diff --git a/.story_kit/work/2_current/199_story_web_ui_submits_all_queued_items_at_once.md b/.story_kit/work/2_current/199_story_web_ui_submits_all_queued_items_at_once.md
new file mode 100644
index 0000000..2203c01
--- /dev/null
+++ b/.story_kit/work/2_current/199_story_web_ui_submits_all_queued_items_at_once.md
@@ -0,0 +1,20 @@
+---
+name: "Web UI submits all queued items at once"
+---
+
+# Story 199: Web UI submits all queued items at once
+
+## User Story
+
+As a user, I want the web UI to submit all queued items at once when there are multiple waiting items, so that I don't have to submit them one at a time.
+
+## Acceptance Criteria
+
+- [ ] When the agent finishes responding and there are multiple queued messages, all queued messages are submitted at once (not one at a time)
+- [ ] All queued messages are appended to the conversation history as sequential user turns before sending
+- [ ] After draining the queue, no queued message indicators remain visible
+- [ ] Queue draining also works when the agent finishes with an error
+
+## Out of Scope
+
+- TBD
diff --git a/frontend/src/components/Chat.test.tsx b/frontend/src/components/Chat.test.tsx
index cecf20b..e1f87db 100644
--- a/frontend/src/components/Chat.test.tsx
+++ b/frontend/src/components/Chat.test.tsx
@@ -851,7 +851,7 @@ describe("Chat message queue (Story 155)", () => {
 		expect(indicators[1]).toHaveTextContent("Queue 2");
 	});
 
-	it("queued messages are delivered in order (Bug 168)", async () => {
+	it("all queued messages are drained at once when agent responds (Story 199)", async () => {
 		render(<Chat projectPath="/tmp/project" onCloseProject={vi.fn()} />);
 
 		await waitFor(() => expect(capturedWsHandlers).not.toBeNull());
@@ -866,7 +866,7 @@ describe("Chat message queue (Story 155)", () => {
 			fireEvent.keyDown(input, { key: "Enter", shiftKey: false });
 		});
 
-		// Queue two messages
+		// Queue two messages while loading
 		await act(async () => {
 			fireEvent.change(input, { target: { value: "Second" } });
 		});
@@ -886,7 +886,7 @@ describe("Chat message queue (Story 155)", () => {
 		expect(indicators[0]).toHaveTextContent("Second");
 		expect(indicators[1]).toHaveTextContent("Third");
 
-		// Simulate first response completing — "Second" is sent next
+		// Simulate first response completing — both "Second" and "Third" are drained at once
 		act(() => {
 			capturedWsHandlers?.onUpdate([
 				{ role: "user", content: "First" },
@@ -894,11 +894,10 @@ describe("Chat message queue (Story 155)", () => {
 			]);
 		});
 
-		// "Third" should remain queued; "Second" was consumed
+		// Both queued indicators should be gone — entire queue drained in one shot
 		await waitFor(() => {
 			const remaining = screen.queryAllByTestId("queued-message-indicator");
-			expect(remaining).toHaveLength(1);
-			expect(remaining[0]).toHaveTextContent("Third");
+			expect(remaining).toHaveLength(0);
 		});
 	});
 
diff --git a/frontend/src/components/Chat.tsx b/frontend/src/components/Chat.tsx
index 45010ec..f07d845 100644
--- a/frontend/src/components/Chat.tsx
+++ b/frontend/src/components/Chat.tsx
@@ -192,8 +192,10 @@ export function Chat({ projectPath, onCloseProject }: ChatProps) {
 	// Ref so stale WebSocket callbacks can read the current queued messages
 	const queuedMessagesRef = useRef<{ id: string; text: string }[]>([]);
 	const queueIdCounterRef = useRef(0);
-	// Trigger state: set to a message string to fire auto-send after loading ends
-	const [pendingAutoSend, setPendingAutoSend] = useState<string | null>(null);
+	// Trigger state: set to a batch of message strings to fire auto-send after loading ends
+	const [pendingAutoSendBatch, setPendingAutoSendBatch] = useState<
+		string[] | null
+	>(null);
 
 	const wsRef = useRef<ChatWebSocket | null>(null);
 	const messagesEndRef = useRef<HTMLDivElement>(null);
@@ -294,10 +296,11 @@ export function Chat({ projectPath, onCloseProject }: ChatProps) {
 				if (last?.role === "assistant" && !last.tool_calls) {
 					setLoading(false);
 					setActivityStatus(null);
-					const nextQueued = queuedMessagesRef.current.shift();
-					if (nextQueued !== undefined) {
-						setQueuedMessages([...queuedMessagesRef.current]);
-						setPendingAutoSend(nextQueued.text);
+					if (queuedMessagesRef.current.length > 0) {
+						const batch = queuedMessagesRef.current.map((item) => item.text);
+						queuedMessagesRef.current = [];
+						setQueuedMessages([]);
+						setPendingAutoSendBatch(batch);
 					}
 				}
 			},
@@ -308,10 +311,11 @@ export function Chat({ projectPath, onCloseProject }: ChatProps) {
 				console.error("WebSocket error:", message);
 				setLoading(false);
 				setActivityStatus(null);
-				const nextQueued = queuedMessagesRef.current.shift();
-				if (nextQueued !== undefined) {
-					setQueuedMessages([...queuedMessagesRef.current]);
-					setPendingAutoSend(nextQueued.text);
+				if (queuedMessagesRef.current.length > 0) {
+					const batch = queuedMessagesRef.current.map((item) => item.text);
+					queuedMessagesRef.current = [];
+					setQueuedMessages([]);
+					setPendingAutoSendBatch(batch);
 				}
 			},
 			onPipelineState: (state) => {
@@ -395,14 +399,14 @@ export function Chat({ projectPath, onCloseProject }: ChatProps) {
 		}
 	}, [autoScrollKey, scrollToBottom]);
 
-	// Auto-send queued message when loading ends
+	// Auto-send all queued messages as a batch when loading ends
 	useEffect(() => {
-		if (pendingAutoSend) {
-			const msg = pendingAutoSend;
-			setPendingAutoSend(null);
-			sendMessage(msg);
+		if (pendingAutoSendBatch && pendingAutoSendBatch.length > 0) {
+			const batch = pendingAutoSendBatch;
+			setPendingAutoSendBatch(null);
+			sendMessageBatch(batch);
 		}
-	}, [pendingAutoSend]);
+	}, [pendingAutoSendBatch]);
 
 	useEffect(() => {
 		const handleResize = () =>
@@ -498,6 +502,51 @@ export function Chat({ projectPath, onCloseProject }: ChatProps) {
 		}
 	};
 
+	const sendMessageBatch = async (messageTexts: string[]) => {
+		if (messageTexts.length === 0) return;
+
+		const userMsgs: Message[] = messageTexts.map((text) => ({
+			role: "user",
+			content: text,
+		}));
+		const newHistory = [...messages, ...userMsgs];
+
+		setMessages(newHistory);
+		setLoading(true);
+		setStreamingContent("");
+		setStreamingThinking("");
+		setActivityStatus(null);
+
+		try {
+			const isClaudeCode = model === "claude-code-pty";
+			const provider = isClaudeCode
+				? "claude-code"
+				: model.startsWith("claude-")
+					? "anthropic"
+					: "ollama";
+			const config: ProviderConfig = {
+				provider,
+				model,
+				base_url: "http://localhost:11434",
+				enable_tools: enableTools,
+				...(isClaudeCode && claudeSessionId
+					? { session_id: claudeSessionId }
+					: {}),
+			};
+			wsRef.current?.sendChat(newHistory, config);
+		} catch (e) {
+			console.error("Chat error:", e);
+			const errorMessage = String(e);
+			if (!errorMessage.includes("Chat cancelled by user")) {
+				setMessages((prev: Message[]) => [
+					...prev,
+					{ role: "assistant", content: `**Error:** ${e}` },
+				]);
+			}
+			setLoading(false);
+		}
+	};
+
 	const handleSaveApiKey = async () => {
 		if (!apiKeyInput.trim()) return;