diff --git a/surfsense_web/tests/connectors/composio/calendar/journey.spec.ts b/surfsense_web/tests/connectors/composio/calendar/journey.spec.ts
new file mode 100644
index 000000000..700463fd2
--- /dev/null
+++ b/surfsense_web/tests/connectors/composio/calendar/journey.spec.ts
@@ -0,0 +1,59 @@
+import { expect, composioCalendarWithChatTest as test } from "../../../fixtures";
+import { streamChatToCompletion } from "../../../helpers/api/chat";
+import { listConnectors } 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 Calendar wiring from OAuth fixture -> live Calendar tools -> chat.
+ *
+ * Composio Calendar is a live connector: it should not index documents into
+ * the knowledge base. Chat should call Calendar tools against the connected
+ * Composio account when the user asks about events.
+ */
+test.describe("Composio Calendar journey", () => {
+	test("user connects Calendar and chats through live Calendar tools with the canary token", async ({
+		page,
+		request,
+		apiToken,
+		searchSpace,
+		composioCalendarConnector,
+		chatThread,
+	}) => {
+		test.setTimeout(90_000); // worker cold-start + live tool chat
+
+		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 beforeChatDocs = await listDocuments(request, apiToken, searchSpace.id);
+		expect(beforeChatDocs).toHaveLength(0);
+
+		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 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 === composioCalendarConnector.id);
+		expect(refreshed?.last_indexed_at).toBeNull();
+
+		const afterChatDocs = await listDocuments(request, apiToken, searchSpace.id);
+		expect(afterChatDocs).toHaveLength(0);
+	});
+});
diff --git a/surfsense_web/tests/fixtures/connectors/composio-calendar.fixture.ts b/surfsense_web/tests/fixtures/connectors/composio-calendar.fixture.ts
new file mode 100644
index 000000000..663692495
--- /dev/null
+++ b/surfsense_web/tests/fixtures/connectors/composio-calendar.fixture.ts
@@ -0,0 +1,33 @@
+import { type ConnectorRow, deleteConnector, runComposioOAuth } from "../../helpers/api/connectors";
+import { searchSpaceFixtures } from "../search-space.fixture";
+
+export type ComposioCalendarFixtures = {
+	/**
+	 * A pre-connected Composio Google Calendar connector inside the
+	 * fixture's `searchSpace`. OAuth uses the strict fake and is cleaned
+	 * up automatically after the test.
+	 */
+	composioCalendarConnector: ConnectorRow;
+};
+
+export const composioCalendarFixtures = searchSpaceFixtures.extend<ComposioCalendarFixtures>({
+	composioCalendarConnector: async ({ request, apiToken, searchSpace }, use) => {
+		const { connector } = await runComposioOAuth(
+			request,
+			apiToken,
+			searchSpace.id,
+			"googlecalendar"
+		);
+		if (!connector) {
+			throw new Error(
+				"composioCalendarConnector 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);
+		}
+	},
+});
diff --git a/surfsense_web/tests/fixtures/index.ts b/surfsense_web/tests/fixtures/index.ts
index 411abb69a..97174f12d 100644
--- a/surfsense_web/tests/fixtures/index.ts
+++ b/surfsense_web/tests/fixtures/index.ts
@@ -12,6 +12,8 @@
  *         │   └─ composioDriveWithChatTest — chatThread
  *         └─ composioGmailFixtures — composioGmailConnector
  *             └─ composioGmailWithChatTest — chatThread
+ *         └─ composioCalendarFixtures — composioCalendarConnector
+ *             └─ composioCalendarWithChatTest — chatThread
  *
  * To add a new connector (Gmail, Slack, manual upload, etc.):
  *   1. Add a fixture file under `fixtures/connectors/<name>.fixture.ts`.
@@ -20,11 +22,13 @@
  */
 export { expect } from "@playwright/test";
 export { chatThreadFixtures } from "./chat-thread.fixture";
+export { composioCalendarFixtures } from "./connectors/composio-calendar.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 { composioCalendarFixtures } from "./connectors/composio-calendar.fixture";
 import { composioDriveFixtures } from "./connectors/composio-drive.fixture";
 import { composioGmailFixtures } from "./connectors/composio-gmail.fixture";
 import { searchSpaceFixtures } from "./search-space.fixture";
@@ -41,3 +45,8 @@ export const composioGmailTest = composioGmailFixtures;
 /** `test` for Gmail specs that also need a chat thread. */
 export const composioGmailWithChatTest =
 	composioGmailFixtures.extend<ChatThreadFixtures>(chatThreadFixtures);
+/** `test` for specs that also need a pre-connected Composio Calendar connector. */
+export const composioCalendarTest = composioCalendarFixtures;
+/** `test` for Calendar specs that also need a chat thread. */
+export const composioCalendarWithChatTest =
+	composioCalendarFixtures.extend<ChatThreadFixtures>(chatThreadFixtures);