diff --git a/surfsense_web/tests/connectors/google/calendar/journey.spec.ts b/surfsense_web/tests/connectors/google/calendar/journey.spec.ts
new file mode 100644
index 000000000..6c076a89a
--- /dev/null
+++ b/surfsense_web/tests/connectors/google/calendar/journey.spec.ts
@@ -0,0 +1,75 @@
+import { expect, nativeCalendarWithChatTest 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_CALENDAR_EVENTS } from "../../../helpers/canary";
+import { openConnectorPopup } from "../../../helpers/ui/connector-popup";
+
+/**
+ * Proves the native Calendar wiring from Google OAuth fixture -> live Calendar
+ * tools -> chat.
+ *
+ * Native Calendar is live-tool only: the public indexing route returns
+ * indexing_started=false and chat should call Calendar tools.
+ */
+test.describe("Native Google Calendar journey", () => {
+	test("user connects native Calendar and chats through live Calendar tools with indexing disabled", async ({
+		page,
+		request,
+		apiToken,
+		searchSpace,
+		nativeCalendarConnector,
+		chatThread,
+	}) => {
+		test.setTimeout(90_000); // worker cold-start + live tool chat
+
+		expect(nativeCalendarConnector.connector_type).toBe("GOOGLE_CALENDAR_CONNECTOR");
+		expect(nativeCalendarConnector.is_indexable).toBe(false);
+		expect(nativeCalendarConnector.config._token_encrypted).toBe(true);
+		expect(nativeCalendarConnector.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,
+			nativeCalendarConnector.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 Calendar event mentions ${CANARY_TOKENS.calendarCanary} next week? ` +
+				`The event title is "${FAKE_CALENDAR_EVENTS.canary.summary}".`,
+		});
+		expect(
+			chat.assistantText,
+			`chat agent should surface native Calendar canary token from live tools; got: ${chat.assistantText.slice(0, 200)}`
+		).toContain(CANARY_TOKENS.calendarCanary);
+
+		const eventText = JSON.stringify(chat.events);
+		expect(eventText).toContain("search_calendar_events");
+
+		const refreshedConnectors = await listConnectors(request, apiToken, searchSpace.id);
+		const refreshed = refreshedConnectors.find((c) => c.id === nativeCalendarConnector.id);
+		expect(refreshed?.connector_type).toBe("GOOGLE_CALENDAR_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);
+	});
+});