diff --git a/workspaces/intelligent-assistant/.changeset/bright-tigers-dance.md b/workspaces/intelligent-assistant/.changeset/bright-tigers-dance.md
new file mode 100644
index 00000000000..be494c67173
--- /dev/null
+++ b/workspaces/intelligent-assistant/.changeset/bright-tigers-dance.md
@@ -0,0 +1,5 @@
+---
+'@red-hat-developer-hub/backstage-plugin-intelligent-assistant': patch
+---
+
+Improve notebook UI: enhance AddDocumentModal, OverwriteConfirmModal, NotebookCard, and NotebookView components with better UX text, document count formatting, and fix translation type errors
diff --git a/workspaces/intelligent-assistant/e2e-tests/lightspeed.notebooks.test.ts b/workspaces/intelligent-assistant/e2e-tests/lightspeed.notebooks.test.ts
index b0efce6648c..c8abab62f0a 100644
--- a/workspaces/intelligent-assistant/e2e-tests/lightspeed.notebooks.test.ts
+++ b/workspaces/intelligent-assistant/e2e-tests/lightspeed.notebooks.test.ts
@@ -100,7 +100,7 @@ test.describe('Intelligent assistant notebooks', () => {
     await uploadModal.selectFilesViaBrowsePicker(
       notebookElevenFileStagingPaths(),
     );
-    await expect(uploadModal.dialog().getByRole('alert')).toContainText(
+    await expect(uploadModal.errorAlert()).toContainText(
       substituteNotebookTemplate(
         translations['notebook.upload.error.tooManyFiles'],
         { max: NOTEBOOK_SESSION_MAX_DOCUMENTS },
@@ -115,7 +115,7 @@ test.describe('Intelligent assistant notebooks', () => {
     await uploadModal.selectFilesViaBrowsePicker([
       notebookUnsupportedTypeFixturePath(),
     ]);
-    await expect(uploadModal.dialog().getByRole('alert')).toContainText(
+    await expect(uploadModal.errorAlert()).toContainText(
       translations['notebook.upload.error.unsupportedType'],
     );
     await uploadModal.clickCancel();
@@ -136,19 +136,27 @@ test.describe('Intelligent assistant notebooks', () => {
     await notebooks.clickOpenUploadDocumentModal();
     uploadModal = notebooks.uploadDocumentModal();
     await uploadModal.selectFilesViaBrowsePicker([absolutePath]);
+    await uploadModal.clickAddFilesForStagedCount(1);
 
     const overwriteModal = notebooks.notebookOverwriteConfirmModal();
     await overwriteModal.expectDialogVisible();
     await overwriteModal.expectListedOverwriteFile(fileName);
-    await overwriteModal.clickCancel();
-    await sharedPage.waitForTimeout(200);
+    await overwriteModal.clickBack();
     await uploadModal.clickCancel();
 
     await notebooks.deleteFirstListedDocumentFromSidebarOverflowMenu();
     await notebooks.expectNotebookEditorUploadResourceButtonVisible();
   });
 
-  test('grid: close editor, rename, delete', async () => {
+  test('grid: close editor, rename, delete', async ({}, testInfo) => {
+    const { absolutePath } = localeNotebookUpload1Path(testInfo.project.name);
+
+    await notebooks.clickOpenUploadDocumentModal();
+    const uploadModal = notebooks.uploadDocumentModal();
+    await uploadModal.selectFilesViaBrowsePicker([absolutePath]);
+    await uploadModal.clickAddFilesForStagedCount(1);
+    await sharedPage.waitForTimeout(1000);
+
     const untitledBefore = await notebooks.untitledNotebookCards().count();
 
     await notebooks.clickCloseNotebookEditor();
@@ -157,7 +165,7 @@ test.describe('Intelligent assistant notebooks', () => {
     await expect(notebooks.newestUntitledNotebookCard()).toBeVisible();
 
     await notebooks.expectNotebookListShowsDocumentCountSummaryAndUpdatedToday(
-      0,
+      1,
     );
 
     await notebooks
@@ -188,8 +196,19 @@ test.describe('Intelligent assistant notebooks', () => {
     await notebooks.expectUntitledNotebookCardCount(untitledBefore);
   });
 
-  test('grid: click card title triggers inline rename', async () => {
+  test('grid: click card title triggers inline rename', async ({}, testInfo) => {
+    const { absolutePath, fileName } = localeNotebookUpload1Path(
+      testInfo.project.name,
+    );
+
     await notebooks.clickPrimaryNotebookCreate();
+
+    await notebooks.clickOpenUploadDocumentModal();
+    const uploadModal = notebooks.uploadDocumentModal();
+    await uploadModal.selectFilesViaBrowsePicker([absolutePath]);
+    await uploadModal.clickAddFilesForStagedCount(1);
+    await notebooks.expectDocumentFileListedInSidebar(fileName);
+
     await notebooks.clickCloseNotebookEditor();
 
     const card = notebooks.newestUntitledNotebookCard();
@@ -215,8 +234,19 @@ test.describe('Intelligent assistant notebooks', () => {
     await notebooks.expectNotebookCardAbsent(newName);
   });
 
-  test('grid: Escape cancels inline rename', async () => {
+  test('grid: Escape cancels inline rename', async ({}, testInfo) => {
+    const { absolutePath, fileName } = localeNotebookUpload1Path(
+      testInfo.project.name,
+    );
+
     await notebooks.clickPrimaryNotebookCreate();
+
+    await notebooks.clickOpenUploadDocumentModal();
+    const uploadModal = notebooks.uploadDocumentModal();
+    await uploadModal.selectFilesViaBrowsePicker([absolutePath]);
+    await uploadModal.clickAddFilesForStagedCount(1);
+    await notebooks.expectDocumentFileListedInSidebar(fileName);
+
     await notebooks.clickCloseNotebookEditor();
 
     const card = notebooks.newestUntitledNotebookCard();
@@ -245,8 +275,19 @@ test.describe('Intelligent assistant notebooks', () => {
     await confirmDelete.confirmDeletion();
   });
 
-  test('grid: blur saves inline rename', async () => {
+  test('grid: blur saves inline rename', async ({}, testInfo) => {
+    const { absolutePath, fileName } = localeNotebookUpload1Path(
+      testInfo.project.name,
+    );
+
     await notebooks.clickPrimaryNotebookCreate();
+
+    await notebooks.clickOpenUploadDocumentModal();
+    const uploadModal = notebooks.uploadDocumentModal();
+    await uploadModal.selectFilesViaBrowsePicker([absolutePath]);
+    await uploadModal.clickAddFilesForStagedCount(1);
+    await notebooks.expectDocumentFileListedInSidebar(fileName);
+
     await notebooks.clickCloseNotebookEditor();
 
     const card = notebooks.newestUntitledNotebookCard();
@@ -273,8 +314,19 @@ test.describe('Intelligent assistant notebooks', () => {
     await notebooks.expectNotebookCardAbsent(newName);
   });
 
-  test('grid: empty or unchanged name cancels rename', async () => {
+  test('grid: empty or unchanged name cancels rename', async ({}, testInfo) => {
+    const { absolutePath, fileName } = localeNotebookUpload1Path(
+      testInfo.project.name,
+    );
+
     await notebooks.clickPrimaryNotebookCreate();
+
+    await notebooks.clickOpenUploadDocumentModal();
+    const uploadModal = notebooks.uploadDocumentModal();
+    await uploadModal.selectFilesViaBrowsePicker([absolutePath]);
+    await uploadModal.clickAddFilesForStagedCount(1);
+    await notebooks.expectDocumentFileListedInSidebar(fileName);
+
     await notebooks.clickCloseNotebookEditor();
 
     const card = notebooks.newestUntitledNotebookCard();
@@ -339,4 +391,47 @@ test.describe('Intelligent assistant notebooks', () => {
     await confirmDelete.confirmDeletion();
     await notebooks.expectNotebookCardAbsent(newName);
   });
+
+  test('auto-delete: empty untitled notebook is discarded on close', async () => {
+    await notebooks.gotoFullscreenNotebooksTab();
+    const cardsBefore = await notebooks.untitledNotebookCards().count();
+
+    await notebooks.clickCreateNotebookFromEmptyList();
+    await expect(sharedPage).toHaveURL(NOTEBOOK_EDITOR_URL_RE);
+
+    await notebooks.clickCloseNotebookEditor();
+
+    await notebooks.expectUntitledNotebookCardCount(cardsBefore);
+  });
+
+  test('auto-delete: notebook with uploaded file persists on close', async ({}, testInfo) => {
+    const { absolutePath, fileName } = localeNotebookUpload1Path(
+      testInfo.project.name,
+    );
+    const cardsBefore = await notebooks.untitledNotebookCards().count();
+
+    await notebooks.clickCreateNotebookFromEmptyList();
+    await expect(sharedPage).toHaveURL(NOTEBOOK_EDITOR_URL_RE);
+
+    await notebooks.clickOpenUploadDocumentModal();
+    const uploadModal = notebooks.uploadDocumentModal();
+    await uploadModal.selectFilesViaBrowsePicker([absolutePath]);
+    await uploadModal.clickAddFilesForStagedCount(1);
+    await notebooks.expectDocumentFileListedInSidebar(fileName);
+    await sharedPage.waitForTimeout(2000);
+
+    await notebooks.clickCloseNotebookEditor();
+
+    await notebooks.expectUntitledNotebookCardCount(cardsBefore + 1);
+
+    await notebooks
+      .notebookCardOverflowMenuButton(notebooks.newestUntitledNotebookCard())
+      .click();
+    await notebooks.deleteNotebookOverflowMenuItem().click();
+    const confirmDelete = notebooks.notebookDeleteConfirmationDialog(
+      NOTEBOOK_UNTITLED_GRID_NAME,
+    );
+    await confirmDelete.confirmDeletion();
+    await notebooks.expectUntitledNotebookCardCount(cardsBefore);
+  });
 });
diff --git a/workspaces/intelligent-assistant/e2e-tests/pages/NotebookAddDocumentModalPage.ts b/workspaces/intelligent-assistant/e2e-tests/pages/NotebookAddDocumentModalPage.ts
index 69f75276fba..5f6e8f8ede9 100644
--- a/workspaces/intelligent-assistant/e2e-tests/pages/NotebookAddDocumentModalPage.ts
+++ b/workspaces/intelligent-assistant/e2e-tests/pages/NotebookAddDocumentModalPage.ts
@@ -44,32 +44,24 @@ export class NotebookAddDocumentModalPage {
     );
   }
 
-  separatorBetweenDragZoneAndBrowse(): Locator {
-    return this.dialog().getByText(this.t['notebook.upload.modal.separator'], {
-      exact: true,
-    });
-  }
-
-  browseFilesButton(): Locator {
-    return this.dialog().getByRole('button', {
-      name: this.t['notebook.upload.modal.browseButton'],
-      exact: true,
-    });
+  supportedFormatsLabel(): Locator {
+    return this.dialog().getByText(
+      this.t['notebook.upload.modal.supportedFormats'],
+    );
   }
 
-  acceptedFileTypesParagraph(): Locator {
-    return this.dialog().getByText(this.t['notebook.upload.modal.infoText'], {
-      exact: true,
-    });
+  maxFileSizeText(): Locator {
+    return this.dialog().getByText(this.t['notebook.upload.modal.maxFileSize']);
   }
 
   addFilesButton(stagedCount: number): Locator {
-    const label = substituteNotebookTemplate(
-      this.t['notebook.upload.modal.addButton'],
-      {
-        count: stagedCount,
-      },
-    );
+    const label =
+      stagedCount > 0
+        ? substituteNotebookTemplate(
+            this.t['notebook.upload.modal.addButton'],
+            { count: stagedCount },
+          )
+        : this.t['notebook.upload.modal.addButtonEmpty'];
     return this.dialog().getByRole('button', { name: label });
   }
 
@@ -82,9 +74,8 @@ export class NotebookAddDocumentModalPage {
   /** Drop-zone copy, “or”, browse button, accepted file types paragraph. */
   async expectUploadAreaFullyDescribed(): Promise<void> {
     await expect(this.dragAndDropInstructions()).toBeVisible();
-    await expect(this.separatorBetweenDragZoneAndBrowse()).toBeVisible();
-    await expect(this.browseFilesButton()).toBeVisible();
-    await expect(this.acceptedFileTypesParagraph()).toBeVisible();
+    await expect(this.supportedFormatsLabel()).toBeVisible();
+    await expect(this.maxFileSizeText()).toBeVisible();
   }
 
   async expectModalTitleBarMatchesAriaSnapshot(): Promise<void> {
@@ -102,7 +93,7 @@ export class NotebookAddDocumentModalPage {
   async selectFilesViaBrowsePicker(filePaths: string[]): Promise<void> {
     const [fileChooser] = await Promise.all([
       this.page.waitForEvent('filechooser'),
-      this.browseFilesButton().click(),
+      this.dragAndDropInstructions().click(),
     ]);
     await fileChooser.setFiles(filePaths);
   }
@@ -132,7 +123,7 @@ export class NotebookAddDocumentModalPage {
   }
 
   errorAlert(): Locator {
-    return this.dialog().getByRole('alert');
+    return this.dialog().locator('[data-ouia-component-type="PF6/Alert"]');
   }
 
   async expectValidationAlertsInclude(text: string): Promise<void> {
diff --git a/workspaces/intelligent-assistant/e2e-tests/pages/NotebookOverwriteConfirmModalPage.ts b/workspaces/intelligent-assistant/e2e-tests/pages/NotebookOverwriteConfirmModalPage.ts
index 7ac948257e2..4a359548a75 100644
--- a/workspaces/intelligent-assistant/e2e-tests/pages/NotebookOverwriteConfirmModalPage.ts
+++ b/workspaces/intelligent-assistant/e2e-tests/pages/NotebookOverwriteConfirmModalPage.ts
@@ -17,9 +17,10 @@
 import { expect, type Locator, type Page } from '@playwright/test';
 
 import type { LightspeedMessages } from '../utils/translations';
+import { substituteNotebookTemplate } from '../utils/notebookTranslation';
 
 /**
- * “Overwrite Files?” confirmation when staging a file whose name already exists in the notebook (`OverwriteConfirmModal.tsx`).
+ * "File already exists" confirmation when uploading a file whose name already exists in the notebook (`OverwriteConfirmModal.tsx`).
  */
 export class NotebookOverwriteConfirmModalPage {
   constructor(
@@ -28,7 +29,6 @@ export class NotebookOverwriteConfirmModalPage {
   ) {}
 
   dialog(): Locator {
-    /** MUI dialogs may not use the plain title as the whole accessible name across engines. */
     return this.page.getByRole('dialog').filter({
       has: this.page.getByRole('heading', {
         name: this.t['notebook.overwrite.modal.title'],
@@ -39,16 +39,14 @@ export class NotebookOverwriteConfirmModalPage {
 
   async expectDialogVisible(timeout = 15_000): Promise<void> {
     await expect(this.dialog()).toBeVisible({ timeout });
-    await expect(
-      this.dialog().getByText(this.t['notebook.overwrite.modal.description'], {
-        exact: true,
-      }),
-    ).toBeVisible();
   }
 
-  async clickCancel(): Promise<void> {
+  async clickBack(): Promise<void> {
     await this.dialog()
-      .getByRole('button', { name: this.t['common.cancel'], exact: true })
+      .getByRole('button', {
+        name: this.t['notebook.overwrite.modal.back'],
+        exact: true,
+      })
       .click();
   }
 
@@ -58,12 +56,19 @@ export class NotebookOverwriteConfirmModalPage {
     ).toBeVisible();
   }
 
-  async clickOverwrite(): Promise<void> {
+  uploadButtonPattern(): RegExp {
+    const escaped = substituteNotebookTemplate(
+      this.t['notebook.overwrite.modal.action'],
+      { count: '\\d+' },
+    )
+      .replace('(', '\\(')
+      .replace(')', '\\)');
+    return new RegExp(escaped);
+  }
+
+  async clickUpload(): Promise<void> {
     await this.dialog()
-      .getByRole('button', {
-        name: this.t['notebook.overwrite.modal.action'],
-        exact: true,
-      })
+      .getByRole('button', { name: this.uploadButtonPattern() })
       .click();
   }
 }
diff --git a/workspaces/intelligent-assistant/e2e-tests/pages/NotebookSurfacePage.ts b/workspaces/intelligent-assistant/e2e-tests/pages/NotebookSurfacePage.ts
index 5a1c7dd7b18..e413028016d 100644
--- a/workspaces/intelligent-assistant/e2e-tests/pages/NotebookSurfacePage.ts
+++ b/workspaces/intelligent-assistant/e2e-tests/pages/NotebookSurfacePage.ts
@@ -17,6 +17,7 @@
 import { expect, type Locator, type Page } from '@playwright/test';
 
 import type { LightspeedMessages } from '../utils/translations';
+import { substituteNotebookTemplate } from '../utils/notebookTranslation';
 import { openLightspeed } from '../utils/testHelper';
 
 import { NotebookAddDocumentModalPage } from './NotebookAddDocumentModalPage';
@@ -341,12 +342,12 @@ export class NotebookSurfacePage {
     });
   }
 
-  /**
-   * Shown on each card as count + plural label (same pattern as NotebookCard.tsx:
-   * `{ document_count } { t('notebooks.documents') }`, not `notebook.view.documents.count`).
-   */
   formatNotebookCardDocumentsSummary(documentCount: number): string {
-    return `${documentCount} ${this.t['notebooks.documents']}`;
+    if (documentCount === 0) return this.t['notebooks.documents.none'];
+    if (documentCount === 1) return this.t['notebooks.documents.one'];
+    return substituteNotebookTemplate(this.t['notebooks.documents.other'], {
+      count: documentCount,
+    });
   }
 
   async expectUntitledNotebookCardCount(expected: number): Promise<void> {
diff --git a/workspaces/intelligent-assistant/plugins/intelligent-assistant/report-alpha.api.md b/workspaces/intelligent-assistant/plugins/intelligent-assistant/report-alpha.api.md
index f05c7c0c4d8..33dfb93f538 100644
--- a/workspaces/intelligent-assistant/plugins/intelligent-assistant/report-alpha.api.md
+++ b/workspaces/intelligent-assistant/plugins/intelligent-assistant/report-alpha.api.md
@@ -51,6 +51,9 @@ export const intelligentAssistantTranslationRef: TranslationRef<
     readonly 'notebooks.empty.description': string;
     readonly 'notebooks.empty.action': string;
     readonly 'notebooks.documents': string;
+    readonly 'notebooks.documents.none': string;
+    readonly 'notebooks.documents.one': string;
+    readonly 'notebooks.documents.other': string;
     readonly 'notebooks.actions.rename': string;
     readonly 'notebooks.actions.delete': string;
     readonly 'notebooks.rename.inline.tooltip': string;
@@ -86,15 +89,25 @@ export const intelligentAssistantTranslationRef: TranslationRef<
     readonly 'notebook.upload.modal.browseButton': string;
     readonly 'notebook.upload.modal.separator': string;
     readonly 'notebook.upload.modal.infoText': string;
+    readonly 'notebook.upload.modal.supportedFormats': string;
+    readonly 'notebook.upload.modal.maxFileSize': string;
     readonly 'notebook.upload.modal.selectedFiles': string;
     readonly 'notebook.upload.modal.addButton': string;
+    readonly 'notebook.upload.modal.addButtonEmpty': string;
     readonly 'notebook.upload.modal.removeFile': string;
     readonly 'notebook.upload.error.unsupportedType': string;
     readonly 'notebook.upload.error.fileTooLarge': string;
     readonly 'notebook.upload.error.tooManyFiles': string;
     readonly 'notebook.overwrite.modal.title': string;
+    readonly 'notebook.overwrite.modal.title.one': string;
+    readonly 'notebook.overwrite.modal.title.other': string;
     readonly 'notebook.overwrite.modal.description': string;
+    readonly 'notebook.overwrite.modal.description.one': string;
+    readonly 'notebook.overwrite.modal.description.other': string;
+    readonly 'notebook.overwrite.modal.replace': string;
+    readonly 'notebook.overwrite.modal.ignore': string;
     readonly 'notebook.overwrite.modal.action': string;
+    readonly 'notebook.overwrite.modal.back': string;
     readonly 'notebook.document.delete': string;
     readonly 'notebook.document.delete.title': string;
     readonly 'notebook.document.delete.description': string;
diff --git a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/LightSpeedChat.tsx b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/LightSpeedChat.tsx
index c275ca126de..5aa4554583d 100644
--- a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/LightSpeedChat.tsx
+++ b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/LightSpeedChat.tsx
@@ -292,7 +292,7 @@ const useStyles = makeStyles(theme => ({
     },
   },
   notebookCardHeader: {
-    padding: theme.spacing(2),
+    padding: theme.spacing(3),
     paddingBottom: 0,
     alignItems: 'center',
   },
@@ -301,16 +301,14 @@ const useStyles = makeStyles(theme => ({
     marginTop: theme.spacing(1),
   },
   notebookCardBody: {
-    padding: theme.spacing(2),
-    paddingTop: theme.spacing(1.5),
+    padding: theme.spacing(3),
+    paddingTop: theme.spacing(2),
   },
   notebookDocuments: {
     paddingTop: theme.spacing(1),
-    paddingLeft: theme.spacing(2),
   },
   notebookUpdated: {
-    paddingBottom: theme.spacing(5),
-    paddingLeft: theme.spacing(2),
+    paddingBottom: theme.spacing(3),
     paddingTop: theme.spacing(2),
   },
   notebookTitle: {
diff --git a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/__tests__/AddDocumentModal.test.tsx b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/__tests__/AddDocumentModal.test.tsx
index 2930e443c36..0725a64f485 100644
--- a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/__tests__/AddDocumentModal.test.tsx
+++ b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/__tests__/AddDocumentModal.test.tsx
@@ -50,8 +50,10 @@ describe('AddDocumentModal', () => {
   it('should render the modal when open', () => {
     render(<AddDocumentModal {...defaultProps} />);
 
-    expect(screen.getByText('Add a resource to Notebook')).toBeInTheDocument();
-    expect(screen.getByText('Drag and drop files here')).toBeInTheDocument();
+    expect(screen.getByText('Add resources')).toBeInTheDocument();
+    expect(
+      screen.getByText('Drag and drop files here, or click to browse'),
+    ).toBeInTheDocument();
   });
 
   it('should not render when isOpen is false', () => {
@@ -64,13 +66,13 @@ describe('AddDocumentModal', () => {
     render(<AddDocumentModal {...defaultProps} />);
 
     expect(screen.getByRole('button', { name: 'Cancel' })).toBeInTheDocument();
-    expect(screen.getByRole('button', { name: 'Add (0)' })).toBeInTheDocument();
+    expect(screen.getByRole('button', { name: 'Add' })).toBeInTheDocument();
   });
 
   it('should have Add button disabled when no files selected', () => {
     render(<AddDocumentModal {...defaultProps} />);
 
-    const addButton = screen.getByRole('button', { name: 'Add (0)' });
+    const addButton = screen.getByRole('button', { name: 'Add' });
     expect(addButton).toBeDisabled();
   });
 
@@ -96,7 +98,7 @@ describe('AddDocumentModal', () => {
     render(<AddDocumentModal {...defaultProps} />);
 
     const dropzone = screen
-      .getByText('Drag and drop files here')
+      .getByText('Drag and drop files here, or click to browse')
       .closest('div');
     const file = new File(['content'], 'test-file.txt', { type: 'text/plain' });
 
@@ -116,7 +118,7 @@ describe('AddDocumentModal', () => {
     render(<AddDocumentModal {...defaultProps} />);
 
     const dropzone = screen
-      .getByText('Drag and drop files here')
+      .getByText('Drag and drop files here, or click to browse')
       .closest('div');
     const file = new File(['content'], 'test-file.txt', { type: 'text/plain' });
 
@@ -138,7 +140,7 @@ describe('AddDocumentModal', () => {
     render(<AddDocumentModal {...defaultProps} />);
 
     const dropzone = screen
-      .getByText('Drag and drop files here')
+      .getByText('Drag and drop files here, or click to browse')
       .closest('div');
     const file = new File(['content'], 'test-file.txt', { type: 'text/plain' });
 
@@ -160,7 +162,7 @@ describe('AddDocumentModal', () => {
     render(<AddDocumentModal {...defaultProps} />);
 
     const dropzone = screen
-      .getByText('Drag and drop files here')
+      .getByText('Drag and drop files here, or click to browse')
       .closest('div');
     const file = new File(['content'], 'test-file.txt', { type: 'text/plain' });
 
@@ -193,7 +195,7 @@ describe('AddDocumentModal', () => {
     render(<AddDocumentModal {...defaultProps} />);
 
     const dropzone = screen
-      .getByText('Drag and drop files here')
+      .getByText('Drag and drop files here, or click to browse')
       .closest('div');
     const file = new File(['content'], 'test-file.txt', { type: 'text/plain' });
 
@@ -215,7 +217,7 @@ describe('AddDocumentModal', () => {
 
     await waitFor(() => {
       expect(screen.queryByText('test-file.txt')).not.toBeInTheDocument();
-      expect(screen.getByRole('button', { name: 'Add (0)' })).toBeDisabled();
+      expect(screen.getByRole('button', { name: 'Add' })).toBeDisabled();
     });
   });
 
@@ -223,7 +225,7 @@ describe('AddDocumentModal', () => {
     const { rerender } = render(<AddDocumentModal {...defaultProps} />);
 
     const dropzone = screen
-      .getByText('Drag and drop files here')
+      .getByText('Drag and drop files here, or click to browse')
       .closest('div');
     const file = new File(['content'], 'test-file.txt', { type: 'text/plain' });
 
@@ -245,7 +247,23 @@ describe('AddDocumentModal', () => {
     expect(screen.queryByText('test-file.txt')).not.toBeInTheDocument();
   });
 
-  it('should call onDuplicatesFound for files that already exist', async () => {
+  it('should show disabled dropzone with tooltip when file limit is reached', () => {
+    const existingNames = Array.from({ length: 10 }, (_, i) => `file-${i}.txt`);
+    render(
+      <AddDocumentModal
+        {...defaultProps}
+        existingDocumentNames={existingNames}
+      />,
+    );
+
+    expect(
+      screen.getByText('Drag and drop files here, or click to browse'),
+    ).toBeInTheDocument();
+    expect(screen.getByText('Maximum file size is 25 MB.')).toBeInTheDocument();
+    expect(screen.getByText('Supported formats:')).toBeInTheDocument();
+  });
+
+  it('should call onDuplicatesFound when Add is clicked with duplicate files', async () => {
     render(
       <AddDocumentModal
         {...defaultProps}
@@ -254,7 +272,7 @@ describe('AddDocumentModal', () => {
     );
 
     const dropzone = screen
-      .getByText('Drag and drop files here')
+      .getByText('Drag and drop files here, or click to browse')
       .closest('div');
     const existingFile = new File(['content'], 'existing-file.txt', {
       type: 'text/plain',
@@ -271,11 +289,17 @@ describe('AddDocumentModal', () => {
     });
 
     await waitFor(() => {
-      expect(defaultProps.onDuplicatesFound).toHaveBeenCalledWith([
-        existingFile,
-      ]);
       expect(screen.getByText('new-file.txt')).toBeInTheDocument();
-      expect(screen.queryByText('existing-file.txt')).not.toBeInTheDocument();
+      expect(screen.getByText('existing-file.txt')).toBeInTheDocument();
+    });
+
+    fireEvent.click(screen.getByRole('button', { name: 'Add (2)' }));
+
+    await waitFor(() => {
+      expect(defaultProps.onDuplicatesFound).toHaveBeenCalledWith(
+        [existingFile],
+        [existingFile, newFile],
+      );
     });
   });
 });
diff --git a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/__tests__/NotebookCard.test.tsx b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/__tests__/NotebookCard.test.tsx
index a2823cfcb77..b65562b2001 100644
--- a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/__tests__/NotebookCard.test.tsx
+++ b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/__tests__/NotebookCard.test.tsx
@@ -75,9 +75,39 @@ describe('NotebookCard', () => {
     expect(screen.getByText('My Notebook')).toBeInTheDocument();
   });
 
-  it('should render the document count', () => {
+  it('should render the resource count for multiple resources', () => {
     render(<NotebookCard {...defaultProps} />);
-    expect(screen.getByText(/2/)).toBeInTheDocument();
+    expect(screen.getByText('2 resources')).toBeInTheDocument();
+  });
+
+  it('should render "No resources" when document_count is 0', () => {
+    render(
+      <NotebookCard
+        {...defaultProps}
+        notebook={{ ...mockNotebook, document_count: 0 }}
+      />,
+    );
+    expect(screen.getByText('No resources')).toBeInTheDocument();
+  });
+
+  it('should render "1 resource" when document_count is 1', () => {
+    render(
+      <NotebookCard
+        {...defaultProps}
+        notebook={{ ...mockNotebook, document_count: 1 }}
+      />,
+    );
+    expect(screen.getByText('1 resource')).toBeInTheDocument();
+  });
+
+  it('should render "No resources" when document_count is undefined', () => {
+    render(
+      <NotebookCard
+        {...defaultProps}
+        notebook={{ ...mockNotebook, document_count: undefined }}
+      />,
+    );
+    expect(screen.getByText('No resources')).toBeInTheDocument();
   });
 
   it('should call onClick with notebook when card is clicked', () => {
@@ -225,6 +255,6 @@ describe('NotebookCard', () => {
 
   it('should render document_count from the notebook session', () => {
     render(<NotebookCard {...defaultProps} />);
-    expect(screen.getByText(/2/)).toBeInTheDocument();
+    expect(screen.getByText('2 resources')).toBeInTheDocument();
   });
 });
diff --git a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/__tests__/OverwriteConfirmModal.test.tsx b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/__tests__/OverwriteConfirmModal.test.tsx
index 076cdd46065..b6c0c491b3d 100644
--- a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/__tests__/OverwriteConfirmModal.test.tsx
+++ b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/__tests__/OverwriteConfirmModal.test.tsx
@@ -23,131 +23,195 @@ jest.mock('../../hooks/useTranslation', () => ({
   useTranslation: jest.fn(() => mockUseTranslation()),
 }));
 
+const createFile = (name: string) =>
+  new File(['content'], name, { type: 'text/plain' });
+
 describe('OverwriteConfirmModal', () => {
   const onClose = jest.fn();
   const onConfirm = jest.fn();
-  const fileNames = ['report.pdf', 'data.yaml', 'notes.txt'];
+  const onBack = jest.fn();
+
+  const allFiles = [
+    createFile('report.pdf'),
+    createFile('data.yaml'),
+    createFile('notes.txt'),
+  ];
+  const duplicateFileNames = ['report.pdf', 'data.yaml'];
 
   beforeEach(() => {
     jest.clearAllMocks();
   });
 
-  it('should render the modal with file list when open', () => {
+  const renderModal = (props = {}) =>
     render(
       <OverwriteConfirmModal
         isOpen
         onClose={onClose}
         onConfirm={onConfirm}
-        fileNames={fileNames}
+        onBack={onBack}
+        allFiles={allFiles}
+        duplicateFileNames={duplicateFileNames}
+        {...props}
       />,
     );
 
+  it('should render the modal with all files when open', () => {
+    renderModal();
+
     expect(screen.getByText('report.pdf')).toBeInTheDocument();
     expect(screen.getByText('data.yaml')).toBeInTheDocument();
     expect(screen.getByText('notes.txt')).toBeInTheDocument();
   });
 
   it('should not render when isOpen is false', () => {
-    render(
-      <OverwriteConfirmModal
-        isOpen={false}
-        onClose={onClose}
-        onConfirm={onConfirm}
-        fileNames={fileNames}
-      />,
-    );
+    renderModal({ isOpen: false });
 
     expect(screen.queryByRole('dialog')).not.toBeInTheDocument();
   });
 
   it('should render a warning alert', () => {
-    render(
-      <OverwriteConfirmModal
-        isOpen
-        onClose={onClose}
-        onConfirm={onConfirm}
-        fileNames={fileNames}
-      />,
-    );
+    renderModal();
 
-    expect(screen.getByRole('alert')).toBeInTheDocument();
+    expect(screen.getByText(/2 files already exist/)).toBeInTheDocument();
+  });
+
+  it('should render radio options for replace and ignore', () => {
+    renderModal();
+
+    expect(screen.getByLabelText('Replace existing files')).toBeInTheDocument();
+    expect(
+      screen.getByLabelText('Ignore duplicated files'),
+    ).toBeInTheDocument();
   });
 
   it('should render FileTypeIcon badges for each file', () => {
-    render(
-      <OverwriteConfirmModal
-        isOpen
-        onClose={onClose}
-        onConfirm={onConfirm}
-        fileNames={fileNames}
-      />,
-    );
+    renderModal();
 
     expect(screen.getByText('pdf')).toBeInTheDocument();
     expect(screen.getByText('yaml')).toBeInTheDocument();
     expect(screen.getByText('txt')).toBeInTheDocument();
   });
 
-  it('should call onConfirm when overwrite button is clicked', () => {
-    render(
-      <OverwriteConfirmModal
-        isOpen
-        onClose={onClose}
-        onConfirm={onConfirm}
-        fileNames={fileNames}
-      />,
-    );
+  it('should call onConfirm with all files when replace is selected', () => {
+    renderModal();
 
-    const overwriteButton = screen.getByRole('button', {
-      name: 'Overwrite',
+    const uploadButton = screen.getByRole('button', {
+      name: /Upload \(3\)/,
     });
-    fireEvent.click(overwriteButton);
+    fireEvent.click(uploadButton);
 
-    expect(onConfirm).toHaveBeenCalledTimes(1);
+    expect(onConfirm).toHaveBeenCalledWith(allFiles);
   });
 
-  it('should call onClose when cancel button is clicked', () => {
-    render(
-      <OverwriteConfirmModal
-        isOpen
-        onClose={onClose}
-        onConfirm={onConfirm}
-        fileNames={fileNames}
-      />,
-    );
+  it('should call onConfirm with only new files when ignore is selected', () => {
+    renderModal();
 
-    const cancelButton = screen.getByRole('button', { name: 'Cancel' });
-    fireEvent.click(cancelButton);
+    const ignoreRadio = screen.getByLabelText('Ignore duplicated files');
+    fireEvent.click(ignoreRadio);
 
-    expect(onClose).toHaveBeenCalledTimes(1);
+    const uploadButton = screen.getByRole('button', {
+      name: /Upload \(1\)/,
+    });
+    fireEvent.click(uploadButton);
+
+    expect(onConfirm).toHaveBeenCalledWith([allFiles[2]]);
+  });
+
+  it('should call onBack when Back button is clicked', () => {
+    renderModal();
+
+    const backButton = screen.getByRole('button', { name: 'Back' });
+    fireEvent.click(backButton);
+
+    expect(onBack).toHaveBeenCalledTimes(1);
   });
 
   it('should call onClose when close icon button is clicked', () => {
-    render(
+    renderModal();
+
+    const closeButton = screen.getByRole('button', { name: 'Close' });
+    fireEvent.click(closeButton);
+
+    expect(onClose).toHaveBeenCalledTimes(1);
+  });
+
+  it('should update upload count when switching from ignore back to replace', () => {
+    renderModal();
+
+    const ignoreRadio = screen.getByLabelText('Ignore duplicated files');
+    fireEvent.click(ignoreRadio);
+    expect(
+      screen.getByRole('button', { name: /Upload \(1\)/ }),
+    ).toBeInTheDocument();
+
+    const replaceRadio = screen.getByLabelText('Replace existing files');
+    fireEvent.click(replaceRadio);
+    expect(
+      screen.getByRole('button', { name: /Upload \(3\)/ }),
+    ).toBeInTheDocument();
+  });
+
+  it('should render an empty file list gracefully when no files provided', () => {
+    renderModal({ allFiles: [], duplicateFileNames: [] });
+
+    expect(screen.queryByRole('listitem')).not.toBeInTheDocument();
+  });
+
+  it('should disable Upload button when all files are duplicates and ignore is selected', () => {
+    renderModal({
+      allFiles: [createFile('dup1.txt'), createFile('dup2.txt')],
+      duplicateFileNames: ['dup1.txt', 'dup2.txt'],
+    });
+
+    const ignoreRadio = screen.getByLabelText('Ignore duplicated files');
+    fireEvent.click(ignoreRadio);
+
+    const uploadButton = screen.getByRole('button', {
+      name: /Upload \(0\)/,
+    });
+    expect(uploadButton).toBeDisabled();
+  });
+
+  it('should reset radio to replace when modal reopens', () => {
+    const { rerender } = render(
       <OverwriteConfirmModal
         isOpen
         onClose={onClose}
         onConfirm={onConfirm}
-        fileNames={fileNames}
+        onBack={onBack}
+        allFiles={allFiles}
+        duplicateFileNames={duplicateFileNames}
       />,
     );
 
-    const closeButton = screen.getByRole('button', { name: 'Close' });
-    fireEvent.click(closeButton);
-
-    expect(onClose).toHaveBeenCalledTimes(1);
-  });
+    fireEvent.click(screen.getByLabelText('Ignore duplicated files'));
+    expect(
+      screen.getByRole('button', { name: /Upload \(1\)/ }),
+    ).toBeInTheDocument();
 
-  it('should render an empty list for no files', () => {
-    render(
+    rerender(
+      <OverwriteConfirmModal
+        isOpen={false}
+        onClose={onClose}
+        onConfirm={onConfirm}
+        onBack={onBack}
+        allFiles={allFiles}
+        duplicateFileNames={duplicateFileNames}
+      />,
+    );
+    rerender(
       <OverwriteConfirmModal
         isOpen
         onClose={onClose}
         onConfirm={onConfirm}
-        fileNames={[]}
+        onBack={onBack}
+        allFiles={allFiles}
+        duplicateFileNames={duplicateFileNames}
       />,
     );
 
-    expect(screen.queryByRole('listitem')).not.toBeInTheDocument();
+    expect(
+      screen.getByRole('button', { name: /Upload \(3\)/ }),
+    ).toBeInTheDocument();
   });
 });
diff --git a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/AddDocumentModal.tsx b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/AddDocumentModal.tsx
index 7b85fbb5946..1a3958dc49a 100644
--- a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/AddDocumentModal.tsx
+++ b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/AddDocumentModal.tsx
@@ -14,12 +14,11 @@
  * limitations under the License.
  */
 
-import { useEffect, useState } from 'react';
+import { useContext, useEffect, useState } from 'react';
 import { FileRejection } from 'react-dropzone';
 
 import { makeStyles } from '@material-ui/core/styles';
 import CloseIcon from '@mui/icons-material/Close';
-import Alert from '@mui/material/Alert';
 import Box from '@mui/material/Box';
 import Button from '@mui/material/Button';
 import Dialog from '@mui/material/Dialog';
@@ -29,20 +28,31 @@ import DialogTitle from '@mui/material/DialogTitle';
 import IconButton from '@mui/material/IconButton';
 import Typography from '@mui/material/Typography';
 import {
+  Alert,
   MultipleFileUpload,
+  MultipleFileUploadContext,
   MultipleFileUploadMain,
+  Tooltip,
 } from '@patternfly/react-core';
 import { UploadIcon } from '@patternfly/react-icons';
 
-import { NOTEBOOK_MAX_FILES } from '../../const';
+import {
+  NOTEBOOK_EXTENSION_TO_FILE_TYPE,
+  NOTEBOOK_MAX_FILES,
+} from '../../const';
 import { useUploadDocument } from '../../hooks/notebooks/useUploadDocument';
 import { useTranslation } from '../../hooks/useTranslation';
+import { runFileUploads } from '../../utils/notebook-upload-runner';
 import {
   getNotebookAcceptedFileTypes,
   validateFiles,
 } from '../../utils/notebook-upload-utils';
 import { FileListItem } from './FileListItem';
 
+const UNIQUE_FILE_TYPE_LABELS = [
+  ...new Set(Object.values(NOTEBOOK_EXTENSION_TO_FILE_TYPE)),
+].map(t => t.toUpperCase());
+
 const useStyles = makeStyles(theme => ({
   dialogPaper: {
     borderRadius: 24,
@@ -68,17 +78,30 @@ const useStyles = makeStyles(theme => ({
   },
   errorAlert: {
     marginBottom: theme.spacing(2),
+    '--pf-v6-c-alert--PaddingBlockEnd': '0',
+    '& .pf-v6-c-alert__title': {
+      marginBlockStart: 0,
+    },
   },
   dropzone: {
-    '& .pf-v6-c-multiple-file-upload__main': {
-      borderColor: 'var(--pf-t--global--border--color--brand--default)',
-      transition: 'background-color 0.2s ease',
-      cursor: 'pointer',
-    },
-    '& .pf-v6-c-multiple-file-upload__main:hover': {
+    borderColor: 'var(--pf-t--global--border--color--brand--default)',
+    borderWidth: 2,
+    borderStyle: 'dashed',
+    borderRadius: theme.spacing(1),
+    padding: theme.spacing(2),
+    transition: 'background-color 0.2s ease',
+    cursor: 'pointer',
+    '&:hover': {
       backgroundColor:
         'color-mix(in srgb, var(--pf-t--global--color--brand--default) 10%, transparent)',
     },
+    '& .pf-v6-c-multiple-file-upload__main': {
+      border: 'none',
+      paddingBottom: 0,
+    },
+    '& .pf-v6-c-multiple-file-upload__title-icon': {
+      fontSize: '2rem',
+    },
   },
   fileListContainer: {
     marginTop: theme.spacing(2),
@@ -97,7 +120,7 @@ const useStyles = makeStyles(theme => ({
   },
   dialogActions: {
     padding: '16px 24px',
-    justifyContent: 'flex-end',
+    justifyContent: 'flex-start',
     gap: theme.spacing(1),
   },
   addButton: {
@@ -106,8 +129,83 @@ const useStyles = makeStyles(theme => ({
   cancelButton: {
     textTransform: 'none',
   },
+  uploadIcon: {
+    color: 'var(--pf-t--global--icon--color--brand--default)',
+  },
+  supportedFormatsLabel: {
+    fontSize: '0.875rem',
+    color: theme.palette.text.secondary,
+    textAlign: 'center',
+    marginTop: theme.spacing(1),
+  },
+  chipContainer: {
+    display: 'flex',
+    flexWrap: 'wrap',
+    gap: theme.spacing(0.75),
+    justifyContent: 'center',
+    marginTop: theme.spacing(0.5),
+  },
+  fileTypeChip: {
+    display: 'inline-block',
+    padding: '2px 10px',
+    borderRadius: 12,
+    fontSize: '0.75rem',
+    fontWeight: 500,
+    backgroundColor:
+      theme.palette.type === 'dark'
+        ? 'rgba(255, 255, 255, 0.1)'
+        : 'rgba(0, 0, 0, 0.08)',
+    color: theme.palette.text.secondary,
+  },
+  maxFileSizeText: {
+    fontSize: '0.875rem',
+    color: theme.palette.text.secondary,
+    textAlign: 'center',
+    marginTop: theme.spacing(1),
+  },
+  dropzoneDisabled: {
+    opacity: 0.5,
+    pointerEvents: 'none',
+    cursor: 'default',
+    '&:hover': {
+      backgroundColor: 'transparent',
+    },
+  },
 }));
 
+const DropzoneClickArea = ({
+  children,
+  isDisabled,
+  ariaLabel,
+}: {
+  children: React.ReactNode;
+  isDisabled?: boolean;
+  ariaLabel?: string;
+}) => {
+  const { open } = useContext(MultipleFileUploadContext);
+  return (
+    <div
+      role="button"
+      aria-label={ariaLabel}
+      tabIndex={isDisabled ? -1 : 0}
+      onClick={isDisabled ? undefined : open}
+      onKeyDown={
+        isDisabled
+          ? undefined
+          : e => {
+              if (e.key === 'Enter' || e.key === ' ') {
+                e.preventDefault();
+                open();
+              }
+            }
+      }
+      style={{ cursor: isDisabled ? 'default' : 'pointer' }}
+    >
+      {children}
+    </div>
+  );
+};
+
 type AddDocumentModalProps = {
   isOpen: boolean;
   onClose: () => void;
@@ -117,7 +215,7 @@ type AddDocumentModalProps = {
   onFilesUploading?: (files: File[]) => void;
   onUploadStarted?: (info: { fileName: string; documentId: string }) => void;
   onUploadFailed?: (fileName: string) => void;
-  onDuplicatesFound?: (files: File[]) => void;
+  onDuplicatesFound?: (duplicateFiles: File[], allFiles: File[]) => void;
   filesToAdd?: File[];
   onFilesAdded?: () => void;
 };
@@ -145,6 +243,13 @@ export const AddDocumentModal = ({
     existingDocumentNames.length + selectedFiles.length;
   const remainingSlots = NOTEBOOK_MAX_FILES - totalExistingAndSelected;
 
+  useEffect(() => {
+    if (!isOpen) {
+      setSelectedFiles([]);
+      setValidationErrors([]);
+    }
+  }, [isOpen]);
+
   useEffect(() => {
     if (filesToAdd && filesToAdd.length > 0) {
       setSelectedFiles(prev => [...prev, ...filesToAdd]);
@@ -164,18 +269,8 @@ export const AddDocumentModal = ({
 
     if (valid.length === 0) return;
 
-    const existingNamesSet = new Set([
-      ...existingDocumentNames,
-      ...selectedFiles.map(f => f.name),
-    ]);
-    const newFiles = valid.filter(f => !existingNamesSet.has(f.name));
-    const duplicateFiles = valid.filter(f =>
-      existingDocumentNames.includes(f.name),
-    );
-
-    if (duplicateFiles.length > 0) {
-      onDuplicatesFound?.(duplicateFiles);
-    }
+    const alreadySelectedNames = new Set(selectedFiles.map(f => f.name));
+    const newFiles = valid.filter(f => !alreadySelectedNames.has(f.name));
 
     if (newFiles.length > 0) {
       setSelectedFiles(prev => [...prev, ...newFiles]);
@@ -189,21 +284,21 @@ export const AddDocumentModal = ({
   const handleAddFiles = () => {
     if (selectedFiles.length === 0) return;
 
-    onFilesUploading?.(selectedFiles);
-    for (const file of selectedFiles) {
-      uploadMutation
-        .mutateAsync({ sessionId, file })
-        .then(data => {
-          onUploadStarted?.({
-            fileName: file.name,
-            documentId: data.document_id,
-          });
-        })
-        .catch(() => {
-          onUploadFailed?.(file.name);
-        });
+    const duplicateFiles = selectedFiles.filter(f =>
+      existingDocumentNames.includes(f.name),
+    );
+
+    if (duplicateFiles.length > 0) {
+      onDuplicatesFound?.(duplicateFiles, selectedFiles);
+      return;
     }
 
+    runFileUploads(uploadMutation, sessionId, selectedFiles, {
+      onUploading: onFilesUploading,
+      onStarted: onUploadStarted,
+      onFailed: onUploadFailed,
+    });
+
     setSelectedFiles([]);
     setValidationErrors([]);
     onClose();
@@ -251,8 +346,11 @@ export const AddDocumentModal = ({
 
       <DialogContent className={classes.dialogContent}>
         {validationErrors.length > 0 && (
-          <Alert severity="error" className={classes.errorAlert}>
-            {validationErrors
+          <Alert
+            variant="danger"
+            isInline
+            className={classes.errorAlert}
+            title={validationErrors
               .map(errorKey => {
                 const message = (t as Function)(errorKey) as string;
                 return errorKey === 'notebook.upload.error.tooManyFiles'
@@ -260,33 +358,67 @@ export const AddDocumentModal = ({
                   : message;
               })
               .join('\n')}
-          </Alert>
+          />
         )}
 
         {hasUploadsInProgress && (
-          <Alert severity="info" className={classes.errorAlert}>
-            {t('notebook.view.documents.uploadsInProgress')}
-          </Alert>
+          <Alert
+            variant="info"
+            isInline
+            className={classes.errorAlert}
+            title={t('notebook.view.documents.uploadsInProgress')}
+          />
         )}
 
-        {remainingSlots > 0 && (
-          <MultipleFileUpload
-            className={classes.dropzone}
-            dropzoneProps={{
-              accept: getNotebookAcceptedFileTypes(),
-              onDropRejected: handleDropRejected,
-            }}
-            onFileDrop={handleFileDrop}
-          >
-            <MultipleFileUploadMain
-              titleIcon={<UploadIcon />}
-              titleText={t('notebook.upload.modal.dragDropTitle')}
-              titleTextSeparator={t('notebook.upload.modal.separator')}
-              infoText={t('notebook.upload.modal.infoText')}
-              browseButtonText={t('notebook.upload.modal.browseButton')}
-            />
-          </MultipleFileUpload>
-        )}
+        {(() => {
+          const isDropzoneDisabled = remainingSlots <= 0;
+          const dropzoneContent = (
+            <MultipleFileUpload
+              className={`${classes.dropzone} ${isDropzoneDisabled ? classes.dropzoneDisabled : ''}`}
+              dropzoneProps={{
+                accept: getNotebookAcceptedFileTypes(),
+                onDropRejected: handleDropRejected,
+                disabled: isDropzoneDisabled,
+              }}
+              onFileDrop={handleFileDrop}
+            >
+              <DropzoneClickArea
+                isDisabled={isDropzoneDisabled}
+                ariaLabel={t('notebook.upload.modal.dragDropTitle')}
+              >
+                <MultipleFileUploadMain
+                  titleIcon={<UploadIcon className={classes.uploadIcon} />}
+                  titleText={t('notebook.upload.modal.dragDropTitle')}
+                  isUploadButtonHidden
+                />
+                <Typography className={classes.supportedFormatsLabel}>
+                  {t('notebook.upload.modal.supportedFormats')}
+                </Typography>
+                <div className={classes.chipContainer}>
+                  {UNIQUE_FILE_TYPE_LABELS.map(label => (
+                    <span key={label} className={classes.fileTypeChip}>
+                      {label}
+                    </span>
+                  ))}
+                </div>
+                <Typography className={classes.maxFileSizeText}>
+                  {t('notebook.upload.modal.maxFileSize')}
+                </Typography>
+              </DropzoneClickArea>
+            </MultipleFileUpload>
+          );
+
+          return isDropzoneDisabled ? (
+            <Tooltip
+              content={t('notebook.view.documents.maxReached')}
+              position="top"
+            >
+              <div>{dropzoneContent}</div>
+            </Tooltip>
+          ) : (
+            dropzoneContent
+          );
+        })()}
 
         {selectedFiles.length > 0 && (
           <Box className={classes.fileListContainer}>
@@ -316,13 +448,6 @@ export const AddDocumentModal = ({
       </DialogContent>
 
       <DialogActions className={classes.dialogActions}>
-        <Button
-          onClick={handleClose}
-          className={classes.cancelButton}
-          color="inherit"
-        >
-          {t('common.cancel')}
-        </Button>
         <Button
           onClick={handleAddFiles}
           className={classes.addButton}
@@ -330,9 +455,18 @@ export const AddDocumentModal = ({
           color="primary"
           disabled={selectedFiles.length === 0 || hasUploadsInProgress}
         >
-          {(t as Function)('notebook.upload.modal.addButton', {
-            count: selectedFiles.length,
-          })}
+          {selectedFiles.length > 0
+            ? (t as Function)('notebook.upload.modal.addButton', {
+                count: selectedFiles.length,
+              })
+            : t('notebook.upload.modal.addButtonEmpty')}
+        </Button>
+        <Button
+          onClick={handleClose}
+          className={classes.cancelButton}
+          color="inherit"
+        >
+          {t('common.cancel')}
         </Button>
       </DialogActions>
     </Dialog>
diff --git a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/DocumentSidebar.tsx b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/DocumentSidebar.tsx
index b9b0ab6cbb5..93ea12da507 100644
--- a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/DocumentSidebar.tsx
+++ b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/DocumentSidebar.tsx
@@ -27,7 +27,7 @@ import {
   TextInput,
   Tooltip,
 } from '@patternfly/react-core';
-import { EllipsisVIcon, PlusCircleIcon } from '@patternfly/react-icons';
+import { AddCircleOIcon, EllipsisVIcon } from '@patternfly/react-icons';
 
 import { NOTEBOOK_MAX_FILES } from '../../const';
 import { useInlineEdit } from '../../hooks/notebooks/useInlineEdit';
@@ -252,7 +252,7 @@ export const DocumentSidebar = ({
               <Button
                 variant="link"
                 className={classes.addButton}
-                icon={<PlusCircleIcon />}
+                icon={<AddCircleOIcon />}
                 isDisabled
               >
                 {t('notebook.view.documents.add')}
@@ -263,7 +263,7 @@ export const DocumentSidebar = ({
           <Button
             variant="link"
             className={classes.addButton}
-            icon={<PlusCircleIcon />}
+            icon={<AddCircleOIcon />}
             onClick={onAddDocument}
           >
             {t('notebook.view.documents.add')}
diff --git a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/FileListItem.tsx b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/FileListItem.tsx
index de0c59b8306..60143528696 100644
--- a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/FileListItem.tsx
+++ b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/FileListItem.tsx
@@ -15,10 +15,9 @@
  */
 
 import { makeStyles } from '@material-ui/core/styles';
-import CloseIcon from '@mui/icons-material/Close';
 import Box from '@mui/material/Box';
-import IconButton from '@mui/material/IconButton';
 import Typography from '@mui/material/Typography';
+import { TimesIcon } from '@patternfly/react-icons';
 
 import { FileTypeIcon } from './FileTypeIcon';
 
@@ -28,7 +27,9 @@ const useStyles = makeStyles(theme => ({
     alignItems: 'center',
     padding: '8px 12px',
     borderRadius: 8,
-    backgroundColor: theme.palette.type === 'dark' ? '#2a2a2a' : '#f5f5f5',
+    border: '1px solid var(--pf-t--global--border--color--default)',
+    backgroundColor:
+      'var(--pf-t--global--background--color--secondary--default)',
     marginBottom: 8,
     '&:last-child': {
       marginBottom: 0,
@@ -56,11 +57,17 @@ const useStyles = makeStyles(theme => ({
     marginRight: 8,
   },
   removeButton: {
+    background: 'none',
+    border: 'none',
+    cursor: 'pointer',
     padding: 4,
-    color: theme.palette.action.active,
+    color: 'var(--pf-t--global--icon--color--subtle)',
     '&:hover': {
-      color: theme.palette.error.main,
+      color: 'var(--pf-t--global--icon--color--regular)',
     },
+    display: 'inline-flex',
+    alignItems: 'center',
+    fontFamily: 'inherit',
   },
 }));
 
@@ -112,14 +119,14 @@ export const FileListItem = ({
       <Typography className={classes.fileSize}>
         {formatFileSize(file.size)}
       </Typography>
-      <IconButton
+      <button
+        type="button"
         className={classes.removeButton}
         onClick={onRemove}
         aria-label={removeAriaLabel}
-        size="small"
       >
-        <CloseIcon fontSize="small" />
-      </IconButton>
+        <TimesIcon style={{ width: 12, height: 12 }} />
+      </button>
     </Box>
   );
 };
diff --git a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/NotebookCard.tsx b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/NotebookCard.tsx
index 90d2cb2ea34..9e31298eaa7 100644
--- a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/NotebookCard.tsx
+++ b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/NotebookCard.tsx
@@ -30,8 +30,12 @@ import {
   MenuToggle,
   TextInput,
 } from '@patternfly/react-core';
-import { EllipsisVIcon } from '@patternfly/react-icons';
-import { CatalogIcon } from '@patternfly/react-icons/dist/esm/icons';
+import {
+  CatalogIcon,
+  EllipsisVIcon,
+  PenIcon,
+  TrashIcon,
+} from '@patternfly/react-icons';
 
 import { useInlineEdit } from '../../hooks/notebooks/useInlineEdit';
 import { intelligentAssistantTranslationRef } from '../../translations/ref';
@@ -103,12 +107,22 @@ export const NotebookCard = ({
     }
   };
 
+  const count = notebook.document_count ?? 0;
+  const getDocumentCountText = () => {
+    if (count === 0) return t('notebooks.documents.none');
+    if (count === 1) return t('notebooks.documents.one');
+    return (t as Function)('notebooks.documents.other', { count });
+  };
+  const documentCountText = getDocumentCountText();
+
   return (
     <Card
       className={classes.notebookCard}
       component="div"
       tabIndex={0}
-      aria-label={t('notebooks.card.openAria' as any, { name: notebook.name })}
+      aria-label={(t as Function)('notebooks.card.openAria', {
+        name: notebook.name,
+      })}
       onClick={handleCardClick}
       onKeyDown={handleCardKeyDown}
     >
@@ -149,6 +163,7 @@ export const NotebookCard = ({
               <DropdownList className={classes.notebookDropdownList}>
                 <DropdownItem
                   className={classes.notebookDropdownItem}
+                  icon={<PenIcon />}
                   onClick={event => {
                     event.stopPropagation();
                     startEditing();
@@ -158,6 +173,7 @@ export const NotebookCard = ({
                 </DropdownItem>
                 <DropdownItem
                   className={classes.notebookDropdownItem}
+                  icon={<TrashIcon />}
                   onClick={event => {
                     event.stopPropagation();
                     onDelete(notebook.session_id);
@@ -204,9 +220,7 @@ export const NotebookCard = ({
       <CardBody className={classes.notebookCardBody}>
         <div>
           <div className={classes.notebookDocuments}>
-            <Typography variant="body2">
-              {notebook.document_count ?? 0} {t('notebooks.documents')}
-            </Typography>
+            <Typography variant="body2">{documentCountText}</Typography>
           </div>
           <div className={classes.notebookUpdated}>
             <Typography variant="caption">
diff --git a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/NotebookView.tsx b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/NotebookView.tsx
index afd236379c5..232ba80eb18 100644
--- a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/NotebookView.tsx
+++ b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/NotebookView.tsx
@@ -38,7 +38,7 @@ import {
   Tooltip,
   type AlertProps,
 } from '@patternfly/react-core';
-import { TimesIcon } from '@patternfly/react-icons';
+import { PlusIcon, TimesIcon } from '@patternfly/react-icons';
 import { useQueryClient } from '@tanstack/react-query';
 
 import { notebooksApiRef } from '../../api/notebooksApi';
@@ -53,12 +53,15 @@ import {
   type PendingUpload,
 } from '../../hooks/notebooks/useDocumentStatusPolling';
 import { useRenameNotebookWithAlert } from '../../hooks/notebooks/useRenameNotebookWithAlert';
+import { useUploadDocument } from '../../hooks/notebooks/useUploadDocument';
 import { useConversationMessages } from '../../hooks/useConversationMessages';
 import { CreateMessageVariables } from '../../hooks/useCreateCoversationMessage';
 import { useNotebookWelcomePrompts } from '../../hooks/useNotebookWelcomePrompts';
+import { useStopConversation } from '../../hooks/useStopConversation';
 import { useTranslation } from '../../hooks/useTranslation';
 import { NotebookSessionMetadata, SessionDocument } from '../../types';
 import { ChatbotFootnoteWithIcon } from '../../utils/lightspeed-chatbox-utils';
+import { runFileUploads } from '../../utils/notebook-upload-runner';
 import { LightspeedChatBox } from '../LightspeedChatBox';
 import { AddDocumentModal } from './AddDocumentModal';
 import { DeleteDocumentModal } from './DeleteDocumentModal';
@@ -257,11 +260,34 @@ const useStyles = makeStyles(theme => ({
           ? theme.palette.grey[100]
           : 'var(--pf-t--global--background--color--secondary--default)',
     },
-    '& .pf-chatbot__button--send, & .pf-chatbot__button--microphone': {
-      '--pf-v6-c-button--BorderRadius':
-        'var(--pf-t--global--border--radius--pill)',
-      borderRadius: 'var(--pf-t--global--border--radius--pill) !important',
+    '& .pf-chatbot__button--stop, & .pf-chatbot__button--attach, & .pf-chatbot__button--send, & .pf-chatbot__button--microphone':
+      {
+        '--pf-v6-c-button--BorderRadius':
+          'var(--pf-t--global--border--radius--pill)',
+        borderRadius: 'var(--pf-t--global--border--radius--pill) !important',
+      },
+  },
+  messageBar: {
+    border: '1px solid var(--pf-t--global--border--color--default)',
+    borderRadius: 24,
+    padding: theme.spacing(0.5),
+    '&::after': {
+      display: 'none',
+    },
+  },
+  addResourceButton: {
+    background: 'none',
+    border: 'none',
+    cursor: 'pointer',
+    padding: 4,
+    display: 'inline-flex',
+    alignItems: 'center',
+    color: 'inherit',
+    '&:focus-visible': {
+      outline: '2px solid var(--pf-t--global--border--color--brand--default)',
+      outlineOffset: 2,
     },
+    marginLeft: theme.spacing(2),
   },
   chatContent: {
     minHeight: 0,
@@ -316,6 +342,9 @@ export const NotebookView = ({
     metadata?.conversation_id ?? TEMP_CONVERSATION_ID,
   );
   const [isSendButtonDisabled, setIsSendButtonDisabled] = useState(false);
+  const [requestId, setRequestId] = useState('');
+  const { mutate: stopConversation } = useStopConversation();
+  const wasStoppedByUserRef = useRef(false);
   const [announcement, setAnnouncement] = useState<string | undefined>(
     undefined,
   );
@@ -334,7 +363,10 @@ export const NotebookView = ({
   const onComplete = useCallback(
     (message: string) => {
       setIsSendButtonDisabled(false);
-      setAnnouncement(`Message from Bot: ${message}`);
+      if (!wasStoppedByUserRef.current) {
+        setAnnouncement(`Message from Bot: ${message}`);
+      }
+      wasStoppedByUserRef.current = false;
       queryClient.invalidateQueries({
         queryKey: ['conversationMessages', conversationId],
       });
@@ -356,6 +388,10 @@ export const NotebookView = ({
     [notebookCreateMessage, sessionId],
   );
 
+  const onRequestIdReady = useCallback((rid: string) => {
+    setRequestId(rid);
+  }, []);
+
   const { conversationMessages, handleInputPrompt, scrollToBottomRef } =
     useConversationMessages(
       conversationId,
@@ -366,6 +402,7 @@ export const NotebookView = ({
       onComplete,
       onStart,
       createMessageAdapter,
+      onRequestIdReady,
     );
 
   const [messages, setMessages] =
@@ -377,6 +414,7 @@ export const NotebookView = ({
 
   const sendMessage = useCallback(
     (message: string | number) => {
+      wasStoppedByUserRef.current = false;
       setAnnouncement(
         t('conversation.announcement.userMessage' as any, {
           prompt: message.toString(),
@@ -388,12 +426,24 @@ export const NotebookView = ({
     [handleInputPrompt, t],
   );
 
+  const handleStopButton = useCallback(() => {
+    wasStoppedByUserRef.current = true;
+    if (requestId) {
+      stopConversation(requestId);
+      setRequestId('');
+    }
+    setIsSendButtonDisabled(false);
+    setAnnouncement(t('conversation.announcement.responseStopped'));
+  }, [requestId, stopConversation, t]);
+
   const notebookPrompts = useNotebookWelcomePrompts();
   const welcomePrompts = notebookPrompts.map(title => ({
     title,
     onClick: () => sendMessage(title),
   }));
 
+  const uploadMutation = useUploadDocument();
+
   const [sidebarCollapsed, setSidebarCollapsed] = useState(false);
   const [isUploadModalOpen, setIsUploadModalOpen] = useState(false);
   const [uploadingFileNames, setUploadingFileNames] = useState<string[]>([]);
@@ -404,6 +454,7 @@ export const NotebookView = ({
     new Set(),
   );
   const [filesToOverwrite, setFilesToOverwrite] = useState<File[]>([]);
+  const [allFilesForOverwrite, setAllFilesForOverwrite] = useState<File[]>([]);
   const [isOverwriteModalOpen, setIsOverwriteModalOpen] = useState(false);
   const [filesToAddToModal, setFilesToAddToModal] = useState<File[]>([]);
 
@@ -444,6 +495,26 @@ export const NotebookView = ({
   const handleOpenUploadModal = () => setIsUploadModalOpen(true);
   const handleCloseUploadModal = () => setIsUploadModalOpen(false);
 
+  const handleCloseNotebook = async () => {
+    const isUntitled = notebookName === UNTITLED_NOTEBOOK_NAME;
+    const hasNoDocuments =
+      documents.length === 0 && completedFileNames.size === 0;
+    const hasNoPendingUploads = !pendingUploads.length;
+    const hasNoUploading = !uploadingFileNames.length;
+    const hasNoChat = conversationId === TEMP_CONVERSATION_ID;
+
+    if (
+      isUntitled &&
+      hasNoDocuments &&
+      hasNoPendingUploads &&
+      hasNoUploading &&
+      hasNoChat
+    ) {
+      await notebooksApi.deleteSession(sessionId).catch(() => {});
+    }
+    onClose();
+  };
+
   const handleFilesUploading = (files: File[]) => {
     setUploadingFileNames(prev => {
       const newNames = files
@@ -478,28 +549,43 @@ export const NotebookView = ({
     ]);
   };
 
-  const handleDuplicatesFound = (files: File[]) => {
-    setFilesToOverwrite(files);
+  const handleDuplicatesFound = (duplicateFiles: File[], allFiles: File[]) => {
+    setFilesToOverwrite(duplicateFiles);
+    setAllFilesForOverwrite(allFiles);
+    setIsUploadModalOpen(false);
     setIsOverwriteModalOpen(true);
   };
 
-  const handleOverwriteConfirm = () => {
-    const files = filesToOverwrite;
+  const handleOverwriteConfirm = (filesToUpload: File[]) => {
     setIsOverwriteModalOpen(false);
     setFilesToOverwrite([]);
+    setAllFilesForOverwrite([]);
 
-    if (files.length === 0) return;
+    if (filesToUpload.length === 0) return;
 
-    setFilesToAddToModal(files);
+    runFileUploads(uploadMutation, sessionId, filesToUpload, {
+      onUploading: handleFilesUploading,
+      onStarted: handleUploadStarted,
+      onFailed: handleUploadFailed,
+    });
   };
 
   const handleFilesAddedToModal = () => {
     setFilesToAddToModal([]);
   };
 
+  const handleOverwriteBack = () => {
+    setIsOverwriteModalOpen(false);
+    setFilesToAddToModal(allFilesForOverwrite);
+    setFilesToOverwrite([]);
+    setAllFilesForOverwrite([]);
+    setIsUploadModalOpen(true);
+  };
+
   const handleOverwriteCancel = () => {
     setIsOverwriteModalOpen(false);
     setFilesToOverwrite([]);
+    setAllFilesForOverwrite([]);
   };
 
   const pollingResults = useDocumentStatusPolling(sessionId, pendingUploads);
@@ -747,7 +833,7 @@ export const NotebookView = ({
                   <Button
                     variant="link"
                     className={classes.closeButton}
-                    onClick={onClose}
+                    onClick={handleCloseNotebook}
                     icon={<TimesIcon />}
                     iconPosition="end"
                   >
@@ -762,33 +848,70 @@ export const NotebookView = ({
                   renderNotebookDisclaimerAlert()}
 
                 <ChatbotFooter className={classes.footer}>
-                  {hasNoDocuments ? (
-                    <Tooltip
-                      content={t('notebook.view.input.disabledTooltip')}
-                      position="top"
-                    >
-                      <div>
-                        <MessageBar
-                          hasAttachButton={false}
-                          hasMicrophoneButton={false}
-                          hasStopButton={false}
-                          isSendButtonDisabled
-                          isDisabled
-                          onSendMessage={sendMessage}
-                          placeholder={t('notebook.view.input.placeholder')}
-                        />
-                      </div>
-                    </Tooltip>
-                  ) : (
-                    <MessageBar
-                      hasAttachButton={false}
-                      hasMicrophoneButton
-                      hasStopButton={false}
-                      isSendButtonDisabled={isSendButtonDisabled}
-                      onSendMessage={sendMessage}
-                      placeholder={t('notebook.view.input.placeholder')}
-                    />
-                  )}
+                  {(() => {
+                    const addResourceAction = (
+                      <button
+                        type="button"
+                        onClick={() => handleOpenUploadModal()}
+                        aria-label={t('notebook.view.documents.add')}
+                        className={classes.addResourceButton}
+                      >
+                        <PlusIcon style={{ width: 16, height: 16 }} />
+                      </button>
+                    );
+                    return hasNoDocuments ? (
+                      <Tooltip
+                        content={t('notebook.view.input.disabledTooltip')}
+                        position="top"
+                      >
+                        <div>
+                          <MessageBar
+                            className={classes.messageBar}
+                            hasAttachButton={false}
+                            hasMicrophoneButton={false}
+                            hasStopButton={false}
+                            isSendButtonDisabled
+                            isDisabled
+                            onSendMessage={sendMessage}
+                            placeholder={t('notebook.view.input.placeholder')}
+                            forceMultilineLayout
+                            additionalActions={addResourceAction}
+                            buttonProps={{
+                              send: {
+                                tooltipContent: t('tooltip.send'),
+                              },
+                            }}
+                          />
+                        </div>
+                      </Tooltip>
+                    ) : (
+                      <MessageBar
+                        className={classes.messageBar}
+                        hasAttachButton={false}
+                        hasMicrophoneButton
+                        hasStopButton={isSendButtonDisabled}
+                        handleStopButton={
+                          isSendButtonDisabled ? handleStopButton : undefined
+                        }
+                        isSendButtonDisabled={isSendButtonDisabled}
+                        onSendMessage={sendMessage}
+                        placeholder={t('notebook.view.input.placeholder')}
+                        forceMultilineLayout
+                        additionalActions={addResourceAction}
+                        buttonProps={{
+                          microphone: {
+                            tooltipContent: {
+                              active: t('tooltip.microphone.active'),
+                              inactive: t('tooltip.microphone.inactive'),
+                            },
+                          },
+                          send: {
+                            tooltipContent: t('tooltip.send'),
+                          },
+                        }}
+                      />
+                    );
+                  })()}
                   <ChatbotFootnoteWithIcon label={t('footer.accuracy.label')} />
                 </ChatbotFooter>
               </div>
@@ -815,7 +938,9 @@ export const NotebookView = ({
         isOpen={isOverwriteModalOpen}
         onClose={handleOverwriteCancel}
         onConfirm={handleOverwriteConfirm}
-        fileNames={filesToOverwrite.map(f => f.name)}
+        onBack={handleOverwriteBack}
+        allFiles={allFilesForOverwrite}
+        duplicateFileNames={filesToOverwrite.map(f => f.name)}
       />
 
       <DeleteDocumentModal
diff --git a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/OverwriteConfirmModal.tsx b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/OverwriteConfirmModal.tsx
index 61327087ef8..e8322152e85 100644
--- a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/OverwriteConfirmModal.tsx
+++ b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/OverwriteConfirmModal.tsx
@@ -14,16 +14,17 @@
  * limitations under the License.
  */
 
+import { useEffect, useMemo, useState } from 'react';
+
 import { makeStyles } from '@material-ui/core/styles';
 import CloseIcon from '@mui/icons-material/Close';
-import Alert from '@mui/material/Alert';
-import Button from '@mui/material/Button';
 import Dialog from '@mui/material/Dialog';
-import DialogActions from '@mui/material/DialogActions';
 import DialogContent from '@mui/material/DialogContent';
 import DialogTitle from '@mui/material/DialogTitle';
 import IconButton from '@mui/material/IconButton';
 import Typography from '@mui/material/Typography';
+import { Alert, Button } from '@patternfly/react-core';
+import { ExclamationTriangleIcon } from '@patternfly/react-icons';
 
 import { useTranslation } from '../../hooks/useTranslation';
 import { FileTypeIcon } from './FileTypeIcon';
@@ -51,19 +52,44 @@ const useStyles = makeStyles(theme => ({
   dialogContent: {
     padding: '0 24px 24px',
   },
+  warningAlert: {
+    '--pf-v6-c-alert--PaddingBlockEnd': '0',
+    marginBottom: theme.spacing(2),
+    '& .pf-v6-c-alert__title': {
+      marginTop: 0,
+    },
+  },
+  radioGroup: {
+    display: 'flex',
+    flexDirection: 'column',
+    gap: theme.spacing(1),
+    marginBottom: theme.spacing(2),
+    '& label': {
+      display: 'flex',
+      alignItems: 'center',
+      gap: theme.spacing(1),
+      cursor: 'pointer',
+      fontSize: '0.875rem',
+    },
+    '& input[type="radio"]': {
+      cursor: 'pointer',
+    },
+  },
   fileList: {
     margin: 0,
     padding: 0,
     listStyle: 'none',
+    maxHeight: 300,
+    overflowY: 'auto',
   },
   fileItem: {
     display: 'flex',
     alignItems: 'center',
     gap: theme.spacing(1),
-    padding: `${theme.spacing(2)}px 0`,
-    borderBottom:
-      '1px solid var(--pf-t--global--border--color--default, #c7c7c7)',
-    cursor: 'pointer',
+    padding: `${theme.spacing(1.5)}px ${theme.spacing(1.5)}px`,
+    border: '1px solid var(--pf-t--global--border--color--default)',
+    borderRadius: 8,
+    marginBottom: theme.spacing(1),
   },
   fileName: {
     flex: 1,
@@ -74,44 +100,69 @@ const useStyles = makeStyles(theme => ({
     fontSize: '0.875rem',
     lineHeight: '1.25rem',
   },
+  warningIcon: {
+    color: 'var(--pf-t--global--color--status--warning--default)',
+    fontSize: '1rem',
+    flexShrink: 0,
+  },
   dialogActions: {
-    justifyContent: 'left',
-    padding: theme.spacing(2.5),
+    display: 'flex',
+    justifyContent: 'flex-start',
+    padding: '16px 24px',
     gap: theme.spacing(1),
   },
-  overwriteButton: {
-    textTransform: 'none',
-    borderRadius: 999,
-  },
-  cancelButton: {
-    textTransform: 'none',
-    borderRadius: 999,
-  },
-  warningAlert: {
-    borderRadius: '6px',
-  },
 }));
 
 type OverwriteConfirmModalProps = {
   isOpen: boolean;
   onClose: () => void;
-  onConfirm: () => void;
-  fileNames: string[];
+  onConfirm: (filesToUpload: File[]) => void;
+  onBack: () => void;
+  allFiles: File[];
+  duplicateFileNames: string[];
 };
 
 export const OverwriteConfirmModal = ({
   isOpen,
   onClose,
   onConfirm,
-  fileNames,
+  onBack,
+  allFiles,
+  duplicateFileNames,
 }: OverwriteConfirmModalProps) => {
   const classes = useStyles();
   const { t } = useTranslation();
+  const [duplicateAction, setDuplicateAction] = useState<'replace' | 'ignore'>(
+    'replace',
+  );
+
+  useEffect(() => {
+    if (isOpen) setDuplicateAction('replace');
+  }, [isOpen]);
+
+  const duplicateSet = useMemo(
+    () => new Set(duplicateFileNames),
+    [duplicateFileNames],
+  );
+  const newFiles = allFiles.filter(f => !duplicateSet.has(f.name));
+  const duplicateFiles = allFiles.filter(f => duplicateSet.has(f.name));
+
+  const filesToUpload = duplicateAction === 'replace' ? allFiles : newFiles;
+
+  const handleConfirm = () => {
+    onConfirm(filesToUpload);
+    setDuplicateAction('replace');
+  };
+
+  const handleClose = () => {
+    setDuplicateAction('replace');
+    onClose();
+  };
 
   return (
     <Dialog
       open={isOpen}
-      onClose={onClose}
+      onClose={handleClose}
       aria-labelledby="overwrite-confirm-modal-title"
       PaperProps={{
         className: classes.dialogPaper,
@@ -119,11 +170,15 @@ export const OverwriteConfirmModal = ({
     >
       <DialogTitle className={classes.dialogTitle}>
         <Typography component="h2" className={classes.titleText}>
-          {t('notebook.overwrite.modal.title')}
+          {(t as Function)(
+            duplicateFiles.length === 1
+              ? 'notebook.overwrite.modal.title.one'
+              : 'notebook.overwrite.modal.title.other',
+          )}
         </Typography>
         <IconButton
           aria-label={t('common.close')}
-          onClick={onClose}
+          onClick={handleClose}
           className={classes.closeButton}
           size="small"
         >
@@ -132,37 +187,69 @@ export const OverwriteConfirmModal = ({
       </DialogTitle>
 
       <DialogContent className={classes.dialogContent}>
-        <Alert severity="warning" className={classes.warningAlert}>
-          {t('notebook.overwrite.modal.description')}
-        </Alert>
+        <Alert
+          variant="warning"
+          isInline
+          title={(t as Function)(
+            duplicateFiles.length === 1
+              ? 'notebook.overwrite.modal.description.one'
+              : 'notebook.overwrite.modal.description.other',
+            {
+              duplicateCount: duplicateFiles.length,
+              newCount: newFiles.length,
+            },
+          )}
+          className={classes.warningAlert}
+        />
+
+        <div className={classes.radioGroup}>
+          <label>
+            <input
+              type="radio"
+              name="duplicate-action"
+              checked={duplicateAction === 'replace'}
+              onChange={() => setDuplicateAction('replace')}
+            />
+            {t('notebook.overwrite.modal.replace')}
+          </label>
+          <label>
+            <input
+              type="radio"
+              name="duplicate-action"
+              checked={duplicateAction === 'ignore'}
+              onChange={() => setDuplicateAction('ignore')}
+            />
+            {t('notebook.overwrite.modal.ignore')}
+          </label>
+        </div>
 
         <ul className={classes.fileList}>
-          {fileNames.map(name => (
-            <li key={name} className={classes.fileItem}>
-              <FileTypeIcon fileName={name} />
-              <Typography className={classes.fileName}>{name}</Typography>
+          {allFiles.map(file => (
+            <li key={file.name} className={classes.fileItem}>
+              <FileTypeIcon fileName={file.name} />
+              <Typography className={classes.fileName}>{file.name}</Typography>
+              {duplicateSet.has(file.name) && (
+                <ExclamationTriangleIcon className={classes.warningIcon} />
+              )}
             </li>
           ))}
         </ul>
       </DialogContent>
 
-      <DialogActions className={classes.dialogActions}>
+      <div className={classes.dialogActions}>
         <Button
-          variant="contained"
-          color="error"
-          className={classes.overwriteButton}
-          onClick={onConfirm}
+          variant="primary"
+          onClick={handleConfirm}
+          isDisabled={filesToUpload.length === 0}
         >
-          {t('notebook.overwrite.modal.action')}
+          {(t as Function)('notebook.overwrite.modal.action', {
+            count: filesToUpload.length,
+          })}
         </Button>
-        <Button
-          variant="outlined"
-          className={classes.cancelButton}
-          onClick={onClose}
-        >
-          {t('common.cancel')}
+        <Button variant="link" onClick={onBack}>
+          {t('notebook.overwrite.modal.back')}
         </Button>
-      </DialogActions>
+      </div>
     </Dialog>
   );
 };
diff --git a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/UploadResourceScreen.tsx b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/UploadResourceScreen.tsx
index 2653946517a..c3dca669e0a 100644
--- a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/UploadResourceScreen.tsx
+++ b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/components/notebooks/UploadResourceScreen.tsx
@@ -97,7 +97,6 @@ export const UploadResourceScreen = ({
             variant="secondary"
             className={classes.uploadButton}
             icon={<AddCircleOIcon />}
-            iconPosition="end"
             onClick={onUploadClick}
           >
             {t('notebook.view.upload.action')}
diff --git a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/translations/de.ts b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/translations/de.ts
index 37fbec9b75e..3c72a8a837c 100644
--- a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/translations/de.ts
+++ b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/translations/de.ts
@@ -209,10 +209,19 @@ const intelligentAssistantTranslationDe = createTranslationMessages({
     'notebook.document.delete.success':
       '„{{documentName}}" wurde erfolgreich entfernt.',
     'notebook.document.delete.title': 'Ressource entfernen?',
-    'notebook.overwrite.modal.action': 'Überschreiben',
+    'notebook.overwrite.modal.action': 'Hochladen ({{count}})',
+    'notebook.overwrite.modal.back': 'Zurück',
     'notebook.overwrite.modal.description':
-      'Die folgenden Dateien existieren bereits in diesem Notizbuch. Möchten Sie sie mit den neuen Versionen überschreiben?',
-    'notebook.overwrite.modal.title': 'Dateien überschreiben?',
+      '{{duplicateCount}} Dateien existieren bereits in diesem Notizbuch. {{newCount}} neue Ressourcen werden trotzdem hinzugefügt.',
+    'notebook.overwrite.modal.ignore': 'Doppelte Dateien ignorieren',
+    'notebook.overwrite.modal.replace': 'Bestehende Dateien ersetzen',
+    'notebook.overwrite.modal.title': 'Datei existiert bereits',
+    'notebook.overwrite.modal.title.one': 'Datei existiert bereits',
+    'notebook.overwrite.modal.title.other': 'Dateien existieren bereits',
+    'notebook.overwrite.modal.description.one':
+      '{{duplicateCount}} Datei existiert bereits in diesem Notizbuch. {{newCount}} neue Ressourcen werden trotzdem hinzugefügt.',
+    'notebook.overwrite.modal.description.other':
+      '{{duplicateCount}} Dateien existieren bereits in diesem Notizbuch. {{newCount}} neue Ressourcen werden trotzdem hinzugefügt.',
     'notebook.upload.error.fileTooLarge':
       'Upload-Fehler: Dateigröße überschreitet das Limit von 25 MB.',
     'notebook.upload.error.tooManyFiles':
@@ -221,15 +230,19 @@ const intelligentAssistantTranslationDe = createTranslationMessages({
       'Upload-Fehler: Nicht unterstützte Dateitypen gefunden. Bitte laden Sie nur unterstützte Dateitypen hoch.',
     'notebook.upload.failed': 'Hochladen von "{{fileName}}" fehlgeschlagen.',
     'notebook.upload.modal.addButton': 'Hinzufügen ({{count}})',
+    'notebook.upload.modal.addButtonEmpty': 'Hinzufügen',
     'notebook.upload.modal.browseButton': 'Hochladen',
-    'notebook.upload.modal.dragDropTitle': 'Dateien hierher ziehen und ablegen',
+    'notebook.upload.modal.dragDropTitle':
+      'Dateien hierher ziehen und ablegen oder zum Durchsuchen klicken',
     'notebook.upload.modal.infoText':
       'Akzeptierte Dateitypen: .md, .txt, .pdf, .json, .yaml, .log',
+    'notebook.upload.modal.maxFileSize': 'Maximale Dateigröße beträgt 25 MB.',
+    'notebook.upload.modal.supportedFormats': 'Unterstützte Formate:',
     'notebook.upload.modal.removeFile': '{{fileName}} entfernen',
     'notebook.upload.modal.selectedFiles':
       '{{count}} von {{max}} Dateien ausgewählt',
     'notebook.upload.modal.separator': 'oder',
-    'notebook.upload.modal.title': 'Ressource zum Notizbuch hinzufügen',
+    'notebook.upload.modal.title': 'Ressourcen hinzufügen',
     'notebook.view.close': 'Notizbuch schließen',
     'notebook.view.documents.add': 'Hinzufügen',
     'notebook.view.documents.count': '{{count}} Ressourcen',
@@ -243,12 +256,12 @@ const intelligentAssistantTranslationDe = createTranslationMessages({
     'notebook.view.sidebar.expand': 'Seitenleiste ausklappen',
     'notebook.view.sidebar.resize': 'Größe der Seitenleiste ändern',
     'notebook.view.title': 'Unbenanntes Notizbuch',
-    'notebook.view.upload.action': 'Ressource hochladen',
+    'notebook.view.upload.action': 'Ressource hinzufügen',
     'notebook.view.processing.description':
       'Ihre Dateien werden indexiert. Sie können Fragen stellen, sobald die Verarbeitung abgeschlossen ist.',
     'notebook.view.processing.heading': 'Ressourcen werden verarbeitet...',
     'notebook.view.upload.heading':
-      'Laden Sie eine Ressource hoch, um zu beginnen',
+      'Fügen Sie eine Ressource hinzu, um zu beginnen',
     'notebooks.actions.delete': 'Löschen',
     'notebooks.actions.rename': 'Umbenennen',
     'notebooks.card.openAria': 'Notizbuch {{name}} öffnen',
@@ -258,6 +271,9 @@ const intelligentAssistantTranslationDe = createTranslationMessages({
     'notebooks.delete.title': '{{name}} löschen?',
     'notebooks.delete.toast': 'Notizbuch gelöscht!',
     'notebooks.documents': 'Ressourcen',
+    'notebooks.documents.none': 'Keine Ressourcen',
+    'notebooks.documents.one': '1 Ressource',
+    'notebooks.documents.other': '{{count}} Ressourcen',
     'notebooks.empty.action': 'Neues Notizbuch erstellen',
     'notebooks.empty.description':
       'Erstellen Sie ein neues Notizbuch, um Ihre Quellen zu organisieren und KI-gestützte Erkenntnisse zu gewinnen.',
diff --git a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/translations/es.ts b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/translations/es.ts
index 61c78bffdb7..112f6dbaec1 100644
--- a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/translations/es.ts
+++ b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/translations/es.ts
@@ -205,10 +205,19 @@ const intelligentAssistantTranslationEs = createTranslationMessages({
     'notebook.document.delete.success':
       '«{{documentName}}» se eliminó correctamente.',
     'notebook.document.delete.title': '¿Eliminar recurso?',
-    'notebook.overwrite.modal.action': 'Sobrescribir',
+    'notebook.overwrite.modal.action': 'Subir ({{count}})',
+    'notebook.overwrite.modal.back': 'Atrás',
     'notebook.overwrite.modal.description':
-      'Los siguientes archivos ya existen en este cuaderno. ¿Desea sobrescribirlos con las nuevas versiones?',
-    'notebook.overwrite.modal.title': '¿Sobrescribir archivos?',
+      '{{duplicateCount}} archivos ya existen en este cuaderno. {{newCount}} nuevos recursos se agregarán de todos modos.',
+    'notebook.overwrite.modal.ignore': 'Ignorar archivos duplicados',
+    'notebook.overwrite.modal.replace': 'Reemplazar archivos existentes',
+    'notebook.overwrite.modal.title': 'El archivo ya existe',
+    'notebook.overwrite.modal.title.one': 'El archivo ya existe',
+    'notebook.overwrite.modal.title.other': 'Los archivos ya existen',
+    'notebook.overwrite.modal.description.one':
+      '{{duplicateCount}} archivo ya existe en este cuaderno. {{newCount}} nuevos recursos se agregarán de todos modos.',
+    'notebook.overwrite.modal.description.other':
+      '{{duplicateCount}} archivos ya existen en este cuaderno. {{newCount}} nuevos recursos se agregarán de todos modos.',
     'notebook.upload.error.fileTooLarge':
       'Error de carga: el tamaño del archivo supera el límite de 25 MB.',
     'notebook.upload.error.tooManyFiles':
@@ -217,16 +226,20 @@ const intelligentAssistantTranslationEs = createTranslationMessages({
       'Error de carga: se encontraron tipos de archivo no compatibles. Suba solo tipos de archivo compatibles.',
     'notebook.upload.failed': 'Error al subir "{{fileName}}".',
     'notebook.upload.modal.addButton': 'Agregar ({{count}})',
+    'notebook.upload.modal.addButtonEmpty': 'Agregar',
     'notebook.upload.modal.browseButton': 'Subir',
     'notebook.upload.modal.dragDropTitle':
-      'Arrastra y suelta los archivos aquí',
+      'Arrastra y suelta los archivos aquí, o haz clic para explorar',
     'notebook.upload.modal.infoText':
       'Tipos de archivo aceptados: .md, .txt, .pdf, .json, .yaml, .log',
+    'notebook.upload.modal.maxFileSize':
+      'El tamaño máximo del archivo es 25 MB.',
+    'notebook.upload.modal.supportedFormats': 'Formatos compatibles:',
     'notebook.upload.modal.removeFile': 'Eliminar {{fileName}}',
     'notebook.upload.modal.selectedFiles':
       '{{count}} de {{max}} archivos seleccionados',
     'notebook.upload.modal.separator': 'o',
-    'notebook.upload.modal.title': 'Agregar un recurso al cuaderno',
+    'notebook.upload.modal.title': 'Agregar recursos',
     'notebook.view.close': 'Cerrar cuaderno',
     'notebook.view.documents.add': 'Agregar',
     'notebook.view.documents.count': '{{count}} Recursos',
@@ -240,11 +253,11 @@ const intelligentAssistantTranslationEs = createTranslationMessages({
     'notebook.view.sidebar.expand': 'Expandir barra lateral',
     'notebook.view.sidebar.resize': 'Redimensionar barra lateral',
     'notebook.view.title': 'Cuaderno sin título',
-    'notebook.view.upload.action': 'Subir un recurso',
+    'notebook.view.upload.action': 'Agregar un recurso',
     'notebook.view.processing.description':
       'Sus archivos están siendo indexados. Puede comenzar a hacer preguntas una vez que se complete el procesamiento.',
     'notebook.view.processing.heading': 'Procesando recursos...',
-    'notebook.view.upload.heading': 'Sube un recurso para empezar',
+    'notebook.view.upload.heading': 'Agrega un recurso para empezar',
     'notebooks.actions.delete': 'Eliminar',
     'notebooks.actions.rename': 'Renombrar',
     'notebooks.card.openAria': 'Abrir el cuaderno {{name}}',
@@ -254,6 +267,9 @@ const intelligentAssistantTranslationEs = createTranslationMessages({
     'notebooks.delete.title': '¿Eliminar {{name}}?',
     'notebooks.delete.toast': '¡Cuaderno eliminado!',
     'notebooks.documents': 'Recursos',
+    'notebooks.documents.none': 'Sin recursos',
+    'notebooks.documents.one': '1 recurso',
+    'notebooks.documents.other': '{{count}} recursos',
     'notebooks.empty.action': 'Crear un cuaderno nuevo',
     'notebooks.empty.description':
       'Crea un nuevo cuaderno para organizar tus fuentes y generar información con IA.',
diff --git a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/translations/fr.ts b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/translations/fr.ts
index 23599d21420..97f1e837c6f 100644
--- a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/translations/fr.ts
+++ b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/translations/fr.ts
@@ -208,10 +208,19 @@ const intelligentAssistantTranslationFr = createTranslationMessages({
     'notebook.document.delete.success':
       '« {{documentName}} » supprimé avec succès.',
     'notebook.document.delete.title': 'Supprimer la ressource ?',
-    'notebook.overwrite.modal.action': 'Écraser',
+    'notebook.overwrite.modal.action': 'Charger ({{count}})',
+    'notebook.overwrite.modal.back': 'Retour',
     'notebook.overwrite.modal.description':
-      'Les fichiers suivants existent déjà dans ce carnet. Voulez-vous les écraser avec les nouvelles versions ?',
-    'notebook.overwrite.modal.title': 'Écraser les fichiers ?',
+      '{{duplicateCount}} fichiers existent déjà dans ce carnet. {{newCount}} nouvelles ressources seront ajoutées quand même.',
+    'notebook.overwrite.modal.ignore': 'Ignorer les fichiers en double',
+    'notebook.overwrite.modal.replace': 'Remplacer les fichiers existants',
+    'notebook.overwrite.modal.title': 'Le fichier existe déjà',
+    'notebook.overwrite.modal.title.one': 'Le fichier existe déjà',
+    'notebook.overwrite.modal.title.other': 'Les fichiers existent déjà',
+    'notebook.overwrite.modal.description.one':
+      '{{duplicateCount}} fichier existe déjà dans ce carnet. {{newCount}} nouvelles ressources seront ajoutées quand même.',
+    'notebook.overwrite.modal.description.other':
+      '{{duplicateCount}} fichiers existent déjà dans ce carnet. {{newCount}} nouvelles ressources seront ajoutées quand même.',
     'notebook.upload.error.fileTooLarge':
       'Erreur de chargement : la taille du fichier dépasse la limite de 25 Mo.',
     'notebook.upload.error.tooManyFiles':
@@ -220,15 +229,20 @@ const intelligentAssistantTranslationFr = createTranslationMessages({
       'Erreur de chargement : type(s) de fichier non pris en charge. Veuillez charger uniquement des types de fichiers pris en charge.',
     'notebook.upload.failed': 'Échec du chargement de "{{fileName}}".',
     'notebook.upload.modal.addButton': 'Ajouter ({{count}})',
+    'notebook.upload.modal.addButtonEmpty': 'Ajouter',
     'notebook.upload.modal.browseButton': 'Charger',
-    'notebook.upload.modal.dragDropTitle': 'Glissez-déposez les fichiers ici',
+    'notebook.upload.modal.dragDropTitle':
+      'Glissez-déposez les fichiers ici ou cliquez pour parcourir',
     'notebook.upload.modal.infoText':
       'Types de fichiers acceptés : .md, .txt, .pdf, .json, .yaml, .log',
+    'notebook.upload.modal.maxFileSize':
+      'La taille maximale du fichier est de 25 Mo.',
+    'notebook.upload.modal.supportedFormats': 'Formats pris en charge :',
     'notebook.upload.modal.removeFile': 'Supprimer {{fileName}}',
     'notebook.upload.modal.selectedFiles':
       '{{count}} sur {{max}} fichiers sélectionnés',
     'notebook.upload.modal.separator': 'ou',
-    'notebook.upload.modal.title': 'Ajouter une ressource au carnet',
+    'notebook.upload.modal.title': 'Ajouter des ressources',
     'notebook.view.close': 'Fermer le carnet',
     'notebook.view.documents.add': 'Ajouter',
     'notebook.view.documents.count': '{{count}} Ressources',
@@ -243,11 +257,11 @@ const intelligentAssistantTranslationFr = createTranslationMessages({
     'notebook.view.sidebar.expand': 'Développer la barre latérale',
     'notebook.view.sidebar.resize': 'Redimensionner la barre latérale',
     'notebook.view.title': 'Carnet sans titre',
-    'notebook.view.upload.action': 'Charger une ressource',
+    'notebook.view.upload.action': 'Ajouter une ressource',
     'notebook.view.processing.description':
       'Vos fichiers sont en cours d’indexation. Vous pourrez poser des questions une fois le traitement terminé.',
     'notebook.view.processing.heading': 'Traitement des ressources...',
-    'notebook.view.upload.heading': 'Chargez une ressource pour commencer',
+    'notebook.view.upload.heading': 'Ajoutez une ressource pour commencer',
     'notebooks.actions.delete': 'Supprimer',
     'notebooks.actions.rename': 'Renommer',
     'notebooks.card.openAria': 'Ouvrir le carnet {{name}}',
@@ -257,6 +271,9 @@ const intelligentAssistantTranslationFr = createTranslationMessages({
     'notebooks.delete.title': 'Supprimer {{name}} ?',
     'notebooks.delete.toast': 'Carnet supprimé !',
     'notebooks.documents': 'Ressources',
+    'notebooks.documents.none': 'Aucune ressource',
+    'notebooks.documents.one': '1 ressource',
+    'notebooks.documents.other': '{{count}} ressources',
     'notebooks.empty.action': 'Créer un nouveau carnet',
     'notebooks.empty.description':
       'Créez un nouveau carnet pour organiser vos sources et générer des informations alimentées par l’IA.',
diff --git a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/translations/it.ts b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/translations/it.ts
index 1ab1f5e4196..5b7bb31bc73 100644
--- a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/translations/it.ts
+++ b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/translations/it.ts
@@ -206,10 +206,19 @@ const intelligentAssistantTranslationIt = createTranslationMessages({
     'notebook.document.delete.success':
       '«{{documentName}}» rimosso con successo.',
     'notebook.document.delete.title': 'Rimuovere la risorsa?',
-    'notebook.overwrite.modal.action': 'Sovrascrivi',
+    'notebook.overwrite.modal.action': 'Carica ({{count}})',
+    'notebook.overwrite.modal.back': 'Indietro',
     'notebook.overwrite.modal.description':
-      'I seguenti file esistono già in questo quaderno. Vuoi sovrascriverli con le nuove versioni?',
-    'notebook.overwrite.modal.title': 'Sovrascrivere i file?',
+      '{{duplicateCount}} file esistono già in questo quaderno. {{newCount}} nuove risorse verranno aggiunte comunque.',
+    'notebook.overwrite.modal.ignore': 'Ignora file duplicati',
+    'notebook.overwrite.modal.replace': 'Sostituisci file esistenti',
+    'notebook.overwrite.modal.title': 'Il file esiste già',
+    'notebook.overwrite.modal.title.one': 'Il file esiste già',
+    'notebook.overwrite.modal.title.other': 'I file esistono già',
+    'notebook.overwrite.modal.description.one':
+      '{{duplicateCount}} file esiste già in questo quaderno. {{newCount}} nuove risorse verranno aggiunte comunque.',
+    'notebook.overwrite.modal.description.other':
+      '{{duplicateCount}} file esistono già in questo quaderno. {{newCount}} nuove risorse verranno aggiunte comunque.',
     'notebook.upload.error.fileTooLarge':
       'Errore di caricamento: la dimensione del file supera il limite di 25 MB.',
     'notebook.upload.error.tooManyFiles':
@@ -218,15 +227,20 @@ const intelligentAssistantTranslationIt = createTranslationMessages({
       'Errore di caricamento: trovati tipi di file non supportati. Caricare solo tipi di file supportati.',
     'notebook.upload.failed': 'Caricamento di "{{fileName}}" non riuscito.',
     'notebook.upload.modal.addButton': 'Aggiungi ({{count}})',
+    'notebook.upload.modal.addButtonEmpty': 'Aggiungi',
     'notebook.upload.modal.browseButton': 'Carica',
-    'notebook.upload.modal.dragDropTitle': 'Trascina e rilascia i file qui',
+    'notebook.upload.modal.dragDropTitle':
+      'Trascina e rilascia i file qui o fai clic per sfogliare',
     'notebook.upload.modal.infoText':
       'Tipi di file accettati: .md, .txt, .pdf, .json, .yaml, .log',
+    'notebook.upload.modal.maxFileSize':
+      'La dimensione massima del file è 25 MB.',
+    'notebook.upload.modal.supportedFormats': 'Formati supportati:',
     'notebook.upload.modal.removeFile': 'Rimuovi {{fileName}}',
     'notebook.upload.modal.selectedFiles':
       '{{count}} di {{max}} file selezionati',
     'notebook.upload.modal.separator': 'o',
-    'notebook.upload.modal.title': 'Aggiungi una risorsa al quaderno',
+    'notebook.upload.modal.title': 'Aggiungi risorse',
     'notebook.view.close': 'Chiudi quaderno',
     'notebook.view.documents.add': 'Aggiungi',
     'notebook.view.documents.count': '{{count}} Risorse',
@@ -241,11 +255,11 @@ const intelligentAssistantTranslationIt = createTranslationMessages({
     'notebook.view.sidebar.expand': 'Espandi barra laterale',
     'notebook.view.sidebar.resize': 'Ridimensiona barra laterale',
     'notebook.view.title': 'Quaderno senza titolo',
-    'notebook.view.upload.action': 'Carica una risorsa',
+    'notebook.view.upload.action': 'Aggiungi una risorsa',
     'notebook.view.processing.description':
       'I tuoi file sono in fase di indicizzazione. Potrai iniziare a fare domande una volta completata l’elaborazione.',
     'notebook.view.processing.heading': 'Elaborazione delle risorse...',
-    'notebook.view.upload.heading': 'Carica una risorsa per iniziare',
+    'notebook.view.upload.heading': 'Aggiungi una risorsa per iniziare',
     'notebooks.actions.delete': 'Elimina',
     'notebooks.actions.rename': 'Rinomina',
     'notebooks.card.openAria': 'Apri il taccuino {{name}}',
@@ -255,6 +269,9 @@ const intelligentAssistantTranslationIt = createTranslationMessages({
     'notebooks.delete.title': 'Eliminare {{name}}?',
     'notebooks.delete.toast': 'Quaderno eliminato!',
     'notebooks.documents': 'Risorse',
+    'notebooks.documents.none': 'Nessuna risorsa',
+    'notebooks.documents.one': '1 risorsa',
+    'notebooks.documents.other': '{{count}} risorse',
     'notebooks.empty.action': 'Crea un nuovo quaderno',
     'notebooks.empty.description':
       'Crea un nuovo quaderno per organizzare le tue fonti e generare insight basati su IA.',
diff --git a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/translations/ja.ts b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/translations/ja.ts
index d86e572a830..15c16c9198f 100644
--- a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/translations/ja.ts
+++ b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/translations/ja.ts
@@ -202,10 +202,19 @@ const intelligentAssistantTranslationJa = createTranslationMessages({
     'notebook.document.delete.success':
       '「{{documentName}}」が正常に削除されました。',
     'notebook.document.delete.title': 'リソースを削除しますか？',
-    'notebook.overwrite.modal.action': '上書き',
+    'notebook.overwrite.modal.action': 'アップロード ({{count}})',
+    'notebook.overwrite.modal.back': '戻る',
     'notebook.overwrite.modal.description':
-      '以下のファイルはこのノートブックに既に存在します。新しいバージョンで上書きしますか？',
-    'notebook.overwrite.modal.title': 'ファイルを上書きしますか？',
+      '{{duplicateCount}} 件のファイルがこのノートブックに既に存在します。{{newCount}} 件の新しいリソースはそのまま追加されます。',
+    'notebook.overwrite.modal.ignore': '重複ファイルを無視',
+    'notebook.overwrite.modal.replace': '既存のファイルを置換',
+    'notebook.overwrite.modal.title': 'ファイルが既に存在します',
+    'notebook.overwrite.modal.title.one': 'ファイルが既に存在します',
+    'notebook.overwrite.modal.title.other': 'ファイルが既に存在します',
+    'notebook.overwrite.modal.description.one':
+      '{{duplicateCount}} 件のファイルがこのノートブックに既に存在します。{{newCount}} 件の新しいリソースはそのまま追加されます。',
+    'notebook.overwrite.modal.description.other':
+      '{{duplicateCount}} 件のファイルがこのノートブックに既に存在します。{{newCount}} 件の新しいリソースはそのまま追加されます。',
     'notebook.upload.error.fileTooLarge':
       'アップロードエラー: ファイルサイズが 25 MB の制限を超えています。',
     'notebook.upload.error.tooManyFiles':
@@ -214,15 +223,19 @@ const intelligentAssistantTranslationJa = createTranslationMessages({
       'アップロードエラー: サポートされていないファイル形式が見つかりました。サポートされているファイル形式のみをアップロードしてください。',
     'notebook.upload.failed': '「{{fileName}}」のアップロードに失敗しました。',
     'notebook.upload.modal.addButton': '追加 ({{count}})',
+    'notebook.upload.modal.addButtonEmpty': '追加',
     'notebook.upload.modal.browseButton': 'アップロード',
-    'notebook.upload.modal.dragDropTitle': 'ここにファイルをドラッグ&ドロップ',
+    'notebook.upload.modal.dragDropTitle':
+      'ここにファイルをドラッグ&ドロップ、またはクリックして参照',
     'notebook.upload.modal.infoText':
       '対応ファイル形式: .md, .txt, .pdf, .json, .yaml, .log',
+    'notebook.upload.modal.maxFileSize': '最大ファイルサイズは 25 MB です。',
+    'notebook.upload.modal.supportedFormats': 'サポートされている形式:',
     'notebook.upload.modal.removeFile': '{{fileName}} を削除',
     'notebook.upload.modal.selectedFiles':
       '{{max}} 件中 {{count}} 件のファイルを選択',
     'notebook.upload.modal.separator': 'または',
-    'notebook.upload.modal.title': 'ノートブックにリソースを追加',
+    'notebook.upload.modal.title': 'リソースを追加',
     'notebook.view.close': 'ノートブックを閉じる',
     'notebook.view.documents.add': '追加',
     'notebook.view.documents.count': '{{count}} 件のリソース',
@@ -236,12 +249,11 @@ const intelligentAssistantTranslationJa = createTranslationMessages({
     'notebook.view.sidebar.expand': 'サイドバーを展開する',
     'notebook.view.sidebar.resize': 'サイドバーのサイズを変更する',
     'notebook.view.title': '無題のノートブック',
-    'notebook.view.upload.action': 'リソースをアップロード',
+    'notebook.view.upload.action': 'リソースを追加',
     'notebook.view.processing.description':
       'ファイルをインデックスしています。処理が完了すると質問を開始できます。',
     'notebook.view.processing.heading': 'リソースを処理中...',
-    'notebook.view.upload.heading':
-      'リソースをアップロードして開始してください',
+    'notebook.view.upload.heading': 'リソースを追加して開始してください',
     'notebooks.actions.delete': '削除',
     'notebooks.actions.rename': '名前の変更',
     'notebooks.card.openAria': 'ノートブック {{name}} を開く',
@@ -251,6 +263,9 @@ const intelligentAssistantTranslationJa = createTranslationMessages({
     'notebooks.delete.title': '{{name}} を削除しますか?',
     'notebooks.delete.toast': 'ノートブックを削除しました！',
     'notebooks.documents': 'リソース',
+    'notebooks.documents.none': 'リソースなし',
+    'notebooks.documents.one': '1 件のリソース',
+    'notebooks.documents.other': '{{count}} 件のリソース',
     'notebooks.empty.action': '新しいノートブックを作成',
     'notebooks.empty.description':
       '新しいノートブックを作成してソースを整理し、AI による洞察を生成します。',
diff --git a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/translations/ref.ts b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/translations/ref.ts
index aefd87cd1a4..af46fcf13ea 100644
--- a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/translations/ref.ts
+++ b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/translations/ref.ts
@@ -36,6 +36,9 @@ export const intelligentAssistantMessages = {
     'Start a new notebook to organize your sources and generate AI-powered insights.',
   'notebooks.empty.action': 'Create a new notebook',
   'notebooks.documents': 'Resources',
+  'notebooks.documents.none': 'No resources',
+  'notebooks.documents.one': '1 resource',
+  'notebooks.documents.other': '{{count}} resources',
   'notebooks.actions.rename': 'Rename',
   'notebooks.actions.delete': 'Delete',
   'notebooks.rename.inline.tooltip': 'Click to rename',
@@ -61,8 +64,8 @@ export const intelligentAssistantMessages = {
   'notebook.view.close': 'Close notebook',
   'notebook.view.documents.count': '{{count}} Resources',
   'notebook.view.documents.add': 'Add',
-  'notebook.view.upload.heading': 'Upload a resource to get started',
-  'notebook.view.upload.action': 'Upload a resource',
+  'notebook.view.upload.heading': 'Add a resource to get started',
+  'notebook.view.upload.action': 'Add a resource',
   'notebook.view.processing.heading': 'Processing resources...',
   'notebook.view.processing.description':
     'Your files are being indexed. You can start asking questions once processing is complete.',
@@ -80,14 +83,18 @@ export const intelligentAssistantMessages = {
   'notebook.upload.failed': '"{{fileName}}" upload failed.',
 
   // Notebook upload modal
-  'notebook.upload.modal.title': 'Add a resource to Notebook',
-  'notebook.upload.modal.dragDropTitle': 'Drag and drop files here',
+  'notebook.upload.modal.title': 'Add resources',
+  'notebook.upload.modal.dragDropTitle':
+    'Drag and drop files here, or click to browse',
   'notebook.upload.modal.browseButton': 'Upload',
   'notebook.upload.modal.separator': 'or',
   'notebook.upload.modal.infoText':
     'Accepted file types: .md, .txt, .pdf, .json, .yaml, .log',
+  'notebook.upload.modal.supportedFormats': 'Supported formats:',
+  'notebook.upload.modal.maxFileSize': 'Maximum file size is 25 MB.',
   'notebook.upload.modal.selectedFiles': '{{count}} of {{max}} files selected',
   'notebook.upload.modal.addButton': 'Add ({{count}})',
+  'notebook.upload.modal.addButtonEmpty': 'Add',
   'notebook.upload.modal.removeFile': 'Remove {{fileName}}',
   'notebook.upload.error.unsupportedType':
     'Upload error: Unsupported file type(s) found. Please upload only supported file types.',
@@ -97,10 +104,19 @@ export const intelligentAssistantMessages = {
     'Upload error: Maximum of {{max}} files allowed.',
 
   // Notebook overwrite modal
-  'notebook.overwrite.modal.title': 'Overwrite Files?',
+  'notebook.overwrite.modal.title': 'File already exists',
+  'notebook.overwrite.modal.title.one': 'File already exists',
+  'notebook.overwrite.modal.title.other': 'Files already exist',
   'notebook.overwrite.modal.description':
-    'The following files already exist in this notebook. Do you want to overwrite them with the new versions?',
-  'notebook.overwrite.modal.action': 'Overwrite',
+    '{{duplicateCount}} files already exist in this notebook. {{newCount}} new resources will be added regardless.',
+  'notebook.overwrite.modal.description.one':
+    '{{duplicateCount}} file already exists in this notebook. {{newCount}} new resources will be added regardless.',
+  'notebook.overwrite.modal.description.other':
+    '{{duplicateCount}} files already exist in this notebook. {{newCount}} new resources will be added regardless.',
+  'notebook.overwrite.modal.replace': 'Replace existing files',
+  'notebook.overwrite.modal.ignore': 'Ignore duplicated files',
+  'notebook.overwrite.modal.action': 'Upload ({{count}})',
+  'notebook.overwrite.modal.back': 'Back',
   'notebook.document.delete': 'Delete',
   'notebook.document.delete.title': 'Remove resource?',
   'notebook.document.delete.description':
diff --git a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/utils/__tests__/notebook-upload-runner.test.ts b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/utils/__tests__/notebook-upload-runner.test.ts
new file mode 100644
index 00000000000..2d8767f59fb
--- /dev/null
+++ b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/utils/__tests__/notebook-upload-runner.test.ts
@@ -0,0 +1,104 @@
+/*
+ * Copyright Red Hat, Inc.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *     http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+import { runFileUploads } from '../notebook-upload-runner';
+
+const createFile = (name: string) =>
+  new File(['content'], name, { type: 'text/plain' });
+
+describe('runFileUploads', () => {
+  const sessionId = 'test-session';
+  const files = [createFile('a.txt'), createFile('b.txt')];
+
+  it('should call onUploading with all files', () => {
+    const mutation = {
+      mutateAsync: jest.fn().mockResolvedValue({ document_id: 'doc-1' }),
+    };
+    const onUploading = jest.fn();
+
+    runFileUploads(mutation, sessionId, files, { onUploading });
+
+    expect(onUploading).toHaveBeenCalledWith(files);
+  });
+
+  it('should call mutateAsync for each file with sessionId', () => {
+    const mutation = {
+      mutateAsync: jest.fn().mockResolvedValue({ document_id: 'doc-1' }),
+    };
+
+    runFileUploads(mutation, sessionId, files, {});
+
+    expect(mutation.mutateAsync).toHaveBeenCalledTimes(2);
+    expect(mutation.mutateAsync).toHaveBeenCalledWith({
+      sessionId,
+      file: files[0],
+    });
+    expect(mutation.mutateAsync).toHaveBeenCalledWith({
+      sessionId,
+      file: files[1],
+    });
+  });
+
+  it('should call onStarted with fileName and documentId on success', async () => {
+    const mutation = {
+      mutateAsync: jest
+        .fn()
+        .mockResolvedValueOnce({ document_id: 'doc-a' })
+        .mockResolvedValueOnce({ document_id: 'doc-b' }),
+    };
+    const onStarted = jest.fn();
+
+    runFileUploads(mutation, sessionId, files, { onStarted });
+
+    await new Promise(resolve => setTimeout(resolve, 0));
+
+    expect(onStarted).toHaveBeenCalledTimes(2);
+    expect(onStarted).toHaveBeenCalledWith({
+      fileName: 'a.txt',
+      documentId: 'doc-a',
+    });
+    expect(onStarted).toHaveBeenCalledWith({
+      fileName: 'b.txt',
+      documentId: 'doc-b',
+    });
+  });
+
+  it('should call onFailed with fileName on error', async () => {
+    const mutation = {
+      mutateAsync: jest
+        .fn()
+        .mockResolvedValueOnce({ document_id: 'doc-a' })
+        .mockRejectedValueOnce(new Error('upload failed')),
+    };
+    const onFailed = jest.fn();
+
+    runFileUploads(mutation, sessionId, files, { onFailed });
+
+    await new Promise(resolve => setTimeout(resolve, 0));
+
+    expect(onFailed).toHaveBeenCalledTimes(1);
+    expect(onFailed).toHaveBeenCalledWith('b.txt');
+  });
+
+  it('should work with no callbacks provided', () => {
+    const mutation = {
+      mutateAsync: jest.fn().mockResolvedValue({ document_id: 'doc-1' }),
+    };
+
+    expect(() => runFileUploads(mutation, sessionId, files, {})).not.toThrow();
+    expect(mutation.mutateAsync).toHaveBeenCalledTimes(2);
+  });
+});
diff --git a/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/utils/notebook-upload-runner.ts b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/utils/notebook-upload-runner.ts
new file mode 100644
index 00000000000..baca941149b
--- /dev/null
+++ b/workspaces/intelligent-assistant/plugins/intelligent-assistant/src/utils/notebook-upload-runner.ts
@@ -0,0 +1,50 @@
+/*
+ * Copyright Red Hat, Inc.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *     http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+type UploadMutation = {
+  mutateAsync: (args: {
+    sessionId: string;
+    file: File;
+  }) => Promise<{ document_id: string }>;
+};
+
+type UploadCallbacks = {
+  onUploading?: (files: File[]) => void;
+  onStarted?: (info: { fileName: string; documentId: string }) => void;
+  onFailed?: (fileName: string) => void;
+};
+
+export function runFileUploads(
+  mutation: UploadMutation,
+  sessionId: string,
+  files: File[],
+  callbacks: UploadCallbacks,
+): void {
+  callbacks.onUploading?.(files);
+  for (const file of files) {
+    mutation
+      .mutateAsync({ sessionId, file })
+      .then(data => {
+        callbacks.onStarted?.({
+          fileName: file.name,
+          documentId: data.document_id,
+        });
+      })
+      .catch(() => {
+        callbacks.onFailed?.(file.name);
+      });
+  }
+}