test(web): add native Google Gmail live-tool journey

surfsense_web/tests/connectors/google/gmail/journey.spec.ts

@@ -0,0 +1,74 @@
+import { expect, nativeGmailWithChatTest as test } from "../../../fixtures";
+import { streamChatToCompletion } from "../../../helpers/api/chat";
+import { listConnectors, triggerIndexExpectDisabled } from "../../../helpers/api/connectors";
+import { listDocuments } from "../../../helpers/api/documents";
+import { CANARY_TOKENS, FAKE_GMAIL_MESSAGES } from "../../../helpers/canary";
+import { openConnectorPopup } from "../../../helpers/ui/connector-popup";
+
+/**
+ * Proves the native Gmail wiring from Google OAuth fixture -> live Gmail
+ * tools -> chat.
+ *
+ * Native Gmail is currently live-tool only: the public indexing route
+ * returns indexing_started=false and chat should call Gmail tools.
+ */
+test.describe("Native Google Gmail journey", () => {
+	test("user connects native Gmail and chats through live Gmail tools with indexing disabled", async ({
+		page,
+		request,
+		apiToken,
+		searchSpace,
+		nativeGmailConnector,
+		chatThread,
+	}) => {
+		test.setTimeout(90_000); // worker cold-start + live tool chat
+
+		expect(nativeGmailConnector.connector_type).toBe("GOOGLE_GMAIL_CONNECTOR");
+		expect(nativeGmailConnector.is_indexable).toBe(false);
+		expect(nativeGmailConnector.config._token_encrypted).toBe(true);
+		expect(nativeGmailConnector.config.composio_connected_account_id).toBeUndefined();
+
+		await page.goto(`/dashboard/${searchSpace.id}/new-chat`, {
+			waitUntil: "domcontentloaded",
+		});
+		await openConnectorPopup(page);
+		const connectorDialog = page.getByRole("dialog", { name: "Manage Connectors" });
+		await expect(connectorDialog).toBeVisible();
+		await expect(connectorDialog.getByRole("button", { name: "Manage" })).toBeVisible();
+
+		const beforeDocs = await listDocuments(request, apiToken, searchSpace.id);
+		expect(beforeDocs).toHaveLength(0);
+
+		const disabledIndex = await triggerIndexExpectDisabled(
+			request,
+			apiToken,
+			nativeGmailConnector.id,
+			searchSpace.id
+		);
+		expect(disabledIndex.message ?? "").toContain("real-time agent tools");
+		expect(disabledIndex.message ?? "").toContain("background indexing is disabled");
+
+		const chat = await streamChatToCompletion(request, apiToken, {
+			searchSpaceId: searchSpace.id,
+			threadId: chatThread.id,
+			query: `What is in my Gmail message titled "${FAKE_GMAIL_MESSAGES.canary.subject}"?`,
+		});
+		expect(
+			chat.assistantText,
+			`chat agent should surface native Gmail canary token from live tools; got: ${chat.assistantText.slice(0, 200)}`
+		).toContain(CANARY_TOKENS.gmailCanary);
+
+		const eventText = JSON.stringify(chat.events);
+		expect(eventText).toContain("search_gmail");
+		expect(eventText).toContain("read_gmail_email");
+
+		const refreshedConnectors = await listConnectors(request, apiToken, searchSpace.id);
+		const refreshed = refreshedConnectors.find((c) => c.id === nativeGmailConnector.id);
+		expect(refreshed?.connector_type).toBe("GOOGLE_GMAIL_CONNECTOR");
+		expect(refreshed?.is_indexable).toBe(false);
+		expect(refreshed?.last_indexed_at).toBeNull();
+
+		const afterDocs = await listDocuments(request, apiToken, searchSpace.id);
+		expect(afterDocs).toHaveLength(0);
+	});
+});

surfsense_web/tests/fixtures/connectors/native-drive.fixture.ts

@@ -20,7 +20,7 @@ export const nativeDriveFixtures = searchSpaceFixtures.extend<NativeDriveFixture
 		if (!connector) {
 			throw new Error(
 				"nativeDriveConnector fixture: OAuth completed but no GOOGLE_DRIVE_CONNECTOR was created. " +
-					"Check the backend log — the native Google Drive fake likely rejected an unmodelled call."
+					"Check the backend log — the native Google fake likely rejected an unmodelled call."
 			);
 		}
 		try {

surfsense_web/tests/fixtures/connectors/native-gmail.fixture.ts

@@ -0,0 +1,32 @@
+import {
+	type ConnectorRow,
+	deleteConnector,
+	runNativeGoogleGmailOAuth,
+} from "../../helpers/api/connectors";
+import { searchSpaceFixtures } from "../search-space.fixture";
+
+export type NativeGmailFixtures = {
+	/**
+	 * A pre-connected native Google Gmail connector inside the fixture's
+	 * `searchSpace`. OAuth uses E2E native Google fakes and is cleaned up
+	 * automatically after the test.
+	 */
+	nativeGmailConnector: ConnectorRow;
+};
+
+export const nativeGmailFixtures = searchSpaceFixtures.extend<NativeGmailFixtures>({
+	nativeGmailConnector: async ({ request, apiToken, searchSpace }, use) => {
+		const { connector } = await runNativeGoogleGmailOAuth(request, apiToken, searchSpace.id);
+		if (!connector) {
+			throw new Error(
+				"nativeGmailConnector fixture: OAuth completed but no GOOGLE_GMAIL_CONNECTOR was created. " +
+					"Check the backend log — the native Google fake likely rejected an unmodelled call."
+			);
+		}
+		try {
+			await use(connector);
+		} finally {
+			await deleteConnector(request, apiToken, connector.id);
+		}
+	},
+});

surfsense_web/tests/fixtures/index.ts

@@ -16,6 +16,8 @@
  *             └─ composioCalendarWithChatTest — chatThread
  *         └─ nativeDriveFixtures — nativeDriveConnector
  *             └─ nativeDriveWithChatTest — chatThread
+ *         └─ nativeGmailFixtures — nativeGmailConnector
+ *             └─ nativeGmailWithChatTest — chatThread
  *
  * To add a new connector (Gmail, Slack, manual upload, etc.):
  *   1. Add a fixture file under `fixtures/connectors/<name>.fixture.ts`.
@@ -28,6 +30,7 @@ export { composioCalendarFixtures } from "./connectors/composio-calendar.fixture
 export { composioDriveFixtures } from "./connectors/composio-drive.fixture";
 export { composioGmailFixtures } from "./connectors/composio-gmail.fixture";
 export { nativeDriveFixtures } from "./connectors/native-drive.fixture";
+export { nativeGmailFixtures } from "./connectors/native-gmail.fixture";
 export { searchSpaceFixtures } from "./search-space.fixture";
 
 import { type ChatThreadFixtures, chatThreadFixtures } from "./chat-thread.fixture";
@@ -35,6 +38,7 @@ import { composioCalendarFixtures } from "./connectors/composio-calendar.fixture
 import { composioDriveFixtures } from "./connectors/composio-drive.fixture";
 import { composioGmailFixtures } from "./connectors/composio-gmail.fixture";
 import { nativeDriveFixtures } from "./connectors/native-drive.fixture";
+import { nativeGmailFixtures } from "./connectors/native-gmail.fixture";
 import { searchSpaceFixtures } from "./search-space.fixture";
 
 /** Default `test` for specs that just need auth + a clean search space. */
@@ -59,3 +63,8 @@ export const nativeDriveTest = nativeDriveFixtures;
 /** `test` for native Drive specs that also need a chat thread. */
 export const nativeDriveWithChatTest =
 	nativeDriveFixtures.extend<ChatThreadFixtures>(chatThreadFixtures);
+/** `test` for specs that also need a pre-connected native Gmail connector. */
+export const nativeGmailTest = nativeGmailFixtures;
+/** `test` for native Gmail specs that also need a chat thread. */
+export const nativeGmailWithChatTest =
+	nativeGmailFixtures.extend<ChatThreadFixtures>(chatThreadFixtures);

surfsense_web/tests/helpers/api/connectors.ts

@@ -126,6 +126,31 @@ export async function triggerIndex(
 	return { ok: true };
 }
 
+export async function triggerIndexExpectDisabled(
+	request: APIRequestContext,
+	token: string,
+	connectorId: number,
+	searchSpaceId: number,
+	body: IndexBody = {}
+): Promise<{ indexing_started: false; message?: string }> {
+	const response = await request.post(
+		`${BACKEND_URL}/api/v1/search-source-connectors/${connectorId}/index?search_space_id=${searchSpaceId}`,
+		{ headers: authHeaders(token), data: body }
+	);
+	if (!response.ok()) {
+		throw new Error(
+			`triggerIndexExpectDisabled(${connectorId}) failed (${response.status()}): ${await response.text()}`
+		);
+	}
+	const payload = (await response.json()) as { indexing_started?: boolean; message?: string };
+	if (payload.indexing_started !== false) {
+		throw new Error(
+			`triggerIndexExpectDisabled(${connectorId}) expected indexing_started=false, got ${JSON.stringify(payload)}`
+		);
+	}
+	return { indexing_started: false, message: payload.message };
+}
+
 /**
  * Drives the OAuth flow for a Composio toolkit programmatically.
  *
@@ -230,3 +255,45 @@ export async function runNativeGoogleDriveOAuth(
 
 	return { authUrl: auth_url, finalUrl: location, connector };
 }
+
+/**
+ * Drives the native Google Gmail OAuth flow programmatically.
+ *
+ * The E2E backend patches Google OAuth so the returned auth_url points
+ * straight back to the backend callback with a deterministic code/state.
+ */
+export async function runNativeGoogleGmailOAuth(
+	request: APIRequestContext,
+	token: string,
+	searchSpaceId: number
+): Promise<{
+	authUrl: string;
+	finalUrl: string;
+	connector: ConnectorRow | null;
+}> {
+	const initiateResp = await request.get(
+		`${BACKEND_URL}/api/v1/auth/google/gmail/connector/add?space_id=${searchSpaceId}`,
+		{ headers: authHeaders(token) }
+	);
+	if (!initiateResp.ok()) {
+		throw new Error(
+			`native Google Gmail initiate failed (${initiateResp.status()}): ${await initiateResp.text()}`
+		);
+	}
+	const { auth_url } = (await initiateResp.json()) as { auth_url: string };
+	if (!auth_url) {
+		throw new Error("native Google Gmail initiate response missing auth_url");
+	}
+
+	const callbackResp = await request.get(auth_url, {
+		headers: authHeaders(token),
+		maxRedirects: 0,
+		failOnStatusCode: false,
+	});
+	const location = callbackResp.headers().location ?? auth_url;
+
+	const connectors = await listConnectors(request, token, searchSpaceId);
+	const connector = connectors.find((c) => c.connector_type === "GOOGLE_GMAIL_CONNECTOR") ?? null;
+
+	return { authUrl: auth_url, finalUrl: location, connector };
+}