diff --git a/src/component/FileManager/ContextMenu/ContextMenu.tsx b/src/component/FileManager/ContextMenu/ContextMenu.tsx
index ba87167..d7e74c9 100644
--- a/src/component/FileManager/ContextMenu/ContextMenu.tsx
+++ b/src/component/FileManager/ContextMenu/ContextMenu.tsx
@@ -1,20 +1,10 @@
-import {
-  Box,
-  Divider,
-  ListItemIcon,
-  ListItemText,
-  Menu,
-  MenuItem,
-  styled,
-  Typography,
-  useTheme,
-} from "@mui/material";
-import { useAppDispatch, useAppSelector } from "../../../redux/hooks.ts";
-import { closeContextMenu } from "../../../redux/fileManagerSlice.ts";
-import useActionDisplayOpt from "./useActionDisplayOpt.ts";
+import { Box, Divider, ListItemIcon, ListItemText, Menu, MenuItem, styled, Typography, useTheme } from "@mui/material";
 import { useCallback, useMemo } from "react";
-import DeleteOutlined from "../../Icons/DeleteOutlined.tsx";
 import { useTranslation } from "react-i18next";
+import { closeContextMenu } from "../../../redux/fileManagerSlice.ts";
+import { CreateNewDialogType } from "../../../redux/globalStateSlice.ts";
+import { useAppDispatch, useAppSelector } from "../../../redux/hooks.ts";
+import { downloadFiles } from "../../../redux/thunks/download.ts";
 import {
   batchGetDirectLinks,
   createNew,
@@ -30,44 +20,40 @@ import {
   renameFile,
   restoreFile,
 } from "../../../redux/thunks/file.ts";
-import RenameOutlined from "../../Icons/RenameOutlined.tsx";
-import BinFullOutlined from "../../Icons/BinFullOutlined.tsx";
-import { CascadingSubmenu } from "./CascadingMenu.tsx";
-import HistoryOutlined from "../../Icons/HistoryOutlined.tsx";
-import CopyOutlined from "../../Icons/CopyOutlined.tsx";
-import Tag from "../../Icons/Tag.tsx";
-import TagMenuItems from "./TagMenuItems.tsx";
-import Download from "../../Icons/Download.tsx";
-import ShareOutlined from "../../Icons/ShareOutlined.tsx";
-import FolderLink from "../../Icons/FolderLink.tsx";
-import { downloadFiles } from "../../../redux/thunks/download.ts";
-import Info from "../../Icons/Info.tsx";
-import WrenchSettings from "../../Icons/WrenchSettings.tsx";
-import Open from "../../Icons/Open.tsx";
+import { refreshFileList, uploadClicked, uploadFromClipboard } from "../../../redux/thunks/filemanager.ts";
 import { openViewers } from "../../../redux/thunks/viewer.ts";
 import AppFolder from "../../Icons/AppFolder.tsx";
-import OrganizeMenuItems from "./OrganizeMenuItems.tsx";
-import MoreMenuItems from "./MoreMenuItems.tsx";
-import OpenWithMenuItems from "./OpenWithMenuItems.tsx";
-import {
-  refreshFileList,
-  uploadClicked,
-  uploadFromClipboard,
-} from "../../../redux/thunks/filemanager.ts";
-import ArrowSync from "../../Icons/ArrowSync.tsx";
-import FolderAdd from "../../Icons/FolderAdd.tsx";
-import { CreateNewDialogType } from "../../../redux/globalStateSlice.ts";
-import FileAdd from "../../Icons/FileAdd.tsx";
-import NewFileTemplateMenuItems from "./NewFileTemplateMenuItems.tsx";
-import Upload from "../../Icons/Upload.tsx";
-import FolderArrowUp from "../../Icons/FolderArrowUp.tsx";
-import { SelectType } from "../../Uploader/core";
-import Clipboard from "../../Icons/Clipboard.tsx";
 import ArchiveArrow from "../../Icons/ArchiveArrow.tsx";
+import ArrowSync from "../../Icons/ArrowSync.tsx";
+import BinFullOutlined from "../../Icons/BinFullOutlined.tsx";
+import Clipboard from "../../Icons/Clipboard.tsx";
 import CloudDownloadOutlined from "../../Icons/CloudDownloadOutlined.tsx";
+import CopyOutlined from "../../Icons/CopyOutlined.tsx";
+import DeleteOutlined from "../../Icons/DeleteOutlined.tsx";
+import Download from "../../Icons/Download.tsx";
 import Enter from "../../Icons/Enter.tsx";
+import FileAdd from "../../Icons/FileAdd.tsx";
+import FolderAdd from "../../Icons/FolderAdd.tsx";
+import FolderArrowUp from "../../Icons/FolderArrowUp.tsx";
+import FolderLink from "../../Icons/FolderLink.tsx";
 import FolderOutlined from "../../Icons/FolderOutlined.tsx";
+import HistoryOutlined from "../../Icons/HistoryOutlined.tsx";
+import Info from "../../Icons/Info.tsx";
 import LinkOutlined from "../../Icons/LinkOutlined.tsx";
+import Open from "../../Icons/Open.tsx";
+import RenameOutlined from "../../Icons/RenameOutlined.tsx";
+import ShareOutlined from "../../Icons/ShareOutlined.tsx";
+import Tag from "../../Icons/Tag.tsx";
+import Upload from "../../Icons/Upload.tsx";
+import WrenchSettings from "../../Icons/WrenchSettings.tsx";
+import { SelectType } from "../../Uploader/core";
+import { CascadingSubmenu } from "./CascadingMenu.tsx";
+import MoreMenuItems from "./MoreMenuItems.tsx";
+import NewFileTemplateMenuItems from "./NewFileTemplateMenuItems.tsx";
+import OpenWithMenuItems from "./OpenWithMenuItems.tsx";
+import OrganizeMenuItems from "./OrganizeMenuItems.tsx";
+import TagMenuItems from "./TagMenuItems.tsx";
+import useActionDisplayOpt from "./useActionDisplayOpt.ts";
 
 export const SquareMenu = styled(Menu)(() => ({
   "& .MuiPaper-root": {
@@ -75,13 +61,11 @@ export const SquareMenu = styled(Menu)(() => ({
   },
 }));
 
-export const SquareMenuItem = styled(MenuItem)<{ hoverColor?: string }>(
-  ({ theme, hoverColor }) => ({
-    "&:hover .MuiListItemIcon-root": {
-      color: hoverColor ?? theme.palette.primary.main,
-    },
-  }),
-);
+export const SquareMenuItem = styled(MenuItem)<{ hoverColor?: string }>(({ theme, hoverColor }) => ({
+  "&:hover .MuiListItemIcon-root": {
+    color: hoverColor ?? theme.palette.primary.main,
+  },
+}));
 
 export const DenseDivider = styled(Divider)(() => ({
   margin: "4px 0 !important",
@@ -90,14 +74,9 @@ export const DenseDivider = styled(Divider)(() => ({
 export const EmptyMenu = () => {
   const { t } = useTranslation();
   return (
-    <Box
-      sx={{ py: 0.5, px: 1, display: "flex", alignItems: "center" }}
-      color={"text.secondary"}
-    >
+    <Box sx={{ py: 0.5, px: 1, display: "flex", alignItems: "center" }} color={"text.secondary"}>
       <Info sx={{ mr: 1 }} />
-      <Typography variant="body2">
-        {t("fileManager.noActionsCanBeDone")}
-      </Typography>
+      <Typography variant="body2">{t("fileManager.noActionsCanBeDone")}</Typography>
     </Box>
   );
 };
@@ -110,44 +89,29 @@ const ContextMenu = ({ fmIndex = 0 }: ContextMenuProps) => {
   const { t } = useTranslation();
   const dispatch = useAppDispatch();
   const theme = useTheme();
-  const contextMenuOpen = useAppSelector(
-    (state) => state.fileManager[fmIndex].contextMenuOpen,
-  );
-  const contextMenuType = useAppSelector(
-    (state) => state.fileManager[fmIndex].contextMenuType,
-  );
-  const contextMenuPos = useAppSelector(
-    (state) => state.fileManager[fmIndex].contextMenuPos,
-  );
-  const selected = useAppSelector(
-    (state) => state.fileManager[fmIndex].selected,
-  );
-  const targetOverwrite = useAppSelector(
-    (state) => state.fileManager[fmIndex].contextMenuTargets,
-  );
+  const contextMenuOpen = useAppSelector((state) => state.fileManager[fmIndex].contextMenuOpen);
+  const contextMenuType = useAppSelector((state) => state.fileManager[fmIndex].contextMenuType);
+  const contextMenuPos = useAppSelector((state) => state.fileManager[fmIndex].contextMenuPos);
+  const selected = useAppSelector((state) => state.fileManager[fmIndex].selected);
+  const targetOverwrite = useAppSelector((state) => state.fileManager[fmIndex].contextMenuTargets);
 
   const targets = useMemo(() => {
     const targetsMap = targetOverwrite ?? selected;
     return Object.keys(targetsMap).map((key) => targetsMap[key]);
   }, [targetOverwrite, selected]);
 
-  const parent = useAppSelector(
-    (state) => state.fileManager[fmIndex].list?.parent,
-  );
+  const parent = useAppSelector((state) => state.fileManager[fmIndex].list?.parent);
 
-  const displayOpt = useActionDisplayOpt(
-    targets,
-    contextMenuType,
-    parent,
-    fmIndex,
-  );
+  const displayOpt = useActionDisplayOpt(targets, contextMenuType, parent, fmIndex);
   const onClose = useCallback(() => {
     dispatch(closeContextMenu({ index: fmIndex, value: undefined }));
   }, [dispatch]);
 
+  const showOpenWithCascading = displayOpt.showOpenWithCascading && displayOpt.showOpenWithCascading();
   const showOpenWith = displayOpt.showOpenWith && displayOpt.showOpenWith();
   let part1 =
     displayOpt.showOpen ||
+    showOpenWithCascading ||
     showOpenWith ||
     displayOpt.showEnter ||
     displayOpt.showDownload ||
@@ -163,16 +127,9 @@ const ContextMenu = ({ fmIndex = 0 }: ContextMenuProps) => {
     displayOpt.showCopy ||
     displayOpt.showDirectLink;
   let part3 =
-    displayOpt.showTags ||
-    displayOpt.showOrganize ||
-    displayOpt.showMore ||
-    displayOpt.showNewFileFromTemplate;
-  let part4 =
-    displayOpt.showInfo ||
-    displayOpt.showGoToParent ||
-    displayOpt.showGoToSharedLink;
-  let part5 =
-    displayOpt.showRestore || displayOpt.showDelete || displayOpt.showRefresh;
+    displayOpt.showTags || displayOpt.showOrganize || displayOpt.showMore || displayOpt.showNewFileFromTemplate;
+  let part4 = displayOpt.showInfo || displayOpt.showGoToParent || displayOpt.showGoToSharedLink;
+  let part5 = displayOpt.showRestore || displayOpt.showDelete || displayOpt.showRefresh;
   const showDivider1 = part1 && part2;
   const showDivider2 = part2 && part3;
   const showDivider3 = part3 && part4;
@@ -181,15 +138,11 @@ const ContextMenu = ({ fmIndex = 0 }: ContextMenuProps) => {
   const part1Elements = part1 ? (
     <>
       {displayOpt.showUpload && (
-        <SquareMenuItem
-          onClick={() => dispatch(uploadClicked(0, SelectType.File))}
-        >
+        <SquareMenuItem onClick={() => dispatch(uploadClicked(0, SelectType.File))}>
           <ListItemIcon>
             <Upload fontSize="small" />
           </ListItemIcon>
-          <ListItemText>
-            {t("application:fileManager.uploadFiles")}
-          </ListItemText>
+          <ListItemText>{t("application:fileManager.uploadFiles")}</ListItemText>
         </SquareMenuItem>
       )}
       {displayOpt.showEnter && (
@@ -201,15 +154,11 @@ const ContextMenu = ({ fmIndex = 0 }: ContextMenuProps) => {
         </SquareMenuItem>
       )}
       {displayOpt.showUpload && (
-        <SquareMenuItem
-          onClick={() => dispatch(uploadClicked(0, SelectType.Directory))}
-        >
+        <SquareMenuItem onClick={() => dispatch(uploadClicked(0, SelectType.Directory))}>
           <ListItemIcon>
             <FolderArrowUp fontSize="small" />
           </ListItemIcon>
-          <ListItemText>
-            {t("application:fileManager.uploadFolder")}
-          </ListItemText>
+          <ListItemText>{t("application:fileManager.uploadFolder")}</ListItemText>
         </SquareMenuItem>
       )}
       {displayOpt.showUpload && (
@@ -217,9 +166,7 @@ const ContextMenu = ({ fmIndex = 0 }: ContextMenuProps) => {
           <ListItemIcon>
             <Clipboard fontSize="small" />
           </ListItemIcon>
-          <ListItemText>
-            {t("application:uploader.uploadFromClipboard")}
-          </ListItemText>
+          <ListItemText>{t("application:uploader.uploadFromClipboard")}</ListItemText>
         </SquareMenuItem>
       )}
       {displayOpt.showRemoteDownload && (
@@ -227,22 +174,18 @@ const ContextMenu = ({ fmIndex = 0 }: ContextMenuProps) => {
           <ListItemIcon>
             <CloudDownloadOutlined fontSize="small" />
           </ListItemIcon>
-          <ListItemText>
-            {t("application:fileManager.newRemoteDownloads")}
-          </ListItemText>
+          <ListItemText>{t("application:fileManager.newRemoteDownloads")}</ListItemText>
         </SquareMenuItem>
       )}
       {displayOpt.showOpen && (
-        <SquareMenuItem
-          onClick={() => dispatch(openViewers(fmIndex, targets[0]))}
-        >
+        <SquareMenuItem onClick={() => dispatch(openViewers(fmIndex, targets[0]))}>
           <ListItemIcon>
             <Open fontSize="small" />
           </ListItemIcon>
           <ListItemText>{t("application:fileManager.open")}</ListItemText>
         </SquareMenuItem>
       )}
-      {showOpenWith && (
+      {showOpenWithCascading && (
         <CascadingSubmenu
           popupId={"openWith"}
           title={t("application:fileManager.openWith")}
@@ -251,10 +194,16 @@ const ContextMenu = ({ fmIndex = 0 }: ContextMenuProps) => {
           <OpenWithMenuItems displayOpt={displayOpt} targets={targets} />
         </CascadingSubmenu>
       )}
+      {showOpenWith && (
+        <SquareMenuItem onClick={() => dispatch(openViewers(fmIndex, targets[0], targets[0].size, undefined, true))}>
+          <ListItemIcon>
+            <AppFolder fontSize="small" />
+          </ListItemIcon>
+          <ListItemText>{t("application:fileManager.openWith")}</ListItemText>
+        </SquareMenuItem>
+      )}
       {displayOpt.showDownload && (
-        <SquareMenuItem
-          onClick={() => dispatch(downloadFiles(fmIndex, targets))}
-        >
+        <SquareMenuItem onClick={() => dispatch(downloadFiles(fmIndex, targets))}>
           <ListItemIcon>
             <Download fontSize="small" />
           </ListItemIcon>
@@ -262,27 +211,19 @@ const ContextMenu = ({ fmIndex = 0 }: ContextMenuProps) => {
         </SquareMenuItem>
       )}
       {displayOpt.showExtractArchive && (
-        <SquareMenuItem
-          onClick={() => dispatch(extractArchive(fmIndex, targets[0]))}
-        >
+        <SquareMenuItem onClick={() => dispatch(extractArchive(fmIndex, targets[0]))}>
           <ListItemIcon>
             <ArchiveArrow fontSize="small" />
           </ListItemIcon>
-          <ListItemText>
-            {t("application:fileManager.extractArchive")}
-          </ListItemText>
+          <ListItemText>{t("application:fileManager.extractArchive")}</ListItemText>
         </SquareMenuItem>
       )}
       {displayOpt.showTorrentRemoteDownload && (
-        <SquareMenuItem
-          onClick={() => dispatch(newRemoteDownload(fmIndex, targets[0]))}
-        >
+        <SquareMenuItem onClick={() => dispatch(newRemoteDownload(fmIndex, targets[0]))}>
           <ListItemIcon>
             <CloudDownloadOutlined fontSize="small" />
           </ListItemIcon>
-          <ListItemText>
-            {t("application:fileManager.createRemoteDownloadForTorrent")}
-          </ListItemText>
+          <ListItemText>{t("application:fileManager.createRemoteDownloadForTorrent")}</ListItemText>
         </SquareMenuItem>
       )}
     </>
@@ -291,11 +232,7 @@ const ContextMenu = ({ fmIndex = 0 }: ContextMenuProps) => {
   const part2Elements = part2 ? (
     <>
       {displayOpt.showCreateFolder && (
-        <SquareMenuItem
-          onClick={() =>
-            dispatch(createNew(fmIndex, CreateNewDialogType.folder))
-          }
-        >
+        <SquareMenuItem onClick={() => dispatch(createNew(fmIndex, CreateNewDialogType.folder))}>
           <ListItemIcon>
             <FolderAdd fontSize="small" />
           </ListItemIcon>
@@ -303,9 +240,7 @@ const ContextMenu = ({ fmIndex = 0 }: ContextMenuProps) => {
         </SquareMenuItem>
       )}
       {displayOpt.showCreateFile && (
-        <SquareMenuItem
-          onClick={() => dispatch(createNew(fmIndex, CreateNewDialogType.file))}
-        >
+        <SquareMenuItem onClick={() => dispatch(createNew(fmIndex, CreateNewDialogType.file))}>
           <ListItemIcon>
             <FileAdd fontSize="small" />
           </ListItemIcon>
@@ -313,9 +248,7 @@ const ContextMenu = ({ fmIndex = 0 }: ContextMenuProps) => {
         </SquareMenuItem>
       )}
       {displayOpt.showShare && (
-        <SquareMenuItem
-          onClick={() => dispatch(openShareDialog(fmIndex, targets[0]))}
-        >
+        <SquareMenuItem onClick={() => dispatch(openShareDialog(fmIndex, targets[0]))}>
           <ListItemIcon>
             <ShareOutlined fontSize="small" />
           </ListItemIcon>
@@ -323,9 +256,7 @@ const ContextMenu = ({ fmIndex = 0 }: ContextMenuProps) => {
         </SquareMenuItem>
       )}
       {displayOpt.showRename && (
-        <SquareMenuItem
-          onClick={() => dispatch(renameFile(fmIndex, targets[0]))}
-        >
+        <SquareMenuItem onClick={() => dispatch(renameFile(fmIndex, targets[0]))}>
           <ListItemIcon>
             <RenameOutlined fontSize="small" />
           </ListItemIcon>
@@ -333,9 +264,7 @@ const ContextMenu = ({ fmIndex = 0 }: ContextMenuProps) => {
         </SquareMenuItem>
       )}
       {displayOpt.showCopy && (
-        <SquareMenuItem
-          onClick={() => dispatch(dialogBasedMoveCopy(fmIndex, targets, true))}
-        >
+        <SquareMenuItem onClick={() => dispatch(dialogBasedMoveCopy(fmIndex, targets, true))}>
           <ListItemIcon>
             <CopyOutlined fontSize="small" />
           </ListItemIcon>
@@ -343,15 +272,11 @@ const ContextMenu = ({ fmIndex = 0 }: ContextMenuProps) => {
         </SquareMenuItem>
       )}
       {displayOpt.showDirectLink && (
-        <SquareMenuItem
-          onClick={() => dispatch(batchGetDirectLinks(fmIndex, targets))}
-        >
+        <SquareMenuItem onClick={() => dispatch(batchGetDirectLinks(fmIndex, targets))}>
           <ListItemIcon>
             <LinkOutlined fontSize="small" />
           </ListItemIcon>
-          <ListItemText>
-            {t("application:fileManager.getSourceLink")}
-          </ListItemText>
+          <ListItemText>{t("application:fileManager.getSourceLink")}</ListItemText>
         </SquareMenuItem>
       )}
     </>
@@ -360,11 +285,7 @@ const ContextMenu = ({ fmIndex = 0 }: ContextMenuProps) => {
   const part3Elements = part3 ? (
     <>
       {displayOpt.showTags && (
-        <CascadingSubmenu
-          popupId={"tags"}
-          title={t("application:fileManager.tags")}
-          icon={<Tag fontSize="small" />}
-        >
+        <CascadingSubmenu popupId={"tags"} title={t("application:fileManager.tags")} icon={<Tag fontSize="small" />}>
           <TagMenuItems displayOpt={displayOpt} targets={targets} />
         </CascadingSubmenu>
       )}
@@ -386,24 +307,18 @@ const ContextMenu = ({ fmIndex = 0 }: ContextMenuProps) => {
           <MoreMenuItems displayOpt={displayOpt} targets={targets} />
         </CascadingSubmenu>
       )}
-      {displayOpt.showNewFileFromTemplate && (
-        <NewFileTemplateMenuItems displayOpt={displayOpt} targets={targets} />
-      )}
+      {displayOpt.showNewFileFromTemplate && <NewFileTemplateMenuItems displayOpt={displayOpt} targets={targets} />}
     </>
   ) : undefined;
 
   const part4Elements = part4 ? (
     <>
       {displayOpt.showGoToSharedLink && (
-        <SquareMenuItem
-          onClick={() => dispatch(goToSharedLink(fmIndex, targets[0]))}
-        >
+        <SquareMenuItem onClick={() => dispatch(goToSharedLink(fmIndex, targets[0]))}>
           <ListItemIcon>
             <FolderLink fontSize="small" />
           </ListItemIcon>
-          <ListItemText>
-            {t("application:fileManager.goToSharedLink")}
-          </ListItemText>
+          <ListItemText>{t("application:fileManager.goToSharedLink")}</ListItemText>
         </SquareMenuItem>
       )}
       {displayOpt.showGoToParent && (
@@ -411,21 +326,15 @@ const ContextMenu = ({ fmIndex = 0 }: ContextMenuProps) => {
           <ListItemIcon>
             <FolderOutlined fontSize="small" />
           </ListItemIcon>
-          <ListItemText>
-            {t("application:fileManager.openParentFolder")}
-          </ListItemText>
+          <ListItemText>{t("application:fileManager.openParentFolder")}</ListItemText>
         </SquareMenuItem>
       )}
       {displayOpt.showInfo && (
-        <SquareMenuItem
-          onClick={() => dispatch(openSidebar(fmIndex, targets[0]))}
-        >
+        <SquareMenuItem onClick={() => dispatch(openSidebar(fmIndex, targets[0]))}>
           <ListItemIcon>
             <Info fontSize="small" />
           </ListItemIcon>
-          <ListItemText>
-            {t("application:fileManager.viewDetails")}
-          </ListItemText>
+          <ListItemText>{t("application:fileManager.viewDetails")}</ListItemText>
         </SquareMenuItem>
       )}
     </>
@@ -442,10 +351,7 @@ const ContextMenu = ({ fmIndex = 0 }: ContextMenuProps) => {
         </SquareMenuItem>
       )}
       {displayOpt.showDelete && (
-        <SquareMenuItem
-          hoverColor={theme.palette.error.light}
-          onClick={() => dispatch(deleteFile(fmIndex, targets))}
-        >
+        <SquareMenuItem hoverColor={theme.palette.error.light} onClick={() => dispatch(deleteFile(fmIndex, targets))}>
           <ListItemIcon>
             <DeleteOutlined fontSize="small" />
           </ListItemIcon>
@@ -463,13 +369,9 @@ const ContextMenu = ({ fmIndex = 0 }: ContextMenuProps) => {
     </>
   ) : undefined;
 
-  const allParts = [
-    part1Elements,
-    part2Elements,
-    part3Elements,
-    part4Elements,
-    part5Elements,
-  ].filter((p) => p != undefined);
+  const allParts = [part1Elements, part2Elements, part3Elements, part4Elements, part5Elements].filter(
+    (p) => p != undefined,
+  );
 
   return (
     <SquareMenu
diff --git a/src/component/FileManager/ContextMenu/useActionDisplayOpt.ts b/src/component/FileManager/ContextMenu/useActionDisplayOpt.ts
index 6a4487b..7f332cc 100644
--- a/src/component/FileManager/ContextMenu/useActionDisplayOpt.ts
+++ b/src/component/FileManager/ContextMenu/useActionDisplayOpt.ts
@@ -48,6 +48,7 @@ export interface DisplayOption {
 
   showEnter?: boolean;
   showOpen?: boolean;
+  showOpenWithCascading?: () => boolean;
   showOpenWith?: () => boolean;
   showDownload?: boolean;
   showGoToSharedLink?: boolean;
@@ -228,7 +229,13 @@ export const getActionOpt = (
     display.orCapability &&
     (currentUserAnonymous?.group?.direct_link_batch_size ?? 0) >= targets.length &&
     display.orCapability.enabled(NavigatorCapability.download_file);
-  display.showOpen = targets.length == 1 && display.hasFile && display.showDownload && !!viewerSetting;
+  display.showOpen =
+    targets.length == 1 &&
+    display.hasFile &&
+    display.showDownload &&
+    !!viewerSetting &&
+    !!firstFileSuffix &&
+    !!viewerSetting?.[firstFileSuffix];
   display.showEnter =
     targets.length == 1 &&
     display.hasFolder &&
@@ -249,11 +256,13 @@ export const getActionOpt = (
     groupBs.enabled(GroupPermission.remote_download) &&
     firstFileSuffix == "torrent";
 
-  display.showOpenWith = () => false;
+  display.showOpenWithCascading = () => false;
+  display.showOpenWith = () => targets.length == 1 && !!display.hasFile && !!display.showDownload;
   if (display.showOpen) {
-    display.showOpen = !!firstFileSuffix && !!viewerSetting?.[firstFileSuffix];
+    display.showOpenWithCascading = () =>
+      !!(display.showOpen && viewerSetting && viewerSetting[firstFileSuffix ?? ""]?.length >= 1);
     display.showOpenWith = () =>
-      !!(display.showOpen && viewerSetting && viewerSetting[firstFileSuffix ?? ""]?.length > 1);
+      !!(display.showOpen && viewerSetting && viewerSetting[firstFileSuffix ?? ""]?.length < 1);
   }
   display.showOrganize = display.showPin || display.showMove || display.showChangeFolderColor || display.showChangeIcon;
   display.showGoToSharedLink =
diff --git a/src/component/FileManager/Dialogs/OpenWith.tsx b/src/component/FileManager/Dialogs/OpenWith.tsx
index 732092f..cfc9a43 100644
--- a/src/component/FileManager/Dialogs/OpenWith.tsx
+++ b/src/component/FileManager/Dialogs/OpenWith.tsx
@@ -1,4 +1,3 @@
-import { useTranslation } from "react-i18next";
 import {
   Avatar,
   Box,
@@ -12,25 +11,24 @@ import {
   ListItemText,
   Stack,
 } from "@mui/material";
-import { useAppDispatch, useAppSelector } from "../../../redux/hooks.ts";
 import React, { useCallback, useEffect, useMemo, useState } from "react";
-import DraggableDialog, {
-  StyledDialogContentText,
-} from "../../Dialogs/DraggableDialog.tsx";
-import { closeViewerSelector } from "../../../redux/globalStateSlice.ts";
-import { fileExtension } from "../../../util";
+import { useTranslation } from "react-i18next";
 import { Viewer, ViewerType } from "../../../api/explorer.ts";
-import { builtInViewers, openViewer } from "../../../redux/thunks/viewer.ts";
-import Image from "../../Icons/Image.tsx";
-import AutoHeight from "../../Common/AutoHeight.tsx";
-import Markdown from "../../Icons/Markdown.tsx";
-import DocumentPDF from "../../Icons/DocumentPDF.tsx";
-import Book from "../../Icons/Book.tsx";
-import MusicNote1 from "../../Icons/MusicNote1.tsx";
-import MoreHorizontal from "../../Icons/MoreHorizontal.tsx";
+import { closeViewerSelector } from "../../../redux/globalStateSlice.ts";
+import { useAppDispatch, useAppSelector } from "../../../redux/hooks.ts";
 import { ViewersByID } from "../../../redux/siteConfigSlice.ts";
+import { builtInViewers, openViewer } from "../../../redux/thunks/viewer.ts";
 import SessionManager, { UserSettings } from "../../../session";
+import { fileExtension } from "../../../util";
+import AutoHeight from "../../Common/AutoHeight.tsx";
 import { SecondaryButton } from "../../Common/StyledComponents.tsx";
+import DraggableDialog, { StyledDialogContentText } from "../../Dialogs/DraggableDialog.tsx";
+import Book from "../../Icons/Book.tsx";
+import DocumentPDF from "../../Icons/DocumentPDF.tsx";
+import Image from "../../Icons/Image.tsx";
+import Markdown from "../../Icons/Markdown.tsx";
+import MoreHorizontal from "../../Icons/MoreHorizontal.tsx";
+import MusicNote1 from "../../Icons/MusicNote1.tsx";
 
 export interface ViewerIconProps {
   viewer: Viewer;
@@ -48,11 +46,7 @@ export const ViewerIDWithDefaultIcons = [
   builtInViewers.markdown,
 ];
 
-export const ViewerIcon = ({
-  viewer,
-  size = 32,
-  py = 0.5,
-}: ViewerIconProps) => {
+export const ViewerIcon = ({ viewer, size = 32, py = 0.5 }: ViewerIconProps) => {
   const BuiltinIcons = useMemo(() => {
     if (viewer.icon) {
       return undefined;
@@ -63,23 +57,18 @@ export const ViewerIcon = ({
         case builtInViewers.image:
           return <Image sx={{ width: size, height: size, color: "#d32f2f" }} />;
         case builtInViewers.pdf:
-          return (
-            <DocumentPDF sx={{ width: size, height: size, color: "#f44336" }} />
-          );
+          return <DocumentPDF sx={{ width: size, height: size, color: "#f44336" }} />;
         case builtInViewers.epub:
           return <Book sx={{ width: size, height: size, color: "#81b315" }} />;
         case builtInViewers.music:
-          return (
-            <MusicNote1 sx={{ width: size, height: size, color: "#651fff" }} />
-          );
+          return <MusicNote1 sx={{ width: size, height: size, color: "#651fff" }} />;
         case builtInViewers.markdown:
           return (
             <Markdown
               sx={{
                 width: size,
                 height: size,
-                color: (theme) =>
-                  theme.palette.mode == "dark" ? "#cbcbcb" : "#383838",
+                color: (theme) => (theme.palette.mode == "dark" ? "#cbcbcb" : "#383838"),
               }}
             />
           );
@@ -106,18 +95,14 @@ export const ViewerIcon = ({
 const OpenWith = () => {
   const { t } = useTranslation();
   const dispatch = useAppDispatch();
-  const [selectedViewer, setSelectedViewer] = React.useState<Viewer | null>(
-    null,
-  );
+  const [selectedViewer, setSelectedViewer] = React.useState<Viewer | null>(null);
   const [expanded, setExpanded] = useState(false);
 
-  const selectorState = useAppSelector(
-    (state) => state.globalState.viewerSelector,
-  );
+  const selectorState = useAppSelector((state) => state.globalState.viewerSelector);
 
   useEffect(() => {
     if (selectorState?.open) {
-      setExpanded(false);
+      setExpanded(!selectorState.viewers);
       setSelectedViewer(null);
     }
   }, [selectorState]);
@@ -140,10 +125,7 @@ const OpenWith = () => {
     }
 
     if (always) {
-      SessionManager.set(
-        UserSettings.OpenWithPrefix + ext,
-        viewer?.id ?? selectedViewer?.id,
-      );
+      SessionManager.set(UserSettings.OpenWithPrefix + ext, viewer?.id ?? selectedViewer?.id);
     }
 
     dispatch(
@@ -157,6 +139,15 @@ const OpenWith = () => {
     dispatch(closeViewerSelector());
   };
 
+  const onViewerClick = (viewer: Viewer) => {
+    if (selectorState?.viewers) {
+      setSelectedViewer(viewer);
+    } else {
+      // For files without matching viewers, open the selected viewer without asking for preference
+      openWith(false, viewer);
+    }
+  };
+
   return (
     <DraggableDialog
       title={t("application:fileManager.openWith")}
@@ -183,16 +174,12 @@ const OpenWith = () => {
               overflow: "auto",
             }}
           >
-            {(
-              (expanded
-                ? Object.values(ViewersByID)
-                : selectorState?.viewers) ?? emptyViewer
-            ).map((viewer) => (
+            {((expanded ? Object.values(ViewersByID) : selectorState?.viewers) ?? emptyViewer).map((viewer) => (
               <ListItem
                 disablePadding
                 key={viewer.id}
                 onDoubleClick={() => openWith(false, viewer)}
-                onClick={() => setSelectedViewer(viewer)}
+                onClick={() => onViewerClick(viewer)}
               >
                 <ListItemButton selected={viewer.id == selectedViewer?.id}>
                   <ListItemAvatar sx={{ minWidth: "48px" }}>
@@ -221,20 +208,12 @@ const OpenWith = () => {
             <Divider />
             <Grid container spacing={2} sx={{ p: 2 }}>
               <Grid md={6} xs={12} item>
-                <SecondaryButton
-                  fullWidth
-                  variant={"contained"}
-                  onClick={() => openWith(true)}
-                >
+                <SecondaryButton fullWidth variant={"contained"} onClick={() => openWith(true)}>
                   {t("modals.always")}
                 </SecondaryButton>
               </Grid>
               <Grid md={6} xs={12} item>
-                <SecondaryButton
-                  fullWidth
-                  variant={"contained"}
-                  onClick={() => openWith(false)}
-                >
+                <SecondaryButton fullWidth variant={"contained"} onClick={() => openWith(false)}>
                   {t("modals.justOnce")}
                 </SecondaryButton>
               </Grid>
diff --git a/src/redux/thunks/viewer.ts b/src/redux/thunks/viewer.ts
index a366678..dabf2a7 100644
--- a/src/redux/thunks/viewer.ts
+++ b/src/redux/thunks/viewer.ts
@@ -78,25 +78,16 @@ export function openViewers(
     }
 
     const viewerOptions = Viewers[ext];
-    if (!viewerOptions) {
-      return;
-    }
-
-    if (viewerOptions.length > 1) {
-      // open viewer selection dialog
-      dispatch(
-        setViewerSelector({
-          open: true,
-          file,
-          entitySize,
-          viewers: viewerOptions,
-          version: preferredVersion,
-        }),
-      );
-      return;
-    }
-
-    dispatch(openViewer(file, viewerOptions[0], entitySize, preferredVersion));
+    // open viewer selection dialog
+    dispatch(
+      setViewerSelector({
+        open: true,
+        file,
+        entitySize,
+        viewers: viewerOptions,
+        version: preferredVersion,
+      }),
+    );
   };
 }