diff --git a/web/src/components/MemoEditor/Toolbar/InsertMenu.tsx b/web/src/components/MemoEditor/Toolbar/InsertMenu.tsx
index d960e999f..f7433ee57 100644
--- a/web/src/components/MemoEditor/Toolbar/InsertMenu.tsx
+++ b/web/src/components/MemoEditor/Toolbar/InsertMenu.tsx
@@ -13,6 +13,7 @@ import {
   DropdownMenuSubContent,
   DropdownMenuSubTrigger,
   DropdownMenuTrigger,
+  useDropdownMenuSubHoverDelay,
 } from "@/components/ui/dropdown-menu";
 import type { Location, MemoRelation } from "@/types/proto/api/v1/memo_service_pb";
 import { useTranslate } from "@/utils/i18n";
@@ -35,10 +36,13 @@ const InsertMenu = observer((props: Props) => {
 
   const [linkDialogOpen, setLinkDialogOpen] = useState(false);
   const [locationDialogOpen, setLocationDialogOpen] = useState(false);
+  const [moreSubmenuOpen, setMoreSubmenuOpen] = useState(false);
 
   // Abort controller for canceling geocoding requests
   const { abort: abortGeocoding, abortAndCreate: createGeocodingSignal } = useAbortController();
 
+  const { handleTriggerEnter, handleTriggerLeave, handleContentEnter, handleContentLeave } = useDropdownMenuSubHoverDelay(150, setMoreSubmenuOpen);
+
   const { fileInputRef, selectingFlag, handleFileInputChange, handleUploadClick } = useFileUpload((newFiles: LocalFile[]) => {
     if (context.addLocalFiles) {
       context.addLocalFiles(newFiles);
@@ -138,7 +142,7 @@ const InsertMenu = observer((props: Props) => {
 
   return (
     <>
-      <DropdownMenu>
+      <DropdownMenu modal={false}>
         <DropdownMenuTrigger asChild>
           <Button variant="outline" size="icon" className="shadow-none" disabled={isUploading}>
             {isUploading ? <LoaderIcon className="size-4 animate-spin" /> : <PlusIcon className="size-4" />}
@@ -158,13 +162,18 @@ const InsertMenu = observer((props: Props) => {
             {t("tooltip.select-location")}
           </DropdownMenuItem>
           {/* View submenu with Focus Mode */}
-          <DropdownMenuSub>
-            <DropdownMenuSubTrigger>
+          <DropdownMenuSub open={moreSubmenuOpen} onOpenChange={setMoreSubmenuOpen}>
+            <DropdownMenuSubTrigger onPointerEnter={handleTriggerEnter} onPointerLeave={handleTriggerLeave}>
               <MoreHorizontalIcon className="w-4 h-4" />
               {t("common.more")}
             </DropdownMenuSubTrigger>
-            <DropdownMenuSubContent>
-              <DropdownMenuItem onClick={props.onToggleFocusMode}>
+            <DropdownMenuSubContent onPointerEnter={handleContentEnter} onPointerLeave={handleContentLeave}>
+              <DropdownMenuItem
+                onClick={() => {
+                  props.onToggleFocusMode?.();
+                  setMoreSubmenuOpen(false);
+                }}
+              >
                 <Maximize2Icon className="w-4 h-4" />
                 {t("editor.focus-mode")}
                 <span className="ml-auto text-xs text-muted-foreground opacity-60">⌘⇧F</span>
diff --git a/web/src/components/ui/dropdown-menu.tsx b/web/src/components/ui/dropdown-menu.tsx
index 0a724533b..ca35079e7 100644
--- a/web/src/components/ui/dropdown-menu.tsx
+++ b/web/src/components/ui/dropdown-menu.tsx
@@ -1,6 +1,7 @@
 import * as DropdownMenuPrimitive from "@radix-ui/react-dropdown-menu";
 import { CheckIcon, ChevronRightIcon, CircleIcon } from "lucide-react";
 import * as React from "react";
+import { useEffect, useRef } from "react";
 import { cn } from "@/lib/utils";
 
 const DropdownMenu = React.forwardRef<
@@ -200,6 +201,58 @@ function DropdownMenuSubContent({ className, ...props }: React.ComponentProps<ty
   );
 }
 
+/**
+ * Hook for managing submenu hover behavior with delayed close.
+ * Prevents accidental submenu closure on quick mouse movements.
+ *
+ * @param closeDelay - Delay in ms before closing submenu when leaving trigger/content
+ * @param onOpenChange - Callback to update submenu open state
+ * @returns Object with event handlers and state management utilities
+ */
+function useDropdownMenuSubHoverDelay(closeDelay = 150, onOpenChange?: (open: boolean) => void) {
+  const closeTimeoutRef = useRef<number | null>(null);
+
+  const clearCloseTimeout = () => {
+    if (closeTimeoutRef.current) {
+      clearTimeout(closeTimeoutRef.current);
+      closeTimeoutRef.current = null;
+    }
+  };
+
+  const scheduleClose = (delay = 0) => {
+    clearCloseTimeout();
+    closeTimeoutRef.current = window.setTimeout(() => onOpenChange?.(false), delay);
+  };
+
+  const handleTriggerEnter = () => {
+    clearCloseTimeout();
+    onOpenChange?.(true);
+  };
+
+  const handleTriggerLeave = () => {
+    scheduleClose(closeDelay);
+  };
+
+  const handleContentEnter = () => {
+    clearCloseTimeout();
+  };
+
+  const handleContentLeave = () => {
+    scheduleClose();
+  };
+
+  useEffect(() => {
+    return () => clearCloseTimeout();
+  }, []);
+
+  return {
+    handleTriggerEnter,
+    handleTriggerLeave,
+    handleContentEnter,
+    handleContentLeave,
+  };
+}
+
 export {
   DropdownMenu,
   DropdownMenuPortal,
@@ -216,4 +269,5 @@ export {
   DropdownMenuSub,
   DropdownMenuSubTrigger,
   DropdownMenuSubContent,
+  useDropdownMenuSubHoverDelay,
 };