diff --git a/src/apps/chat/components/ChatMessageList.tsx b/src/apps/chat/components/ChatMessageList.tsx
index 3cf7a9287..a8d011233 100644
--- a/src/apps/chat/components/ChatMessageList.tsx
+++ b/src/apps/chat/components/ChatMessageList.tsx
@@ -12,7 +12,7 @@ import type { ConversationHandler } from '~/common/chat-overlay/ConversationHand
 import { DConversationId, excludeSystemMessages } from '~/common/stores/chat/chat.conversation';
 import { ShortcutKey, useGlobalShortcuts } from '~/common/components/shortcuts/useGlobalShortcuts';
 import { convertFilesToDAttachmentFragments } from '~/common/attachment-drafts/attachment.pipeline';
-import { createDMessageFromFragments, createDMessageTextContent, DMessage, DMessageId, DMessageUserFlag, DMetaReferenceItem, MESSAGE_FLAG_AIX_SKIP } from '~/common/stores/chat/chat.message';
+import { createDMessageFromFragments, createDMessageTextContent, DMessage, DMessageId, DMessageUserFlag, DMetaReferenceItem, MESSAGE_FLAG_AIX_SKIP, messageHasUserFlag } from '~/common/stores/chat/chat.message';
 import { createTextContentFragment, DMessageFragment, DMessageFragmentId } from '~/common/stores/chat/chat.fragments';
 import { openFileForAttaching } from '~/common/components/ButtonAttachFiles';
 import { optimaOpenPreferences } from '~/common/layout/optima/useOptima';
@@ -223,6 +223,16 @@ export function ChatMessageList(props: {
 
   // operate on the local selection set
 
+  const areAllSelectedMessagesHidden = React.useMemo(() => {
+    if (selectedMessages.size === 0) return false;
+    for (const messageId of selectedMessages) {
+      const message = conversationMessages.find(m => m.id === messageId);
+      if (message && !messageHasUserFlag(message, MESSAGE_FLAG_AIX_SKIP))
+        return false;
+    }
+    return true;
+  }, [selectedMessages, conversationMessages]);
+
   const handleSelectAll = (selected: boolean) => {
     const newSelected = new Set<string>();
     if (selected)
@@ -242,11 +252,11 @@ export function ChatMessageList(props: {
     setSelectedMessages(new Set());
   }, [conversationHandler, selectedMessages]);
 
-  const handleSelectionHide = React.useCallback(() => {
+  const handleSelectionToggleVisibility = React.useCallback(() => {
     for (let selectedMessage of Array.from(selectedMessages))
-      conversationHandler?.messageSetUserFlag(selectedMessage, MESSAGE_FLAG_AIX_SKIP, true, true);
+      conversationHandler?.messageSetUserFlag(selectedMessage, MESSAGE_FLAG_AIX_SKIP, !areAllSelectedMessagesHidden, true);
     setSelectedMessages(new Set());
-  }, [conversationHandler, selectedMessages]);
+  }, [conversationHandler, selectedMessages, areAllSelectedMessagesHidden]);
 
   const { isMessageSelectionMode, setIsMessageSelectionMode } = props;
 
@@ -324,7 +334,8 @@ export function ChatMessageList(props: {
           onClose={() => props.setIsMessageSelectionMode(false)}
           onSelectAll={handleSelectAll}
           onDeleteMessages={handleSelectionDelete}
-          onHideMessages={handleSelectionHide}
+          onToggleVisibility={handleSelectionToggleVisibility}
+          areAllMessagesHidden={areAllSelectedMessagesHidden}
         />
       )}
 
diff --git a/src/apps/chat/components/message/CleanerMessage.tsx b/src/apps/chat/components/message/CleanerMessage.tsx
index 8f637157d..3d30778bb 100644
--- a/src/apps/chat/components/message/CleanerMessage.tsx
+++ b/src/apps/chat/components/message/CleanerMessage.tsx
@@ -3,6 +3,7 @@ import * as React from 'react';
 import { Box, Button, Checkbox, IconButton, ListItem, Sheet, Typography } from '@mui/joy';
 import ClearIcon from '@mui/icons-material/Clear';
 import DeleteOutlineIcon from '@mui/icons-material/DeleteOutline';
+import VisibilityIcon from '@mui/icons-material/Visibility';
 import VisibilityOffIcon from '@mui/icons-material/VisibilityOff';
 
 import { DMessage, MESSAGE_FLAG_AIX_SKIP, messageFragmentsReduceText, messageHasUserFlag } from '~/common/stores/chat/chat.message';
@@ -16,7 +17,15 @@ import { messageSkippedSx } from './ChatMessage';
 /**
  * Header bar for controlling the operations during the Selection mode
  */
-export const MessagesSelectionHeader = (props: { hasSelected: boolean, sumTokens: number, onClose: () => void, onSelectAll: (selected: boolean) => void, onDeleteMessages: () => void, onHideMessages: () => void }) =>
+export const MessagesSelectionHeader = (props: {
+  hasSelected: boolean,
+  sumTokens: number,
+  onClose: () => void,
+  onSelectAll: (selected: boolean) => void,
+  onDeleteMessages: () => void,
+  onToggleVisibility: () => void,
+  areAllMessagesHidden: boolean,
+}) =>
   <Sheet color='warning' variant='solid' invertedColors sx={{
     position: 'sticky', top: 0, left: 0, right: 0, zIndex: 101 /* Cleanup Selection Header on top of messages */,
     boxShadow: 'md',
@@ -30,8 +39,14 @@ export const MessagesSelectionHeader = (props: { hasSelected: boolean, sumTokens
     <Box sx={{ fontSize: 'sm' }}>Select all ({props.sumTokens?.toLocaleString()})</Box>
 
     <Box sx={{ mx: 'auto', display: 'flex', gap: 1 }}>
-      <Button size='sm' disabled={!props.hasSelected} onClick={props.onHideMessages} sx={{ minWidth: { md: 120 } }} endDecorator={<VisibilityOffIcon />}>
-        Hide
+      <Button
+        size='sm'
+        disabled={!props.hasSelected}
+        onClick={props.onToggleVisibility}
+        sx={{ minWidth: { md: 120 } }}
+        endDecorator={props.areAllMessagesHidden ? <VisibilityIcon /> : <VisibilityOffIcon />}
+      >
+        {props.areAllMessagesHidden ? 'Show' : 'Hide'}
       </Button>
       <Button size='sm' disabled={!props.hasSelected} onClick={props.onDeleteMessages} sx={{ minWidth: { md: 120 } }} endDecorator={<DeleteOutlineIcon />}>
         Delete