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streamable client: Connect blocks far past its context deadline against an unresponsive server (detached-context cleanup) #1189

Description

@ibetitsmike

What

Client.Connect with a context deadline can block far past that deadline against a server that accepts TCP connections but never responds (black-holed peer). Observed: a 2s deadline returns after ~12s with the default HTTP client in a local test; in production, with connections crossing a NAT that silently dropped packets, a 10s deadline stretched to ~125s (kernel TCP timeout).

The caller's deadline bounds the initialize request itself, but not the error-path cleanup that follows. StreamableClientTransport.Connect detaches the incoming context for the connection's lifecycle (connCtx, cancel := context.WithCancel(xcontext.Detach(ctx)), mcp/streamable.go ~L2045 in v1.7.0). That detachment is intentional and documented for keeping the standalone SSE stream alive past a short connect deadline. However, when initialize fails at the deadline, the cleanup work that runs before Connect returns (the notifications/cancelled write for the abandoned call and session.Close()) issues HTTP requests bound to the detached connection context, not to the caller's expired one. Against a black-holed server those requests block until the HTTP transport or the kernel gives up, so Connect overshoots its deadline by minutes with a default http.Client (no ResponseHeaderTimeout).

Related: #1183 covers the same detached-context ordering problem for Close() specifically. This report is about Connect not honoring its own deadline on the error path.

Repro

func TestConnectOvershootsDeadline(t *testing.T) {
	// Accepts TCP connections, never responds to any request.
	ln, err := net.Listen("tcp", "127.0.0.1:0")
	if err != nil {
		t.Fatal(err)
	}
	defer ln.Close()
	go func() {
		for {
			conn, err := ln.Accept()
			if err != nil {
				return
			}
			defer conn.Close()
		}
	}()

	client := mcp.NewClient(&mcp.Implementation{Name: "c", Version: "0"}, nil)
	tr := &mcp.StreamableClientTransport{Endpoint: "http://" + ln.Addr().String()}
	ctx, cancel := context.WithTimeout(context.Background(), 2*time.Second)
	defer cancel()

	start := time.Now()
	_, err = client.Connect(ctx, tr, nil)
	elapsed := time.Since(start)
	t.Logf("Connect returned after %s, err=%v", elapsed, err)
	if elapsed > 4*time.Second {
		t.Fatalf("Connect blocked %s past a 2s deadline", elapsed)
	}
}

With go-sdk v1.7.0 and Go 1.24 this fails: Connect returned after 12.03s, err=context deadline exceeded; sending "notifications/cancelled": rejected by transport: Post "http://127.0.0.1:...": context deadline exceeded.

Expected

Connect(ctx, ...) returns within (approximately) ctx's deadline regardless of server behavior. Error-path cleanup for a session that never initialized could be best-effort/asynchronous, or bounded by the caller's context rather than the detached connection context.

Workaround

We now run Connect+ListTools in a goroutine and select on the deadline, abandoning the goroutine on timeout, plus a cloned http.Transport with ResponseHeaderTimeout and a short dial timeout (coder/coder#28400).

🤖 Filed by Mux (AI agent) on behalf of @ibetitsmike.

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