diff --git a/surfsense_web/tests/connectors/jira/journey.spec.ts b/surfsense_web/tests/connectors/jira/journey.spec.ts
new file mode 100644
index 000000000..8d88ee706
--- /dev/null
+++ b/surfsense_web/tests/connectors/jira/journey.spec.ts
@@ -0,0 +1,85 @@
+import { expect, jiraWithChatTest 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_JIRA_ISSUES } from "../../helpers/canary";
+import { openConnectorPopup } from "../../helpers/ui/connector-popup";
+
+/**
+ * Proves Jira MCP OAuth -> live MCP tool discovery/call -> chat.
+ *
+ * Jira is live-tool only: the public indexing route returns
+ * indexing_started=false and chat should call Jira MCP tools.
+ */
+test.describe("Jira connector journey", () => {
+	test("user connects Jira and chats through live MCP tools with indexing disabled", async ({
+		page,
+		request,
+		apiToken,
+		searchSpace,
+		jiraConnector,
+		chatThread,
+	}) => {
+		test.setTimeout(90_000); // worker cold-start + live tool chat
+
+		expect(jiraConnector.connector_type).toBe("JIRA_CONNECTOR");
+		expect(jiraConnector.is_indexable).toBe(false);
+		expect(jiraConnector.config._token_encrypted).toBe(true);
+		expect(jiraConnector.config.mcp_service).toBe("jira");
+		expect(jiraConnector.config.server_config).toMatchObject({
+			transport: "streamable-http",
+			url: "https://mcp.atlassian.com/v1/mcp",
+		});
+		expect(jiraConnector.config.mcp_oauth).toMatchObject({
+			client_id: "fake-jira-mcp-client-id",
+			token_endpoint: "https://cf.mcp.atlassian.com/v1/token",
+		});
+		expect((jiraConnector.config.mcp_oauth as Record<string, unknown>).access_token).toBeTruthy();
+		expect(jiraConnector.config.access_token).toBeUndefined();
+		expect(jiraConnector.config.refresh_token).toBeUndefined();
+
+		await page.goto(`/dashboard/${searchSpace.id}/new-chat`, {
+			waitUntil: "domcontentloaded",
+		});
+		await openConnectorPopup(page);
+		const connectorDialog = page.getByRole("dialog", { name: "Manage Connectors" });
+		await expect(connectorDialog).toBeVisible();
+		await connectorDialog.getByPlaceholder("Search").fill("Jira");
+		await expect(connectorDialog.getByText("Jira", { exact: true })).toBeVisible();
+		await expect(connectorDialog.getByText("1 Account")).toBeVisible();
+
+		const beforeDocs = await listDocuments(request, apiToken, searchSpace.id);
+		expect(beforeDocs).toHaveLength(0);
+
+		const disabledIndex = await triggerIndexExpectDisabled(
+			request,
+			apiToken,
+			jiraConnector.id,
+			searchSpace.id
+		);
+		expect(disabledIndex.message ?? "").toContain("real-time agent tools");
+		expect(disabledIndex.message ?? "").toContain("background indexing is disabled");
+
+		const chat = await streamChatToCompletion(request, apiToken, {
+			searchSpaceId: searchSpace.id,
+			threadId: chatThread.id,
+			query: `What is in my Jira issue titled "${FAKE_JIRA_ISSUES.canary.summary}"?`,
+		});
+		expect(
+			chat.assistantText,
+			`chat agent should surface Jira canary token from live MCP tools; got: ${chat.assistantText.slice(0, 200)}`
+		).toContain(CANARY_TOKENS.jiraCanary);
+
+		const eventText = JSON.stringify(chat.events);
+		expect(eventText).toContain("searchJiraIssuesUsingJql");
+
+		const refreshedConnectors = await listConnectors(request, apiToken, searchSpace.id);
+		const refreshed = refreshedConnectors.find((c) => c.id === jiraConnector.id);
+		expect(refreshed?.connector_type).toBe("JIRA_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);
+	});
+});
diff --git a/surfsense_web/tests/helpers/canary.ts b/surfsense_web/tests/helpers/canary.ts
index 6d08c4911..59c6d482e 100644
--- a/surfsense_web/tests/helpers/canary.ts
+++ b/surfsense_web/tests/helpers/canary.ts
@@ -22,6 +22,7 @@ export const CANARY_TOKENS = {
 	calendarCanary: "SURFSENSE_E2E_CANARY_TOKEN_CALENDAR_001",
 	notionCanary: "SURFSENSE_E2E_CANARY_TOKEN_NOTION_001",
 	linearCanary: "SURFSENSE_E2E_CANARY_TOKEN_LINEAR_001",
+	jiraCanary: "SURFSENSE_E2E_CANARY_TOKEN_JIRA_001",
 } as const;
 
 /**
@@ -113,6 +114,20 @@ export const FAKE_LINEAR_ISSUES = {
 	},
 } as const;
 
+/**
+ * Fake Jira issue IDs that match what the backend MCP fake returns from
+ * searchJiraIssuesUsingJql.
+ */
+export const FAKE_JIRA_ISSUES = {
+	canary: {
+		id: "fake-jira-issue-canary-001",
+		key: "E2E-101",
+		summary: "E2E Canary Jira Issue",
+		cloudId: "fake-jira-cloud-001",
+		siteUrl: "https://surfsense-e2e.atlassian.net",
+	},
+} 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)}`;