diff --git a/src/app.css b/src/app.css
index 81f4293f9f..5c03d7cf27 100644
--- a/src/app.css
+++ b/src/app.css
@@ -937,7 +937,8 @@ html.high-contrast:not(.dark)
 	:is(
 		#sidebar .hover\:bg-gray-100:hover,
 		#sidebar .group:hover .group-hover\:bg-gray-100,
-		.app-dropdown-menu :is(button, a):hover
+		.app-dropdown-menu :is(button, a):not(.user-menu-row *):hover,
+		.app-dropdown-menu .user-menu-row:hover
 	) {
 	background-color: var(--color-gray-200) !important;
 }
@@ -946,7 +947,8 @@ html.high-contrast.dark
 	:is(
 		#sidebar .dark\:hover\:bg-gray-900:hover,
 		#sidebar .group:hover .dark\:group-hover\:bg-gray-900,
-		.app-dropdown-menu :is(button, a):hover
+		.app-dropdown-menu :is(button, a):not(.user-menu-row *):hover,
+		.app-dropdown-menu .user-menu-row:hover
 	) {
 	background-color: var(--color-gray-800) !important;
 }
diff --git a/src/lib/components/layout/Sidebar/UserMenu.svelte b/src/lib/components/layout/Sidebar/UserMenu.svelte
index 18c6f88ea4..e3a25ba1e9 100644
--- a/src/lib/components/layout/Sidebar/UserMenu.svelte
+++ b/src/lib/components/layout/Sidebar/UserMenu.svelte
@@ -118,7 +118,7 @@
 			{#if $user}
 				<div>
 					<button
-						class="flex h-[1.6875rem] items-center gap-2 rounded-xl px-2 text-xs w-full hover:bg-gray-100 dark:hover:bg-gray-900 transition cursor-pointer select-none text-left"
+						class="flex h-[1.6875rem] items-center gap-2 rounded-xl px-2 text-xs w-full hover:bg-gray-50/60 dark:hover:bg-gray-800/60 transition cursor-pointer select-none text-left"
 						type="button"
 						on:click={async () => {
 							show = false;
@@ -166,7 +166,7 @@
 				{#if $user?.status_emoji || $user?.status_message}
 					<div class="user-menu-status">
 						<button
-							class="w-full h-[1.6875rem] gap-2 rounded-xl px-2 hover:bg-gray-100 dark:hover:bg-gray-900 transition cursor-pointer select-none text-xs flex items-center text-left"
+							class="w-full h-[1.6875rem] gap-2 rounded-xl px-2 hover:bg-gray-50/60 dark:hover:bg-gray-800/60 transition cursor-pointer select-none text-xs flex items-center text-left"
 							type="button"
 							on:click={() => {
 								show = false;
@@ -218,7 +218,7 @@
 				{:else}
 					<div class="user-menu-status">
 						<button
-							class="w-full h-[1.6875rem] gap-2 rounded-xl px-2 hover:bg-gray-100 dark:hover:bg-gray-900 transition cursor-pointer select-none text-xs flex items-center text-left"
+							class="w-full h-[1.6875rem] gap-2 rounded-xl px-2 hover:bg-gray-50/60 dark:hover:bg-gray-800/60 transition cursor-pointer select-none text-xs flex items-center text-left"
 							type="button"
 							on:click={() => {
 								show = false;
@@ -239,11 +239,13 @@
 			{/if}
 
 			{#if $user?.role === 'admin' || $user?.permissions?.workspace?.models || $user?.permissions?.workspace?.knowledge || $user?.permissions?.workspace?.prompts || $user?.permissions?.workspace?.tools || $user?.permissions?.workspace?.skills}
-				<div class="flex items-center w-full">
+				<div
+					class="user-menu-row flex items-center w-full rounded-xl hover:bg-gray-50/60 dark:hover:bg-gray-800/60 transition-colors"
+				>
 					<a
 						href="/workspace"
 						draggable="false"
-						class="flex flex-1 h-[1.6875rem] items-center gap-2 rounded-xl px-2 text-[0.8125rem] hover:bg-gray-100 dark:hover:bg-gray-900 transition cursor-pointer select-none"
+						class="flex flex-1 min-w-0 h-[1.6875rem] items-center gap-2 rounded-xl px-2 text-[0.8125rem] cursor-pointer select-none"
 						on:click={async (e) => {
 							if (e.metaKey || e.ctrlKey || e.shiftKey || e.button === 1) return;
 							e.preventDefault();
@@ -283,11 +285,13 @@
 			{/if}
 
 			{#if ($config?.features?.enable_notes ?? false) && ($user?.role === 'admin' || ($user?.permissions?.features?.notes ?? true))}
-				<div class="flex items-center w-full">
+				<div
+					class="user-menu-row flex items-center w-full rounded-xl hover:bg-gray-50/60 dark:hover:bg-gray-800/60 transition-colors"
+				>
 					<a
 						href="/notes"
 						draggable="false"
-						class="flex flex-1 h-[1.6875rem] items-center gap-2 rounded-xl px-2 text-[0.8125rem] hover:bg-gray-100 dark:hover:bg-gray-900 transition cursor-pointer select-none"
+						class="flex flex-1 min-w-0 h-[1.6875rem] items-center gap-2 rounded-xl px-2 text-[0.8125rem] cursor-pointer select-none"
 						on:click={async (e) => {
 							if (e.metaKey || e.ctrlKey || e.shiftKey || e.button === 1) return;
 							e.preventDefault();
@@ -327,11 +331,13 @@
 			{/if}
 
 			{#if $config?.features?.enable_calendar && ($user?.role === 'admin' || $user?.permissions?.features?.calendar)}
-				<div class="flex items-center w-full">
+				<div
+					class="user-menu-row flex items-center w-full rounded-xl hover:bg-gray-50/60 dark:hover:bg-gray-800/60 transition-colors"
+				>
 					<a
 						href="/calendar"
 						draggable="false"
-						class="flex flex-1 h-[1.6875rem] items-center gap-2 rounded-xl px-2 text-[0.8125rem] hover:bg-gray-100 dark:hover:bg-gray-900 transition cursor-pointer select-none"
+						class="flex flex-1 min-w-0 h-[1.6875rem] items-center gap-2 rounded-xl px-2 text-[0.8125rem] cursor-pointer select-none"
 						on:click={async (e) => {
 							if (e.metaKey || e.ctrlKey || e.shiftKey || e.button === 1) return;
 							e.preventDefault();
@@ -371,11 +377,13 @@
 			{/if}
 
 			{#if $config?.features?.enable_automations && ($user?.role === 'admin' || $user?.permissions?.features?.automations)}
-				<div class="flex items-center w-full">
+				<div
+					class="user-menu-row flex items-center w-full rounded-xl hover:bg-gray-50/60 dark:hover:bg-gray-800/60 transition-colors"
+				>
 					<a
 						href="/automations"
 						draggable="false"
-						class="flex flex-1 h-[1.6875rem] items-center gap-2 rounded-xl px-2 text-[0.8125rem] hover:bg-gray-100 dark:hover:bg-gray-900 transition cursor-pointer select-none"
+						class="flex flex-1 min-w-0 h-[1.6875rem] items-center gap-2 rounded-xl px-2 text-[0.8125rem] cursor-pointer select-none"
 						on:click={async (e) => {
 							if (e.metaKey || e.ctrlKey || e.shiftKey || e.button === 1) return;
 							e.preventDefault();
@@ -415,11 +423,13 @@
 			{/if}
 
 			{#if role === 'admin'}
-				<div class="flex items-center w-full">
+				<div
+					class="user-menu-row flex items-center w-full rounded-xl hover:bg-gray-50/60 dark:hover:bg-gray-800/60 transition-colors"
+				>
 					<a
 						href="/playground"
 						draggable="false"
-						class="flex flex-1 h-[1.6875rem] items-center gap-2 rounded-xl px-2 text-[0.8125rem] hover:bg-gray-100 dark:hover:bg-gray-900 transition cursor-pointer select-none"
+						class="flex flex-1 min-w-0 h-[1.6875rem] items-center gap-2 rounded-xl px-2 text-[0.8125rem] cursor-pointer select-none"
 						on:click={async (e) => {
 							if (e.metaKey || e.ctrlKey || e.shiftKey || e.button === 1) return;
 							e.preventDefault();
@@ -468,7 +478,7 @@
 						href="https://docs.openwebui.com"
 						target="_blank"
 						draggable="false"
-						class="flex h-[1.6875rem] items-center gap-2 rounded-xl px-2 text-[0.8125rem] w-full hover:bg-gray-100 dark:hover:bg-gray-900 transition cursor-pointer select-none"
+						class="flex h-[1.6875rem] items-center gap-2 rounded-xl px-2 text-[0.8125rem] w-full hover:bg-gray-50/60 dark:hover:bg-gray-800/60 transition cursor-pointer select-none"
 						id="chat-share-button"
 						on:click={() => {
 							show = false;
@@ -485,7 +495,7 @@
 						href="https://github.com/open-webui/open-webui/releases"
 						target="_blank"
 						draggable="false"
-						class="flex h-[1.6875rem] items-center gap-2 rounded-xl px-2 text-[0.8125rem] w-full hover:bg-gray-100 dark:hover:bg-gray-900 transition cursor-pointer select-none"
+						class="flex h-[1.6875rem] items-center gap-2 rounded-xl px-2 text-[0.8125rem] w-full hover:bg-gray-50/60 dark:hover:bg-gray-800/60 transition cursor-pointer select-none"
 						id="chat-share-button"
 						on:click={() => {
 							show = false;
@@ -499,7 +509,7 @@
 				{/if}
 
 				<button
-					class="flex h-[1.6875rem] items-center gap-2 rounded-xl px-2 text-[0.8125rem] w-full hover:bg-gray-100 dark:hover:bg-gray-900 transition cursor-pointer select-none"
+					class="flex h-[1.6875rem] items-center gap-2 rounded-xl px-2 text-[0.8125rem] w-full hover:bg-gray-50/60 dark:hover:bg-gray-800/60 transition cursor-pointer select-none"
 					type="button"
 					id="chat-share-button"
 					on:click={async () => {
@@ -525,7 +535,7 @@
 				<a
 					href="/admin"
 					draggable="false"
-					class="flex h-[1.6875rem] items-center gap-2 rounded-xl px-2 text-[0.8125rem] w-full hover:bg-gray-100 dark:hover:bg-gray-900 transition cursor-pointer select-none"
+					class="flex h-[1.6875rem] items-center gap-2 rounded-xl px-2 text-[0.8125rem] w-full hover:bg-gray-50/60 dark:hover:bg-gray-800/60 transition cursor-pointer select-none"
 					on:click={async (e) => {
 						if (e.metaKey || e.ctrlKey || e.shiftKey || e.button === 1) {
 							return;
@@ -547,7 +557,7 @@
 			{/if}
 
 			<button
-				class="flex h-[1.6875rem] items-center gap-2 rounded-xl px-2 text-[0.8125rem] w-full hover:bg-gray-100 dark:hover:bg-gray-900 transition cursor-pointer select-none"
+				class="flex h-[1.6875rem] items-center gap-2 rounded-xl px-2 text-[0.8125rem] w-full hover:bg-gray-50/60 dark:hover:bg-gray-800/60 transition cursor-pointer select-none"
 				type="button"
 				on:click={async () => {
 					show = false;
@@ -567,7 +577,7 @@
 			</button>
 
 			<button
-				class="flex h-[1.6875rem] items-center gap-2 rounded-xl px-2 text-[0.8125rem] w-full hover:bg-gray-100 dark:hover:bg-gray-900 transition cursor-pointer select-none"
+				class="flex h-[1.6875rem] items-center gap-2 rounded-xl px-2 text-[0.8125rem] w-full hover:bg-gray-50/60 dark:hover:bg-gray-800/60 transition cursor-pointer select-none"
 				type="button"
 				on:click={async () => {
 					const res = await userSignOut();