diff --git a/src/apps/chat/components/composer/llmattachments/LLMAttachmentButton.tsx b/src/apps/chat/components/composer/llmattachments/LLMAttachmentButton.tsx
index 5facff657..9188f02f4 100644
--- a/src/apps/chat/components/composer/llmattachments/LLMAttachmentButton.tsx
+++ b/src/apps/chat/components/composer/llmattachments/LLMAttachmentButton.tsx
@@ -19,7 +19,8 @@ import WarningRoundedIcon from '@mui/icons-material/WarningRounded';
 import { RenderImageURL } from '~/modules/blocks/image/RenderImageURL';
 
 import { GoodTooltip } from '~/common/components/GoodTooltip';
-import { LiveFileIcon } from '~/common/livefile/LiveFileIcon';
+import { LiveFileIcon } from '~/common/livefile/LiveFileIcons';
+import { TooltipOutlined } from '~/common/components/TooltipOutlined';
 import { ellipsizeFront, ellipsizeMiddle } from '~/common/util/textUtils';
 import { liveFileInAttachmentFragment } from '~/common/livefile/liveFile';
 
@@ -139,9 +140,13 @@ function attachmentIcons(attachmentDraft: AttachmentDraft): React.ReactNode {
     {/*))}*/}
 
     {/*{activeConterters.some(c => c.id.startsWith('url-page-')) ? <LanguageIcon sx={{ opacity: 0.2, ml: -2.5 }} /> : null}*/}
-    {activeConterters.map(c => {
-      const Icon = converterTypeToIconMap[c.id] ?? null;
-      return Icon ? <Icon key={c.id} sx={{ width: 20, height: 20 }} /> : null;
+    {activeConterters.map((_converter, idx) => {
+      const Icon = converterTypeToIconMap[_converter.id] ?? null;
+      return !Icon ? null : (
+        <TooltipOutlined key={`${_converter.id}-${idx}`} title={`Attached as ${_converter.name}`} placement='top-start'>
+          <Icon sx={{ width: 20, height: 20 }} />
+        </TooltipOutlined>
+      );
     })}
   </Typography>;
 }
@@ -264,7 +269,11 @@ export function LLMAttachmentButton(props: {
                 {isOutputLoading && <CircularProgress color='success' size='sm' />}
 
                 {/* Live file icon */}
-                {hasLiveFile && <LiveFileIcon />}
+                {hasLiveFile && (
+                  <TooltipOutlined title='LiveFile is supported' placement='top-end'>
+                    <LiveFileIcon />
+                  </TooltipOutlined>
+                )}
               </>}
           </Button>
         )}
diff --git a/src/apps/chat/components/composer/llmattachments/LLMAttachmentMenu.tsx b/src/apps/chat/components/composer/llmattachments/LLMAttachmentMenu.tsx
index a02a22e70..6104f5b9e 100644
--- a/src/apps/chat/components/composer/llmattachments/LLMAttachmentMenu.tsx
+++ b/src/apps/chat/components/composer/llmattachments/LLMAttachmentMenu.tsx
@@ -14,7 +14,7 @@ import { showImageDataRefInNewTab } from '~/modules/blocks/image/RenderImageRefD
 
 import { CloseableMenu } from '~/common/components/CloseableMenu';
 import { DMessageAttachmentFragment, isDocPart, isImageRefPart } from '~/common/stores/chat/chat.fragments';
-import { LiveFileIcon } from '~/common/livefile/LiveFileIcon';
+import { LiveFileIcon } from '~/common/livefile/LiveFileIcons';
 import { copyToClipboard } from '~/common/util/clipboardUtils';
 import { liveFileInAttachmentFragment } from '~/common/livefile/liveFile';
 import { showImageDataURLInNewTab } from '~/common/util/imageUtils';
@@ -184,12 +184,6 @@ export function LLMAttachmentMenu(props: {
           </Typography>
         ) : (
           <Box sx={{ my: 0.5 }}>
-            {/* LiveFile notice */}
-            {hasLiveFile && !!draftInput && (
-              <Typography level='body-sm' sx={{ mb: 1 }} startDecorator={<LiveFileIcon sx={{ width: 16, height: 16 }} />}>
-                LiveFile is supported
-              </Typography>
-            )}
 
             {/* <- inputs */}
             {!!draftInput && (
@@ -271,6 +265,14 @@ export function LLMAttachmentMenu(props: {
                 </Typography>
               )}
             </Box>
+
+            {/* LiveFile notice */}
+            {hasLiveFile && !!draftInput && (
+              <Typography level='body-sm' sx={{ mt: 1 }} startDecorator={<LiveFileIcon sx={{ width: 16, height: 16 }} />}>
+                LiveFile is supported
+              </Typography>
+            )}
+
           </Box>
         )}
       </MenuItem>
diff --git a/src/apps/chat/components/message/fragments-attachment-doc/DocAttachmentFragmentButton.tsx b/src/apps/chat/components/message/fragments-attachment-doc/DocAttachmentFragmentButton.tsx
index 6b46e36a3..0b98a23c1 100644
--- a/src/apps/chat/components/message/fragments-attachment-doc/DocAttachmentFragmentButton.tsx
+++ b/src/apps/chat/components/message/fragments-attachment-doc/DocAttachmentFragmentButton.tsx
@@ -1,7 +1,7 @@
 import * as React from 'react';
 
 import type { SxProps } from '@mui/joy/styles/types';
-import { Box, Button, ColorPaletteProp, Tooltip } from '@mui/joy';
+import { Box, Button, ColorPaletteProp } from '@mui/joy';
 import AbcIcon from '@mui/icons-material/Abc';
 import CodeIcon from '@mui/icons-material/Code';
 import ExpandCircleDownIcon from '@mui/icons-material/ExpandCircleDown';
@@ -13,7 +13,8 @@ import TextureIcon from '@mui/icons-material/Texture';
 
 import { ContentScaling, themeScalingMap } from '~/common/app.theme';
 import { DMessageAttachmentFragment, DMessageFragmentId, isDocPart } from '~/common/stores/chat/chat.fragments';
-import { LiveFileIcon } from '~/common/livefile/LiveFileIcon';
+import { LiveFileIcon } from '~/common/livefile/LiveFileIcons';
+import { TooltipOutlined } from '~/common/components/TooltipOutlined';
 import { ellipsizeMiddle } from '~/common/util/textUtils';
 import { liveFileInAttachmentFragment } from '~/common/livefile/liveFile';
 
@@ -124,9 +125,9 @@ export function DocAttachmentFragmentButton(props: {
         {/*</Box>*/}
       </Box>
       {liveFileInAttachmentFragment(fragment) && (
-        <Tooltip color='success' disableInteractive title='Supports LiveFile' placement='top-end' arrow>
+        <TooltipOutlined title='LiveFile is supported' color='success' placement='top-end'>
           <LiveFileIcon color={isSelected ? undefined : 'success'} sx={{ mr: '0.5rem' }} />
-        </Tooltip>
+        </TooltipOutlined>
       )}
     </Button>
   );
diff --git a/src/apps/chat/components/message/fragments-attachment-doc/useLiveFile.tsx b/src/apps/chat/components/message/fragments-attachment-doc/useLiveFile.tsx
index cc4ef055a..bb772f5f4 100644
--- a/src/apps/chat/components/message/fragments-attachment-doc/useLiveFile.tsx
+++ b/src/apps/chat/components/message/fragments-attachment-doc/useLiveFile.tsx
@@ -2,12 +2,13 @@ import * as React from 'react';
 import { fileOpen } from 'browser-fs-access';
 import { cleanupEfficiency, makeDiff } from '@sanity/diff-match-patch';
 
-import { Alert, Box, Button, CircularProgress, ColorPaletteProp, IconButton, Tooltip } from '@mui/joy';
+import { Alert, Box, Button, CircularProgress, ColorPaletteProp, IconButton } from '@mui/joy';
 import CloseRoundedIcon from '@mui/icons-material/CloseRounded';
 import WarningRoundedIcon from '@mui/icons-material/WarningRounded';
 
 import type { DMessageAttachmentFragment } from '~/common/stores/chat/chat.fragments';
-import { LiveFileIcon, LiveFileReloadIcon, LiveFileSaveIcon } from '~/common/livefile/LiveFileIcon';
+import { LiveFileChooseIcon, LiveFileIcon, LiveFileReloadIcon, LiveFileSaveIcon } from '~/common/livefile/LiveFileIcons';
+import { TooltipOutlined } from '~/common/components/TooltipOutlined';
 import { liveFileCreate } from '~/common/livefile/liveFile';
 
 
@@ -155,19 +156,37 @@ export function useLiveFile(
 
 
   const liveFileSyncButton = React.useMemo(() => (
-    <Tooltip disableInteractive enterDelay={600} arrow color={isPreviewMode ? 'primary' : 'success'} placement='top-end' title={!fileSystemFileHandle ? 'Setup LiveFile file association' : <>LiveFile connected.<br />Click to compare with file content.</>}>
+    <TooltipOutlined
+      title={
+        isPreviewMode ? 'Click to update the comparison.'
+          : fileSystemFileHandle ? 'Click compare with the File contents.'
+            : 'Setup LiveFile association.'
+      }
+      color={isPreviewMode ? 'primary' : 'success'}
+      variant={isPreviewMode ? undefined : 'solid'}
+      placement='top-end'
+    >
       <Button
         variant='soft'
         color={isPreviewMode ? 'primary' : 'success'}
         size='sm'
         disabled={isWorking}
         onClick={handleSyncButtonClick}
-        startDecorator={isPreviewMode ? <LiveFileIcon /> : (isWorking ? <CircularProgress sx={{ '--CircularProgress-size': '16px' }} /> : <LiveFileIcon />)}
+        startDecorator={
+          isPreviewMode ? <LiveFileIcon />
+            : (isWorking ? <CircularProgress sx={{ '--CircularProgress-size': '16px' }} />
+              : fileSystemFileHandle ? <LiveFileIcon />
+                : <LiveFileChooseIcon />)
+        }
         aria-label={fileSystemFileHandle ? 'Sync File' : 'Choose File'}
       >
-        {isPreviewMode ? 'Refresh' : (fileSystemFileHandle ? 'Sync File' : 'Choose File')}
+        {
+          isPreviewMode ? 'Refresh'
+            : fileSystemFileHandle ? 'Sync File'
+              : 'Pair File'
+        }
       </Button>
-    </Tooltip>
+    </TooltipOutlined>
   ), [fileSystemFileHandle, handleSyncButtonClick, isPreviewMode, isWorking]);
 
 
@@ -195,7 +214,7 @@ export function useLiveFile(
       >
         <Box sx={{ display: 'flex', gap: 0.5, alignItems: 'center' }}>
           {isPreviewMode && !!fileSystemFileHandle && (
-            <IconButton size='sm' color={statusColor} onClick={handleSyncButtonClick}>
+            <IconButton size='sm' onClick={handleSyncButtonClick}>
               <LiveFileIcon />
             </IconButton>
           )}
@@ -204,9 +223,10 @@ export function useLiveFile(
 
 
         <Box sx={{ ml: 'auto', display: 'flex', gap: 1 }}>
+          {/* Load from File */}
           {(diffSummary && (diffSummary.insertions > 0 || diffSummary.deletions > 0)) && (
             <Button
-              variant='plain'
+              variant={isMobile ? 'outlined' : 'plain'}
               color='primary'
               size='sm'
               disabled={isWorking}
@@ -214,12 +234,14 @@ export function useLiveFile(
               startDecorator={<LiveFileReloadIcon />}
               aria-label='Load content from disk'
             >
-              {isMobile ? 'Load File' : 'Load from File'}
+              {isMobile ? 'Update' : 'Load from File'}
             </Button>
           )}
+
+          {/* Save to File */}
           {(diffSummary && (diffSummary.insertions > 0 || diffSummary.deletions > 0)) && (
             <Button
-              variant='plain'
+              variant={isMobile ? 'outlined' : 'plain'}
               color='danger'
               size='sm'
               disabled={isWorking}
@@ -227,14 +249,23 @@ export function useLiveFile(
               startDecorator={<LiveFileSaveIcon />}
               aria-label='Save content to disk'
             >
-              {isMobile ? 'Save File' : 'Save to File'}
+              {isMobile ? 'Save' : 'Save to File'}
             </Button>
           )}
 
+          {/* Reassign File button */}
+          <TooltipOutlined title='Pair a different File.' placement='top-end'>
+            <IconButton size='sm' onClick={associateAndPreviewFile}>
+              <LiveFileChooseIcon />
+            </IconButton>
+          </TooltipOutlined>
+
           {/* Close button */}
-          <IconButton size='sm' color={statusColor} onClick={resetState}>
-            <CloseRoundedIcon />
-          </IconButton>
+          <TooltipOutlined title='Close LiveFile.' placement='top-end'>
+            <IconButton size='sm' onClick={resetState}>
+              <CloseRoundedIcon />
+            </IconButton>
+          </TooltipOutlined>
         </Box>
       </Alert>
     );
diff --git a/src/common/components/TooltipOutlined.tsx b/src/common/components/TooltipOutlined.tsx
new file mode 100644
index 000000000..9cd9fe650
--- /dev/null
+++ b/src/common/components/TooltipOutlined.tsx
@@ -0,0 +1,25 @@
+import * as React from 'react';
+
+import { Tooltip, TooltipProps } from '@mui/joy';
+
+
+export function TooltipOutlined(props: {
+  title: React.ReactNode;
+  color?: TooltipProps['color'];
+  variant?: TooltipProps['variant'];
+  placement?: TooltipProps['placement'];
+  children: React.JSX.Element;
+}) {
+  return (
+    <Tooltip
+      title={props.title}
+      color={props.color}
+      variant={props.variant ?? 'outlined'}
+      arrow
+      disableInteractive
+      placement={props.placement ?? 'top'}
+    >
+      {props.children}
+    </Tooltip>
+  );
+}
diff --git a/src/common/livefile/LiveFileIcon.ts b/src/common/livefile/LiveFileIcons.ts
similarity index 55%
rename from src/common/livefile/LiveFileIcon.ts
rename to src/common/livefile/LiveFileIcons.ts
index 24469e7be..e65825f86 100644
--- a/src/common/livefile/LiveFileIcon.ts
+++ b/src/common/livefile/LiveFileIcons.ts
@@ -1,7 +1,13 @@
+import { styled } from '@mui/joy';
+import FileOpenOutlinedIcon from '@mui/icons-material/FileOpenOutlined';
 import MultipleStopIcon from '@mui/icons-material/MultipleStop';
 import SystemUpdateAltIcon from '@mui/icons-material/SystemUpdateAlt';
 import UploadFileIcon from '@mui/icons-material/UploadFile';
 
-export { MultipleStopIcon as LiveFileIcon };
-export { UploadFileIcon as LiveFileSaveIcon };
+export const LiveFileIcon = styled(MultipleStopIcon)({
+  rotate: '90deg',
+});
+
+export { FileOpenOutlinedIcon as LiveFileChooseIcon };
 export { SystemUpdateAltIcon as LiveFileReloadIcon };
+export { UploadFileIcon as LiveFileSaveIcon };