diff --git a/app/javascript/dashboard/components-next/captain/assistant/DocumentCard.vue b/app/javascript/dashboard/components-next/captain/assistant/DocumentCard.vue
index d6e546581..bb5f03451 100644
--- a/app/javascript/dashboard/components-next/captain/assistant/DocumentCard.vue
+++ b/app/javascript/dashboard/components-next/captain/assistant/DocumentCard.vue
@@ -4,6 +4,10 @@ import { useToggle } from '@vueuse/core';
 import { useI18n } from 'vue-i18n';
 import { dynamicTime } from 'shared/helpers/timeHelper';
 import { usePolicy } from 'dashboard/composables/usePolicy';
+import {
+  isPdfDocument,
+  formatDocumentLink,
+} from 'shared/helpers/documentHelper';
 
 import CardLayout from 'dashboard/components-next/CardLayout.vue';
 import DropdownMenu from 'dashboard/components-next/dropdown-menu/DropdownMenu.vue';
@@ -63,6 +67,11 @@ const menuItems = computed(() => {
 
 const createdAt = computed(() => dynamicTime(props.createdAt));
 
+const displayLink = computed(() => formatDocumentLink(props.externalLink));
+const linkIcon = computed(() =>
+  isPdfDocument(props.externalLink) ? 'i-ph-file-pdf' : 'i-ph-link-simple'
+);
+
 const handleAction = ({ action, value }) => {
   toggleDropdown(false);
   emit('action', { action, value, id: props.id });
@@ -71,14 +80,14 @@ const handleAction = ({ action, value }) => {
 
 <template>
   <CardLayout>
-    <div class="flex justify-between w-full gap-1">
+    <div class="flex gap-1 justify-between w-full">
       <span class="text-base text-n-slate-12 line-clamp-1">
         {{ name }}
       </span>
-      <div class="flex items-center gap-2">
+      <div class="flex gap-2 items-center">
         <div
           v-on-clickaway="() => toggleDropdown(false)"
-          class="relative flex items-center group"
+          class="flex relative items-center group"
         >
           <Button
             icon="i-lucide-ellipsis-vertical"
@@ -90,26 +99,26 @@ const handleAction = ({ action, value }) => {
           <DropdownMenu
             v-if="showActionsDropdown"
             :menu-items="menuItems"
-            class="mt-1 ltr:right-0 rtl:left-0 xl:ltr:right-0 xl:rtl:left-0 top-full"
+            class="top-full mt-1 ltr:right-0 rtl:left-0 xl:ltr:right-0 xl:rtl:left-0"
             @action="handleAction($event)"
           />
         </div>
       </div>
     </div>
-    <div class="flex items-center justify-between w-full gap-4">
+    <div class="flex gap-4 justify-between items-center w-full">
       <span
-        class="text-sm shrink-0 truncate text-n-slate-11 flex items-center gap-1"
+        class="flex gap-1 items-center text-sm truncate shrink-0 text-n-slate-11"
       >
         <i class="i-woot-captain" />
         {{ assistant?.name || '' }}
       </span>
       <span
-        class="text-n-slate-11 text-sm truncate flex justify-start flex-1 items-center gap-1"
+        class="flex flex-1 gap-1 justify-start items-center text-sm truncate text-n-slate-11"
       >
-        <i class="i-ph-link-simple shrink-0" />
-        <span class="truncate">{{ externalLink }}</span>
+        <i :class="linkIcon" class="shrink-0" />
+        <span class="truncate">{{ displayLink }}</span>
       </span>
-      <div class="shrink-0 text-sm text-n-slate-11 line-clamp-1">
+      <div class="text-sm shrink-0 text-n-slate-11 line-clamp-1">
         {{ createdAt }}
       </div>
     </div>
diff --git a/app/javascript/dashboard/components-next/captain/pageComponents/document/CreateDocumentDialog.vue b/app/javascript/dashboard/components-next/captain/pageComponents/document/CreateDocumentDialog.vue
index 7db74f523..9f701a149 100644
--- a/app/javascript/dashboard/components-next/captain/pageComponents/document/CreateDocumentDialog.vue
+++ b/app/javascript/dashboard/components-next/captain/pageComponents/document/CreateDocumentDialog.vue
@@ -3,6 +3,7 @@ import { ref } from 'vue';
 import { useStore } from 'dashboard/composables/store';
 import { useAlert } from 'dashboard/composables';
 import { useI18n } from 'vue-i18n';
+import { parseAPIErrorResponse } from 'dashboard/store/utils/api';
 
 import Dialog from 'dashboard/components-next/dialog/Dialog.vue';
 import DocumentForm from './DocumentForm.vue';
@@ -12,7 +13,6 @@ const { t } = useI18n();
 const store = useStore();
 
 const dialogRef = ref(null);
-const documentForm = ref(null);
 
 const i18nKey = 'CAPTAIN.DOCUMENTS.CREATE';
 
@@ -23,7 +23,7 @@ const handleSubmit = async newDocument => {
     dialogRef.value.close();
   } catch (error) {
     const errorMessage =
-      error?.response?.message || t(`${i18nKey}.ERROR_MESSAGE`);
+      parseAPIErrorResponse(error) || t(`${i18nKey}.ERROR_MESSAGE`);
     useAlert(errorMessage);
   }
 };
@@ -48,11 +48,7 @@ defineExpose({ dialogRef });
     :show-confirm-button="false"
     @close="handleClose"
   >
-    <DocumentForm
-      ref="documentForm"
-      @submit="handleSubmit"
-      @cancel="handleCancel"
-    />
+    <DocumentForm @submit="handleSubmit" @cancel="handleCancel" />
     <template #footer />
   </Dialog>
 </template>
diff --git a/app/javascript/dashboard/components-next/captain/pageComponents/document/DocumentForm.vue b/app/javascript/dashboard/components-next/captain/pageComponents/document/DocumentForm.vue
index d85ba8a06..784b3aad2 100644
--- a/app/javascript/dashboard/components-next/captain/pageComponents/document/DocumentForm.vue
+++ b/app/javascript/dashboard/components-next/captain/pageComponents/document/DocumentForm.vue
@@ -1,9 +1,10 @@
 <script setup>
-import { reactive, computed } from 'vue';
+import { reactive, computed, ref, nextTick } from 'vue';
 import { useI18n } from 'vue-i18n';
 import { useVuelidate } from '@vuelidate/core';
-import { required, minLength, url } from '@vuelidate/validators';
+import { required, minLength, requiredIf, url } from '@vuelidate/validators';
 import { useMapGetter } from 'dashboard/composables/store';
+import { useAlert } from 'dashboard/composables';
 
 import Input from 'dashboard/components-next/input/Input.vue';
 import Button from 'dashboard/components-next/button/Button.vue';
@@ -11,6 +12,8 @@ import ComboBox from 'dashboard/components-next/combobox/ComboBox.vue';
 
 const emit = defineEmits(['submit', 'cancel']);
 
+const MAX_FILE_SIZE = 10 * 1024 * 1024; // 10MB
+
 const { t } = useI18n();
 
 const formState = {
@@ -20,14 +23,25 @@ const formState = {
 
 const initialState = {
   name: '',
+  url: '',
   assistantId: null,
+  documentType: 'url',
+  pdfFile: null,
 };
 
 const state = reactive({ ...initialState });
+const fileInputRef = ref(null);
 
 const validationRules = {
-  url: { required, url, minLength: minLength(1) },
+  url: {
+    required: requiredIf(() => state.documentType === 'url'),
+    url: requiredIf(() => state.documentType === 'url' && url),
+    minLength: requiredIf(() => state.documentType === 'url' && minLength(1)),
+  },
   assistantId: { required },
+  pdfFile: {
+    required: requiredIf(() => state.documentType === 'pdf'),
+  },
 };
 
 const assistantList = computed(() =>
@@ -37,10 +51,17 @@ const assistantList = computed(() =>
   }))
 );
 
+const documentTypeOptions = [
+  { value: 'url', label: t('CAPTAIN.DOCUMENTS.FORM.TYPE.URL') },
+  { value: 'pdf', label: t('CAPTAIN.DOCUMENTS.FORM.TYPE.PDF') },
+];
+
 const v$ = useVuelidate(validationRules, state);
 
 const isLoading = computed(() => formState.uiFlags.value.creatingItem);
 
+const hasPdfFileError = computed(() => v$.value.pdfFile.$error);
+
 const getErrorMessage = (field, errorKey) => {
   return v$.value[field].$error
     ? t(`CAPTAIN.DOCUMENTS.FORM.${errorKey}.ERROR`)
@@ -50,14 +71,57 @@ const getErrorMessage = (field, errorKey) => {
 const formErrors = computed(() => ({
   url: getErrorMessage('url', 'URL'),
   assistantId: getErrorMessage('assistantId', 'ASSISTANT'),
+  pdfFile: getErrorMessage('pdfFile', 'PDF_FILE'),
 }));
 
 const handleCancel = () => emit('cancel');
 
-const prepareDocumentDetails = () => ({
-  external_link: state.url,
-  assistant_id: state.assistantId,
-});
+const handleFileChange = event => {
+  const file = event.target.files[0];
+  if (file) {
+    if (file.type !== 'application/pdf') {
+      useAlert(t('CAPTAIN.DOCUMENTS.FORM.PDF_FILE.INVALID_TYPE'));
+      event.target.value = '';
+      return;
+    }
+    if (file.size > MAX_FILE_SIZE) {
+      // 10MB
+      useAlert(t('CAPTAIN.DOCUMENTS.FORM.PDF_FILE.TOO_LARGE'));
+      event.target.value = '';
+      return;
+    }
+    state.pdfFile = file;
+    state.name = file.name.replace(/\.pdf$/i, '');
+  }
+};
+
+const openFileDialog = () => {
+  // Use nextTick to ensure the ref is available
+  nextTick(() => {
+    if (fileInputRef.value) {
+      fileInputRef.value.click();
+    }
+  });
+};
+
+const prepareDocumentDetails = () => {
+  const formData = new FormData();
+  formData.append('document[assistant_id]', state.assistantId);
+
+  if (state.documentType === 'url') {
+    formData.append('document[external_link]', state.url);
+    formData.append('document[name]', state.name || state.url);
+  } else {
+    formData.append('document[pdf_file]', state.pdfFile);
+    formData.append(
+      'document[name]',
+      state.name || state.pdfFile.name.replace('.pdf', '')
+    );
+    // No need to send external_link for PDF - it's auto-generated in the backend
+  }
+
+  return formData;
+};
 
 const handleSubmit = async () => {
   const isFormValid = await v$.value.$validate();
@@ -71,13 +135,89 @@ const handleSubmit = async () => {
 
 <template>
   <form class="flex flex-col gap-4" @submit.prevent="handleSubmit">
+    <div class="flex flex-col gap-1">
+      <label
+        for="documentType"
+        class="mb-0.5 text-sm font-medium text-n-slate-12"
+      >
+        {{ t('CAPTAIN.DOCUMENTS.FORM.TYPE.LABEL') }}
+      </label>
+      <ComboBox
+        id="documentType"
+        v-model="state.documentType"
+        :options="documentTypeOptions"
+        class="[&>div>button]:bg-n-alpha-black2"
+      />
+    </div>
+
     <Input
+      v-if="state.documentType === 'url'"
       v-model="state.url"
       :label="t('CAPTAIN.DOCUMENTS.FORM.URL.LABEL')"
       :placeholder="t('CAPTAIN.DOCUMENTS.FORM.URL.PLACEHOLDER')"
       :message="formErrors.url"
       :message-type="formErrors.url ? 'error' : 'info'"
     />
+
+    <div v-if="state.documentType === 'pdf'" class="flex flex-col gap-2">
+      <label class="text-sm font-medium text-n-slate-12">
+        {{ t('CAPTAIN.DOCUMENTS.FORM.PDF_FILE.LABEL') }}
+      </label>
+      <div class="relative">
+        <input
+          ref="fileInputRef"
+          type="file"
+          accept=".pdf"
+          class="hidden"
+          @change="handleFileChange"
+        />
+        <Button
+          type="button"
+          :color="hasPdfFileError ? 'ruby' : 'slate'"
+          :variant="hasPdfFileError ? 'outline' : 'solid'"
+          class="!w-full !h-auto !justify-between !py-4"
+          @click="openFileDialog"
+        >
+          <template #default>
+            <div class="flex gap-2 items-center">
+              <div
+                class="flex justify-center items-center w-10 h-10 rounded-lg bg-n-slate-3"
+              >
+                <i class="text-xl i-ph-file-pdf text-n-slate-11" />
+              </div>
+              <div class="flex flex-col flex-1 gap-1 items-start">
+                <p class="m-0 text-sm font-medium text-n-slate-12">
+                  {{
+                    state.pdfFile
+                      ? state.pdfFile.name
+                      : t('CAPTAIN.DOCUMENTS.FORM.PDF_FILE.CHOOSE_FILE')
+                  }}
+                </p>
+                <p class="m-0 text-xs text-n-slate-11">
+                  {{
+                    state.pdfFile
+                      ? `${(state.pdfFile.size / 1024 / 1024).toFixed(2)} MB`
+                      : t('CAPTAIN.DOCUMENTS.FORM.PDF_FILE.HELP_TEXT')
+                  }}
+                </p>
+              </div>
+            </div>
+
+            <i class="i-lucide-upload text-n-slate-11" />
+          </template>
+        </Button>
+      </div>
+      <p v-if="formErrors.pdfFile" class="text-xs text-n-ruby-9">
+        {{ formErrors.pdfFile }}
+      </p>
+    </div>
+
+    <Input
+      v-model="state.name"
+      :label="t('CAPTAIN.DOCUMENTS.FORM.NAME.LABEL')"
+      :placeholder="t('CAPTAIN.DOCUMENTS.FORM.NAME.PLACEHOLDER')"
+    />
+
     <div class="flex flex-col gap-1">
       <label for="assistant" class="mb-0.5 text-sm font-medium text-n-slate-12">
         {{ t('CAPTAIN.DOCUMENTS.FORM.ASSISTANT.LABEL') }}
@@ -88,12 +228,12 @@ const handleSubmit = async () => {
         :options="assistantList"
         :has-error="!!formErrors.assistantId"
         :placeholder="t('CAPTAIN.DOCUMENTS.FORM.ASSISTANT.PLACEHOLDER')"
-        class="[&>div>button]:bg-n-alpha-black2 [&>div>button:not(.focused)]:dark:outline-n-weak [&>div>button:not(.focused)]:hover:!outline-n-slate-6"
+        class="[&>div>button]:bg-n-alpha-black2"
         :message="formErrors.assistantId"
       />
     </div>
 
-    <div class="flex items-center justify-between w-full gap-3">
+    <div class="flex gap-3 justify-between items-center w-full">
       <Button
         type="button"
         variant="faded"
diff --git a/app/javascript/dashboard/components-next/combobox/ComboBox.vue b/app/javascript/dashboard/components-next/combobox/ComboBox.vue
index 026a63a70..76296ddde 100644
--- a/app/javascript/dashboard/components-next/combobox/ComboBox.vue
+++ b/app/javascript/dashboard/components-next/combobox/ComboBox.vue
@@ -96,8 +96,12 @@ watch(
         :label="selectedLabel"
         trailing-icon
         :disabled="disabled"
-        class="justify-between w-full !px-3 !py-2.5 text-n-slate-12 font-normal group-hover/combobox:border-n-slate-6 [&:not(.focused)]:hover:enabled:outline-n-slate-6 [&:not(.focused)]:dark:hover:enabled:outline-n-slate-6 [&:not(.focused)]:dark:outline-n-weak focus:outline-n-brand"
-        :class="{ focused: open }"
+        class="justify-between w-full !px-3 !py-2.5 text-n-slate-12 font-normal group-hover/combobox:border-n-slate-6 focus:outline-n-brand"
+        :class="{
+          focused: open,
+          '[&:not(.focused)]:dark:outline-n-weak [&:not(.focused)]:hover:enabled:outline-n-slate-6 [&:not(.focused)]:dark:hover:enabled:outline-n-slate-6':
+            !hasError,
+        }"
         :icon="open ? 'i-lucide-chevron-up' : 'i-lucide-chevron-down'"
         @click="toggleDropdown"
       />
diff --git a/app/javascript/dashboard/i18n/locale/en/helpCenter.json b/app/javascript/dashboard/i18n/locale/en/helpCenter.json
index fd2b1a788..16f108c0e 100644
--- a/app/javascript/dashboard/i18n/locale/en/helpCenter.json
+++ b/app/javascript/dashboard/i18n/locale/en/helpCenter.json
@@ -807,6 +807,58 @@
           "ERROR_MESSAGE": "Unable to update portal"
         }
       }
+    },
+    "PDF_UPLOAD": {
+      "TITLE": "Upload PDF Document",
+      "DESCRIPTION": "Upload a PDF document to automatically generate FAQs using AI",
+      "DRAG_DROP_TEXT": "Drag and drop your PDF file here, or click to select",
+      "SELECT_FILE": "Select PDF File",
+      "ADDITIONAL_CONTEXT_LABEL": "Additional Context (Optional)",
+      "ADDITIONAL_CONTEXT_PLACEHOLDER": "Provide any additional context or instructions for FAQ generation...",
+      "UPLOADING": "Uploading...",
+      "UPLOAD": "Upload & Process",
+      "CANCEL": "Cancel",
+      "ERROR_INVALID_TYPE": "Please select a valid PDF file",
+      "ERROR_FILE_TOO_LARGE": "File size must be less than 512MB",
+      "ERROR_UPLOAD_FAILED": "Failed to upload PDF. Please try again."
+    },
+    "PDF_DOCUMENTS": {
+      "TITLE": "PDF Documents",
+      "DESCRIPTION": "Manage uploaded PDF documents and generate FAQs from them",
+      "UPLOAD_PDF": "Upload PDF",
+      "UPLOAD_FIRST_PDF": "Upload your first PDF",
+      "UPLOADED_BY": "Uploaded by",
+      "GENERATE_FAQS": "Generate FAQs",
+      "GENERATING": "Generating...",
+      "CONFIRM_DELETE": "Are you sure you want to delete {filename}?",
+      "EMPTY_STATE": {
+        "TITLE": "No PDF documents yet",
+        "DESCRIPTION": "Upload PDF documents to automatically generate FAQs using AI"
+      },
+      "STATUS": {
+        "UPLOADED": "Ready",
+        "PROCESSING": "Processing",
+        "PROCESSED": "Completed", 
+        "FAILED": "Failed"
+      }
+    },
+    "CONTENT_GENERATION": {
+      "TITLE": "Content Generation",
+      "DESCRIPTION": "Upload PDF documents to automatically generate FAQ content using AI",
+      "UPLOAD_TITLE": "Upload PDF Document",
+      "DRAG_DROP": "Drag and drop your PDF file here, or click to select",
+      "SELECT_FILE": "Select PDF File",
+      "UPLOADING": "Processing document...",
+      "UPLOAD_SUCCESS": "Document processed successfully!",
+      "UPLOAD_ERROR": "Failed to upload document. Please try again.",
+      "INVALID_FILE_TYPE": "Please select a valid PDF file",
+      "FILE_TOO_LARGE": "File size must be less than 512MB",
+      "GENERATED_CONTENT": "Generated FAQ Content",
+      "PUBLISH_SELECTED": "Publish Selected",
+      "PUBLISHING": "Publishing...",
+      "FROM_DOCUMENT": "From document",
+      "NO_CONTENT": "No generated content available. Upload a PDF document to get started.",
+      "LOADING": "Loading generated content..."
     }
   }
 }
diff --git a/app/javascript/dashboard/i18n/locale/en/integrations.json b/app/javascript/dashboard/i18n/locale/en/integrations.json
index d1c5b0903..c4399b0e9 100644
--- a/app/javascript/dashboard/i18n/locale/en/integrations.json
+++ b/app/javascript/dashboard/i18n/locale/en/integrations.json
@@ -701,11 +701,28 @@
         "ERROR_MESSAGE": "There was an error creating the document, please try again."
       },
       "FORM": {
+        "TYPE": {
+          "LABEL": "Document Type",
+          "URL": "URL",
+          "PDF": "PDF File"
+        },
         "URL": {
           "LABEL": "URL",
           "PLACEHOLDER": "Enter the URL of the document",
           "ERROR": "Please provide a valid URL for the document"
         },
+        "PDF_FILE": {
+          "LABEL": "PDF File",
+          "CHOOSE_FILE": "Choose PDF file",
+          "ERROR": "Please select a PDF file",
+          "HELP_TEXT": "Maximum file size: 10MB",
+          "INVALID_TYPE": "Please select a valid PDF file",
+          "TOO_LARGE": "File size exceeds 10MB limit"
+        },
+        "NAME": {
+          "LABEL": "Document Name (Optional)",
+          "PLACEHOLDER": "Enter a name for the document"
+        },
         "ASSISTANT": {
           "LABEL": "Assistant",
           "PLACEHOLDER": "Select the assistant",
diff --git a/app/javascript/shared/helpers/documentHelper.js b/app/javascript/shared/helpers/documentHelper.js
new file mode 100644
index 000000000..f050ad54d
--- /dev/null
+++ b/app/javascript/shared/helpers/documentHelper.js
@@ -0,0 +1,38 @@
+/**
+ * Document Helper - utilities for document display and formatting
+ */
+
+// Constants for document processing
+const PDF_PREFIX = 'PDF:';
+const TIMESTAMP_PATTERN = /_\d{14}(?=\.pdf$)/; // Format: _YYYYMMDDHHMMSS before .pdf extension
+
+/**
+ * Checks if a document is a PDF based on its external link
+ * @param {string} externalLink - The external link string
+ * @returns {boolean} True if the document is a PDF
+ */
+export const isPdfDocument = externalLink => {
+  if (!externalLink) return false;
+  return externalLink.startsWith(PDF_PREFIX);
+};
+
+/**
+ * Formats the display link for documents
+ * For PDF documents: removes 'PDF:' prefix and timestamp suffix
+ * For regular URLs: returns as-is
+ *
+ * @param {string} externalLink - The external link string
+ * @returns {string} Formatted display link
+ */
+export const formatDocumentLink = externalLink => {
+  if (!externalLink) return '';
+
+  if (isPdfDocument(externalLink)) {
+    // Remove 'PDF:' prefix
+    const fullName = externalLink.substring(PDF_PREFIX.length);
+    // Remove timestamp suffix if present
+    return fullName.replace(TIMESTAMP_PATTERN, '');
+  }
+
+  return externalLink;
+};
diff --git a/app/javascript/shared/helpers/specs/documentHelper.spec.js b/app/javascript/shared/helpers/specs/documentHelper.spec.js
new file mode 100644
index 000000000..64baf7069
--- /dev/null
+++ b/app/javascript/shared/helpers/specs/documentHelper.spec.js
@@ -0,0 +1,111 @@
+import {
+  isPdfDocument,
+  formatDocumentLink,
+} from 'shared/helpers/documentHelper';
+
+describe('documentHelper', () => {
+  describe('#isPdfDocument', () => {
+    it('returns true for PDF documents', () => {
+      expect(isPdfDocument('PDF:document.pdf')).toBe(true);
+      expect(isPdfDocument('PDF:my-file_20241227123045.pdf')).toBe(true);
+      expect(isPdfDocument('PDF:report with spaces_20241227123045.pdf')).toBe(
+        true
+      );
+    });
+
+    it('returns false for regular URLs', () => {
+      expect(isPdfDocument('https://example.com')).toBe(false);
+      expect(isPdfDocument('http://docs.example.com/file.pdf')).toBe(false);
+      expect(isPdfDocument('ftp://files.example.com/document.pdf')).toBe(false);
+    });
+
+    it('returns false for empty or null values', () => {
+      expect(isPdfDocument('')).toBe(false);
+      expect(isPdfDocument(null)).toBe(false);
+      expect(isPdfDocument(undefined)).toBe(false);
+    });
+
+    it('returns false for strings that contain PDF but do not start with PDF:', () => {
+      expect(isPdfDocument('document PDF:file.pdf')).toBe(false);
+      expect(isPdfDocument('My PDF:file.pdf')).toBe(false);
+    });
+  });
+
+  describe('#formatDocumentLink', () => {
+    describe('PDF documents', () => {
+      it('removes PDF: prefix from PDF documents', () => {
+        expect(formatDocumentLink('PDF:document.pdf')).toBe('document.pdf');
+        expect(formatDocumentLink('PDF:my-file.pdf')).toBe('my-file.pdf');
+      });
+
+      it('removes timestamp suffix from PDF documents', () => {
+        expect(formatDocumentLink('PDF:document_20241227123045.pdf')).toBe(
+          'document.pdf'
+        );
+        expect(formatDocumentLink('PDF:report_20231215094530.pdf')).toBe(
+          'report.pdf'
+        );
+      });
+
+      it('handles PDF documents with spaces in filename', () => {
+        expect(formatDocumentLink('PDF:my document_20241227123045.pdf')).toBe(
+          'my document.pdf'
+        );
+        expect(
+          formatDocumentLink('PDF:Annual Report 2024_20241227123045.pdf')
+        ).toBe('Annual Report 2024.pdf');
+      });
+
+      it('handles PDF documents without timestamp suffix', () => {
+        expect(formatDocumentLink('PDF:document.pdf')).toBe('document.pdf');
+        expect(formatDocumentLink('PDF:simple-file.pdf')).toBe(
+          'simple-file.pdf'
+        );
+      });
+
+      it('handles PDF documents with partial timestamp patterns', () => {
+        expect(formatDocumentLink('PDF:document_202412.pdf')).toBe(
+          'document_202412.pdf'
+        );
+        expect(formatDocumentLink('PDF:file_123.pdf')).toBe('file_123.pdf');
+      });
+
+      it('handles edge cases with timestamp pattern', () => {
+        expect(
+          formatDocumentLink('PDF:doc_20241227123045_final_20241227123045.pdf')
+        ).toBe('doc_20241227123045_final.pdf');
+      });
+    });
+
+    describe('Regular URLs', () => {
+      it('returns regular URLs unchanged', () => {
+        expect(formatDocumentLink('https://example.com')).toBe(
+          'https://example.com'
+        );
+        expect(formatDocumentLink('http://docs.example.com/api')).toBe(
+          'http://docs.example.com/api'
+        );
+        expect(formatDocumentLink('https://github.com/user/repo')).toBe(
+          'https://github.com/user/repo'
+        );
+      });
+
+      it('handles URLs with query parameters', () => {
+        expect(formatDocumentLink('https://example.com?param=value')).toBe(
+          'https://example.com?param=value'
+        );
+        expect(
+          formatDocumentLink(
+            'https://api.example.com/docs?version=v1&format=json'
+          )
+        ).toBe('https://api.example.com/docs?version=v1&format=json');
+      });
+
+      it('handles URLs with fragments', () => {
+        expect(formatDocumentLink('https://example.com/docs#section1')).toBe(
+          'https://example.com/docs#section1'
+        );
+      });
+    });
+  });
+});