diff --git a/src/lib/components/layout/Sidebar.svelte b/src/lib/components/layout/Sidebar.svelte
index c7a905b48f..e4e004f461 100644
--- a/src/lib/components/layout/Sidebar.svelte
+++ b/src/lib/components/layout/Sidebar.svelte
@@ -826,7 +826,7 @@
 						aria-label={$showSidebar ? $i18n.t('Close Sidebar') : $i18n.t('Open Sidebar')}
 					>
 						<div
-							class=" self-center flex size-[30px] items-center justify-center rounded-lg transition group-hover:bg-gray-50/40 dark:group-hover:bg-gray-800/40"
+							class=" self-center flex size-[30px] items-center justify-center rounded-lg transition group-hover:bg-gray-50 dark:group-hover:bg-gray-900"
 						>
 							<img
 								src="{WEBUI_BASE_URL}/static/favicon.png"
@@ -857,7 +857,7 @@
 							aria-label={$i18n.t('New Chat')}
 						>
 							<div
-								class=" self-center flex size-[30px] items-center justify-center rounded-lg transition group-hover:bg-gray-50/40 dark:group-hover:bg-gray-800/40"
+								class=" self-center flex size-[30px] items-center justify-center rounded-lg transition group-hover:bg-gray-50 dark:group-hover:bg-gray-900"
 							>
 								<EditPencilIcon className="size-4" strokeWidth="1.5" />
 							</div>
@@ -879,7 +879,7 @@
 							aria-label={$i18n.t('Search')}
 						>
 							<div
-								class=" self-center flex size-[30px] items-center justify-center rounded-lg transition group-hover:bg-gray-50/40 dark:group-hover:bg-gray-800/40"
+								class=" self-center flex size-[30px] items-center justify-center rounded-lg transition group-hover:bg-gray-50 dark:group-hover:bg-gray-900"
 							>
 								<SearchIcon className="size-4" strokeWidth="1.5" />
 							</div>
@@ -893,10 +893,7 @@
 						<div class="">
 							<Tooltip content={$i18n.t(meta.label)} placement="right">
 								<a
-									class=" cursor-pointer flex size-8 items-center justify-center transition group {itemId ===
-									activeMenuItemId
-										? 'text-gray-900 dark:text-gray-100'
-										: ''}"
+									class=" cursor-pointer flex size-8 items-center justify-center transition group"
 									href={meta.href}
 									on:click={async (e) => {
 										e.stopImmediatePropagation();
@@ -910,8 +907,10 @@
 									<div
 										class=" self-center flex size-[30px] items-center justify-center rounded-lg transition {itemId ===
 										activeMenuItemId
-											? 'bg-gray-100/80 dark:bg-gray-850/50'
-											: 'group-hover:bg-gray-50/40 dark:group-hover:bg-gray-800/40'}"
+											? ($settings?.highContrastMode ?? false)
+												? 'bg-black/[0.035] dark:bg-white/[0.06]'
+												: 'bg-black/[0.035] dark:bg-white/[0.045]'
+											: 'group-hover:bg-gray-50 dark:group-hover:bg-gray-900'}"
 									>
 										{#if itemId === 'notes'}
 											<NotesIcon className="size-4" strokeWidth="1.5" />
@@ -944,7 +943,7 @@
 								aria-label={$i18n.t('User menu')}
 							>
 								<div
-									class="self-center relative flex size-[30px] items-center justify-center rounded-lg transition group-hover:bg-gray-50/40 dark:group-hover:bg-gray-800/40"
+									class="self-center relative flex size-[30px] items-center justify-center rounded-lg transition group-hover:bg-gray-50 dark:group-hover:bg-gray-900"
 								>
 									<img
 										src={`${WEBUI_API_BASE_URL}/users/${$user?.id}/profile/image`}
@@ -999,7 +998,7 @@
 				class="sidebar px-1 pt-1.5 pb-1 flex justify-between space-x-1 text-gray-600 dark:text-gray-400 sticky top-0 z-10 -mb-2"
 			>
 				<a
-					class="flex items-center rounded-xl size-8.5 h-full justify-center hover:bg-gray-50/60 dark:hover:bg-gray-800/40 transition no-drag-region"
+					class="flex items-center rounded-xl size-8.5 h-full justify-center hover:bg-gray-50 dark:hover:bg-gray-900 transition no-drag-region"
 					href="/"
 					draggable="false"
 					on:click={newChatHandler}
@@ -1025,7 +1024,7 @@
 					placement="bottom"
 				>
 					<button
-						class="flex size-[30px] justify-center items-center rounded-lg hover:bg-gray-50/60 dark:hover:bg-gray-800/40 transition {isWindows
+						class="flex size-[30px] justify-center items-center rounded-lg hover:bg-gray-50 dark:hover:bg-gray-900 transition {isWindows
 							? 'cursor-pointer'
 							: 'cursor-[w-resize]'}"
 						on:click={() => {
@@ -1060,7 +1059,7 @@
 					<div class="px-1 flex justify-center text-gray-700 dark:text-gray-300">
 						<a
 							id="sidebar-new-chat-button"
-							class="group grow flex items-center space-x-2 rounded-xl px-2 py-1.5 hover:bg-gray-50/40 dark:hover:bg-gray-800/40 transition outline-none"
+							class="group grow flex items-center space-x-2 rounded-xl px-2 py-1.5 hover:bg-gray-50 dark:hover:bg-gray-900 transition outline-none"
 							href="/"
 							draggable="false"
 							on:click={newChatHandler}
@@ -1081,7 +1080,7 @@
 					<div class="px-1 flex justify-center text-gray-700 dark:text-gray-300">
 						<button
 							id="sidebar-search-button"
-							class="group grow flex items-center space-x-2 rounded-xl px-2 py-1.5 hover:bg-gray-50/40 dark:hover:bg-gray-800/40 transition outline-none"
+							class="group grow flex items-center space-x-2 rounded-xl px-2 py-1.5 hover:bg-gray-50 dark:hover:bg-gray-900 transition outline-none"
 							on:click={() => {
 								showSearch.set(true);
 							}}
@@ -1104,17 +1103,17 @@
 							{@const meta = getMenuItemMeta(itemId)}
 							{#if meta && isMenuItemVisible(itemId)}
 								<div
-									class="px-1 flex justify-center {itemId === activeMenuItemId
-										? 'text-gray-900 dark:text-gray-100'
-										: 'text-gray-700 dark:text-gray-300'}"
+									class="px-1 flex justify-center text-gray-700 dark:text-gray-300"
 									data-id={itemId}
 								>
 									<a
 										id="sidebar-{itemId}-button"
 										class="grow flex items-center space-x-2 rounded-xl px-2 py-1.5 transition {itemId ===
 										activeMenuItemId
-											? 'bg-gray-100/80 dark:bg-gray-850/50'
-											: 'hover:bg-gray-50/40 dark:hover:bg-gray-800/40'}"
+											? ($settings?.highContrastMode ?? false)
+												? 'bg-black/[0.035] dark:bg-white/[0.06]'
+												: 'bg-black/[0.035] dark:bg-white/[0.045]'
+											: 'hover:bg-gray-50 dark:hover:bg-gray-900'}"
 										href={meta.href}
 										on:click={itemClickHandler}
 										draggable="false"
@@ -1527,7 +1526,7 @@
 						>
 							<button
 								type="button"
-								class=" flex items-center rounded-xl py-1.5 px-1.5 w-full hover:bg-gray-50/40 dark:hover:bg-gray-800/40 transition"
+								class=" flex items-center rounded-xl py-1.5 px-1.5 w-full hover:bg-gray-50 dark:hover:bg-gray-900 transition"
 								aria-label={$i18n.t('User menu')}
 							>
 								<div class=" self-center mr-3 relative flex-shrink-0">