diff --git a/src/servers/mcp-server.ts b/src/servers/mcp-server.ts
index b4b4886..54b3b88 100644
--- a/src/servers/mcp-server.ts
+++ b/src/servers/mcp-server.ts
@@ -3,6 +3,7 @@ import type {
 	ReadResourceRequestSchema,
 } from "@modelcontextprotocol/sdk/types.js";
 import { SpanStatusCode, context, trace } from "@opentelemetry/api";
+import type { AgentConversation } from "@thoughtspot/rest-api-sdk";
 import type { z } from "zod";
 import { TrackEvent } from "../metrics";
 import type { ApiVersionMode } from "../metrics/runtime/metric-types";
@@ -381,10 +382,22 @@ Provide this url to the user as a link to view the liveboard in ThoughtSpot.`;
 		);
 		span?.setAttribute("data_source_id", data_source_id ?? "(none)");
 
-		const response =
-			await this.getThoughtSpotService(recorder).createAgentConversation(
-				data_source_id,
+		let response: AgentConversation;
+		try {
+			response =
+				await this.getThoughtSpotService(recorder).createAgentConversation(
+					data_source_id,
+				);
+		} catch (error) {
+			if (!(error as any)?.message?.includes("failed with status 401")) {
+				throw error;
+			}
+
+			return this.createErrorResponse(
+				"Your authentication has expired, please reauthenticate and try again. You may need to disconnect and reconnect the MCP Server if you don't have any other way to reauthenticate.",
+				"User authentication has expired, prompting them to reauthenticate",
 			);
+		}
 		recorder.setAnalyticsContext({
 			analyticalSessionId: response.conversation_id,
 		});
diff --git a/test/servers/mcp-server.spec.ts b/test/servers/mcp-server.spec.ts
index 1eb50d7..32cbe54 100644
--- a/test/servers/mcp-server.spec.ts
+++ b/test/servers/mcp-server.spec.ts
@@ -1278,6 +1278,50 @@ describe("MCP Server", () => {
 				}),
 			).rejects.toThrow("Failed to create conversation");
 		});
+
+		it("should return auth-expired error response when service throws 401 error", async () => {
+			vi.spyOn(thoughtspotClient, "getThoughtSpotClient").mockReturnValue({
+				getSessionInfo: vi.fn().mockResolvedValue({
+					clusterId: "test-cluster-123",
+					clusterName: "test-cluster",
+					releaseVersion: "10.13.0.cl-110",
+					userGUID: "test-user-123",
+					configInfo: {
+						mixpanelConfig: {
+							devSdkKey: "test-dev-token",
+							prodSdkKey: "test-prod-token",
+							production: false,
+						},
+						selfClusterName: "test-cluster",
+						selfClusterId: "test-cluster-123",
+						enableSpotterDataSourceDiscovery: true,
+					},
+					userName: "test-user",
+					currentOrgId: "test-org",
+					privileges: [],
+				}),
+				createAgentConversationWithAutoMode: vi
+					.fn()
+					.mockRejectedValue(
+						new Error(
+							"createAgentConversationWithAutoMode failed with status 401",
+						),
+					),
+				instanceUrl: "https://test.thoughtspot.cloud",
+			} as any);
+
+			await server.init();
+
+			const result = await server.callCreateAnalysisSession({
+				method: "tools/call",
+				params: { name: "create_analysis_session", arguments: {} },
+			});
+
+			expect(result.isError).toBe(true);
+			expect((result.content[0] as any).text).toContain(
+				"Your authentication has expired",
+			);
+		});
 	});
 
 	describe("Caching", () => {