diff --git a/surfsense_web/components/documents/DocumentNode.tsx b/surfsense_web/components/documents/DocumentNode.tsx
index e55512e96..4acdcf662 100644
--- a/surfsense_web/components/documents/DocumentNode.tsx
+++ b/surfsense_web/components/documents/DocumentNode.tsx
@@ -1,7 +1,7 @@
 "use client";
 
 import { AlertCircle, Clock, Eye, MoreHorizontal, Move, PenLine, Trash2 } from "lucide-react";
-import React, { useCallback, useRef } from "react";
+import React, { useCallback, useRef, useState } from "react";
 import { useDrag } from "react-dnd";
 import { getDocumentTypeIcon } from "@/app/dashboard/[search_space_id]/documents/(manage)/components/DocumentTypeIcon";
 import { Button } from "@/components/ui/button";
@@ -78,6 +78,7 @@ export const DocumentNode = React.memo(function DocumentNode({
 	);
 
 	const isProcessing = statusState === "pending" || statusState === "processing";
+	const [dropdownOpen, setDropdownOpen] = useState(false);
 	const rowRef = useRef<HTMLButtonElement>(null);
 
 	const attachRef = useCallback(
@@ -95,9 +96,9 @@ export const DocumentNode = React.memo(function DocumentNode({
 					type="button"
 					ref={attachRef}
 					className={cn(
-						"group flex h-8 w-full items-center gap-2.5 rounded-md px-1 text-sm hover:bg-accent/50 cursor-pointer select-none text-left",
-						isMentioned && "bg-accent/30",
-						isDragging && "opacity-40"
+					"group flex h-8 w-full items-center gap-2.5 rounded-md px-1 text-sm hover:bg-accent/50 cursor-pointer select-none text-left",
+					isMentioned && "bg-accent/30",
+					isDragging && "opacity-40"
 					)}
 					style={{ paddingLeft: `${depth * 16 + 4}px` }}
 					onClick={handleCheckChange}
@@ -160,14 +161,17 @@ export const DocumentNode = React.memo(function DocumentNode({
 						)}
 					</span>
 
-					<DropdownMenu>
-						<DropdownMenuTrigger asChild>
-							<Button
-								variant="ghost"
-								size="icon"
-								className="hidden sm:inline-flex h-6 w-6 shrink-0 opacity-0 group-hover:opacity-100 transition-opacity"
-								onClick={(e) => e.stopPropagation()}
-							>
+				<DropdownMenu open={dropdownOpen} onOpenChange={setDropdownOpen}>
+					<DropdownMenuTrigger asChild>
+						<Button
+							variant="ghost"
+							size="icon"
+							className={cn(
+								"hidden sm:inline-flex h-6 w-6 shrink-0 transition-opacity hover:bg-transparent",
+								dropdownOpen ? "opacity-100 bg-accent hover:bg-accent" : "opacity-0 group-hover:opacity-100"
+							)}
+							onClick={(e) => e.stopPropagation()}
+						>
 								<MoreHorizontal className="h-3.5 w-3.5" />
 							</Button>
 						</DropdownMenuTrigger>
diff --git a/surfsense_web/components/layout/ui/sidebar/AllPrivateChatsSidebar.tsx b/surfsense_web/components/layout/ui/sidebar/AllPrivateChatsSidebar.tsx
index fc5fb3873..65a24208b 100644
--- a/surfsense_web/components/layout/ui/sidebar/AllPrivateChatsSidebar.tsx
+++ b/surfsense_web/components/layout/ui/sidebar/AllPrivateChatsSidebar.tsx
@@ -396,10 +396,13 @@ export function AllPrivateChatsSidebarContent({
 												variant="ghost"
 												size="icon"
 												className={cn(
-													"h-6 w-6 shrink-0",
+													"h-6 w-6 shrink-0 hover:bg-transparent",
 													isMobile
 														? "opacity-0 pointer-events-none absolute"
-														: "md:opacity-0 md:group-hover:opacity-100 md:focus:opacity-100",
+														: openDropdownId === thread.id
+															? "opacity-100"
+															: "md:opacity-0 md:group-hover:opacity-100 md:focus:opacity-100",
+													openDropdownId === thread.id && "bg-accent hover:bg-accent",
 													"transition-opacity"
 												)}
 												disabled={isBusy}
diff --git a/surfsense_web/components/layout/ui/sidebar/AllSharedChatsSidebar.tsx b/surfsense_web/components/layout/ui/sidebar/AllSharedChatsSidebar.tsx
index 03673955a..ce0e45e81 100644
--- a/surfsense_web/components/layout/ui/sidebar/AllSharedChatsSidebar.tsx
+++ b/surfsense_web/components/layout/ui/sidebar/AllSharedChatsSidebar.tsx
@@ -396,10 +396,13 @@ export function AllSharedChatsSidebarContent({
 												variant="ghost"
 												size="icon"
 												className={cn(
-													"h-6 w-6 shrink-0",
+													"h-6 w-6 shrink-0 hover:bg-transparent",
 													isMobile
 														? "opacity-0 pointer-events-none absolute"
-														: "md:opacity-0 md:group-hover:opacity-100 md:focus:opacity-100",
+														: openDropdownId === thread.id
+															? "opacity-100"
+															: "md:opacity-0 md:group-hover:opacity-100 md:focus:opacity-100",
+													openDropdownId === thread.id && "bg-accent hover:bg-accent",
 													"transition-opacity"
 												)}
 												disabled={isBusy}
diff --git a/surfsense_web/components/layout/ui/sidebar/ChatListItem.tsx b/surfsense_web/components/layout/ui/sidebar/ChatListItem.tsx
index fc0520745..7f3089a89 100644
--- a/surfsense_web/components/layout/ui/sidebar/ChatListItem.tsx
+++ b/surfsense_web/components/layout/ui/sidebar/ChatListItem.tsx
@@ -79,14 +79,21 @@ export function ChatListItem({
 						: "bg-gradient-to-l from-sidebar from-60% to-transparent group-hover/item:from-accent",
 					isMobile
 						? "opacity-0"
-						: isActive
+						: isActive || dropdownOpen
 							? "opacity-100"
 							: "opacity-0 group-hover/item:opacity-100"
 				)}
 			>
 				<DropdownMenu open={dropdownOpen} onOpenChange={setDropdownOpen}>
 					<DropdownMenuTrigger asChild>
-						<Button variant="ghost" size="icon" className="pointer-events-auto h-6 w-6">
+						<Button
+							variant="ghost"
+							size="icon"
+							className={cn(
+								"pointer-events-auto h-6 w-6 hover:bg-transparent",
+								dropdownOpen && "bg-accent hover:bg-accent"
+							)}
+						>
 							<MoreHorizontal className="h-3.5 w-3.5 text-muted-foreground" />
 							<span className="sr-only">{t("more_options")}</span>
 						</Button>