diff --git a/.changeset/legacy-fallback-early-abort.md b/.changeset/legacy-fallback-early-abort.md
new file mode 100644
index 0000000000..145fa1c443
--- /dev/null
+++ b/.changeset/legacy-fallback-early-abort.md
@@ -0,0 +1,5 @@
+---
+'@modelcontextprotocol/server': patch
+---
+
+The stateless legacy fallback of `createMcpHandler` now answers `499` with no body, closes the per-request transport and server, and runs nothing when the client aborted the request while the factory or `connect()` was still running. Before, that abort was never seen: the request ran to completion and `ctx.mcpReq.signal` never aborted. The modern path already answered `499` in this case.
diff --git a/packages/server/src/server/createMcpHandler.ts b/packages/server/src/server/createMcpHandler.ts
index 4ef836c636..042163516e 100644
--- a/packages/server/src/server/createMcpHandler.ts
+++ b/packages/server/src/server/createMcpHandler.ts
@@ -358,6 +358,11 @@ function createLegacyStatelessFallback(
             // Tear the per-request pair down when the client goes away before
             // the exchange completes.
             request.signal?.addEventListener('abort', teardown, { once: true });
+            // An abort that fired during the awaits above has no event left to deliver.
+            if (request.signal?.aborted) {
+                teardown();
+                return new Response(null, { status: 499 });
+            }
 
             const response = await transport.handleRequest(request, {
                 ...(options?.authInfo !== undefined && { authInfo: options.authInfo }),
diff --git a/packages/server/test/server/legacyStatelessFallback.test.ts b/packages/server/test/server/legacyStatelessFallback.test.ts
index efd1177cff..42c89c6ced 100644
--- a/packages/server/test/server/legacyStatelessFallback.test.ts
+++ b/packages/server/test/server/legacyStatelessFallback.test.ts
@@ -161,6 +161,39 @@ describe('legacyStatelessFallback', () => {
         });
     });
 
+    it('tears the per-request pair down without running the request when the client aborted before the handler subscribed', async () => {
+        let toolRan = false;
+        let productClosed = false;
+        const handler = legacyStatelessFallback(() => {
+            const mcpServer = new McpServer({ name: 'fallback-early-abort', version: '1.0.0' });
+            mcpServer.registerTool('echo', { inputSchema: z.object({}) }, async () => {
+                toolRan = true;
+                return { content: [{ type: 'text', text: 'ran' }] };
+            });
+            mcpServer.server.onclose = () => {
+                productClosed = true;
+            };
+            return mcpServer;
+        });
+
+        const request = new Request('http://localhost/mcp', {
+            method: 'POST',
+            headers: {
+                'Content-Type': 'application/json',
+                Accept: 'application/json, text/event-stream'
+            },
+            body: JSON.stringify({ jsonrpc: '2.0', id: 1, method: 'tools/call', params: { name: 'echo', arguments: {} } }),
+            signal: AbortSignal.abort()
+        });
+
+        const response = await handler(request);
+        expect(response.status).toBe(499);
+        await vi.waitFor(() => {
+            expect(productClosed).toBe(true);
+        });
+        expect(toolRan).toBe(false);
+    });
+
     it('answers factory failures with a 500 internal error body', async () => {
         const handler = legacyStatelessFallback(() => {
             throw new Error('factory exploded');