From f02f64725e1108ce3dc777d4badcaa7eedfbe5c8 Mon Sep 17 00:00:00 2001
From: Anish Sarkar <104695310+AnishSarkar22@users.noreply.github.com>
Date: Fri, 8 May 2026 13:13:35 +0530
Subject: [PATCH] test(e2e): cover ClickUp live MCP journey

---
 .../tests/connectors/clickup/journey.spec.ts  | 83 +++++++++++++++++++
 1 file changed, 83 insertions(+)
 create mode 100644 surfsense_web/tests/connectors/clickup/journey.spec.ts

diff --git a/surfsense_web/tests/connectors/clickup/journey.spec.ts b/surfsense_web/tests/connectors/clickup/journey.spec.ts
new file mode 100644
index 000000000..6ed2017a6
--- /dev/null
+++ b/surfsense_web/tests/connectors/clickup/journey.spec.ts
@@ -0,0 +1,83 @@
+import { expect, clickupWithChatTest 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_CLICKUP_TASKS } from "../../helpers/canary";
+import { openConnectorPopup } from "../../helpers/ui/connector-popup";
+
+/**
+ * Proves ClickUp MCP OAuth -> live MCP tool discovery/call -> chat.
+ *
+ * ClickUp is live-tool only: the public indexing route returns
+ * indexing_started=false and chat should call ClickUp MCP tools.
+ */
+test.describe("ClickUp connector journey", () => {
+	test("user connects ClickUp and chats through live MCP tools with indexing disabled", async ({
+		page,
+		request,
+		apiToken,
+		searchSpace,
+		clickupConnector,
+		chatThread,
+	}) => {
+		test.setTimeout(90_000); // worker cold-start + live tool chat
+
+		expect(clickupConnector.connector_type).toBe("CLICKUP_CONNECTOR");
+		expect(clickupConnector.is_indexable).toBe(false);
+		expect(clickupConnector.config._token_encrypted).toBe(true);
+		expect(clickupConnector.config.mcp_service).toBe("clickup");
+		expect(clickupConnector.config.server_config).toMatchObject({
+			transport: "streamable-http",
+			url: "https://mcp.clickup.com/mcp",
+		});
+		expect(clickupConnector.config.mcp_oauth).toMatchObject({
+			client_id: "fake-clickup-mcp-client-id",
+			token_endpoint: "https://mcp.clickup.com/token",
+		});
+		expect((clickupConnector.config.mcp_oauth as Record<string, unknown>).access_token).toBeTruthy();
+		expect(clickupConnector.config.access_token).toBeUndefined();
+		expect(clickupConnector.config.refresh_token).toBeUndefined();
+
+		await page.goto(`/dashboard/${searchSpace.id}/new-chat`, {
+			waitUntil: "domcontentloaded",
+		});
+		await openConnectorPopup(page);
+		const connectorDialog = page.getByRole("dialog", { name: "Manage Connectors" });
+		await expect(connectorDialog).toBeVisible();
+		await expect(connectorDialog.getByText("ClickUp")).toBeVisible();
+
+		const beforeDocs = await listDocuments(request, apiToken, searchSpace.id);
+		expect(beforeDocs).toHaveLength(0);
+
+		const disabledIndex = await triggerIndexExpectDisabled(
+			request,
+			apiToken,
+			clickupConnector.id,
+			searchSpace.id
+		);
+		expect(disabledIndex.message ?? "").toContain("real-time agent tools");
+		expect(disabledIndex.message ?? "").toContain("background indexing is disabled");
+
+		const chat = await streamChatToCompletion(request, apiToken, {
+			searchSpaceId: searchSpace.id,
+			threadId: chatThread.id,
+			query: `What is in my ClickUp task titled "${FAKE_CLICKUP_TASKS.canary.name}"?`,
+		});
+		expect(
+			chat.assistantText,
+			`chat agent should surface ClickUp canary token from live MCP tools; got: ${chat.assistantText.slice(0, 200)}`
+		).toContain(CANARY_TOKENS.clickupCanary);
+
+		const eventText = JSON.stringify(chat.events);
+		expect(eventText).toContain("clickup_search");
+
+		const refreshedConnectors = await listConnectors(request, apiToken, searchSpace.id);
+		const refreshed = refreshedConnectors.find((c) => c.id === clickupConnector.id);
+		expect(refreshed?.connector_type).toBe("CLICKUP_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);
+	});
+});