diff --git a/packages/mcp/src/transport/http.ts b/packages/mcp/src/transport/http.ts
index b01a194..696d545 100644
--- a/packages/mcp/src/transport/http.ts
+++ b/packages/mcp/src/transport/http.ts
@@ -1,19 +1,48 @@
 import { randomUUID } from "node:crypto";
-import { createServer as createHttpServer } from "node:http";
+import {
+	createServer as createHttpServer,
+	type IncomingMessage,
+	type RequestListener,
+	type ServerResponse,
+} from "node:http";
 import type { McpServer } from "@modelcontextprotocol/sdk/server/mcp.js";
 import { StreamableHTTPServerTransport } from "@modelcontextprotocol/sdk/server/streamableHttp.js";
 
+/** Minimal transport surface the request listener depends on. */
+interface RequestHandlingTransport {
+	handleRequest(req: IncomingMessage, res: ServerResponse): Promise<unknown>;
+}
+
+/**
+ * Build the Node HTTP request listener that drives the MCP transport.
+ *
+ * Extracted so the error path can be exercised in isolation. When
+ * handleRequest rejects, the client must receive a structured response rather
+ * than a hung connection that only times out at the socket level.
+ */
+export function createRequestListener(transport: RequestHandlingTransport): RequestListener {
+	return (req, res) => {
+		transport.handleRequest(req, res).catch((err: unknown) => {
+			const message = err instanceof Error ? err.message : String(err);
+			process.stderr.write(`HTTP handler error: ${message}\n`);
+			if (!res.headersSent) {
+				res.statusCode = 500;
+				res.setHeader("Content-Type", "application/json");
+				res.end(JSON.stringify({ error: "Internal MCP server error", detail: message }));
+			} else if (!res.writableEnded) {
+				res.end();
+			}
+		});
+	};
+}
+
 export async function startHttp(server: McpServer, port: number): Promise<void> {
 	const transport = new StreamableHTTPServerTransport({
 		sessionIdGenerator: () => randomUUID(),
 	});
 	await server.connect(transport);
 
-	const httpServer = createHttpServer((req, res) => {
-		transport.handleRequest(req, res).catch((err: unknown) => {
-			process.stderr.write(`HTTP handler error: ${String(err)}\n`);
-		});
-	});
+	const httpServer = createHttpServer(createRequestListener(transport));
 
 	httpServer.listen(port, () => {
 		process.stderr.write(`@logic-md/mcp listening on http://localhost:${port}\n`);
diff --git a/packages/mcp/tests/server.test.mjs b/packages/mcp/tests/server.test.mjs
index d92d8cd..de7e401 100644
--- a/packages/mcp/tests/server.test.mjs
+++ b/packages/mcp/tests/server.test.mjs
@@ -1,10 +1,14 @@
 import { strict as assert } from "node:assert";
 import { symlinkSync, unlinkSync } from "node:fs";
+import { createServer as createHttpServer, request as httpRequest } from "node:http";
 import { join } from "node:path";
 import { describe, it } from "node:test";
 import { Client } from "@modelcontextprotocol/sdk/client/index.js";
 import { InMemoryTransport } from "@modelcontextprotocol/sdk/inMemory.js";
 import { createServer } from "../dist/server.js";
+// Imported from source: exercises the real request listener with an injected
+// transport. Node strips the TypeScript types on import (>=22.18 default).
+import { createRequestListener } from "../src/transport/http.ts";
 
 // Ensure templates directory is resolved relative to this test file so
 // list_templates works regardless of the cwd when tests are invoked.
@@ -370,3 +374,78 @@ describe("MCP server integration", () => {
 		});
 	});
 });
+
+// -----------------------------------------------------------------------------
+// Issue #66: HTTP transport must respond on handler error, not hang
+// -----------------------------------------------------------------------------
+
+/**
+ * POST a payload and resolve with {status, contentType, body}. Rejects if no
+ * response arrives within timeoutMs, which is how a hung connection (the bug)
+ * surfaces as a test failure rather than waiting on a socket-level timeout.
+ */
+function postWithTimeout(port, payload, timeoutMs) {
+	return new Promise((resolve, reject) => {
+		const req = httpRequest(
+			{
+				host: "127.0.0.1",
+				port,
+				method: "POST",
+				path: "/",
+				headers: {
+					"Content-Type": "application/json",
+					"Content-Length": Buffer.byteLength(payload),
+				},
+			},
+			(res) => {
+				let data = "";
+				res.on("data", (chunk) => {
+					data += chunk;
+				});
+				res.on("end", () => {
+					resolve({
+						status: res.statusCode,
+						contentType: res.headers["content-type"],
+						body: data,
+					});
+				});
+			},
+		);
+		req.setTimeout(timeoutMs, () => {
+			req.destroy(new Error(`request timed out after ${timeoutMs}ms (hung connection)`));
+		});
+		req.on("error", reject);
+		req.write(payload);
+		req.end();
+	});
+}
+
+describe("HTTP transport error response (issue #66)", () => {
+	it("responds 500 with a structured JSON body when handleRequest rejects", async () => {
+		// Stub transport whose handleRequest rejects, simulating the failure
+		// path. Before the fix the listener only logs to stderr and never ends
+		// the response, so the client hangs until its socket timeout.
+		const rejectingTransport = {
+			async handleRequest() {
+				throw new Error("simulated handler failure");
+			},
+		};
+		const httpServer = createHttpServer(createRequestListener(rejectingTransport));
+		await new Promise((resolve) => httpServer.listen(0, "127.0.0.1", resolve));
+		const { port } = httpServer.address();
+
+		try {
+			const res = await postWithTimeout(port, '{"jsonrpc":"2.0","method":"x","id":1}', 2000);
+			assert.strictEqual(res.status, 500, `expected status 500, got ${res.status}`);
+			assert.ok(
+				res.contentType?.includes("application/json"),
+				`expected application/json content-type, got: ${res.contentType}`,
+			);
+			const parsed = JSON.parse(res.body);
+			assert.ok(parsed.error, `expected an error field in body, got: ${res.body}`);
+			assert.ok("detail" in parsed, `expected a detail field in body, got: ${res.body}`);
+		} finally {
+			await new Promise((resolve) => httpServer.close(resolve));
+		}
+	});
+});