diff --git a/src/Controller/Administrative/Disposition/DocumentUploadController.php b/src/Controller/Administrative/Disposition/DocumentUploadController.php
new file mode 100644
index 0000000..e090c1a
--- /dev/null
+++ b/src/Controller/Administrative/Disposition/DocumentUploadController.php
@@ -0,0 +1,117 @@
+<?php
+
+namespace App\Controller\Administrative\Disposition;
+
+use App\Entity\Disposition;
+use App\Entity\Upload;
+use App\Event\DocumentUploadedEvent;
+use App\Htmx\HxRedirectResponse;
+use App\Service\Upload\UploadHandler;
+use Doctrine\ORM\EntityManagerInterface;
+use Psr\Log\LoggerInterface;
+use Symfony\Bundle\FrameworkBundle\Controller\AbstractController;
+use Symfony\Component\DependencyInjection\Attribute\Target;
+use Symfony\Component\HttpFoundation\Request;
+use Symfony\Component\HttpFoundation\Response;
+use Symfony\Component\Routing\Attribute\Route;
+use Symfony\Component\Security\Http\Attribute\IsGranted;
+use Symfony\Component\Workflow\WorkflowInterface;
+use Symfony\Contracts\EventDispatcher\EventDispatcherInterface;
+
+class DocumentUploadController extends AbstractController
+{
+    public function __construct(
+        private readonly UploadHandler $uploadHandler,
+        private readonly EntityManagerInterface $entityManager,
+        #[Target('disposition')]
+        private readonly WorkflowInterface $workflow,
+        private readonly EventDispatcherInterface $eventDispatcher,
+        private readonly LoggerInterface $logger,
+    ) {
+    }
+
+    #[Route(
+        path: '/administrative/disposition/document-upload/{uuid}',
+        name: 'app_administrative_disposition_document_upload'
+    )]
+    #[IsGranted('ROLE_ADMINISTRATIVE')]
+    public function index(Disposition $disposition, Request $request): Response
+    {
+        if (true === $this->workflow->can($disposition, 'upload_contract')) {
+            $uploadType = Upload::TYPE_CONTRACT;
+            $uploadTypeLabel = 'Honorarvertrag';
+            $uploaderRoute = '_uploader_upload_contract';
+        } elseif (true === $this->workflow->can($disposition, 'upload_invoice')) {
+            $uploadType = Upload::TYPE_INVOICE;
+            $uploadTypeLabel = 'Honoranote';
+            $uploaderRoute = '_uploader_upload_invoice';
+        } else {
+            $this->addFlash('error', 'Kein Upload möglich beim aktuellen Status der Einteilung');
+
+            return $this->getRedirectResponse($disposition);
+        }
+
+        $teamer = $disposition->getTeamer();
+        $modalTitle = sprintf('%s für %s hochladen', $uploadTypeLabel, $teamer);
+
+        $form = $this->createFormBuilder()->getForm();
+        $form->handleRequest($request);
+
+        if ($form->isSubmitted() && $form->isValid()) {
+            $this->processUpload($disposition, $uploadType);
+
+            $this->addFlash('success', sprintf('%s wurde hochgeladen', $uploadTypeLabel));
+
+            return $this->getRedirectResponse($disposition);
+        }
+
+        return $this->render('administrative/disposition/modal_document_upload.html.twig', [
+            'disposition' => $disposition,
+            'modalTitle' => $modalTitle,
+            'uploaderRoute' => $uploaderRoute,
+            'form' => $form->createView(),
+        ]);
+    }
+
+    private function processUpload(Disposition $disposition, string $uploadType): void
+    {
+        if (null !== $existingUpload = $disposition->getDocumentByType($uploadType)) {
+            $this->entityManager->remove($existingUpload);
+        }
+
+        $teamer = $disposition->getTeamer();
+        $user = $teamer->getUser();
+
+        $uploadSession = $this->uploadHandler->getUploadSession();
+
+        $upload = Upload::fromUploadDto($uploadSession->getUploads()->first(), $user, $uploadType);
+        $upload->setStatus(Upload::STATUS_NEW);
+
+        $disposition->addDocument($upload);
+
+        $transitionName = sprintf('upload_%s', $uploadType);
+        $this->workflow->apply($disposition, $transitionName);
+
+        $this->entityManager->flush();
+
+        $this->uploadHandler->moveUploadSessionFilesFromOrphanage($uploadType, $uploadSession);
+        $this->uploadHandler->destroyUploadSession();
+
+        $this->eventDispatcher->dispatch(new DocumentUploadedEvent($upload), DocumentUploadedEvent::NAME);
+
+        $this->logger->info('Document upload for teamer', [
+            'teamer_id' => $teamer->getId(),
+            'teamer_name' => $teamer->getFullName(),
+            'disposition_id' => $disposition->getId(),
+            'document_id' => $upload->getId(),
+            'upload_type' => $uploadType,
+        ]);
+    }
+
+    private function getRedirectResponse(Disposition $disposition): HxRedirectResponse
+    {
+        return new HxRedirectResponse($this->generateUrl('app_administrative_assignment_detail', [
+            'uuid' => $disposition->getAssignment()->getUuid(),
+        ]));
+    }
+}
diff --git a/src/EventListener/DispositionWorkflowGuardSubscriber.php b/src/EventListener/DispositionWorkflowGuardSubscriber.php
index 65fe97d..fbc5859 100644
--- a/src/EventListener/DispositionWorkflowGuardSubscriber.php
+++ b/src/EventListener/DispositionWorkflowGuardSubscriber.php
@@ -4,13 +4,14 @@ namespace App\EventListener;
 
 use App\Entity\Disposition;
 use App\Entity\Upload;
+use Symfony\Bundle\SecurityBundle\Security;
 use Symfony\Component\EventDispatcher\EventSubscriberInterface;
 use Symfony\Component\Workflow\Event\GuardEvent;
 use Symfony\Contracts\Translation\TranslatorInterface;
 
 class DispositionWorkflowGuardSubscriber implements EventSubscriberInterface
 {
-    public function __construct(private readonly TranslatorInterface $translator)
+    public function __construct(private readonly TranslatorInterface $translator, private readonly Security $security)
     {}
 
     public static function getSubscribedEvents(): array
@@ -40,6 +41,11 @@ class DispositionWorkflowGuardSubscriber implements EventSubscriberInterface
 
     public function guardUploadContract(GuardEvent $event): void
     {
+        // no checks for administrative users
+        if ($this->security->isGranted('ROLE_ADMINISTRATIVE')) {
+            return;
+        }
+
         /** @var Disposition $disposition */
         $disposition = $event->getSubject();
         $assignment = $disposition->getAssignment();
@@ -79,6 +85,11 @@ class DispositionWorkflowGuardSubscriber implements EventSubscriberInterface
             $event->setBlocked(true, $message);
         }
 
+        // no further checks for administrative users
+        if ($this->security->isGranted('ROLE_ADMINISTRATIVE')) {
+            return;
+        }
+
         $earliestDate = $destination->getDateTo();
 
         if ($earliestDate > $today) {
diff --git a/templates/administrative/assignment/detail.html.twig b/templates/administrative/assignment/detail.html.twig
index b95deb4..aece30e 100644
--- a/templates/administrative/assignment/detail.html.twig
+++ b/templates/administrative/assignment/detail.html.twig
@@ -179,6 +179,15 @@
                             </td>
                             <td>
                                 <div class="flex items-center justify-end space-x-2">
+                                    {% if workflow_can(disposition, 'upload_contract') or workflow_can(disposition, 'upload_invoice') %}
+                                        <button type="button"
+                                                title="Dokumentenupload"
+                                                hx-get="{{ path('app_administrative_disposition_document_upload', { 'uuid': disposition.uuid }) }}"
+                                                hx-target="body"
+                                                hx-swap="beforeend">
+                                            {{ icon('upload') }}
+                                        </button>
+                                    {% endif %}
                                     {% if is_granted('DELETE', disposition) %}
                                         <button type="button"
                                                 class="text-red-500"
diff --git a/templates/administrative/disposition/modal_document_upload.html.twig b/templates/administrative/disposition/modal_document_upload.html.twig
new file mode 100644
index 0000000..1bb909c
--- /dev/null
+++ b/templates/administrative/disposition/modal_document_upload.html.twig
@@ -0,0 +1,20 @@
+{% extends 'htmx_modal.html.twig' %}
+
+{% block title %}{{ modalTitle }}{% endblock %}
+
+{% block content %}
+    {{ form_start(form, { 'attr': { 'hx-post': app.request.uri, 'hx-target': '#htmx-modal', 'hx-swap': 'outerHTML' }}) }}
+    <div class="pb-4">
+        {% include '_partials/_upload_collection_form.html.twig' with {
+            'endpoint_upload': path(uploaderRoute),
+            'max_filesize': 5,
+            'max_files': 1,
+            'accepted_files': 'image/jpg,image/jpeg,application/pdf',
+        } %}
+    </div>
+    <button type="submit" class="btn">
+        Upload speichern
+    </button>
+    {{ form_rest(form) }}
+    {{ form_end(form) }}
+{% endblock %}
\ No newline at end of file