diff --git a/ui-participant/src/hub/documents/DocumentLibrary.test.tsx b/ui-participant/src/hub/documents/DocumentLibrary.test.tsx
index 70a17f1256..a15bedc39d 100644
--- a/ui-participant/src/hub/documents/DocumentLibrary.test.tsx
+++ b/ui-participant/src/hub/documents/DocumentLibrary.test.tsx
@@ -1,7 +1,7 @@
 import { asMockedFn, MockI18nProvider, setupRouterTest, mockParticipantFile } from '@juniper/ui-core'
 import { usePortalEnv } from 'providers/PortalProvider'
-import { mockUsePortalEnv } from 'test-utils/test-portal-factory'
-import { render, screen, waitFor } from '@testing-library/react'
+import { mockPortal, mockUsePortalEnv } from 'test-utils/test-portal-factory'
+import { act, render, screen, waitFor } from '@testing-library/react'
 import React from 'react'
 import DocumentLibrary from './DocumentLibrary'
 import { useActiveUser } from 'providers/ActiveUserProvider'
@@ -16,7 +16,8 @@ jest.mock('providers/ActiveUserProvider', () => ({
 }))
 
 jest.mock('api/api', () => ({
-  listParticipantFiles: jest.fn()
+  listParticipantFiles: jest.fn(),
+  getPortal: jest.fn()
 }))
 
 beforeEach(() => {
@@ -58,6 +59,11 @@ describe('DocumentLibrary', () => {
       expect(screen.getByText('file1.pdf')).toBeInTheDocument()
     })
 
+    await act(async () => {
+      screen.getByText('Options').click()
+    })
+
+    expect(screen.getByText('Delete')).toBeInTheDocument()
     expect(screen.getByText('{documentDownloadButton}')).toBeInTheDocument()
   })
 
@@ -106,4 +112,71 @@ describe('DocumentLibrary', () => {
     //note: this is looking at the i18n key for the task name
     expect(screen.getByText('{researchSurvey1:1}')).toBeInTheDocument()
   })
+
+  it('allows deleting documents that dont have any associated answers', async () => {
+    asMockedFn(Api.listParticipantFiles).mockResolvedValue([
+      mockParticipantFile('file1.pdf')
+    ])
+
+    asMockedFn(Api.getPortal).mockResolvedValue(mockPortal())
+
+    const { RoutedComponent } = setupRouterTest(
+      <MockI18nProvider><DocumentLibrary/></MockI18nProvider>
+    )
+    render(RoutedComponent)
+
+    await waitFor(() => {
+      expect(screen.getByText('file1.pdf')).toBeInTheDocument()
+    })
+
+    await act(async () => {
+      screen.getByText('Options').click()
+    })
+
+    await act(async () => {
+      screen.getByText('Delete').click()
+    })
+
+    await waitFor(() => {
+      expect(screen.queryByText('Are you sure you want to delete this document?', { exact: false })).toBeInTheDocument()
+    })
+  })
+
+  it('shows a warning message when trying to delete a document that has associated answers', async () => {
+    asMockedFn(Api.listParticipantFiles).mockResolvedValue([
+      mockParticipantFile('file1.pdf', [{
+        format: 'FILE_NAME',
+        surveyVersion: 1,
+        stringValue: 'file1.pdf',
+        questionStableId: 'question1',
+        surveyResponseId: 'taskId1'
+      }])
+    ])
+
+    asMockedFn(Api.getPortal).mockResolvedValue(mockPortal())
+
+    const { RoutedComponent } = setupRouterTest(
+      <MockI18nProvider><DocumentLibrary/></MockI18nProvider>
+    )
+    render(RoutedComponent)
+
+    await waitFor(() => {
+      expect(screen.getByText('file1.pdf')).toBeInTheDocument()
+    })
+
+    await act(async () => {
+      screen.getByText('Options').click()
+    })
+
+    await act(async () => {
+      screen.getByText('Delete').click()
+    })
+
+    await waitFor(() => {
+      expect(screen.queryByText('' +
+          'This document is currently shared in response to at least one survey. ' +
+          'Please remove it from the survey response(s) before deleting it.')
+      ).toBeInTheDocument()
+    })
+  })
 })
diff --git a/ui-participant/src/hub/documents/DocumentLibrary.tsx b/ui-participant/src/hub/documents/DocumentLibrary.tsx
index ff5a38a0c0..4be19a50ba 100644
--- a/ui-participant/src/hub/documents/DocumentLibrary.tsx
+++ b/ui-participant/src/hub/documents/DocumentLibrary.tsx
@@ -203,7 +203,9 @@ const FileOptionsDropdown = ({ studyEnvParams, participantFile, enrollee, loadDo
       onHide={() => setShowConfirmDelete(false)} size={'lg'} animation={true}>
       <Modal.Header>
         <Modal.Title>
-          <h2 className="fw-bold pb-0 mb-0">Are you sure?</h2>
+          <h2 className="fw-bold pb-0 mb-0">
+            {participantFile.associatedAnswers.length === 0 ? 'Are you sure?' : 'This document is in use'}
+          </h2>
         </Modal.Title>
       </Modal.Header>
       <Modal.Body>
diff --git a/ui-participant/src/test-utils/test-portal-factory.tsx b/ui-participant/src/test-utils/test-portal-factory.tsx
index 37e41b6dae..3134fbf92e 100644
--- a/ui-participant/src/test-utils/test-portal-factory.tsx
+++ b/ui-participant/src/test-utils/test-portal-factory.tsx
@@ -108,7 +108,8 @@ export const mockLocalSiteContent = (): LocalSiteContent => {
     landingPage: mockHtmlPage(),
     navLogoCleanFileName: 'navLogo.png',
     navLogoVersion: 1,
-    languageTextOverrides: []
+    languageTextOverrides: [],
+    primaryBrandColor: '#000000'
   }
 }