diff --git a/tools/server/public/index.html.gz b/tools/server/public/index.html.gz
index 64a6402fc9..ae2c8f77a7 100644
Binary files a/tools/server/public/index.html.gz and b/tools/server/public/index.html.gz differ
diff --git a/tools/server/webui/src/lib/components/app/chat/ChatForm/ChatForm.svelte b/tools/server/webui/src/lib/components/app/chat/ChatForm/ChatForm.svelte
index 27ab975cbd..95645295fb 100644
--- a/tools/server/webui/src/lib/components/app/chat/ChatForm/ChatForm.svelte
+++ b/tools/server/webui/src/lib/components/app/chat/ChatForm/ChatForm.svelte
@@ -27,11 +27,13 @@
 	interface Props {
 		class?: string;
 		disabled?: boolean;
+		initialMessage?: string;
 		isLoading?: boolean;
 		onFileRemove?: (fileId: string) => void;
 		onFileUpload?: (files: File[]) => void;
 		onSend?: (message: string, files?: ChatUploadedFile[]) => Promise<boolean>;
 		onStop?: () => void;
+		onSystemPromptAdd?: (draft: { message: string; files: ChatUploadedFile[] }) => void;
 		showHelperText?: boolean;
 		uploadedFiles?: ChatUploadedFile[];
 	}
@@ -39,11 +41,13 @@
 	let {
 		class: className,
 		disabled = false,
+		initialMessage = '',
 		isLoading = false,
 		onFileRemove,
 		onFileUpload,
 		onSend,
 		onStop,
+		onSystemPromptAdd,
 		showHelperText = true,
 		uploadedFiles = $bindable([])
 	}: Props = $props();
@@ -53,15 +57,28 @@
 	let currentConfig = $derived(config());
 	let fileInputRef: ChatFormFileInputInvisible | undefined = $state(undefined);
 	let isRecording = $state(false);
-	let message = $state('');
+	let message = $state(initialMessage);
 	let pasteLongTextToFileLength = $derived.by(() => {
 		const n = Number(currentConfig.pasteLongTextToFileLen);
 		return Number.isNaN(n) ? Number(SETTING_CONFIG_DEFAULT.pasteLongTextToFileLen) : n;
 	});
 	let previousIsLoading = $state(isLoading);
+	let previousInitialMessage = $state(initialMessage);
 	let recordingSupported = $state(false);
 	let textareaRef: ChatFormTextarea | undefined = $state(undefined);
 
+	// Sync message when initialMessage prop changes (e.g., after draft restoration)
+	$effect(() => {
+		if (initialMessage !== previousInitialMessage) {
+			message = initialMessage;
+			previousInitialMessage = initialMessage;
+		}
+	});
+
+	function handleSystemPromptClick() {
+		onSystemPromptAdd?.({ message, files: uploadedFiles });
+	}
+
 	// Check if model is selected (in ROUTER mode)
 	let conversationModel = $derived(
 		chatStore.getConversationModel(activeMessages() as DatabaseMessage[])
@@ -308,6 +325,7 @@
 			onFileUpload={handleFileUpload}
 			onMicClick={handleMicClick}
 			onStop={handleStop}
+			onSystemPromptClick={handleSystemPromptClick}
 		/>
 	</div>
 </form>
diff --git a/tools/server/webui/src/lib/components/app/chat/ChatForm/ChatFormActions/ChatFormActionFileAttachments.svelte b/tools/server/webui/src/lib/components/app/chat/ChatForm/ChatFormActions/ChatFormActionFileAttachments.svelte
index dd37268096..3545b4aebf 100644
--- a/tools/server/webui/src/lib/components/app/chat/ChatForm/ChatFormActions/ChatFormActionFileAttachments.svelte
+++ b/tools/server/webui/src/lib/components/app/chat/ChatForm/ChatFormActions/ChatFormActionFileAttachments.svelte
@@ -1,5 +1,6 @@
 <script lang="ts">
 	import { Paperclip } from '@lucide/svelte';
+	import { MessageSquare } from '@lucide/svelte';
 	import { Button } from '$lib/components/ui/button';
 	import * as DropdownMenu from '$lib/components/ui/dropdown-menu';
 	import * as Tooltip from '$lib/components/ui/tooltip';
@@ -11,6 +12,7 @@
 		hasAudioModality?: boolean;
 		hasVisionModality?: boolean;
 		onFileUpload?: () => void;
+		onSystemPromptClick?: () => void;
 	}
 
 	let {
@@ -18,7 +20,8 @@
 		disabled = false,
 		hasAudioModality = false,
 		hasVisionModality = false,
-		onFileUpload
+		onFileUpload,
+		onSystemPromptClick
 	}: Props = $props();
 
 	const fileUploadTooltipText = $derived.by(() => {
@@ -118,6 +121,23 @@
 					</Tooltip.Content>
 				{/if}
 			</Tooltip.Root>
+			<DropdownMenu.Separator />
+			<Tooltip.Root>
+				<Tooltip.Trigger class="w-full">
+					<DropdownMenu.Item
+						class="flex cursor-pointer items-center gap-2"
+						onclick={() => onSystemPromptClick?.()}
+					>
+						<MessageSquare class="h-4 w-4" />
+
+						<span>System Prompt</span>
+					</DropdownMenu.Item>
+				</Tooltip.Trigger>
+
+				<Tooltip.Content>
+					<p>Add a custom system message for this conversation</p>
+				</Tooltip.Content>
+			</Tooltip.Root>
 		</DropdownMenu.Content>
 	</DropdownMenu.Root>
 </div>
diff --git a/tools/server/webui/src/lib/components/app/chat/ChatForm/ChatFormActions/ChatFormActions.svelte b/tools/server/webui/src/lib/components/app/chat/ChatForm/ChatFormActions/ChatFormActions.svelte
index dde9bda2d8..c621a69e05 100644
--- a/tools/server/webui/src/lib/components/app/chat/ChatForm/ChatFormActions/ChatFormActions.svelte
+++ b/tools/server/webui/src/lib/components/app/chat/ChatForm/ChatFormActions/ChatFormActions.svelte
@@ -27,6 +27,7 @@
 		onFileUpload?: () => void;
 		onMicClick?: () => void;
 		onStop?: () => void;
+		onSystemPromptClick?: () => void;
 	}
 
 	let {
@@ -39,7 +40,8 @@
 		uploadedFiles = [],
 		onFileUpload,
 		onMicClick,
-		onStop
+		onStop,
+		onSystemPromptClick
 	}: Props = $props();
 
 	let currentConfig = $derived(config());
@@ -170,6 +172,7 @@
 		{hasAudioModality}
 		{hasVisionModality}
 		{onFileUpload}
+		{onSystemPromptClick}
 	/>
 
 	<ModelsSelector
diff --git a/tools/server/webui/src/lib/components/app/chat/ChatMessages/ChatMessage.svelte b/tools/server/webui/src/lib/components/app/chat/ChatMessages/ChatMessage.svelte
index 220276fc9e..82ef7de7c7 100644
--- a/tools/server/webui/src/lib/components/app/chat/ChatMessages/ChatMessage.svelte
+++ b/tools/server/webui/src/lib/components/app/chat/ChatMessages/ChatMessage.svelte
@@ -1,6 +1,15 @@
 <script lang="ts">
-	import { chatStore } from '$lib/stores/chat.svelte';
+	import { goto } from '$app/navigation';
+	import {
+		chatStore,
+		pendingEditMessageId,
+		clearPendingEditMessageId,
+		removeSystemPromptPlaceholder
+	} from '$lib/stores/chat.svelte';
+	import { conversationsStore } from '$lib/stores/conversations.svelte';
+	import { DatabaseService } from '$lib/services';
 	import { config } from '$lib/stores/settings.svelte';
+	import { SYSTEM_MESSAGE_PLACEHOLDER } from '$lib/constants/ui';
 	import { copyToClipboard, isIMEComposing, formatMessageForClipboard } from '$lib/utils';
 	import ChatMessageAssistant from './ChatMessageAssistant.svelte';
 	import ChatMessageUser from './ChatMessageUser.svelte';
@@ -92,8 +101,30 @@
 		return null;
 	});
 
-	function handleCancelEdit() {
+	// Auto-start edit mode if this message is the pending edit target
+	$effect(() => {
+		const pendingId = pendingEditMessageId();
+
+		if (pendingId && pendingId === message.id && !isEditing) {
+			handleEdit();
+			clearPendingEditMessageId();
+		}
+	});
+
+	async function handleCancelEdit() {
 		isEditing = false;
+
+		// If canceling a new system message with placeholder content, remove it without deleting children
+		if (message.role === 'system') {
+			const conversationDeleted = await removeSystemPromptPlaceholder(message.id);
+
+			if (conversationDeleted) {
+				goto('/');
+			}
+
+			return;
+		}
+
 		editedContent = message.content;
 		editedExtras = message.extra ? [...message.extra] : [];
 		editedUploadedFiles = [];
@@ -114,8 +145,17 @@
 		onCopy?.(message);
 	}
 
-	function handleConfirmDelete() {
-		onDelete?.(message);
+	async function handleConfirmDelete() {
+		if (message.role === 'system') {
+			const conversationDeleted = await removeSystemPromptPlaceholder(message.id);
+
+			if (conversationDeleted) {
+				goto('/');
+			}
+		} else {
+			onDelete?.(message);
+		}
+
 		showDeleteDialog = false;
 	}
 
@@ -126,7 +166,12 @@
 
 	function handleEdit() {
 		isEditing = true;
-		editedContent = message.content;
+		// Clear placeholder content for system messages
+		editedContent =
+			message.role === 'system' && message.content === SYSTEM_MESSAGE_PLACEHOLDER
+				? ''
+				: message.content;
+		textareaElement?.focus();
 		editedExtras = message.extra ? [...message.extra] : [];
 		editedUploadedFiles = [];
 
@@ -166,7 +211,26 @@
 	}
 
 	async function handleSaveEdit() {
-		if (message.role === 'user' || message.role === 'system') {
+		if (message.role === 'system') {
+			// System messages: update in place without branching
+			const newContent = editedContent.trim();
+
+			// If content is empty or still the placeholder, remove without deleting children
+			if (!newContent) {
+				const conversationDeleted = await removeSystemPromptPlaceholder(message.id);
+				isEditing = false;
+				if (conversationDeleted) {
+					goto('/');
+				}
+				return;
+			}
+
+			await DatabaseService.updateMessage(message.id, { content: newContent });
+			const index = conversationsStore.findMessageIndex(message.id);
+			if (index !== -1) {
+				conversationsStore.updateMessageAtIndex(index, { content: newContent });
+			}
+		} else if (message.role === 'user') {
 			const finalExtras = await getMergedExtras();
 			onEditWithBranching?.(message, editedContent.trim(), finalExtras);
 		} else {
diff --git a/tools/server/webui/src/lib/components/app/chat/ChatMessages/ChatMessageSystem.svelte b/tools/server/webui/src/lib/components/app/chat/ChatMessages/ChatMessageSystem.svelte
index c203822f60..887df5b771 100644
--- a/tools/server/webui/src/lib/components/app/chat/ChatMessages/ChatMessageSystem.svelte
+++ b/tools/server/webui/src/lib/components/app/chat/ChatMessages/ChatMessageSystem.svelte
@@ -116,7 +116,7 @@
 
 				<Button class="h-8 px-3" onclick={onSaveEdit} disabled={!editedContent.trim()} size="sm">
 					<Check class="mr-1 h-3 w-3" />
-					Send
+					Save
 				</Button>
 			</div>
 		</div>
diff --git a/tools/server/webui/src/lib/components/app/chat/ChatScreen/ChatScreen.svelte b/tools/server/webui/src/lib/components/app/chat/ChatScreen/ChatScreen.svelte
index 27439551a1..6e26d510cd 100644
--- a/tools/server/webui/src/lib/components/app/chat/ChatScreen/ChatScreen.svelte
+++ b/tools/server/webui/src/lib/components/app/chat/ChatScreen/ChatScreen.svelte
@@ -71,6 +71,8 @@
 
 	let emptyFileNames = $state<string[]>([]);
 
+	let initialMessage = $state('');
+
 	let isEmpty = $derived(
 		showCenteredEmpty && !activeConversation() && activeMessages().length === 0 && !isLoading()
 	);
@@ -221,6 +223,14 @@
 		}
 	}
 
+	async function handleSystemPromptAdd(draft: { message: string; files: ChatUploadedFile[] }) {
+		if (draft.message || draft.files.length > 0) {
+			chatStore.savePendingDraft(draft.message, draft.files);
+		}
+
+		await chatStore.addSystemPrompt();
+	}
+
 	function handleScroll() {
 		if (disableAutoScroll || !chatScrollContainer) return;
 
@@ -343,6 +353,12 @@
 		if (!disableAutoScroll) {
 			setTimeout(() => scrollChatToBottom('instant'), INITIAL_SCROLL_DELAY);
 		}
+
+		const pendingDraft = chatStore.consumePendingDraft();
+		if (pendingDraft) {
+			initialMessage = pendingDraft.message;
+			uploadedFiles = pendingDraft.files;
+		}
 	});
 
 	$effect(() => {
@@ -428,11 +444,13 @@
 			<div class="conversation-chat-form pointer-events-auto rounded-t-3xl pb-4">
 				<ChatForm
 					disabled={hasPropsError || isEditing()}
+					{initialMessage}
 					isLoading={isCurrentConversationLoading}
 					onFileRemove={handleFileRemove}
 					onFileUpload={handleFileUpload}
 					onSend={handleSendMessage}
 					onStop={() => chatStore.stopGeneration()}
+					onSystemPromptAdd={handleSystemPromptAdd}
 					showHelperText={false}
 					bind:uploadedFiles
 				/>
@@ -486,11 +504,13 @@
 			<div in:fly={{ y: 10, duration: 250, delay: hasPropsError ? 0 : 300 }}>
 				<ChatForm
 					disabled={hasPropsError}
+					{initialMessage}
 					isLoading={isCurrentConversationLoading}
 					onFileRemove={handleFileRemove}
 					onFileUpload={handleFileUpload}
 					onSend={handleSendMessage}
 					onStop={() => chatStore.stopGeneration()}
+					onSystemPromptAdd={handleSystemPromptAdd}
 					showHelperText={true}
 					bind:uploadedFiles
 				/>
diff --git a/tools/server/webui/src/lib/stores/chat.svelte.ts b/tools/server/webui/src/lib/stores/chat.svelte.ts
index 879b2f3245..89de4f080c 100644
--- a/tools/server/webui/src/lib/stores/chat.svelte.ts
+++ b/tools/server/webui/src/lib/stores/chat.svelte.ts
@@ -15,6 +15,7 @@ import {
 } from '$lib/utils';
 import { SvelteMap } from 'svelte/reactivity';
 import { DEFAULT_CONTEXT } from '$lib/constants/default-context';
+import { SYSTEM_MESSAGE_PLACEHOLDER } from '$lib/constants/ui';
 
 /**
  * chatStore - Active AI interaction and streaming state management
@@ -76,6 +77,10 @@ class ChatStore {
 	private isStreamingActive = $state(false);
 	private isEditModeActive = $state(false);
 	private addFilesHandler: ((files: File[]) => void) | null = $state(null);
+	pendingEditMessageId = $state<string | null>(null);
+	// Draft preservation for navigation (e.g., when adding system prompt from welcome page)
+	private _pendingDraftMessage = $state<string>('');
+	private _pendingDraftFiles = $state<ChatUploadedFile[]>([]);
 
 	// ─────────────────────────────────────────────────────────────────────────────
 	// Loading State
@@ -455,6 +460,166 @@ class ChatStore {
 		}
 	}
 
+	/**
+	 * Adds a system message at the top of a conversation and triggers edit mode.
+	 * The system message is inserted between root and the first message of the active branch.
+	 * Creates a new conversation if one doesn't exist.
+	 */
+	async addSystemPrompt(): Promise<void> {
+		let activeConv = conversationsStore.activeConversation;
+
+		// Create conversation if needed
+		if (!activeConv) {
+			await conversationsStore.createConversation();
+			activeConv = conversationsStore.activeConversation;
+		}
+		if (!activeConv) return;
+
+		try {
+			// Get all messages to find the root
+			const allMessages = await conversationsStore.getConversationMessages(activeConv.id);
+			const rootMessage = allMessages.find((m) => m.type === 'root' && m.parent === null);
+			let rootId: string;
+
+			// Create root message if it doesn't exist
+			if (!rootMessage) {
+				rootId = await DatabaseService.createRootMessage(activeConv.id);
+			} else {
+				rootId = rootMessage.id;
+			}
+
+			// Check if there's already a system message as root's child
+			const existingSystemMessage = allMessages.find(
+				(m) => m.role === 'system' && m.parent === rootId
+			);
+
+			if (existingSystemMessage) {
+				// If system message exists, just trigger edit mode on it
+				this.pendingEditMessageId = existingSystemMessage.id;
+
+				// Make sure it's in active messages at the beginning
+				if (!conversationsStore.activeMessages.some((m) => m.id === existingSystemMessage.id)) {
+					conversationsStore.activeMessages.unshift(existingSystemMessage);
+				}
+				return;
+			}
+
+			// Find the first message of the active branch (child of root that's in activeMessages)
+			const activeMessages = conversationsStore.activeMessages;
+			const firstActiveMessage = activeMessages.find((m) => m.parent === rootId);
+
+			// Create new system message with placeholder content (will be edited by user)
+			const systemMessage = await DatabaseService.createSystemMessage(
+				activeConv.id,
+				SYSTEM_MESSAGE_PLACEHOLDER,
+				rootId
+			);
+
+			// If there's a first message in the active branch, re-parent it to the system message
+			if (firstActiveMessage) {
+				// Update the first message's parent to be the system message
+				await DatabaseService.updateMessage(firstActiveMessage.id, {
+					parent: systemMessage.id
+				});
+
+				// Update the system message's children to include the first message
+				await DatabaseService.updateMessage(systemMessage.id, {
+					children: [firstActiveMessage.id]
+				});
+
+				// Remove first message from root's children
+				const updatedRootChildren = rootMessage
+					? rootMessage.children.filter((id: string) => id !== firstActiveMessage.id)
+					: [];
+				// Note: system message was already added to root's children by createSystemMessage
+				await DatabaseService.updateMessage(rootId, {
+					children: [
+						...updatedRootChildren.filter((id: string) => id !== systemMessage.id),
+						systemMessage.id
+					]
+				});
+
+				// Update local state
+				const firstMsgIndex = conversationsStore.findMessageIndex(firstActiveMessage.id);
+				if (firstMsgIndex !== -1) {
+					conversationsStore.updateMessageAtIndex(firstMsgIndex, { parent: systemMessage.id });
+				}
+			}
+
+			// Add system message to active messages at the beginning
+			conversationsStore.activeMessages.unshift(systemMessage);
+
+			// Set pending edit message ID to trigger edit mode
+			this.pendingEditMessageId = systemMessage.id;
+
+			conversationsStore.updateConversationTimestamp();
+		} catch (error) {
+			console.error('Failed to add system prompt:', error);
+		}
+	}
+
+	/**
+	 * Removes a system message placeholder without deleting its children.
+	 * Re-parents children back to the root message.
+	 * If this is a new empty conversation (only root + system placeholder), deletes the entire conversation.
+	 * @returns true if the entire conversation was deleted, false otherwise
+	 */
+	async removeSystemPromptPlaceholder(messageId: string): Promise<boolean> {
+		const activeConv = conversationsStore.activeConversation;
+		if (!activeConv) return false;
+
+		try {
+			const allMessages = await conversationsStore.getConversationMessages(activeConv.id);
+			const systemMessage = allMessages.find((m) => m.id === messageId);
+			if (!systemMessage || systemMessage.role !== 'system') return false;
+
+			const rootMessage = allMessages.find((m) => m.type === 'root' && m.parent === null);
+			if (!rootMessage) return false;
+
+			// Check if this is a new empty conversation (only root + system placeholder)
+			const isEmptyConversation = allMessages.length === 2 && systemMessage.children.length === 0;
+
+			if (isEmptyConversation) {
+				// Delete the entire conversation
+				await conversationsStore.deleteConversation(activeConv.id);
+				return true;
+			}
+
+			// Re-parent system message's children to root
+			for (const childId of systemMessage.children) {
+				await DatabaseService.updateMessage(childId, { parent: rootMessage.id });
+
+				// Update local state
+				const childIndex = conversationsStore.findMessageIndex(childId);
+				if (childIndex !== -1) {
+					conversationsStore.updateMessageAtIndex(childIndex, { parent: rootMessage.id });
+				}
+			}
+
+			// Update root's children: remove system message, add system's children
+			const newRootChildren = [
+				...rootMessage.children.filter((id: string) => id !== messageId),
+				...systemMessage.children
+			];
+			await DatabaseService.updateMessage(rootMessage.id, { children: newRootChildren });
+
+			// Delete the system message (without cascade)
+			await DatabaseService.deleteMessage(messageId);
+
+			// Remove from active messages
+			const systemIndex = conversationsStore.findMessageIndex(messageId);
+			if (systemIndex !== -1) {
+				conversationsStore.activeMessages.splice(systemIndex, 1);
+			}
+
+			conversationsStore.updateConversationTimestamp();
+			return false;
+		} catch (error) {
+			console.error('Failed to remove system prompt placeholder:', error);
+			return false;
+		}
+	}
+
 	private async createAssistantMessage(parentId?: string): Promise<DatabaseMessage | null> {
 		const activeConv = conversationsStore.activeConversation;
 		if (!activeConv) return null;
@@ -916,6 +1081,28 @@ class ChatStore {
 		if (!activeConv)
 			return { totalCount: 0, userMessages: 0, assistantMessages: 0, messageTypes: [] };
 		const allMessages = await conversationsStore.getConversationMessages(activeConv.id);
+		const messageToDelete = allMessages.find((m) => m.id === messageId);
+
+		// For system messages, don't count descendants as they will be preserved (reparented to root)
+		if (messageToDelete?.role === 'system') {
+			const messagesToDelete = allMessages.filter((m) => m.id === messageId);
+			let userMessages = 0,
+				assistantMessages = 0;
+			const messageTypes: string[] = [];
+
+			for (const msg of messagesToDelete) {
+				if (msg.role === 'user') {
+					userMessages++;
+					if (!messageTypes.includes('user message')) messageTypes.push('user message');
+				} else if (msg.role === 'assistant') {
+					assistantMessages++;
+					if (!messageTypes.includes('assistant response')) messageTypes.push('assistant response');
+				}
+			}
+
+			return { totalCount: 1, userMessages, assistantMessages, messageTypes };
+		}
+
 		const descendants = findDescendantMessages(allMessages, messageId);
 		const allToDelete = [messageId, ...descendants];
 		const messagesToDelete = allMessages.filter((m) => allToDelete.includes(m.id));
@@ -1381,6 +1568,31 @@ class ChatStore {
 		return this.addFilesHandler;
 	}
 
+	savePendingDraft(message: string, files: ChatUploadedFile[]): void {
+		this._pendingDraftMessage = message;
+		this._pendingDraftFiles = [...files];
+	}
+
+	consumePendingDraft(): { message: string; files: ChatUploadedFile[] } | null {
+		if (!this._pendingDraftMessage && this._pendingDraftFiles.length === 0) {
+			return null;
+		}
+
+		const draft = {
+			message: this._pendingDraftMessage,
+			files: [...this._pendingDraftFiles]
+		};
+
+		this._pendingDraftMessage = '';
+		this._pendingDraftFiles = [];
+
+		return draft;
+	}
+
+	hasPendingDraft(): boolean {
+		return Boolean(this._pendingDraftMessage) || this._pendingDraftFiles.length > 0;
+	}
+
 	public getAllLoadingChats(): string[] {
 		return Array.from(this.chatLoadingStates.keys());
 	}
@@ -1485,3 +1697,7 @@ export const isEditing = () => chatStore.isEditing();
 export const isLoading = () => chatStore.isLoading;
 export const setEditModeActive = (handler: (files: File[]) => void) =>
 	chatStore.setEditModeActive(handler);
+export const pendingEditMessageId = () => chatStore.pendingEditMessageId;
+export const clearPendingEditMessageId = () => (chatStore.pendingEditMessageId = null);
+export const removeSystemPromptPlaceholder = (messageId: string) =>
+	chatStore.removeSystemPromptPlaceholder(messageId);