diff --git a/.gitignore b/.gitignore
index a06c1377..7b88789e 100644
--- a/.gitignore
+++ b/.gitignore
@@ -33,3 +33,6 @@ pi-*.html
 out.html
 packages/coding-agent/binaries/
 todo.md
+
+# Riptide artifacts (cloud-synced)
+.humanlayer/tasks/
diff --git a/packages/coding-agent/src/core/gateway-runtime.ts b/packages/coding-agent/src/core/gateway-runtime.ts
index c8b15990..cc5149a0 100644
--- a/packages/coding-agent/src/core/gateway-runtime.ts
+++ b/packages/coding-agent/src/core/gateway-runtime.ts
@@ -4,6 +4,12 @@ import { URL } from "node:url";
 import type { ImageContent } from "@mariozechner/pi-ai";
 import type { AgentSession, AgentSessionEvent } from "./agent-session.js";
 import { SessionManager } from "./session-manager.js";
+import {
+	createVercelStreamListener,
+	errorVercelStream,
+	extractUserText,
+	finishVercelStream,
+} from "./vercel-ai-stream.js";
 
 export interface GatewayConfig {
 	bind: string;
@@ -58,6 +64,8 @@ export interface GatewayRuntimeOptions {
 interface GatewayQueuedMessage {
 	request: GatewayMessageRequest;
 	resolve: (result: GatewayMessageResult) => void;
+	onStart?: () => void;
+	onFinish?: () => void;
 }
 
 type GatewayEvent =
@@ -185,18 +193,26 @@ export class GatewayRuntime {
 	}
 
 	async enqueueMessage(request: GatewayMessageRequest): Promise<GatewayMessageResult> {
-		const managedSession = await this.ensureSession(request.sessionKey);
+		return this.enqueueManagedMessage({ request });
+	}
+
+	private async enqueueManagedMessage(queuedMessage: {
+		request: GatewayMessageRequest;
+		onStart?: () => void;
+		onFinish?: () => void;
+	}): Promise<GatewayMessageResult> {
+		const managedSession = await this.ensureSession(queuedMessage.request.sessionKey);
 		if (managedSession.queue.length >= this.config.session.maxQueuePerSession) {
 			return {
 				ok: false,
 				response: "",
 				error: `Queue full (${this.config.session.maxQueuePerSession} pending).`,
-				sessionKey: request.sessionKey,
+				sessionKey: queuedMessage.request.sessionKey,
 			};
 		}
 
 		return new Promise<GatewayMessageResult>((resolve) => {
-			managedSession.queue.push({ request, resolve });
+			managedSession.queue.push({ ...queuedMessage, resolve });
 			this.emitState(managedSession);
 			void this.processNext(managedSession);
 		});
@@ -302,6 +318,7 @@ export class GatewayRuntime {
 		this.emitState(managedSession);
 
 		try {
+			queued.onStart?.();
 			await managedSession.session.prompt(queued.request.text, {
 				images: queued.request.images,
 				source: queued.request.source ?? "extension",
@@ -326,6 +343,7 @@ export class GatewayRuntime {
 				sessionKey: managedSession.sessionKey,
 			});
 		} finally {
+			queued.onFinish?.();
 			managedSession.processing = false;
 			managedSession.lastActiveAt = Date.now();
 			this.emitState(managedSession);
@@ -491,7 +509,7 @@ export class GatewayRuntime {
 			return;
 		}
 
-		const sessionMatch = path.match(/^\/sessions\/([^/]+)(?:\/(events|messages|abort|reset))?$/);
+		const sessionMatch = path.match(/^\/sessions\/([^/]+)(?:\/(events|messages|abort|reset|chat))?$/);
 		if (!sessionMatch) {
 			this.writeJson(response, 404, { error: "Not found" });
 			return;
@@ -511,6 +529,11 @@ export class GatewayRuntime {
 			return;
 		}
 
+		if (action === "chat" && method === "POST") {
+			await this.handleChat(sessionKey, request, response);
+			return;
+		}
+
 		if (action === "messages" && method === "POST") {
 			const body = await this.readJsonBody(request);
 			const text = typeof body.text === "string" ? body.text : "";
@@ -587,6 +610,81 @@ export class GatewayRuntime {
 		});
 	}
 
+	private async handleChat(sessionKey: string, request: IncomingMessage, response: ServerResponse): Promise<void> {
+		const body = await this.readJsonBody(request);
+		const text = extractUserText(body);
+		if (!text) {
+			this.writeJson(response, 400, { error: "Missing user message text" });
+			return;
+		}
+
+		// Set up SSE response headers
+		response.writeHead(200, {
+			"Content-Type": "text/event-stream",
+			"Cache-Control": "no-cache, no-transform",
+			Connection: "keep-alive",
+			"x-vercel-ai-ui-message-stream": "v1",
+		});
+		response.write("\n");
+
+		const listener = createVercelStreamListener(response);
+		let unsubscribe: (() => void) | undefined;
+		let streamingActive = false;
+
+		const stopStreaming = () => {
+			if (!streamingActive) return;
+			streamingActive = false;
+			unsubscribe?.();
+			unsubscribe = undefined;
+		};
+
+		// Clean up on client disconnect
+		let clientDisconnected = false;
+		request.on("close", () => {
+			clientDisconnected = true;
+			stopStreaming();
+		});
+
+		// Drive the session through the existing queue infrastructure
+		try {
+			const managedSession = await this.ensureSession(sessionKey);
+			const result = await this.enqueueManagedMessage({
+				request: {
+					sessionKey,
+					text,
+					source: "extension",
+				},
+				onStart: () => {
+					if (clientDisconnected || streamingActive) return;
+					unsubscribe = managedSession.session.subscribe(listener);
+					streamingActive = true;
+				},
+				onFinish: () => {
+					stopStreaming();
+				},
+			});
+			if (!clientDisconnected) {
+				stopStreaming();
+				if (result.ok) {
+					finishVercelStream(response, "stop");
+				} else {
+					const isAbort = result.error?.includes("aborted");
+					if (isAbort) {
+						finishVercelStream(response, "error");
+					} else {
+						errorVercelStream(response, result.error ?? "Unknown error");
+					}
+				}
+			}
+		} catch (error) {
+			if (!clientDisconnected) {
+				stopStreaming();
+				const message = error instanceof Error ? error.message : String(error);
+				errorVercelStream(response, message);
+			}
+		}
+	}
+
 	private requireAuth(request: IncomingMessage, response: ServerResponse): void {
 		if (!this.config.bearerToken) {
 			return;
diff --git a/packages/coding-agent/src/core/vercel-ai-stream.ts b/packages/coding-agent/src/core/vercel-ai-stream.ts
new file mode 100644
index 00000000..2326cbb6
--- /dev/null
+++ b/packages/coding-agent/src/core/vercel-ai-stream.ts
@@ -0,0 +1,199 @@
+import { randomUUID } from "node:crypto";
+import type { ServerResponse } from "node:http";
+import type { AgentSessionEvent } from "./agent-session.js";
+
+/**
+ * Write a single Vercel AI SDK v5+ SSE chunk to the response.
+ * Format: `data: <JSON>\n\n`
+ * For the terminal [DONE] sentinel: `data: [DONE]\n\n`
+ */
+function writeChunk(response: ServerResponse, chunk: object | string): void {
+	if (response.writableEnded) return;
+	const payload = typeof chunk === "string" ? chunk : JSON.stringify(chunk);
+	response.write(`data: ${payload}\n\n`);
+}
+
+/**
+ * Extract the user's text from the request body.
+ * Supports both useChat format ({ messages: UIMessage[] }) and simple gateway format ({ text: string }).
+ */
+export function extractUserText(body: Record<string, unknown>): string | null {
+	// Simple gateway format
+	if (typeof body.text === "string" && body.text.trim()) {
+		return body.text;
+	}
+	// Convenience format
+	if (typeof body.prompt === "string" && body.prompt.trim()) {
+		return body.prompt;
+	}
+	// Vercel AI SDK useChat format - extract last user message
+	if (Array.isArray(body.messages)) {
+		for (let i = body.messages.length - 1; i >= 0; i--) {
+			const msg = body.messages[i] as Record<string, unknown>;
+			if (msg.role !== "user") continue;
+			// v5+ format with parts array
+			if (Array.isArray(msg.parts)) {
+				for (const part of msg.parts as Array<Record<string, unknown>>) {
+					if (part.type === "text" && typeof part.text === "string") {
+						return part.text;
+					}
+				}
+			}
+			// v4 format with content string
+			if (typeof msg.content === "string" && msg.content.trim()) {
+				return msg.content;
+			}
+		}
+	}
+	return null;
+}
+
+/**
+ * Create an AgentSessionEvent listener that translates events to Vercel AI SDK v5+ SSE
+ * chunks and writes them to the HTTP response.
+ *
+ * Returns the listener function. The caller is responsible for subscribing/unsubscribing.
+ */
+export function createVercelStreamListener(
+	response: ServerResponse,
+	messageId?: string,
+): (event: AgentSessionEvent) => void {
+	// Gate: only forward events within a single prompt's agent_start -> agent_end lifecycle.
+	// handleChat now subscribes this listener immediately before the queued prompt starts,
+	// so these guards only need to bound the stream to that prompt's event span.
+	let active = false;
+	const msgId = messageId ?? randomUUID();
+
+	return (event: AgentSessionEvent) => {
+		if (response.writableEnded) return;
+
+		// Activate on our agent_start, deactivate on agent_end
+		if (event.type === "agent_start") {
+			if (!active) {
+				active = true;
+				writeChunk(response, { type: "start", messageId: msgId });
+			}
+			return;
+		}
+		if (event.type === "agent_end") {
+			active = false;
+			return;
+		}
+
+		// Drop events that don't belong to our message
+		if (!active) return;
+
+		switch (event.type) {
+			case "turn_start":
+				writeChunk(response, { type: "start-step" });
+				return;
+
+			case "message_update": {
+				const inner = event.assistantMessageEvent;
+				switch (inner.type) {
+					case "text_start":
+						writeChunk(response, {
+							type: "text-start",
+							id: `text_${inner.contentIndex}`,
+						});
+						return;
+					case "text_delta":
+						writeChunk(response, {
+							type: "text-delta",
+							id: `text_${inner.contentIndex}`,
+							delta: inner.delta,
+						});
+						return;
+					case "text_end":
+						writeChunk(response, {
+							type: "text-end",
+							id: `text_${inner.contentIndex}`,
+						});
+						return;
+					case "toolcall_start": {
+						const content = inner.partial.content[inner.contentIndex];
+						if (content?.type === "toolCall") {
+							writeChunk(response, {
+								type: "tool-input-start",
+								toolCallId: content.id,
+								toolName: content.name,
+							});
+						}
+						return;
+					}
+					case "toolcall_delta": {
+						const content = inner.partial.content[inner.contentIndex];
+						if (content?.type === "toolCall") {
+							writeChunk(response, {
+								type: "tool-input-delta",
+								toolCallId: content.id,
+								inputTextDelta: inner.delta,
+							});
+						}
+						return;
+					}
+					case "toolcall_end":
+						writeChunk(response, {
+							type: "tool-input-available",
+							toolCallId: inner.toolCall.id,
+							toolName: inner.toolCall.name,
+							input: inner.toolCall.arguments,
+						});
+						return;
+					case "thinking_start":
+						writeChunk(response, {
+							type: "reasoning-start",
+							id: `reasoning_${inner.contentIndex}`,
+						});
+						return;
+					case "thinking_delta":
+						writeChunk(response, {
+							type: "reasoning-delta",
+							id: `reasoning_${inner.contentIndex}`,
+							delta: inner.delta,
+						});
+						return;
+					case "thinking_end":
+						writeChunk(response, {
+							type: "reasoning-end",
+							id: `reasoning_${inner.contentIndex}`,
+						});
+						return;
+				}
+				return;
+			}
+
+			case "turn_end":
+				writeChunk(response, { type: "finish-step" });
+				return;
+
+			case "tool_execution_end":
+				writeChunk(response, {
+					type: "tool-output-available",
+					toolCallId: event.toolCallId,
+					output: event.result,
+				});
+				return;
+		}
+	};
+}
+
+/**
+ * Write the terminal finish sequence and end the response.
+ */
+export function finishVercelStream(response: ServerResponse, finishReason: string = "stop"): void {
+	if (response.writableEnded) return;
+	writeChunk(response, { type: "finish", finishReason });
+	writeChunk(response, "[DONE]");
+	response.end();
+}
+
+/**
+ * Write an error chunk and end the response.
+ */
+export function errorVercelStream(response: ServerResponse, errorText: string): void {
+	if (response.writableEnded) return;
+	writeChunk(response, { type: "error", errorText });
+	writeChunk(response, "[DONE]");
+	response.end();
+}
diff --git a/packages/coding-agent/test/vercel-ai-stream.test.ts b/packages/coding-agent/test/vercel-ai-stream.test.ts
new file mode 100644
index 00000000..1c3ea750
--- /dev/null
+++ b/packages/coding-agent/test/vercel-ai-stream.test.ts
@@ -0,0 +1,149 @@
+import { describe, expect, it } from "vitest";
+import type { AgentSessionEvent } from "../src/core/agent-session.js";
+import { createVercelStreamListener, extractUserText } from "../src/core/vercel-ai-stream.js";
+
+describe("extractUserText", () => {
+	it("extracts text from useChat v5+ format with parts", () => {
+		const body = {
+			messages: [{ role: "user", parts: [{ type: "text", text: "hello world" }] }],
+		};
+		expect(extractUserText(body)).toBe("hello world");
+	});
+
+	it("extracts text from useChat v4 format with content string", () => {
+		const body = {
+			messages: [{ role: "user", content: "hello world" }],
+		};
+		expect(extractUserText(body)).toBe("hello world");
+	});
+
+	it("extracts last user message when multiple messages present", () => {
+		const body = {
+			messages: [
+				{ role: "user", parts: [{ type: "text", text: "first" }] },
+				{ role: "assistant", parts: [{ type: "text", text: "response" }] },
+				{ role: "user", parts: [{ type: "text", text: "second" }] },
+			],
+		};
+		expect(extractUserText(body)).toBe("second");
+	});
+
+	it("extracts text from simple gateway format", () => {
+		expect(extractUserText({ text: "hello" })).toBe("hello");
+	});
+
+	it("extracts text from prompt format", () => {
+		expect(extractUserText({ prompt: "hello" })).toBe("hello");
+	});
+
+	it("returns null for empty body", () => {
+		expect(extractUserText({})).toBeNull();
+	});
+
+	it("returns null for empty messages array", () => {
+		expect(extractUserText({ messages: [] })).toBeNull();
+	});
+
+	it("prefers text field over messages", () => {
+		const body = {
+			text: "direct",
+			messages: [{ role: "user", parts: [{ type: "text", text: "from messages" }] }],
+		};
+		expect(extractUserText(body)).toBe("direct");
+	});
+});
+
+describe("createVercelStreamListener", () => {
+	function createMockResponse() {
+		const chunks: string[] = [];
+		let ended = false;
+		return {
+			writableEnded: false,
+			write(data: string) {
+				chunks.push(data);
+				return true;
+			},
+			end() {
+				ended = true;
+				this.writableEnded = true;
+			},
+			chunks,
+			get ended() {
+				return ended;
+			},
+		} as any;
+	}
+
+	function parseChunks(chunks: string[]): Array<object | string> {
+		return chunks
+			.filter((c) => c.startsWith("data: "))
+			.map((c) => {
+				const payload = c.replace(/^data: /, "").replace(/\n\n$/, "");
+				try {
+					return JSON.parse(payload);
+				} catch {
+					return payload;
+				}
+			});
+	}
+
+	it("translates text streaming events", () => {
+		const response = createMockResponse();
+		const listener = createVercelStreamListener(response, "test-msg-id");
+
+		listener({ type: "agent_start" } as AgentSessionEvent);
+		listener({ type: "turn_start", turnIndex: 0, timestamp: Date.now() } as AgentSessionEvent);
+		listener({
+			type: "message_update",
+			message: {} as any,
+			assistantMessageEvent: { type: "text_start", contentIndex: 0, partial: {} as any },
+		} as AgentSessionEvent);
+		listener({
+			type: "message_update",
+			message: {} as any,
+			assistantMessageEvent: { type: "text_delta", contentIndex: 0, delta: "hello", partial: {} as any },
+		} as AgentSessionEvent);
+		listener({
+			type: "message_update",
+			message: {} as any,
+			assistantMessageEvent: { type: "text_end", contentIndex: 0, content: "hello", partial: {} as any },
+		} as AgentSessionEvent);
+		listener({ type: "turn_end", turnIndex: 0, message: {} as any, toolResults: [] } as AgentSessionEvent);
+
+		const parsed = parseChunks(response.chunks);
+		expect(parsed).toEqual([
+			{ type: "start", messageId: "test-msg-id" },
+			{ type: "start-step" },
+			{ type: "text-start", id: "text_0" },
+			{ type: "text-delta", id: "text_0", delta: "hello" },
+			{ type: "text-end", id: "text_0" },
+			{ type: "finish-step" },
+		]);
+	});
+
+	it("does not write after response has ended", () => {
+		const response = createMockResponse();
+		const listener = createVercelStreamListener(response, "test-msg-id");
+
+		listener({ type: "agent_start" } as AgentSessionEvent);
+		response.end();
+		listener({ type: "turn_start", turnIndex: 0, timestamp: Date.now() } as AgentSessionEvent);
+
+		const parsed = parseChunks(response.chunks);
+		expect(parsed).toEqual([{ type: "start", messageId: "test-msg-id" }]);
+	});
+
+	it("ignores events outside the active prompt lifecycle", () => {
+		const response = createMockResponse();
+		const listener = createVercelStreamListener(response, "test-msg-id");
+
+		listener({ type: "turn_start", turnIndex: 0, timestamp: Date.now() } as AgentSessionEvent);
+		listener({ type: "agent_start" } as AgentSessionEvent);
+		listener({ type: "turn_start", turnIndex: 0, timestamp: Date.now() } as AgentSessionEvent);
+		listener({ type: "agent_end", messages: [] } as AgentSessionEvent);
+		listener({ type: "turn_start", turnIndex: 1, timestamp: Date.now() } as AgentSessionEvent);
+
+		const parsed = parseChunks(response.chunks);
+		expect(parsed).toEqual([{ type: "start", messageId: "test-msg-id" }, { type: "start-step" }]);
+	});
+});