test(web): add Composio Gmail E2E journey

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

@@ -0,0 +1,87 @@
+import { expect, composioGmailWithChatTest as test } from "../../../fixtures";
+import { streamChatToCompletion } from "../../../helpers/api/chat";
+import {
+	listConnectors,
+	triggerIndexByDateRange,
+} from "../../../helpers/api/connectors";
+import { getEditorContent, listDocuments } from "../../../helpers/api/documents";
+import { CANARY_TOKENS, FAKE_GMAIL_MESSAGES } from "../../../helpers/canary";
+import { openConnectorPopup } from "../../../helpers/ui/connector-popup";
+import { waitForDocumentByTitle, waitForIndexingComplete } from "../../../helpers/waits/indexing";
+
+/**
+ * Proves the Gmail wiring from OAuth fixture -> date-range indexing ->
+ * Gmail message markdown -> stored source_markdown -> chat.
+ *
+ * Unlike Drive, Gmail has no file/folder selection config. The E2E
+ * hits the same date-range index contract the production route uses.
+ */
+test.describe("Composio Gmail journey", () => {
+	test("user connects Gmail, indexes messages, and chats with the canary token", async ({
+		page,
+		request,
+		apiToken,
+		searchSpace,
+		composioGmailConnector,
+		chatThread,
+	}) => {
+		test.setTimeout(180_000); // worker cold-start + summarize + embed + chunk
+
+		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();
+
+		await triggerIndexByDateRange(request, apiToken, composioGmailConnector.id, searchSpace.id, {
+			startDate: "2025-01-01",
+			endDate: "2026-12-31",
+		});
+
+		await waitForIndexingComplete(request, apiToken, composioGmailConnector.id, searchSpace.id, {
+			timeoutMs: 150_000,
+			intervalMs: 1_500,
+			minDocuments: 1,
+		});
+
+		await waitForDocumentByTitle(
+			request,
+			apiToken,
+			searchSpace.id,
+			FAKE_GMAIL_MESSAGES.canary.subject,
+			{ timeoutMs: 30_000 }
+		);
+
+		const docs = await listDocuments(request, apiToken, searchSpace.id);
+		const canaryDoc = docs.find((d) => d.title === FAKE_GMAIL_MESSAGES.canary.subject);
+
+		expect(canaryDoc, "canary Gmail document must exist after indexing").toBeDefined();
+		if (!canaryDoc) throw new Error("unreachable: canaryDoc asserted defined above");
+
+		const editor = await getEditorContent(request, apiToken, searchSpace.id, canaryDoc.id);
+		expect(
+			editor.source_markdown,
+			`canary token ${CANARY_TOKENS.gmailCanary} should appear in editor source_markdown; ` +
+				`got first 200 chars: ${editor.source_markdown.slice(0, 200)}`
+		).toContain(CANARY_TOKENS.gmailCanary);
+		expect(editor.source_markdown).toContain(`**From:** ${FAKE_GMAIL_MESSAGES.canary.from}`);
+		expect(editor.source_markdown).toContain("## Message Content");
+		expect(editor.chunk_count).toBeGreaterThan(0);
+
+		const refreshedConnectors = await listConnectors(request, apiToken, searchSpace.id);
+		const refreshed = refreshedConnectors.find((c) => c.id === composioGmailConnector.id);
+		expect(refreshed?.last_indexed_at).not.toBeNull();
+
+		const chat = await streamChatToCompletion(request, apiToken, {
+			searchSpaceId: searchSpace.id,
+			threadId: chatThread.id,
+			query: `What is in my Gmail message titled "${FAKE_GMAIL_MESSAGES.canary.subject}"?`,
+		});
+		expect(
+			chat.assistantText,
+			`chat agent should surface Gmail canary token after indexing; got: ${chat.assistantText.slice(0, 200)}`
+		).toContain(CANARY_TOKENS.gmailCanary);
+	});
+});

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

@@ -0,0 +1,37 @@
+import {
+	type ConnectorRow,
+	deleteConnector,
+	runComposioOAuth,
+} from "../../helpers/api/connectors";
+import { searchSpaceFixtures } from "../search-space.fixture";
+
+export type ComposioGmailFixtures = {
+	/**
+	 * A pre-connected Composio Gmail connector inside the fixture's
+	 * `searchSpace`. OAuth happens against the strict fake (no real
+	 * network). Cleaned up automatically after the test.
+	 */
+	composioGmailConnector: ConnectorRow;
+};
+
+export const composioGmailFixtures = searchSpaceFixtures.extend<ComposioGmailFixtures>({
+	composioGmailConnector: async ({ request, apiToken, searchSpace }, use) => {
+		const { connector } = await runComposioOAuth(
+			request,
+			apiToken,
+			searchSpace.id,
+			"gmail"
+		);
+		if (!connector) {
+			throw new Error(
+				"composioGmailConnector fixture: OAuth completed but no connector was created. " +
+					"Check the backend log — the strict Composio fake likely rejected an unmodelled call."
+			);
+		}
+		try {
+			await use(connector);
+		} finally {
+			await deleteConnector(request, apiToken, connector.id);
+		}
+	},
+});

surfsense_web/tests/fixtures/index.ts

@@ -8,8 +8,10 @@
  * Inheritance chain:
  *   base (@playwright/test)
  *     └─ searchSpaceFixtures   — apiToken, searchSpace
- *         └─ composioDriveFixtures — composioDriveConnector
- *             └─ composioDriveWithChatTest — chatThread
+ *         ├─ composioDriveFixtures — composioDriveConnector
+ *         │   └─ composioDriveWithChatTest — chatThread
+ *         └─ composioGmailFixtures — composioGmailConnector
+ *             └─ composioGmailWithChatTest — chatThread
  *
  * To add a new connector (Gmail, Slack, manual upload, etc.):
  *   1. Add a fixture file under `fixtures/connectors/<name>.fixture.ts`.
@@ -19,16 +21,23 @@
 export { expect } from "@playwright/test";
 export { chatThreadFixtures } from "./chat-thread.fixture";
 export { composioDriveFixtures } from "./connectors/composio-drive.fixture";
+export { composioGmailFixtures } from "./connectors/composio-gmail.fixture";
 export { searchSpaceFixtures } from "./search-space.fixture";
 
 import { type ChatThreadFixtures, chatThreadFixtures } from "./chat-thread.fixture";
 import { composioDriveFixtures } from "./connectors/composio-drive.fixture";
+import { composioGmailFixtures } from "./connectors/composio-gmail.fixture";
 import { searchSpaceFixtures } from "./search-space.fixture";
 
 /** Default `test` for specs that just need auth + a clean search space. */
 export const test = searchSpaceFixtures;
 /** `test` for specs that also need a pre-connected Composio Drive connector. */
 export const composioDriveTest = composioDriveFixtures;
-/** `test` for specs that also need a chat thread. */
+/** `test` for Drive specs that also need a chat thread. */
 export const composioDriveWithChatTest =
 	composioDriveFixtures.extend<ChatThreadFixtures>(chatThreadFixtures);
+/** `test` for specs that also need a pre-connected Composio Gmail connector. */
+export const composioGmailTest = composioGmailFixtures;
+/** `test` for Gmail specs that also need a chat thread. */
+export const composioGmailWithChatTest =
+	composioGmailFixtures.extend<ChatThreadFixtures>(chatThreadFixtures);

surfsense_web/tests/helpers/api/connectors.ts

@@ -128,6 +128,35 @@ export async function triggerIndex(
 	return { ok: true };
 }
 
+export async function triggerIndexByDateRange(
+	request: APIRequestContext,
+	token: string,
+	connectorId: number,
+	searchSpaceId: number,
+	options: { startDate?: string; endDate?: string } = {}
+): Promise<{ ok: true }> {
+	const params = new URLSearchParams({ search_space_id: String(searchSpaceId) });
+	if (options.startDate) params.set("start_date", options.startDate);
+	if (options.endDate) params.set("end_date", options.endDate);
+
+	const response = await request.post(
+		`${BACKEND_URL}/api/v1/search-source-connectors/${connectorId}/index?${params.toString()}`,
+		{ headers: authHeaders(token) }
+	);
+	if (!response.ok()) {
+		throw new Error(
+			`triggerIndexByDateRange(${connectorId}) failed (${response.status()}): ${await response.text()}`
+		);
+	}
+	const body = (await response.json()) as { indexing_started?: boolean; message?: string };
+	if (body.indexing_started === false) {
+		throw new Error(
+			`triggerIndexByDateRange(${connectorId}) did not start indexing: ${body.message ?? "no message"}`
+		);
+	}
+	return { ok: true };
+}
+
 /**
  * Drives the OAuth flow for a Composio toolkit programmatically.
  *

surfsense_web/tests/helpers/canary.ts

@@ -18,6 +18,7 @@ export const CANARY_TOKENS = {
 	driveBudget: "SURFSENSE_E2E_BUDGET_MARKER",
 	driveRoadmap: "SURFSENSE_E2E_ROADMAP_MARKER",
 	driveArchive: "SURFSENSE_E2E_ARCHIVE_MARKER",
+	gmailCanary: "SURFSENSE_E2E_CANARY_TOKEN_GMAIL_001",
 } as const;
 
 /**
@@ -43,6 +44,27 @@ export const FAKE_DRIVE_FOLDERS = {
 	},
 } as const;
 
+/**
+ * Fake Gmail message IDs that match what the backend fake returns from
+ * GMAIL_FETCH_EMAILS / GMAIL_FETCH_MESSAGE_BY_MESSAGE_ID.
+ */
+export const FAKE_GMAIL_MESSAGES = {
+	canary: {
+		id: "fake-msg-canary-001",
+		threadId: "fake-thread-canary-001",
+		subject: "E2E Canary Email",
+		from: "sender@surfsense.example",
+		to: "e2e-fake@surfsense.example",
+	},
+	planning: {
+		id: "fake-msg-planning-001",
+		threadId: "fake-thread-planning-001",
+		subject: "E2E Planning Notes",
+		from: "planner@surfsense.example",
+		to: "e2e-fake@surfsense.example",
+	},
+} as const;
+
 /** Generate a unique-per-run search space name. Keeps parallel tests isolated. */
 export function uniqueSearchSpaceName(prefix = "e2e"): string {
 	return `${prefix}-${randomUUID().slice(0, 8)}`;