getSettings()->admin_cc_email)->send(new BulkAssetCheckoutMail(
+                    $event->assets,
+                    $event->target,
+                    $event->admin,
+                    $event->checkout_at,
+                    $event->expected_checkin,
+                    $event->note,
+                ));
+
+                Log::info('BulkAssetCheckoutMail sent to admin_cc_email');
+            } catch (Exception $e) {
+                Log::debug("Exception caught during BulkAssetCheckoutMail to admin_cc_email: " . $e->getMessage());
+            }
+        }
+    }
+
+    private function shouldSendCheckoutEmailToUser(?User $user, Collection $assets): bool
+    {
+        if (!$user->email) {
+            return false;
+        }
+
+        if ($this->hasAssetWithEula($assets)) {
+            return true;
+        }
+
+        if ($this->hasAssetWithCategorySettingToSendEmail($assets)) {
+            return true;
+        }
+
+        return $this->requiresAcceptance($assets);
+    }
+
+    private function shouldSendEmailToAlertAddress(Collection $assets): bool
+    {
+        $setting = Setting::getSettings();
+
+        if (!$setting) {
+            return false;
+        }
+
+        if ($setting->admin_cc_always) {
+            return true;
+        }
+
+        if (!$this->requiresAcceptance($assets)) {
+            return false;
+        }
+
+        return (bool) $setting->admin_cc_email;
+    }
+
+    private function hasAssetWithEula(Collection $assets): bool
+    {
+        foreach ($assets as $asset) {
+            if ($asset->getEula()) {
+                return true;
+            }
+        }
+
+        return false;
+    }
+
+    private function hasAssetWithCategorySettingToSendEmail(Collection $assets): bool
+    {
+        foreach ($assets as $asset) {
+            if ($asset->checkin_email()) {
+                return true;
+            }
+        }
+
+        return false;
+    }
+
+    private function requiresAcceptance(Collection $assets): bool
+    {
+        return (bool) $assets->reduce(
+            fn($count, $asset) => $count + $asset->requireAcceptance()
+        );
+    }
+
+    private function getNotifiableUser(CheckoutablesCheckedOutInBulk $event)
+    {
+        $target = $event->target;
+
+        if ($target instanceof Asset) {
+            $target->load('assignedTo');
+            return $target->assignedto;
+        }
+
+        if ($target instanceof Location) {
+            return $target->manager;
+        }
+
+        return $target;
+    }
+}
diff --git a/app/Mail/BulkAssetCheckoutMail.php b/app/Mail/BulkAssetCheckoutMail.php
new file mode 100644
index 000000000000..b1a6ff528699
--- /dev/null
+++ b/app/Mail/BulkAssetCheckoutMail.php
@@ -0,0 +1,128 @@
+<?php
+
+namespace App\Mail;
+
+use App\Models\Asset;
+use App\Models\CustomField;
+use App\Models\Location;
+use App\Models\User;
+use Illuminate\Bus\Queueable;
+use Illuminate\Database\Eloquent\Model;
+use Illuminate\Mail\Mailable;
+use Illuminate\Mail\Mailables\Content;
+use Illuminate\Mail\Mailables\Envelope;
+use Illuminate\Queue\SerializesModels;
+use Illuminate\Support\Collection;
+
+class BulkAssetCheckoutMail extends Mailable
+{
+    use Queueable, SerializesModels;
+
+    public bool $requires_acceptance;
+
+    public function __construct(
+        public Collection $assets,
+        public Model $target,
+        public User $admin,
+        public string $checkout_at,
+        public string $expected_checkin,
+        public string $note,
+    ) {
+        $this->requires_acceptance = $this->requiresAcceptance();
+
+        $this->loadCustomFieldsOnAssets();
+    }
+
+    public function envelope(): Envelope
+    {
+        return new Envelope(
+            subject: $this->getSubject(),
+        );
+    }
+
+    public function content(): Content
+    {
+        return new Content(
+            markdown: 'mail.markdown.bulk-asset-checkout-mail',
+            with: [
+                'introduction' => $this->getIntroduction(),
+                'requires_acceptance' => $this->requires_acceptance,
+                'requires_acceptance_wording' => $this->getRequiresAcceptanceWording(),
+                'acceptance_url' => $this->acceptanceUrl(),
+            ],
+        );
+    }
+
+    public function attachments(): array
+    {
+        return [];
+    }
+
+    private function getSubject(): string
+    {
+        if ($this->assets->count() > 1) {
+            return ucfirst(trans('general.assets_checked_out_count'));
+        }
+
+        return trans('mail.Asset_Checkout_Notification', ['tag' => $this->assets->first()->asset_tag]);
+    }
+
+    private function getIntroduction(): string
+    {
+        if ($this->target instanceof Location) {
+            return trans_choice('mail.new_item_checked_location', $this->assets->count(), ['location' => $this->target->name]);
+        }
+
+        return trans_choice('mail.new_item_checked', $this->assets->count());
+    }
+
+    private function acceptanceUrl()
+    {
+        if ($this->assets->count() > 1) {
+            return route('account.accept');
+        }
+
+        return route('account.accept.item', $this->assets->first());
+    }
+
+    private function loadCustomFieldsOnAssets(): void
+    {
+        $this->assets = $this->assets->map(function (Asset $asset) {
+            $fields = $asset->model?->fieldset?->fields->filter(function (CustomField $field) {
+                return $field->show_in_email && !$field->field_encrypted;
+            });
+
+            $asset->setRelation('fields', $fields);
+
+            return $asset;
+        });
+    }
+
+    private function requiresAcceptance(): bool
+    {
+        return (bool) $this->assets->reduce(
+            fn($count, $asset) => $count + $asset->requireAcceptance()
+        );
+    }
+
+    private function getRequiresAcceptanceWording(): array
+    {
+        if (!$this->requiresAcceptance()) {
+            return [];
+        }
+
+        if ($this->assets->count() > 1) {
+            return [
+                // todo: translate
+                trans_choice('mail.items_checked_out_require_acceptance', $this->assets->count()),
+                "**[✔ Click here to review the terms of use and accept the items]({$this->acceptanceUrl()})**",
+            ];
+        }
+
+        return [
+            // todo: translate
+            trans_choice('mail.items_checked_out_require_acceptance', $this->assets->count()),
+            "**[✔ Click here to review the terms of use and accept the item]({$this->acceptanceUrl()})**",
+        ];
+    }
+}
diff --git a/app/Mail/CheckoutAssetMail.php b/app/Mail/CheckoutAssetMail.php
index 324c1c8f29b3..8f7c44c9f738 100644
--- a/app/Mail/CheckoutAssetMail.php
+++ b/app/Mail/CheckoutAssetMail.php
@@ -14,7 +14,6 @@
 use Illuminate\Mail\Mailables\Attachment;
 use Illuminate\Mail\Mailables\Content;
 use Illuminate\Mail\Mailables\Envelope;
-use Illuminate\Notifications\Messages\MailMessage;
 use Illuminate\Queue\SerializesModels;
 
 class CheckoutAssetMail extends Mailable
diff --git a/app/Providers/EventServiceProvider.php b/app/Providers/EventServiceProvider.php
index 1f08b445c9ec..9143cdc8f5a0 100644
--- a/app/Providers/EventServiceProvider.php
+++ b/app/Providers/EventServiceProvider.php
@@ -3,6 +3,7 @@
 namespace App\Providers;
 
 use App\Listeners\CheckoutableListener;
+use App\Listeners\CheckoutablesCheckedOutInBulkListener;
 use App\Listeners\LogListener;
 use Illuminate\Foundation\Support\Providers\EventServiceProvider as ServiceProvider;
 
@@ -31,5 +32,6 @@ class EventServiceProvider extends ServiceProvider
     protected $subscribe = [
         LogListener::class,
         CheckoutableListener::class,
+        CheckoutablesCheckedOutInBulkListener::class,
     ];
 }
diff --git a/database/factories/CategoryFactory.php b/database/factories/CategoryFactory.php
index 733c52668ed4..6ebd8e40746d 100644
--- a/database/factories/CategoryFactory.php
+++ b/database/factories/CategoryFactory.php
@@ -214,4 +214,34 @@ public function doesNotRequireAcceptance()
             'require_acceptance' => false,
         ]);
     }
+
+    public function doesNotSendCheckinEmail()
+    {
+        return $this->state([
+            'checkin_email' => false,
+        ]);
+    }
+
+    public function sendsCheckinEmail()
+    {
+        return $this->state([
+            'checkin_email' => true,
+        ]);
+    }
+
+    public function hasLocalEula()
+    {
+        return $this->state([
+            'use_default_eula' => false,
+            'eula_text' => 'Some EULA text here',
+        ]);
+    }
+
+    public function withNoLocalOrGlobalEula()
+    {
+        return $this->state([
+            'use_default_eula' => false,
+            'eula_text' => '',
+        ]);
+    }
 }
diff --git a/resources/lang/en-US/mail.php b/resources/lang/en-US/mail.php
index 707390e4f0ab..92cce47145ca 100644
--- a/resources/lang/en-US/mail.php
+++ b/resources/lang/en-US/mail.php
@@ -79,6 +79,7 @@
     'new_item_checked' => 'A new item has been checked out under your name, details are below.|:count new items have been checked out under your name, details are below.',
     'new_item_checked_with_acceptance' => 'A new item has been checked out under your name that requires acceptance, details are below.|:count new items have been checked out under your name that requires acceptance, details are below.',
     'new_item_checked_location' => 'A new item has been checked out to :location, details are below.|:count new items have been checked out to :location, details are below.',
+    'items_checked_out_require_acceptance' => 'The checked out item requires acceptance.|One or more items require acceptance.',
     'recent_item_checked' => 'An item was recently checked out under your name that requires acceptance, details are below.',
     'notes' => 'Notes',
     'password' => 'Password',
diff --git a/resources/views/mail/markdown/bulk-asset-checkout-mail.blade.php b/resources/views/mail/markdown/bulk-asset-checkout-mail.blade.php
new file mode 100644
index 000000000000..900a0488186a
--- /dev/null
+++ b/resources/views/mail/markdown/bulk-asset-checkout-mail.blade.php
@@ -0,0 +1,71 @@
+<x-mail::message>
+
+<style>
+    th, td {
+        vertical-align: top;
+    }
+    hr {
+        display: block;
+        height: 1px;
+        border: 0;
+        border-top: 1px solid #ccc;
+        margin: 1em 0;
+        padding: 0;
+    }
+</style>
+
+{{ $introduction }}
+
+@if ($requires_acceptance)
+@foreach($requires_acceptance_wording as $line)
+{{ $line }}<br>
+@endforeach
+@endif
+
+<hr>
+
+@if ((isset($expected_checkin)) && ($expected_checkin!=''))
+**{{ trans('mail.expecting_checkin_date') }}**: {{ Helper::getFormattedDateObject($expected_checkin, 'date', false) }}
+@endif
+
+@if ($note)
+**{{ trans('mail.additional_notes') }}**: {{ $note }}
+@endif
+
+<x-mail::table>
+|        |        |
+| ------------- | ------------- |
+@foreach($assets as $asset)
+| **{{ trans('general.asset_tag') }}** | <a href="{{ route('hardware.show', $asset->id) }}">{{ $asset->display_name }}</a><br><small>{{trans('mail.serial').': '.$asset->serial}}</small> |
+@if (isset($asset->model?->category))
+| **{{ trans('general.category') }}** | {{ $asset->model->category->name }} |
+@endif
+@if (isset($asset->manufacturer))
+| **{{ trans('general.manufacturer') }}** | {{ $asset->manufacturer->name }} |
+@endif
+@if (isset($asset->model))
+| **{{ trans('general.asset_model') }}** | {{ $asset->model->name }} |
+@endif
+@if ((isset($asset->model?->model_number)))
+| **{{ trans('general.model_no') }}** | {{ $asset->model->model_number }} |
+@endif
+@if (isset($asset->assetstatus))
+| **{{ trans('general.status') }}** | {{ $asset->assetstatus->name }} |
+@endif
+@if($asset->fields)
+@foreach($asset->fields as $field)
+@if ($asset->{ $field->db_column_name() } != '')
+| **{{ $field->name }}** | {{ $asset->{ $field->db_column_name() } }} |
+@endif
+@endforeach
+@endif
+| <hr> | <hr> |
+@endforeach
+</x-mail::table>
+
+**{{ trans('general.administrator') }}**: {{ $admin->display_name }}
+
+{{ trans('mail.best_regards') }}<br>
+
+{{ $snipeSettings->site_name }}
+</x-mail::message>
diff --git a/tests/Feature/Checkouts/Ui/BulkAssetCheckoutTest.php b/tests/Feature/Checkouts/Ui/BulkAssetCheckoutTest.php
index 6f6f250b9003..99ea17bb4aca 100644
--- a/tests/Feature/Checkouts/Ui/BulkAssetCheckoutTest.php
+++ b/tests/Feature/Checkouts/Ui/BulkAssetCheckoutTest.php
@@ -2,6 +2,7 @@
 
 namespace Tests\Feature\Checkouts\Ui;
 
+use App\Mail\BulkAssetCheckoutMail;
 use App\Mail\CheckoutAssetMail;
 use App\Models\Asset;
 use App\Models\Company;
@@ -59,10 +60,16 @@ public function testCanBulkCheckoutAssets()
             $asset->last_checkout = $checkoutAt;
             $asset->expected_checkin = $expectedCheckin;
             $this->assertHasTheseActionLogs($asset, ['create', 'checkout']); //Note: '$this' gets auto-bound in closures, so this does work.
+            $this->assertDatabaseHas('checkout_acceptances', [
+                'checkoutable_type' => Asset::class,
+                'checkoutable_id' => $asset->id,
+                'assigned_to_id' => $user->id,
+                'qty' => 1,
+            ]);
         });
 
-        Mail::assertSent(CheckoutAssetMail::class, 2);
-        Mail::assertSent(CheckoutAssetMail::class, function (CheckoutAssetMail $mail) {
+        Mail::assertNotSent(CheckoutAssetMail::class);
+        Mail::assertSent(BulkAssetCheckoutMail::class, function (BulkAssetCheckoutMail $mail) {
             return $mail->hasTo('someone@example.com');
         });
     }
diff --git a/tests/Feature/Notifications/Email/BulkCheckoutEmailTest.php b/tests/Feature/Notifications/Email/BulkCheckoutEmailTest.php
new file mode 100644
index 000000000000..9fb6f4554c34
--- /dev/null
+++ b/tests/Feature/Notifications/Email/BulkCheckoutEmailTest.php
@@ -0,0 +1,249 @@
+<?php
+
+namespace Tests\Feature\Notifications\Email;
+
+use App\Mail\BulkAssetCheckoutMail;
+use App\Mail\CheckoutAssetMail;
+use App\Models\Asset;
+use App\Models\Category;
+use App\Models\Location;
+use App\Models\User;
+use Illuminate\Database\Eloquent\Model;
+use Illuminate\Support\Collection;
+use Illuminate\Support\Facades\Mail;
+use PHPUnit\Framework\Attributes\Group;
+use Tests\TestCase;
+
+#[Group('notifications')]
+class BulkCheckoutEmailTest extends TestCase
+{
+    private Collection $assets;
+    private Model $assignee;
+
+    protected function setUp(): void
+    {
+        parent::setUp();
+
+        Mail::fake();
+
+        $this->settings->disableAdminCC();
+        $this->settings->disableAdminCCAlways();
+
+        $this->assets = Asset::factory()->requiresAcceptance()->count(2)->create();
+        $this->assignee = User::factory()->create(['email' => 'someone@example.com']);
+    }
+
+    public function test_sent_to_user()
+    {
+        $this->sendRequest();
+
+        Mail::assertNotSent(CheckoutAssetMail::class);
+
+        Mail::assertSent(BulkAssetCheckoutMail::class, 1);
+
+        Mail::assertSent(BulkAssetCheckoutMail::class, function (BulkAssetCheckoutMail $mail) {
+            return $mail->hasTo($this->assignee->email);
+        });
+    }
+
+    public function test_sent_to_location_manager()
+    {
+        $manager = User::factory()->create();
+
+        $this->assignee = Location::factory()->for($manager, 'manager')->create();
+
+        $this->sendRequest();
+
+        Mail::assertNotSent(CheckoutAssetMail::class);
+
+        Mail::assertSent(BulkAssetCheckoutMail::class, 1);
+
+        Mail::assertSent(BulkAssetCheckoutMail::class, function (BulkAssetCheckoutMail $mail) use ($manager) {
+            return $mail->hasTo($manager->email);
+        });
+    }
+
+    public function test_sent_to_user_asset_is_checked_out_to()
+    {
+        $user = User::factory()->create();
+
+        $this->assignee = Asset::factory()->assignedToUser($user)->create();
+
+        $this->sendRequest();
+
+        Mail::assertNotSent(CheckoutAssetMail::class);
+
+        Mail::assertSent(BulkAssetCheckoutMail::class, 1);
+
+        Mail::assertSent(BulkAssetCheckoutMail::class, function (BulkAssetCheckoutMail $mail) use ($user) {
+            return $mail->hasTo($user->email);
+        });
+    }
+
+    public function test_not_sent_to_user_when_user_does_not_have_email_address()
+    {
+        $this->assignee = User::factory()->create(['email' => null]);
+
+        $this->sendRequest();
+
+        Mail::assertNotSent(CheckoutAssetMail::class);
+        Mail::assertNotSent(BulkAssetCheckoutMail::class);
+    }
+
+    public function test_not_sent_to_user_if_assets_do_not_require_acceptance()
+    {
+        $this->assets = Asset::factory()->doesNotRequireAcceptance()->count(2)->create();
+
+        $category = Category::factory()
+            ->doesNotRequireAcceptance()
+            ->doesNotSendCheckinEmail()
+            ->withNoLocalOrGlobalEula()
+            ->create();
+
+        $this->assets->each(fn($asset) => $asset->model->category()->associate($category)->save());
+
+        $this->sendRequest();
+
+        Mail::assertNotSent(CheckoutAssetMail::class);
+        Mail::assertNotSent(BulkAssetCheckoutMail::class);
+    }
+
+    public function test_sent_when_assets_do_not_require_acceptance_but_have_a_eula()
+    {
+        $this->assets = Asset::factory()->count(2)->create();
+
+        $category = Category::factory()
+            ->doesNotRequireAcceptance()
+            ->doesNotSendCheckinEmail()
+            ->hasLocalEula()
+            ->create();
+
+        $this->assets->each(fn($asset) => $asset->model->category()->associate($category)->save());
+
+        $this->sendRequest();
+
+        Mail::assertNotSent(CheckoutAssetMail::class);
+
+        Mail::assertSent(BulkAssetCheckoutMail::class, 1);
+
+        Mail::assertSent(BulkAssetCheckoutMail::class, function (BulkAssetCheckoutMail $mail) {
+            return $mail->hasTo($this->assignee->email);
+        });
+    }
+
+    public function test_sent_when_assets_do_not_require_acceptance_or_have_a_eula_but_category_is_set_to_send_email()
+    {
+        $this->assets = Asset::factory()->count(2)->create();
+
+        $category = Category::factory()
+            ->doesNotRequireAcceptance()
+            ->withNoLocalOrGlobalEula()
+            ->sendsCheckinEmail()
+            ->create();
+
+        $this->assets->each(fn($asset) => $asset->model->category()->associate($category)->save());
+
+        $this->sendRequest();
+
+        Mail::assertNotSent(CheckoutAssetMail::class);
+
+        Mail::assertSent(BulkAssetCheckoutMail::class, 1);
+
+        Mail::assertSent(BulkAssetCheckoutMail::class, function (BulkAssetCheckoutMail $mail) {
+            return $mail->hasTo($this->assignee->email);
+        });
+    }
+
+    public function test_sent_to_cc_address_when_assets_require_acceptance()
+    {
+        $this->assets = Asset::factory()->requiresAcceptance()->count(2)->create();
+
+        $this->settings->enableAdminCC('cc@example.com')->disableAdminCCAlways();
+
+        $this->sendRequest();
+
+        Mail::assertNotSent(CheckoutAssetMail::class);
+
+        Mail::assertSent(BulkAssetCheckoutMail::class, 2);
+
+        Mail::assertSent(BulkAssetCheckoutMail::class, function (BulkAssetCheckoutMail $mail) {
+            return $mail->hasTo($this->assignee->email);
+        });
+
+        Mail::assertSent(BulkAssetCheckoutMail::class, function (BulkAssetCheckoutMail $mail) {
+            return $mail->hasTo('cc@example.com');
+        });
+    }
+
+    public function test_sent_to_cc_address_when_assets_do_not_require_acceptance_or_have_eula_but_admin_cc_always_enabled()
+    {
+        $this->settings->enableAdminCC('cc@example.com')->enableAdminCCAlways();
+
+        $this->assets = Asset::factory()->doesNotRequireAcceptance()->count(2)->create();
+
+        $category = Category::factory()
+            ->doesNotRequireAcceptance()
+            ->doesNotSendCheckinEmail()
+            ->withNoLocalOrGlobalEula()
+            ->create();
+
+        $this->assets->each(fn($asset) => $asset->model->category()->associate($category)->save());
+
+        $this->sendRequest();
+
+        Mail::assertNotSent(CheckoutAssetMail::class);
+
+        Mail::assertSent(BulkAssetCheckoutMail::class, function (BulkAssetCheckoutMail $mail) {
+            return $mail->hasTo('cc@example.com');
+        });
+    }
+
+    public function test_not_sent_to_cc_address_if_assets_do_not_require_acceptance()
+    {
+        $this->settings->enableAdminCC('cc@example.com')->disableAdminCCAlways();
+
+        $this->assets = Asset::factory()->doesNotRequireAcceptance()->count(2)->create();
+
+        $category = Category::factory()
+            ->doesNotRequireAcceptance()
+            ->doesNotSendCheckinEmail()
+            ->withNoLocalOrGlobalEula()
+            ->create();
+
+        $this->assets->each(fn($asset) => $asset->model->category()->associate($category)->save());
+
+        $this->sendRequest();
+
+        Mail::assertNotSent(CheckoutAssetMail::class);
+        Mail::assertNotSent(BulkAssetCheckoutMail::class);
+    }
+
+    private function sendRequest()
+    {
+        $assigned = match (get_class($this->assignee)) {
+            User::class => [
+                'checkout_to_type' => 'user',
+                'assigned_user' => $this->assignee->id,
+            ],
+            Location::class => [
+                'checkout_to_type' => 'location',
+                'assigned_location' => $this->assignee->id,
+            ],
+            Asset::class => [
+                'checkout_to_type' => 'asset',
+                'assigned_asset' => $this->assignee->id,
+            ],
+            default => [],
+        };
+
+        $this->actingAs(User::factory()->checkoutAssets()->viewAssets()->create())
+            ->followingRedirects()
+            ->post(route('hardware.bulkcheckout.store'), [
+                    'selected_assets' => $this->assets->pluck('id')->toArray(),
+                    'checkout_at' => now()->subWeek()->format('Y-m-d'),
+                    'expected_checkin' => now()->addWeek()->format('Y-m-d'),
+                    'note' => null,
+                ] + $assigned)
+            ->assertOk();
+    }
+}
diff --git a/tests/Feature/Notifications/Webhooks/WebhookNotificationsUponBulkAssetCheckoutTest.php b/tests/Feature/Notifications/Webhooks/WebhookNotificationsUponBulkAssetCheckoutTest.php
new file mode 100644
index 000000000000..993d33b93257
--- /dev/null
+++ b/tests/Feature/Notifications/Webhooks/WebhookNotificationsUponBulkAssetCheckoutTest.php
@@ -0,0 +1,39 @@
+<?php
+
+namespace Tests\Feature\Notifications\Webhooks;
+
+use App\Models\Asset;
+use App\Models\User;
+use App\Notifications\CheckoutAssetNotification;
+use Illuminate\Support\Facades\Notification;
+use PHPUnit\Framework\Attributes\Group;
+use Tests\TestCase;
+
+#[Group('notifications')]
+class WebhookNotificationsUponBulkAssetCheckoutTest extends TestCase
+{
+    public function test_webbook_is_sent_upon_bulk_asset_checkout()
+    {
+        Notification::fake();
+
+        $this->settings->enableSlackWebhook();
+
+        $assets = Asset::factory()->requiresAcceptance()->count(2)->create();
+
+        $this->actingAs(User::factory()->checkoutAssets()->viewAssets()->create())
+            ->followingRedirects()
+            ->post(route('hardware.bulkcheckout.store'), [
+                'selected_assets' => $assets->pluck('id')->toArray(),
+                'checkout_to_type' => 'user',
+                'assigned_user' => User::factory()->create(['email' => 'someone@example.com'])->id,
+                'assigned_asset' => null,
+                'checkout_at' => now()->subWeek()->format('Y-m-d'),
+                'expected_checkin' => now()->addWeek()->format('Y-m-d'),
+                'note' => null,
+            ])
+            ->assertOk();
+
+        $this->assertSlackNotificationSent(CheckoutAssetNotification::class);
+        Notification::assertSentTimes(CheckoutAssetNotification::class, 2);
+    }
+}