diff --git a/assets/vue/views/documents/DocumentsList.vue b/assets/vue/views/documents/DocumentsList.vue
index f7a91afb4c3..b9237c97e71 100644
--- a/assets/vue/views/documents/DocumentsList.vue
+++ b/assets/vue/views/documents/DocumentsList.vue
@@ -448,6 +448,34 @@
       />
     </form>
   </BaseDialogConfirmCancel>
+  <BaseDialogConfirmCancel
+    v-model:is-visible="isDeleteWarningLpDialogVisible"
+    :title="t('Confirm deletion')"
+    @confirm-clicked="forceDeleteItem"
+    @cancel-clicked="isDeleteWarningLpDialogVisible = false"
+  >
+    <div class="confirmation-content">
+      <BaseIcon
+        class="mr-2"
+        icon="alert"
+        size="big"
+      />
+      <p class="mb-2">
+        {{ t("The following documents are used in learning paths:") }}
+      </p>
+      <ul class="pl-4 mb-4">
+        <li
+          v-for="lp in lpListWarning"
+          :key="lp.lpId + lp.documentTitle"
+        >
+          <b>{{ lp.documentTitle }}</b> → {{ lp.lpTitle }}
+        </li>
+      </ul>
+      <p class="mt-4 font-semibold">
+        {{ t("Do you still want to delete them?") }}
+      </p>
+    </div>
+  </BaseDialogConfirmCancel>
 </template>
 
 <script setup>
@@ -486,7 +514,9 @@ const router = useRouter()
 const securityStore = useSecurityStore()
 
 const platformConfigStore = usePlatformConfig()
-const allowAccessUrlFiles = computed(() => "false" !== platformConfigStore.getSetting("course.access_url_specific_files"))
+const allowAccessUrlFiles = computed(
+  () => "false" !== platformConfigStore.getSetting("course.access_url_specific_files"),
+)
 
 const { t } = useI18n()
 const { filters, options, onUpdateOptions, deleteItem } = useDatatableList("Documents")
@@ -499,6 +529,8 @@ const isAllowedToEdit = ref(false)
 const folders = ref([])
 const selectedFolder = ref(null)
 const isDownloading = ref(false)
+const isDeleteWarningLpDialogVisible = ref(false)
+const lpListWarning = ref([])
 
 const {
   showNewDocumentButton,
@@ -610,7 +642,7 @@ const showBackButtonIfNotRootFolder = computed(() => {
 function goToAddVariation(item) {
   const resourceFileId = item.resourceNode.firstResourceFile.id
   router.push({
-    name: 'DocumentsAddVariation',
+    name: "DocumentsAddVariation",
     params: { resourceFileId, node: route.params.node },
     query: { cid, sid, gid },
   })
@@ -672,9 +704,41 @@ function showDeleteMultipleDialog() {
   isDeleteMultipleDialogVisible.value = true
 }
 
-function confirmDeleteItem(itemToDelete) {
-  item.value = itemToDelete
-  isDeleteItemDialogVisible.value = true
+async function confirmDeleteItem(itemToDelete) {
+  try {
+    const response = await axios.get(`/api/documents/${itemToDelete.iid}/lp-usage`)
+    if (response.data.usedInLp) {
+      lpListWarning.value = response.data.lpList.map((lp) => ({
+        ...lp,
+        documentTitle: itemToDelete.title,
+        documentId: itemToDelete.iid,
+      }))
+      item.value = itemToDelete
+      isDeleteWarningLpDialogVisible.value = true
+    } else {
+      item.value = itemToDelete
+      isDeleteItemDialogVisible.value = true
+    }
+  } catch (error) {
+    console.error("Error checking LP usage for individual item:", error)
+  }
+}
+
+async function forceDeleteItem() {
+  try {
+    const docIdsToDelete = [...new Set(lpListWarning.value.map((lp) => lp.documentId))]
+
+    await Promise.all(docIdsToDelete.map((iid) => axios.delete(`/api/documents/${iid}`)))
+
+    notification.showSuccessNotification(t("Documents deleted"))
+    isDeleteWarningLpDialogVisible.value = false
+    item.value = {}
+    unselectAll()
+    onUpdateOptions(options.value)
+  } catch (error) {
+    console.error("Error deleting documents forcibly:", error)
+    notification.showErrorNotification(t("Error deleting document(s)."))
+  }
 }
 
 async function downloadSelectedItems() {
@@ -688,8 +752,8 @@ async function downloadSelectedItems() {
   try {
     const response = await axios.post(
       "/api/documents/download-selected",
-      { ids: selectedItems.value.map(item => item.iid) },
-      { responseType: "blob" }
+      { ids: selectedItems.value.map((item) => item.iid) },
+      { responseType: "blob" },
     )
 
     const url = window.URL.createObjectURL(new Blob([response.data]))
@@ -705,15 +769,61 @@ async function downloadSelectedItems() {
     console.error("Error downloading selected items:", error)
     notification.showErrorNotification(t("Error downloading selected items."))
   } finally {
-    isDownloading.value = false;
+    isDownloading.value = false
   }
 }
 
 async function deleteMultipleItems() {
-  await store.dispatch("documents/delMultiple", selectedItems.value)
+  const itemsWithoutLp = []
+  const documentsWithLpMap = {}
+
+  for (const item of selectedItems.value) {
+    try {
+      const response = await axios.get(`/api/documents/${item.iid}/lp-usage`)
+      if (response.data.usedInLp) {
+        if (!documentsWithLpMap[item.iid]) {
+          documentsWithLpMap[item.iid] = {
+            iid: item.iid,
+            title: item.title,
+            lpList: [],
+          }
+        }
+        documentsWithLpMap[item.iid].lpList.push(...response.data.lpList)
+      } else {
+        itemsWithoutLp.push(item)
+      }
+    } catch (error) {
+      console.error(`Error checking LP usage for document ${item.iid}:`, error)
+    }
+  }
+
+  const documentsWithLp = Object.values(documentsWithLpMap)
+
+  if (itemsWithoutLp.length > 0) {
+    try {
+      await store.dispatch("documents/delMultiple", itemsWithoutLp)
+    } catch (e) {
+      console.error("Error deleting documents without LP:", e)
+    }
+  }
+
+  if (documentsWithLp.length > 0) {
+    lpListWarning.value = documentsWithLp.flatMap((doc) =>
+      doc.lpList.map((lp) => ({
+        ...lp,
+        documentTitle: doc.title,
+        documentId: doc.iid,
+      })),
+    )
+
+    item.value = {}
+    isDeleteWarningLpDialogVisible.value = true
+  } else {
+    notification.showSuccessNotification(t("Documents deleted"))
+    unselectAll()
+  }
+
   isDeleteMultipleDialogVisible.value = false
-  notification.showSuccessNotification(t("Deleted"))
-  unselectAll()
   onUpdateOptions(options.value)
 }
 
@@ -884,19 +994,19 @@ async function replaceDocument() {
     return
   }
 
-  if (documentToReplace.value.filetype !== 'file') {
+  if (documentToReplace.value.filetype !== "file") {
     notification.showErrorNotification(t("Only files can be replaced."))
     return
   }
 
   const formData = new FormData()
   console.log(selectedReplaceFile.value)
-  formData.append('file', selectedReplaceFile.value)
+  formData.append("file", selectedReplaceFile.value)
 
   try {
     await axios.post(`/api/documents/${documentToReplace.value.iid}/replace`, formData, {
       headers: {
-        'Content-Type': 'multipart/form-data',
+        "Content-Type": "multipart/form-data",
       },
     })
     notification.showSuccessNotification(t("File replaced"))
@@ -911,7 +1021,7 @@ async function replaceDocument() {
 async function fetchFolders(nodeId = null, parentPath = "") {
   const foldersList = [
     {
-      label: t('Documents'),
+      label: t("Documents"),
       value: nodeId || route.params.node || route.query.node || "root-node-id",
     },
   ]
diff --git a/public/main/inc/lib/document.lib.php b/public/main/inc/lib/document.lib.php
index 204f30d6d4b..4ca615e4bd8 100644
--- a/public/main/inc/lib/document.lib.php
+++ b/public/main/inc/lib/document.lib.php
@@ -2294,12 +2294,15 @@ class="moved ui-sortable-handle link_with_id"
             ->innerJoin('node.resourceType', 'type')
             ->innerJoin('node.resourceLinks', 'links')
             ->innerJoin('node.resourceFiles', 'files')
+            ->innerJoin(CDocument::class, 'doc', 'WITH', 'doc.resourceNode = node')
             ->addSelect('files')
             ->where('type = :type')
             ->andWhere('links.course = :course')
-            ->setParameters(['type' => $type, 'course' => $course])
-            ->orderBy('node.parent', 'ASC')
-        ;
+            ->setParameters([
+                'type' => $type,
+                'course' => $course,
+            ])
+            ->orderBy('node.parent', 'ASC');
 
         $sessionId = api_get_session_id();
         if (empty($sessionId)) {
diff --git a/src/CoreBundle/Controller/Api/DocumentLearningPathUsageAction.php b/src/CoreBundle/Controller/Api/DocumentLearningPathUsageAction.php
new file mode 100644
index 00000000000..9f4da2ca3ef
--- /dev/null
+++ b/src/CoreBundle/Controller/Api/DocumentLearningPathUsageAction.php
@@ -0,0 +1,30 @@
+<?php
+
+declare(strict_types=1);
+
+/* For licensing terms, see /license.txt */
+
+namespace Chamilo\CoreBundle\Controller\Api;
+
+use Chamilo\CourseBundle\Repository\CLpItemRepository;
+use Symfony\Bundle\FrameworkBundle\Controller\AbstractController;
+use Symfony\Component\HttpFoundation\JsonResponse;
+use Symfony\Component\HttpKernel\Attribute\AsController;
+
+#[AsController]
+class DocumentLearningPathUsageAction extends AbstractController
+{
+    public function __construct(
+        private CLpItemRepository $lpItemRepo
+    ) {}
+
+    public function __invoke($iid): JsonResponse
+    {
+        $lpUsages = $this->lpItemRepo->findLearningPathsUsingDocument((int) $iid);
+
+        return new JsonResponse([
+            'usedInLp' => !empty($lpUsages),
+            'lpList' => $lpUsages,
+        ]);
+    }
+}
diff --git a/src/CoreBundle/Entity/Listener/ResourceListener.php b/src/CoreBundle/Entity/Listener/ResourceListener.php
index 447e67b1afb..0545811d7f1 100644
--- a/src/CoreBundle/Entity/Listener/ResourceListener.php
+++ b/src/CoreBundle/Entity/Listener/ResourceListener.php
@@ -22,7 +22,9 @@
 use Chamilo\CoreBundle\Tool\ToolChain;
 use Chamilo\CoreBundle\Traits\AccessUrlListenerTrait;
 use Chamilo\CourseBundle\Entity\CCalendarEvent;
+use Chamilo\CourseBundle\Entity\CDocument;
 use Cocur\Slugify\SlugifyInterface;
+use Doctrine\Persistence\Event\LifecycleEventArgs;
 use Doctrine\ORM\Event\PostUpdateEventArgs;
 use Doctrine\ORM\Event\PrePersistEventArgs;
 use Doctrine\ORM\Event\PreUpdateEventArgs;
@@ -350,4 +352,24 @@ private function addCCalendarEventGlobalLink(CCalendarEvent $event, PrePersistEv
             }
         }
     }
+
+    public function preRemove(AbstractResource $resource, LifecycleEventArgs $args): void
+    {
+        if (!$resource instanceof CDocument) {
+            return;
+        }
+
+        $em = $args->getObjectManager();
+        $resourceNode = $resource->getResourceNode();
+
+        if (!$resourceNode) {
+            return;
+        }
+
+        $docID = $resource->getIid();
+        $em->createQuery('DELETE FROM Chamilo\CourseBundle\Entity\CLpItem i WHERE i.path = :path AND i.itemType = :type')
+            ->setParameter('path', $docID)
+            ->setParameter('type', 'document')
+            ->execute();
+    }
 }
diff --git a/src/CoreBundle/Repository/ResourceNodeRepository.php b/src/CoreBundle/Repository/ResourceNodeRepository.php
index d74a8e0c102..d74e2e0f882 100644
--- a/src/CoreBundle/Repository/ResourceNodeRepository.php
+++ b/src/CoreBundle/Repository/ResourceNodeRepository.php
@@ -37,7 +37,7 @@ public function __construct(
         private readonly AccessUrlHelper $accessUrlHelper,
         private readonly SettingsManager $settingsManager
     ) {
-        $this->filesystem = $resourceFilesystem; // Asignar el filesystem correcto
+        $this->filesystem = $resourceFilesystem;
         parent::__construct($manager, $manager->getClassMetadata(ResourceNode::class));
     }
 
diff --git a/src/CoreBundle/Traits/Repository/ORM/NestedTreeRepositoryTrait.php b/src/CoreBundle/Traits/Repository/ORM/NestedTreeRepositoryTrait.php
index ce257805b6b..59d6f9696fa 100644
--- a/src/CoreBundle/Traits/Repository/ORM/NestedTreeRepositoryTrait.php
+++ b/src/CoreBundle/Traits/Repository/ORM/NestedTreeRepositoryTrait.php
@@ -2,6 +2,7 @@
 
 namespace Chamilo\CoreBundle\Traits\Repository\ORM;
 
+use Gedmo\Exception\RuntimeException;
 use Gedmo\Tool\Wrapper\EntityWrapper;
 use Doctrine\ORM\Query;
 use Gedmo\Tree\Strategy;
@@ -668,12 +669,8 @@ public function moveUp($node, $number = 1)
      * UNSAFE: be sure to backup before running this method when necessary
      *
      * Removes given $node from the tree and reparents its descendants
-     *
-     * @param object $node
-     *
-     * @throws \RuntimeException - if something fails in transaction
      */
-    public function removeFromTree($node)
+    public function removeFromTree(object $node): void
     {
         $meta = $this->getClassMetadata();
         $em = $this->getEntityManager();
@@ -685,6 +682,11 @@ public function removeFromTree($node)
             $left = $wrapped->getPropertyValue($config['left']);
             $rootId = isset($config['root']) ? $wrapped->getPropertyValue($config['root']) : null;
 
+            if (!is_numeric($left) || !is_numeric($right)) {
+                $this->removeSingle($wrapped);
+                return;
+            }
+
             if ($right == $left + 1) {
                 $this->removeSingle($wrapped);
                 $this->listener
@@ -775,7 +777,7 @@ public function removeFromTree($node)
             } catch (\Exception $e) {
                 $em->close();
                 $em->getConnection()->rollback();
-                throw new \Gedmo\Exception\RuntimeException('Transaction failed', null, $e);
+                throw new RuntimeException('Transaction failed', null, $e);
             }
         } else {
             throw new InvalidArgumentException("Node is not related to this repository");
diff --git a/src/CourseBundle/Entity/CDocument.php b/src/CourseBundle/Entity/CDocument.php
index 0953749b592..ed1253e2247 100644
--- a/src/CourseBundle/Entity/CDocument.php
+++ b/src/CourseBundle/Entity/CDocument.php
@@ -18,6 +18,7 @@
 use ApiPlatform\Metadata\Put;
 use ApiPlatform\Serializer\Filter\PropertyFilter;
 use Chamilo\CoreBundle\Controller\Api\CreateDocumentFileAction;
+use Chamilo\CoreBundle\Controller\Api\DocumentLearningPathUsageAction;
 use Chamilo\CoreBundle\Controller\Api\DownloadSelectedDocumentsAction;
 use Chamilo\CoreBundle\Controller\Api\ReplaceDocumentFileAction;
 use Chamilo\CoreBundle\Controller\Api\UpdateDocumentFileAction;
@@ -88,6 +89,13 @@
             deserialize: false
         ),
         new Get(security: "is_granted('VIEW', object.resourceNode)"),
+        new Get(
+            uriTemplate: '/documents/{iid}/lp-usage',
+            controller: DocumentLearningPathUsageAction::class,
+            security: "is_granted('ROLE_USER')",
+            read: false,
+            name: 'api_documents_lp_usage'
+        ),
         new Delete(security: "is_granted('DELETE', object.resourceNode)"),
         new Post(
             controller: CreateDocumentFileAction::class,
diff --git a/src/CourseBundle/Entity/CLpItem.php b/src/CourseBundle/Entity/CLpItem.php
index 179e2775c28..35e9487b18e 100644
--- a/src/CourseBundle/Entity/CLpItem.php
+++ b/src/CourseBundle/Entity/CLpItem.php
@@ -18,7 +18,7 @@
  * Items from a learning path (LP).
  */
 #[ORM\Table(name: 'c_lp_item')]
-#[ORM\Index(name: 'lp_id', columns: ['lp_id'])]
+#[ORM\Index(columns: ['lp_id'], name: 'lp_id')]
 #[Gedmo\Tree(type: 'nested')]
 #[ORM\Entity(repositoryClass: CLpItemRepository::class)]
 class CLpItem implements Stringable
diff --git a/src/CourseBundle/Repository/CLpItemRepository.php b/src/CourseBundle/Repository/CLpItemRepository.php
index 25c3b6d4dc1..783632edc0e 100644
--- a/src/CourseBundle/Repository/CLpItemRepository.php
+++ b/src/CourseBundle/Repository/CLpItemRepository.php
@@ -51,4 +51,17 @@ public function findItemsByLearningPathAndType(int $learningPathId, string $item
 
         return $query->getResult();
     }
+
+    public function findLearningPathsUsingDocument(int $resourceFileId): array
+    {
+        return $this->createQueryBuilder('i')
+            ->select('lp.iid AS lpId, lp.title AS lpTitle')
+            ->join('i.lp', 'lp')
+            ->where('i.itemType = :type')
+            ->andWhere('i.path = :path')
+            ->setParameter('type', 'document')
+            ->setParameter('path', $resourceFileId)
+            ->getQuery()
+            ->getArrayResult();
+    }
 }