diff --git a/client/src/components/Chat/Input/Files/FileContainer.tsx b/client/src/components/Chat/Input/Files/FileContainer.tsx
index f146277e051..2386394a132 100644
--- a/client/src/components/Chat/Input/Files/FileContainer.tsx
+++ b/client/src/components/Chat/Input/Files/FileContainer.tsx
@@ -80,7 +80,7 @@ const FileContainer = ({
     'focus-visible:outline-hidden focus-visible:ring-2 focus-visible:ring-inset focus-visible:ring-text-primary';
 
   const details = (
-    <div className="w-56 p-1.5">
+    <div className="w-56 max-w-full p-1.5">
       <div className="flex flex-row items-center gap-2">
         <FilePreview file={file} fileType={fileType} className="relative" />
         <div className="overflow-hidden">
diff --git a/client/src/components/Chat/Messages/Content/Container.tsx b/client/src/components/Chat/Messages/Content/Container.tsx
index 945d8ca1d51..db97b17e17a 100644
--- a/client/src/components/Chat/Messages/Content/Container.tsx
+++ b/client/src/components/Chat/Messages/Content/Container.tsx
@@ -1,18 +1,8 @@
-import { TMessage } from 'librechat-data-provider';
+import type { TMessage } from 'librechat-data-provider';
 import MessageQuotes from './MessageQuotes';
 import SkillPills from './SkillPills';
-import Files from './Files';
 
-const Container = ({
-  children,
-  message,
-  hideFiles = false,
-}: {
-  children: React.ReactNode;
-  message?: TMessage;
-  /** The message editor renders the files itself, as chips that can be removed. */
-  hideFiles?: boolean;
-}) => (
+const Container = ({ children, message }: { children: React.ReactNode; message?: TMessage }) => (
   <div
     data-message-text
     className="flex min-h-[1.25rem] flex-col items-start gap-3 overflow-visible [[data-message-text]+&]:mt-5"
@@ -21,7 +11,6 @@ const Container = ({
     {message?.isCreatedByUser === true && (
       <>
         <MessageQuotes quotes={message.quotes} />
-        {!hideFiles && <Files message={message} />}
         <SkillPills skills={message.alwaysAppliedSkills} source="always-apply" />
         <SkillPills skills={message.manualSkills} source="manual" />
       </>
diff --git a/client/src/components/Chat/Messages/Content/EditMessage.tsx b/client/src/components/Chat/Messages/Content/EditMessage.tsx
index 1c9c397f5ea..e46a81fc90e 100644
--- a/client/src/components/Chat/Messages/Content/EditMessage.tsx
+++ b/client/src/components/Chat/Messages/Content/EditMessage.tsx
@@ -250,7 +250,7 @@ const EditMessage = ({
   );
 
   return (
-    <Container message={message} hideFiles={isUserTurn}>
+    <Container message={message}>
       <section
         aria-label={localize('com_ui_edit_message')}
         className="mt-2 flex w-full flex-col gap-2"
diff --git a/client/src/components/Chat/Messages/Content/Files.tsx b/client/src/components/Chat/Messages/Content/Files.tsx
index f5deee31f64..1497f123317 100644
--- a/client/src/components/Chat/Messages/Content/Files.tsx
+++ b/client/src/components/Chat/Messages/Content/Files.tsx
@@ -36,6 +36,8 @@ const Files = ({ message }: { message?: TMessage }) => {
           <FileContainer
             key={file.file_id}
             file={file as TFile}
+            buttonClassName="border-surface-user-message max-w-full bg-transparent"
+            containerClassName="max-w-full"
             onClick={() => setSelectedFile(file)}
           />
         ))}
@@ -44,6 +46,7 @@ const Files = ({ message }: { message?: TMessage }) => {
           <Image
             key={file.file_id}
             alignRight
+            className="border-surface-user-message mt-0 shadow-none"
             imagePath={file.preview ?? file.filepath ?? ''}
             height={file.height ?? 1920}
             width={file.width ?? 1080}
diff --git a/client/src/components/Chat/Messages/Content/Parts/PendingSteers.tsx b/client/src/components/Chat/Messages/Content/Parts/PendingSteers.tsx
index acd2dcb856c..07401615f8c 100644
--- a/client/src/components/Chat/Messages/Content/Parts/PendingSteers.tsx
+++ b/client/src/components/Chat/Messages/Content/Parts/PendingSteers.tsx
@@ -5,7 +5,7 @@ import { Button, TooltipAnchor } from '@librechat/client';
 import { QueryKeys, type TMessage } from 'librechat-data-provider';
 import type { SteerReceiptState } from '~/components/Chat/Steering/Receipt';
 import useSteerCancel, { useSteerMoveToQueue, useSteerRehome } from '~/hooks/Chat/useSteerCancel';
-import { getMessageRowWidthClass } from '~/components/Chat/Messages/ui/MessageRow';
+import { getMessageRowWidthClass } from '~/components/Chat/Messages/ui/width';
 import EscalateNowButton from '~/components/Chat/Input/EscalateNowButton';
 import { useMessagePartsHost } from '~/Providers/MessagePartsHostContext';
 import useSteerEscalate from '~/hooks/Chat/useSteerEscalate';
diff --git a/client/src/components/Chat/Messages/Content/__tests__/Files.test.tsx b/client/src/components/Chat/Messages/Content/__tests__/Files.test.tsx
index 08b36f767f8..802f3e9f527 100644
--- a/client/src/components/Chat/Messages/Content/__tests__/Files.test.tsx
+++ b/client/src/components/Chat/Messages/Content/__tests__/Files.test.tsx
@@ -11,13 +11,25 @@ jest.mock('~/Providers', () => ({
 jest.mock(
   '~/components/Chat/Input/Files/FileContainer',
   () =>
-    ({ onClick }: { onClick: () => void }) => <button onClick={onClick}>file action</button>,
+    ({ onClick, buttonClassName }: { onClick: () => void; buttonClassName?: string }) => (
+      <button className={buttonClassName} onClick={onClick}>
+        file action
+      </button>
+    ),
+);
+jest.mock(
+  '../Image',
+  () =>
+    ({ alignRight, className }: { alignRight?: boolean; className?: string }) => (
+      <div
+        data-testid="image-preview"
+        data-aligned-right={String(alignRight)}
+        className={className}
+      >
+        image preview
+      </div>
+    ),
 );
-jest.mock('../Image', () => ({ alignRight }: { alignRight?: boolean }) => (
-  <div data-testid="image-preview" data-aligned-right={String(alignRight)}>
-    image preview
-  </div>
-));
 jest.mock(
   '../FilePreviewDialog',
   () =>
@@ -40,6 +52,16 @@ it('exposes extracted image text without changing ordinary image previews', () =
   );
   expect(screen.getAllByText('image preview')).toHaveLength(1);
   expect(screen.getByTestId('image-preview')).toHaveAttribute('data-aligned-right', 'true');
+  expect(screen.getByText('file action')).toHaveClass(
+    'border-surface-user-message',
+    'max-w-full',
+    'bg-transparent',
+  );
+  expect(screen.getByTestId('image-preview')).toHaveClass(
+    'border-surface-user-message',
+    'mt-0',
+    'shadow-none',
+  );
   fireEvent.click(screen.getByText('file action'));
   expect(screen.getByText('preview: text')).toBeInTheDocument();
 });
diff --git a/client/src/components/Chat/Messages/MessageParts.tsx b/client/src/components/Chat/Messages/MessageParts.tsx
index 2c6b0315018..f5a8f782a60 100644
--- a/client/src/components/Chat/Messages/MessageParts.tsx
+++ b/client/src/components/Chat/Messages/MessageParts.tsx
@@ -116,6 +116,7 @@ function MessageParts(props: TMessageProps) {
     >
       <div className="m-auto justify-center px-4 py-3 sm:px-0">
         <MessageRow
+          message={message}
           id={messageId ?? ''}
           icon={author.icon}
           label={author.label}
diff --git a/client/src/components/Chat/Messages/PendingTurn.tsx b/client/src/components/Chat/Messages/PendingTurn.tsx
index 7651a490580..eb85aa2ac90 100644
--- a/client/src/components/Chat/Messages/PendingTurn.tsx
+++ b/client/src/components/Chat/Messages/PendingTurn.tsx
@@ -113,6 +113,7 @@ export default function PendingTurn({
     >
       <div className="m-auto justify-center px-4 py-3 sm:px-0">
         <MessageRow
+          message={message}
           icon={<MessageIcon iconData={iconData} />}
           label={label}
           timestamp={reveal.revealedAt}
diff --git a/client/src/components/Chat/Messages/SearchMessage.tsx b/client/src/components/Chat/Messages/SearchMessage.tsx
index 13f0bbf05a7..e81eab67c7c 100644
--- a/client/src/components/Chat/Messages/SearchMessage.tsx
+++ b/client/src/components/Chat/Messages/SearchMessage.tsx
@@ -2,12 +2,13 @@ import { memo, useMemo } from 'react';
 import { useRecoilValue } from 'recoil';
 import type { TMessage } from 'librechat-data-provider';
 import type { TMessageProps, TMessageIcon } from '~/common';
-import MessageRow, { getMessageRowWidthClass } from '~/components/Chat/Messages/ui/MessageRow';
 import AuthorHeader from '~/components/Chat/Messages/Content/Parts/AuthorHeader';
 import MinimalHoverButtons from '~/components/Chat/Messages/MinimalHoverButtons';
 import { getHeaderModelName } from '~/components/Chat/Messages/ui/HeaderLabel';
+import { getMessageRowWidthClass } from '~/components/Chat/Messages/ui/width';
 import { getHeaderPrefixForScreenReader, getMessageAriaLabel } from '~/utils';
 import SearchContent, { rendersMarkdownLite } from './Content/SearchContent';
+import MessageRow from '~/components/Chat/Messages/ui/MessageRow';
 import Icon from '~/components/Chat/Messages/MessageIcon';
 import { useAuthContext, useLocalize } from '~/hooks';
 import SearchButtons from './SearchButtons';
@@ -121,6 +122,7 @@ function SearchMessage({ message }: Pick<TMessageProps, 'message'>) {
         className={cn('border-border-light mx-auto border-b px-4 py-4', getMessageRowWidthClass())}
       >
         <MessageRow
+          message={message}
           id={message.messageId}
           icon={<Icon iconData={iconData} />}
           label={messageLabel}
diff --git a/client/src/components/Chat/Messages/ui/MessageRender.tsx b/client/src/components/Chat/Messages/ui/MessageRender.tsx
index 077a0724394..f638d393ab6 100644
--- a/client/src/components/Chat/Messages/ui/MessageRender.tsx
+++ b/client/src/components/Chat/Messages/ui/MessageRender.tsx
@@ -168,6 +168,7 @@ const MessageRender = memo(function MessageRender({
     <Row
       task={subagentWakeup}
       conversationId={msg.conversationId ?? conversation?.conversationId ?? ''}
+      message={wakeupDisplay != null ? undefined : msg}
       id={msg.messageId}
       icon={<MessageIcon iconData={iconData} assistant={assistant} agent={agent} />}
       label={messageLabel ?? ''}
diff --git a/client/src/components/Chat/Messages/ui/MessageRow.tsx b/client/src/components/Chat/Messages/ui/MessageRow.tsx
index b6885eda2f3..bc825904e8e 100644
--- a/client/src/components/Chat/Messages/ui/MessageRow.tsx
+++ b/client/src/components/Chat/Messages/ui/MessageRow.tsx
@@ -1,11 +1,16 @@
 import { Zap } from 'lucide-react';
+import { ContentTypes } from 'librechat-data-provider';
+import type { TMessage } from 'librechat-data-provider';
 import type { ReactNode } from 'react';
 import MessageTimestamp from './MessageTimestamp';
+import { getMessageRowWidthClass } from './width';
 import HeaderLabel from './HeaderLabel';
+import Files from '../Content/Files';
 import { cn } from '~/utils';
 
 type MessageRowProps = {
   id?: string;
+  message?: TMessage;
   label: string;
   hoverLabel?: string | null;
   icon: ReactNode;
@@ -74,20 +79,9 @@ function renderAuthorHeader({
   );
 }
 
-export function getMessageRowWidthClass({
-  fullWidth = false,
-  hasParallelContent = false,
-}: {
-  fullWidth?: boolean;
-  hasParallelContent?: boolean;
-} = {}) {
-  if (fullWidth) return 'w-full max-w-full sm:px-2';
-  if (hasParallelContent) return 'w-full sm:px-2 md:max-w-[58rem] xl:max-w-[70rem]';
-  return 'w-full sm:px-2 md:max-w-3xl xl:max-w-4xl';
-}
-
 export default function MessageRow({
   id,
+  message,
   icon,
   label,
   hoverLabel,
@@ -110,6 +104,24 @@ export default function MessageRow({
   const widthClass = getMessageRowWidthClass({ fullWidth, hasParallelContent });
   const isSystem = systemLabel != null && systemLabel !== '';
   const isUserSide = isCreatedByUser && !isSystem;
+  const hasFiles = isUserSide && !isEditing && (message?.files?.length ?? 0) > 0;
+  const hasBody =
+    !hasFiles ||
+    Boolean(
+      message?.text?.trim() ||
+        message?.content?.some(
+          (part) =>
+            part != null &&
+            (part.type !== ContentTypes.TEXT ||
+              (typeof part.text === 'string' ? part.text : part.text?.value)?.trim()),
+        ) ||
+        message?.privacyRevision ||
+        message?.error ||
+        message?.unfinished ||
+        message?.quotes?.length ||
+        message?.alwaysAppliedSkills?.length ||
+        message?.manualSkills?.length,
+    );
 
   return (
     <div
@@ -166,22 +178,32 @@ export default function MessageRow({
           })}
 
         <div className={cn('flex w-full flex-col gap-1', isUserSide && 'items-end')}>
-          <div
-            className={cn(
-              'flex min-h-[1.25rem] max-w-full grow flex-col gap-0',
-              isUserSide && !isEditing
-                ? cn(
-                    'rounded-theme-surface rounded-br-theme-control px-theme-normal w-fit',
-                    isSystem || outlined
-                      ? 'border-border-medium border py-1.5'
-                      : 'bg-surface-user-message py-2.5',
-                  )
-                : 'w-full',
-            )}
-            data-testid="message-body"
-          >
-            {children}
-          </div>
+          {hasFiles && (
+            <div
+              data-testid="message-attachments"
+              className="flex max-w-full flex-col items-end gap-3 pb-2"
+            >
+              <Files message={message} />
+            </div>
+          )}
+          {hasBody && (
+            <div
+              className={cn(
+                'flex min-h-[1.25rem] max-w-full grow flex-col gap-0',
+                isUserSide && !isEditing
+                  ? cn(
+                      'rounded-theme-surface rounded-br-theme-control px-theme-normal w-fit',
+                      isSystem || outlined
+                        ? 'border-border-medium border py-1.5'
+                        : 'bg-surface-user-message py-2.5',
+                    )
+                  : 'w-full',
+              )}
+              data-testid="message-body"
+            >
+              {children}
+            </div>
+          )}
           <div className={cn('w-full', isUserSide && 'flex justify-end')}>{footer}</div>
         </div>
       </div>
diff --git a/client/src/components/Chat/Messages/ui/__tests__/MessageRow.spec.tsx b/client/src/components/Chat/Messages/ui/__tests__/MessageRow.spec.tsx
index 2c95e2e2b45..bd611dfee26 100644
--- a/client/src/components/Chat/Messages/ui/__tests__/MessageRow.spec.tsx
+++ b/client/src/components/Chat/Messages/ui/__tests__/MessageRow.spec.tsx
@@ -1,4 +1,5 @@
 import { render, screen } from '@testing-library/react';
+import type { TMessage } from 'librechat-data-provider';
 import MessageRow from '../MessageRow';
 
 jest.mock('../MessageTimestamp', () => ({
@@ -8,10 +9,24 @@ jest.mock('../MessageTimestamp', () => ({
   ),
 }));
 
+jest.mock('../../Content/Files', () => ({
+  __esModule: true,
+  default: () => <button data-testid="attached-file" />,
+}));
+
 const MESSAGE_BODY = 'Message body';
+const attachedMessage = (overrides: Partial<TMessage> = {}) =>
+  ({
+    messageId: 'message-1',
+    isCreatedByUser: true,
+    text: MESSAGE_BODY,
+    files: [{ file_id: 'file-1', filename: 'notes.txt', type: 'text/plain' }],
+    ...overrides,
+  }) as TMessage;
 
 const renderRow = ({
   isCreatedByUser,
+  message,
   hasParallelContent = false,
   fullWidth = false,
   isEditing = false,
@@ -20,6 +35,7 @@ const renderRow = ({
   outlined,
 }: {
   isCreatedByUser: boolean;
+  message?: TMessage;
   hasParallelContent?: boolean;
   fullWidth?: boolean;
   isEditing?: boolean;
@@ -30,6 +46,7 @@ const renderRow = ({
   render(
     <MessageRow
       id="message-1"
+      message={message}
       label={isCreatedByUser ? 'You' : 'Assistant'}
       hoverLabel={isCreatedByUser ? undefined : 'gpt-5.6'}
       icon={<span data-testid="message-icon" />}
@@ -49,6 +66,56 @@ const renderRow = ({
   );
 
 describe('MessageRow', () => {
+  it('places right-aligned attachments before and outside the text bubble', () => {
+    renderRow({ isCreatedByUser: true, message: attachedMessage() });
+
+    const attachments = screen.getByTestId('message-attachments');
+    const body = screen.getByTestId('message-body');
+    expect(attachments).toHaveClass('items-end', 'max-w-full');
+    expect(attachments).toContainElement(screen.getByTestId('attached-file'));
+    expect(body).not.toContainElement(attachments);
+    expect(attachments.nextElementSibling).toBe(body);
+    expect(body).toHaveClass('bg-surface-user-message');
+    expect(screen.getByTestId('message-actions')).toBeInTheDocument();
+  });
+
+  it.each([
+    { text: '' },
+    { text: '  ', content: [{ type: 'text', text: '' }] },
+    { text: '', content: [{ type: 'text', text: { value: '', annotations: [] } }] },
+  ] as Partial<TMessage>[])(
+    'does not leave an empty bubble for attachments-only messages: %j',
+    (overrides) => {
+      renderRow({ isCreatedByUser: true, message: attachedMessage(overrides) });
+
+      expect(screen.getByTestId('attached-file')).toBeInTheDocument();
+      expect(screen.queryByTestId('message-body')).not.toBeInTheDocument();
+      expect(screen.getByTestId('message-actions')).toBeInTheDocument();
+    },
+  );
+
+  it.each([
+    { content: [{ type: 'text', text: { value: 'Assistant prompt', annotations: [] } }] },
+    { quotes: ['Excerpt'] },
+    { manualSkills: ['review'] },
+    { alwaysAppliedSkills: ['review'] },
+    { error: true },
+    { unfinished: true },
+  ] as Partial<TMessage>[])('keeps the bubble for non-text message content: %j', (overrides) => {
+    renderRow({ isCreatedByUser: true, message: attachedMessage({ text: '', ...overrides }) });
+    expect(screen.getByTestId('message-body')).toHaveClass('bg-surface-user-message');
+  });
+
+  it.each([
+    { isCreatedByUser: true, isEditing: true },
+    { isCreatedByUser: false },
+    { isCreatedByUser: true, systemLabel: 'System' },
+  ])('does not add an attachment strip to editors, assistant or system rows: %j', (props) => {
+    renderRow({ ...props, message: attachedMessage() });
+    expect(screen.queryByTestId('attached-file')).not.toBeInTheDocument();
+    expect(screen.getByTestId('message-body')).toBeInTheDocument();
+  });
+
   it('renders a system row in the transcript under a visible heading', () => {
     renderRow({ isCreatedByUser: true, systemLabel: 'System' });
 
diff --git a/client/src/components/Chat/Messages/ui/__tests__/width.spec.ts b/client/src/components/Chat/Messages/ui/__tests__/width.spec.ts
new file mode 100644
index 00000000000..bd3c7e6e50f
--- /dev/null
+++ b/client/src/components/Chat/Messages/ui/__tests__/width.spec.ts
@@ -0,0 +1,17 @@
+import { getMessageRowWidthClass } from '../width';
+
+it('uses the standard reading column by default', () => {
+  expect(getMessageRowWidthClass()).toBe('w-full sm:px-2 md:max-w-3xl xl:max-w-4xl');
+});
+
+it('widens parallel content', () => {
+  expect(getMessageRowWidthClass({ hasParallelContent: true })).toBe(
+    'w-full sm:px-2 md:max-w-[58rem] xl:max-w-[70rem]',
+  );
+});
+
+it.each([false, true])('prioritizes full width over parallel content: %s', (hasParallelContent) => {
+  expect(getMessageRowWidthClass({ fullWidth: true, hasParallelContent })).toBe(
+    'w-full max-w-full sm:px-2',
+  );
+});
diff --git a/client/src/components/Chat/Messages/ui/width.ts b/client/src/components/Chat/Messages/ui/width.ts
new file mode 100644
index 00000000000..2b4a43e6827
--- /dev/null
+++ b/client/src/components/Chat/Messages/ui/width.ts
@@ -0,0 +1,11 @@
+export function getMessageRowWidthClass({
+  fullWidth = false,
+  hasParallelContent = false,
+}: {
+  fullWidth?: boolean;
+  hasParallelContent?: boolean;
+} = {}) {
+  if (fullWidth) return 'w-full max-w-full sm:px-2';
+  if (hasParallelContent) return 'w-full sm:px-2 md:max-w-[58rem] xl:max-w-[70rem]';
+  return 'w-full sm:px-2 md:max-w-3xl xl:max-w-4xl';
+}
diff --git a/client/src/components/Chat/Subagents/EventSubagentActivityGroup.tsx b/client/src/components/Chat/Subagents/EventSubagentActivityGroup.tsx
index a64a3a51234..c64911d6b44 100644
--- a/client/src/components/Chat/Subagents/EventSubagentActivityGroup.tsx
+++ b/client/src/components/Chat/Subagents/EventSubagentActivityGroup.tsx
@@ -4,7 +4,7 @@ import { Button, cn } from '@librechat/client';
 import { Bot, ChevronDown } from 'lucide-react';
 import type { ParentSubagentSummary } from 'librechat-data-provider';
 import { isLiveSubagentStatus, subagentStatusDotClass, subagentStatusLabelKey } from './status';
-import { getMessageRowWidthClass } from '~/components/Chat/Messages/ui/MessageRow';
+import { getMessageRowWidthClass } from '~/components/Chat/Messages/ui/width';
 import { useChatSurface, useOpenSubagentPanel } from './surface';
 import { useParentSubagents } from './ParentSubagentsProvider';
 import { eventSubagentSelection } from './eventSelection';
diff --git a/client/src/components/Messages/ContentRender.tsx b/client/src/components/Messages/ContentRender.tsx
index 799a9198990..e8484f6f0b6 100644
--- a/client/src/components/Messages/ContentRender.tsx
+++ b/client/src/components/Messages/ContentRender.tsx
@@ -168,6 +168,7 @@ const ContentRender = memo(function ContentRender({
 
   return (
     <MessageRow
+      message={msg}
       id={msg.messageId}
       icon={author.icon}
       label={author.label}
diff --git a/client/src/components/Messages/__tests__/ProtectedAttachments.spec.tsx b/client/src/components/Messages/__tests__/ProtectedAttachments.spec.tsx
new file mode 100644
index 00000000000..7a106d303e2
--- /dev/null
+++ b/client/src/components/Messages/__tests__/ProtectedAttachments.spec.tsx
@@ -0,0 +1,148 @@
+import { RecoilRoot } from 'recoil';
+import { ContentTypes, dataService } from 'librechat-data-provider';
+import { QueryClient, QueryClientProvider } from '@tanstack/react-query';
+import { act, fireEvent, render, screen, within } from '@testing-library/react';
+import type { TMessage } from 'librechat-data-provider';
+import type { TMessageChatContext } from '~/common';
+import { OwnerTextProvider } from '~/components/Chat/Messages/PrivateText';
+import MessageRender from '~/components/Chat/Messages/ui/MessageRender';
+import ContentRender from '../ContentRender';
+
+jest.mock('librechat-data-provider', () => ({
+  ...jest.requireActual('librechat-data-provider'),
+  dataService: {
+    ...jest.requireActual('librechat-data-provider').dataService,
+    getOwnerMessageTexts: jest.fn(),
+  },
+}));
+
+jest.mock('~/hooks/AuthContext', () => ({
+  useAuthContext: () => ({ user: { id: 'owner', tenantId: 'tenant' } }),
+}));
+jest.mock('~/hooks', () => ({
+  useLocalize: () => (key: string) => key,
+  useAttachments: () => ({}),
+  useContentMetadata: () => ({ hasParallelContent: false }),
+  useMessageActions: () => ({
+    edit: false,
+    index: 0,
+    conversation: { conversationId: 'protected-conversation', endpoint: 'agents' },
+    messageLabel: 'You',
+    getCanCopy: () => true,
+  }),
+}));
+jest.mock('~/components/Chat/Messages/MessageIcon', () => ({
+  __esModule: true,
+  default: () => null,
+}));
+jest.mock('~/components/Chat/Messages/HoverButtons', () => ({
+  __esModule: true,
+  default: () => null,
+}));
+jest.mock('~/components/Chat/Messages/SiblingSwitch', () => ({
+  __esModule: true,
+  default: () => null,
+}));
+jest.mock('~/components/Chat/Messages/Elapsed', () => ({
+  __esModule: true,
+  default: () => null,
+  shouldShowElapsed: () => false,
+}));
+
+const canonical: TMessage = {
+  messageId: 'protected-message',
+  parentMessageId: 'parent',
+  conversationId: 'protected-conversation',
+  isCreatedByUser: true,
+  text: '[EMAIL_1_turn]',
+  privacyRevision: 'turn',
+  files: [
+    { file_id: 'notes', filename: 'notes.txt', type: 'text/plain', bytes: 128 },
+    {
+      file_id: 'image',
+      filename: 'preview.png',
+      type: 'image/png',
+      filepath: '/images/preview.png',
+      width: 320,
+      height: 180,
+    },
+  ],
+};
+const original = {
+  messageId: canonical.messageId,
+  canonicalText: canonical.text,
+  revision: 'turn',
+  text: 'alice@example.com',
+};
+const chatContext = { latestMessageId: canonical.messageId } as TMessageChatContext;
+
+for (const [name, Row] of [
+  ['plain', MessageRender],
+  ['structured', ContentRender],
+] as const) {
+  describe(`${name} protected attachments`, () => {
+    const message: TMessage = {
+      ...canonical,
+      ...(name === 'structured'
+        ? { content: [{ type: ContentTypes.TEXT, text: canonical.text }] }
+        : {}),
+    };
+    function renderMessage(overrides: Partial<TMessage> = {}) {
+      const current = { ...message, ...overrides };
+      const queryClient = new QueryClient({ defaultOptions: { queries: { retry: false } } });
+      return render(
+        <QueryClientProvider client={queryClient}>
+          <RecoilRoot>
+            <OwnerTextProvider
+              messages={[current]}
+              conversationId={current.conversationId ?? undefined}
+              isSubmitting={false}
+            >
+              <Row message={current} chatContext={chatContext} currentEditId={null} />
+            </OwnerTextProvider>
+          </RecoilRoot>
+        </QueryClientProvider>,
+      );
+    }
+
+    function expectAttachments() {
+      const attachments = screen.getByTestId('message-attachments');
+      const body = screen.getByTestId('message-body');
+      expect(within(attachments).getByRole('button', { name: 'notes.txt' })).toBeVisible();
+      expect(
+        within(attachments).getByRole('button', { name: 'View preview.png in dialog' }),
+      ).toBeVisible();
+      expect(body).not.toContainElement(attachments);
+      return attachments;
+    }
+
+    it('preserves previews while owner text loads and after it resolves', async () => {
+      let finish!: (value: { messages: (typeof original)[] }) => void;
+      (dataService.getOwnerMessageTexts as jest.Mock).mockReturnValue(
+        new Promise((resolve) => {
+          finish = resolve;
+        }),
+      );
+      renderMessage();
+      expectAttachments();
+      expect(screen.getByRole('status')).toHaveTextContent('com_ui_private_text_loading');
+      await act(async () => finish({ messages: [original] }));
+      expect(await screen.findByText(original.text)).toBeInTheDocument();
+      expectAttachments();
+      expect(message.text).toBe(canonical.text);
+      fireEvent.click(screen.getByRole('button', { name: 'View preview.png in dialog' }));
+      expect(await screen.findByRole('dialog')).toBeVisible();
+    });
+
+    it('keeps attachments and private-text recovery when canonical text is empty', async () => {
+      (dataService.getOwnerMessageTexts as jest.Mock).mockResolvedValue({ messages: [] });
+      renderMessage({ text: '', content: [] });
+      expectAttachments();
+      expect(
+        await screen.findByRole('button', { name: 'com_ui_private_text_retry' }),
+      ).toBeVisible();
+      expect(screen.getByRole('status')).toHaveTextContent('com_ui_private_text_unavailable');
+      expectAttachments();
+    });
+  });
+}
diff --git a/client/src/components/Share/Message.tsx b/client/src/components/Share/Message.tsx
index e3ad8fd5238..f482f62d60a 100644
--- a/client/src/components/Share/Message.tsx
+++ b/client/src/components/Share/Message.tsx
@@ -67,6 +67,7 @@ export default function Message(props: TMessageProps) {
           <Row
             task={subagentWakeup}
             conversationId={message.conversationId ?? conversation?.conversationId ?? ''}
+            message={wakeupDisplay == null ? message : undefined}
             id={messageId}
             icon={<Icon message={message} conversation={conversation} />}
             label={messageLabel}
diff --git a/client/src/routes/Search.tsx b/client/src/routes/Search.tsx
index f25cae8113c..9fd191e8c21 100644
--- a/client/src/routes/Search.tsx
+++ b/client/src/routes/Search.tsx
@@ -7,7 +7,7 @@ import { List, CellMeasurer, CellMeasurerCache } from 'react-virtualized';
 import { EmptyState, Spinner, useRemScale, useToastContext } from '@librechat/client';
 import type { Index, ListRowProps } from 'react-virtualized';
 import type { TMessage } from 'librechat-data-provider';
-import { getMessageRowWidthClass } from '~/components/Chat/Messages/ui/MessageRow';
+import { getMessageRowWidthClass } from '~/components/Chat/Messages/ui/width';
 import { useElementSize, useLocalize, useAuthContext } from '~/hooks';
 import SearchMessage from '~/components/Chat/Messages/SearchMessage';
 import { useMessagesInfiniteQuery } from '~/data-provider';
diff --git a/e2e/specs/mock/scenarios/message-attachments.spec.ts b/e2e/specs/mock/scenarios/message-attachments.spec.ts
new file mode 100644
index 00000000000..bf77a0c2dec
--- /dev/null
+++ b/e2e/specs/mock/scenarios/message-attachments.spec.ts
@@ -0,0 +1,179 @@
+import { randomUUID } from 'crypto';
+import { expect, test } from '@playwright/test';
+import { clickHouseTheme } from '../../../../packages/client/src/theme/themes/clickhouse';
+import {
+  deleteConversations,
+  deleteMessagesByConversation,
+  seedConversations,
+  seedMessages,
+  withMongo,
+} from '../db';
+import { getE2EUser } from '../../../setup/user';
+
+const IMAGE =
+  'data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAAEAAAABCAQAAAC1HAwCAAAAC0lEQVR42mP8/x8AAwMCAO+ip1sAAAAASUVORK5CYII=';
+const TEXT = 'Keep these attachments separate from the text bubble.';
+
+test.use({ viewport: { width: 1280, height: 800 } });
+
+for (const definition of ['stock', 'clickhouse'] as const) {
+  for (const mode of ['light', 'dark'] as const) {
+    test(`message attachments in ${definition} ${mode} @scenario:message-attachments-${definition}-${mode}`, async ({
+      page,
+    }) => {
+      await page.addInitScript(
+        ({ selectedMode, theme }) => {
+          localStorage.setItem('color-theme', selectedMode);
+          localStorage.removeItem('theme-colors');
+          localStorage.removeItem('theme-name');
+          if (theme) {
+            localStorage.setItem('theme-definition', JSON.stringify(theme));
+            localStorage.setItem('theme-source', 'definition');
+          } else {
+            localStorage.removeItem('theme-definition');
+            localStorage.removeItem('theme-source');
+          }
+        },
+        { selectedMode: mode, theme: definition === 'clickhouse' ? clickHouseTheme : null },
+      );
+      const conversationId = randomUUID();
+      const messageId = randomUUID();
+      const structuredId = randomUUID();
+      const filesOnlyId = randomUUID();
+      const { email } = getE2EUser();
+      const files = [
+        { file_id: randomUUID(), filename: 'notes.txt', type: 'text/plain', bytes: 128 },
+        {
+          file_id: randomUUID(),
+          filename: 'preview.png',
+          type: 'image/png',
+          filepath: IMAGE,
+          width: 320,
+          height: 180,
+        },
+      ];
+      await seedConversations(email, [
+        { conversationId, title: 'Separate attachments', updatedAt: new Date() },
+      ]);
+      await seedMessages(email, conversationId, [
+        {
+          messageId,
+          parentMessageId: '00000000-0000-0000-0000-000000000000',
+          text: TEXT,
+          isCreatedByUser: true,
+          sender: 'User',
+          files,
+        },
+        {
+          messageId: structuredId,
+          parentMessageId: messageId,
+          text: TEXT,
+          content: [{ type: 'text', text: TEXT }],
+          isCreatedByUser: true,
+          sender: 'User',
+          files,
+        },
+        {
+          messageId: filesOnlyId,
+          parentMessageId: structuredId,
+          text: '',
+          content: [{ type: 'text', text: '' }],
+          isCreatedByUser: true,
+          sender: 'User',
+          files: [files[0]],
+        },
+      ]);
+      try {
+        await page.goto(`/c/${conversationId}`);
+        const row = page.locator(`[id="${messageId}"]`);
+        const attachments = row.getByTestId('message-attachments');
+        const body = row.getByTestId('message-body');
+        await expect(body).toContainText(TEXT);
+        await expect(attachments.getByRole('button')).toHaveCount(2);
+        const structured = page.locator(`[id="${structuredId}"]`);
+        await expect(structured.getByTestId('message-attachments').getByRole('button')).toHaveCount(
+          2,
+        );
+        await expect(structured.getByTestId('message-body')).toContainText(TEXT);
+        expect(await body.getByRole('button').count()).toBe(0);
+        const bubbleColor = await body.evaluate((node) => getComputedStyle(node).backgroundColor);
+        for (const button of await attachments.getByRole('button').all()) {
+          const border = await button.evaluate((node) => {
+            const style = getComputedStyle(node);
+            return { color: style.borderTopColor, width: style.borderTopWidth };
+          });
+          expect(border).toEqual({ color: bubbleColor, width: '1px' });
+        }
+        await expect(page.locator(`[id="${filesOnlyId}"]`).getByTestId('message-body')).toHaveCount(
+          0,
+        );
+        await test.info().attach(`attachments-${definition}-${mode}`, {
+          body: await row.screenshot({ animations: 'disabled' }),
+          contentType: 'image/png',
+        });
+        await attachments.getByRole('button', { name: 'View preview.png in dialog' }).click();
+        await expect(page.getByRole('dialog')).toBeVisible();
+        await page.keyboard.press('Escape');
+        await expect(page.getByRole('dialog')).toBeHidden();
+        await withMongo(async (db) => {
+          await db
+            .collection('messages')
+            .updateMany(
+              { conversationId, messageId: { $in: [messageId, structuredId] } },
+              { $set: { privacyRevision: 'attachment-revision' } },
+            );
+        });
+        let ownerAvailable = true;
+        const ownerText = 'Owner-only attachment prompt';
+        await page.route(`**/api/messages/${conversationId}/owner-text`, (route) =>
+          route.fulfill({
+            json: {
+              messages: ownerAvailable
+                ? [messageId, structuredId].map((id) => ({
+                    messageId: id,
+                    canonicalText: TEXT,
+                    revision: 'attachment-revision',
+                    text: ownerText,
+                  }))
+                : [],
+            },
+          }),
+        );
+        await page.reload();
+        for (const id of [messageId, structuredId]) {
+          const protectedRow = page.locator(`[id="${id}"]`);
+          await expect(protectedRow.getByTestId('message-body')).toContainText(ownerText);
+          await expect(
+            protectedRow.getByTestId('message-attachments').getByRole('button'),
+          ).toHaveCount(2);
+        }
+        await attachments.getByRole('button', { name: 'View preview.png in dialog' }).click();
+        await expect(page.getByRole('dialog')).toBeVisible();
+        await page.keyboard.press('Escape');
+        await expect(page.getByRole('dialog')).toBeHidden();
+        ownerAvailable = false;
+        await page.reload();
+        for (const id of [messageId, structuredId]) {
+          const protectedRow = page.locator(`[id="${id}"]`);
+          await expect(protectedRow.getByTestId('message-body')).toContainText(TEXT);
+          await expect(
+            protectedRow.getByRole('button', { name: 'Retry loading original' }),
+          ).toBeVisible();
+          await expect(
+            protectedRow.getByTestId('message-attachments').getByRole('button'),
+          ).toHaveCount(2);
+        }
+        await page.setViewportSize({ width: 320, height: 800 });
+        await expect(attachments).toBeVisible();
+        expect(await page.evaluate(() => document.documentElement.scrollWidth)).toBeLessThanOrEqual(
+          320,
+        );
+      } finally {
+        await Promise.all([
+          deleteMessagesByConversation([conversationId]),
+          deleteConversations([conversationId]),
+        ]);
+      }
+    });
+  }
+}