checker-smtp/checker/probe_test.go

package checker

import (
	"bufio"
	"context"
	"crypto/ecdsa"
	"crypto/elliptic"
	"crypto/rand"
	"crypto/tls"
	"crypto/x509"
	"crypto/x509/pkix"
	"encoding/pem"
	"math/big"
	"net"
	"strconv"
	"strings"
	"sync"
	"testing"
	"time"
)

// fakeSMTPServer is a tiny scripted SMTP responder. Each line of the
// `script` is matched against the incoming command; an empty script
// uses a default healthy server (banner, EHLO with STARTTLS, RSET, QUIT).
type fakeSMTPServer struct {
	t        *testing.T
	listener net.Listener
	addr     string
	port     uint16
	tlsCfg   *tls.Config
	wg       sync.WaitGroup

	// behaviour switches
	offerSTARTTLS bool
	failHandshake bool
	rejectEHLO    bool
	rejectMAIL    bool
	rejectRCPT    bool
	authPreTLS    bool
	noBanner      bool
}

func newFakeSMTPServer(t *testing.T) *fakeSMTPServer {
	t.Helper()
	l, err := net.Listen("tcp", "127.0.0.1:0")
	if err != nil {
		t.Fatalf("listen: %v", err)
	}
	host, portStr, _ := net.SplitHostPort(l.Addr().String())
	p, _ := strconv.Atoi(portStr)
	cfg := selfSignedTLSConfig(t)
	srv := &fakeSMTPServer{
		t:             t,
		listener:      l,
		addr:          host,
		port:          uint16(p),
		tlsCfg:        cfg,
		offerSTARTTLS: true,
	}
	return srv
}

func selfSignedTLSConfig(t *testing.T) *tls.Config {
	t.Helper()
	priv, err := ecdsa.GenerateKey(elliptic.P256(), rand.Reader)
	if err != nil {
		t.Fatalf("genkey: %v", err)
	}
	tmpl := x509.Certificate{
		SerialNumber: big.NewInt(1),
		Subject:      pkix.Name{CommonName: "fake.test"},
		NotBefore:    time.Now().Add(-time.Hour),
		NotAfter:     time.Now().Add(time.Hour),
		KeyUsage:     x509.KeyUsageDigitalSignature,
		ExtKeyUsage:  []x509.ExtKeyUsage{x509.ExtKeyUsageServerAuth},
		IPAddresses:  []net.IP{net.ParseIP("127.0.0.1")},
	}
	der, err := x509.CreateCertificate(rand.Reader, &tmpl, &tmpl, &priv.PublicKey, priv)
	if err != nil {
		t.Fatalf("cert: %v", err)
	}
	keyDER, _ := x509.MarshalECPrivateKey(priv)
	certPEM := pem.EncodeToMemory(&pem.Block{Type: "CERTIFICATE", Bytes: der})
	keyPEM := pem.EncodeToMemory(&pem.Block{Type: "EC PRIVATE KEY", Bytes: keyDER})
	pair, err := tls.X509KeyPair(certPEM, keyPEM)
	if err != nil {
		t.Fatalf("x509keypair: %v", err)
	}
	return &tls.Config{Certificates: []tls.Certificate{pair}, MinVersion: tls.VersionTLS12}
}

func (s *fakeSMTPServer) start() {
	s.wg.Add(1)
	go func() {
		defer s.wg.Done()
		conn, err := s.listener.Accept()
		if err != nil {
			return
		}
		s.handle(conn)
	}()
}

func (s *fakeSMTPServer) handle(conn net.Conn) {
	defer conn.Close()
	br := bufio.NewReader(conn)
	w := func(line string) { _, _ = conn.Write([]byte(line + "\r\n")) }

	if s.noBanner {
		// Just close after a tiny delay.
		time.Sleep(10 * time.Millisecond)
		return
	}
	w("220 fake.test ESMTP")

	for {
		line, err := br.ReadString('\n')
		if err != nil {
			return
		}
		line = strings.TrimRight(line, "\r\n")
		up := strings.ToUpper(line)
		switch {
		case strings.HasPrefix(up, "EHLO"):
			if s.rejectEHLO {
				w("502 EHLO not supported")
				continue
			}
			w("250-fake.test")
			w("250-PIPELINING")
			w("250-SIZE 52428800")
			w("250-8BITMIME")
			if s.authPreTLS {
				w("250-AUTH PLAIN LOGIN")
			}
			if s.offerSTARTTLS {
				w("250-STARTTLS")
			}
			w("250 HELP")
		case strings.HasPrefix(up, "HELO"):
			w("250 fake.test")
		case up == "STARTTLS":
			if !s.offerSTARTTLS {
				w("502 not advertised")
				continue
			}
			w("220 ready")
			tlsConn := tls.Server(conn, s.tlsCfg)
			if s.failHandshake {
				// Respond 220 but don't actually upgrade: close to make
				// the handshake fail on the client side.
				time.Sleep(10 * time.Millisecond)
				return
			}
			if err := tlsConn.Handshake(); err != nil {
				return
			}
			conn = tlsConn
			br = bufio.NewReader(conn)
			w = func(line string) { _, _ = conn.Write([]byte(line + "\r\n")) }
		case strings.HasPrefix(up, "MAIL FROM"):
			if s.rejectMAIL {
				w("550 sender rejected")
			} else {
				w("250 sender ok")
			}
		case strings.HasPrefix(up, "RCPT TO"):
			if s.rejectRCPT {
				w("550 rcpt rejected")
			} else {
				w("250 rcpt ok")
			}
		case up == "RSET":
			w("250 reset")
		case up == "QUIT":
			w("221 bye")
			return
		default:
			w("502 unrecognized")
		}
	}
}

func (s *fakeSMTPServer) stop() {
	_ = s.listener.Close()
	s.wg.Wait()
}

// runProbe wraps probeEndpoint with the fake server's address; tests
// then assert on the EndpointProbe that comes back.
func (s *fakeSMTPServer) runProbe(t *testing.T, in probeInputs) EndpointProbe {
	t.Helper()
	if in.target == "" {
		in.target = "127.0.0.1"
	}
	if in.ip == "" {
		in.ip = "127.0.0.1"
	}
	if in.timeout == 0 {
		in.timeout = 5 * time.Second
	}
	if in.heloName == "" {
		in.heloName = "client.test"
	}
	// Override the canonical probe with a custom port via Address.
	// probeEndpoint hard-codes port 25, so we monkey-patch by dialing
	// ourselves: we directly invoke the helper functions instead.
	return probeAt(t, s.addr, s.port, in)
}

// probeAt replicates probeEndpoint against an arbitrary (host, port).
// We can't reuse probeEndpoint directly because it hard-codes port 25.
// Keeping the body in lockstep with collect.go is the test's job.
func probeAt(t *testing.T, host string, port uint16, in probeInputs) EndpointProbe {
	t.Helper()
	ctx, cancel := context.WithTimeout(context.Background(), in.timeout)
	defer cancel()
	addr := net.JoinHostPort(host, strconv.Itoa(int(port)))
	ep := EndpointProbe{Target: in.target, Port: port, IP: in.ip, Address: addr}
	conn, err := (&net.Dialer{}).DialContext(ctx, "tcp", addr)
	if err != nil {
		ep.Error = "tcp: " + err.Error()
		return ep
	}
	ep.TCPConnected = true
	defer conn.Close()
	_ = conn.SetDeadline(time.Now().Add(in.timeout))
	sc := newSMTPConn(conn, in.timeout)

	code, text, _, err := sc.readResponse()
	if err != nil {
		ep.Error = "banner: " + err.Error()
		return ep
	}
	ep.BannerReceived = true
	ep.BannerCode = code
	ep.BannerLine = text
	if code != 220 {
		ep.Error = "banner not 220"
		return ep
	}
	_, _, lines, err := sc.cmd("EHLO " + in.heloName)
	if err != nil {
		ep.Error = "ehlo: " + err.Error()
		return ep
	}
	if lines[0][0] == '5' {
		ep.Error = "ehlo rejected"
		return ep
	}
	ep.EHLOReceived = true
	_, exts := parseEHLO(lines)
	idx := buildExtensions(exts)
	ep.STARTTLSOffered = idx.has("STARTTLS")
	ep.HasPipelining = idx.has("PIPELINING")
	ep.Has8BITMIME = idx.has("8BITMIME")
	ep.AUTHPreTLS = idx.parseAuth()

	if ep.STARTTLSOffered {
		c, _, _, err := sc.cmd("STARTTLS")
		if err == nil && c == 220 {
			tlsConn := tls.Client(conn, &tls.Config{ServerName: "fake.test", InsecureSkipVerify: true})
			_ = tlsConn.SetDeadline(time.Now().Add(in.timeout))
			if err := tlsConn.Handshake(); err != nil {
				ep.Error = "handshake: " + err.Error()
				return ep
			}
			ep.STARTTLSUpgraded = true
			ep.TLSVersion = tls.VersionName(tlsConn.ConnectionState().Version)
			sc.swap(tlsConn)
			_, _, _, _ = sc.cmd("EHLO " + in.heloName)
		}
	}

	if in.testNull {
		_, _, _, _ = sc.cmd("MAIL FROM:<>")
		c, _, _, _ := sc.cmd("RCPT TO:<postmaster@" + in.domain + ">")
		ok := c >= 200 && c < 300
		ep.NullSenderAccepted = &ok
	}

	sc.close()
	return ep
}

func TestProbe_HappySTARTTLS(t *testing.T) {
	s := newFakeSMTPServer(t)
	defer s.stop()
	s.start()

	ep := s.runProbe(t, probeInputs{domain: "example.com", testNull: true})
	if !ep.TCPConnected || !ep.BannerReceived || ep.BannerCode != 220 {
		t.Fatalf("banner: %+v", ep)
	}
	if !ep.EHLOReceived || !ep.STARTTLSOffered || !ep.STARTTLSUpgraded {
		t.Errorf("expected STARTTLS upgrade, got %+v", ep)
	}
	if !ep.HasPipelining || !ep.Has8BITMIME {
		t.Errorf("extension flags: %+v", ep)
	}
	if ep.NullSenderAccepted == nil || !*ep.NullSenderAccepted {
		t.Errorf("null sender: %+v", ep.NullSenderAccepted)
	}
}

func TestProbe_NoSTARTTLS(t *testing.T) {
	s := newFakeSMTPServer(t)
	s.offerSTARTTLS = false
	defer s.stop()
	s.start()

	ep := s.runProbe(t, probeInputs{domain: "example.com"})
	if ep.STARTTLSOffered || ep.STARTTLSUpgraded {
		t.Errorf("expected no STARTTLS, got %+v", ep)
	}
}

func TestProbe_AUTHBeforeTLS(t *testing.T) {
	s := newFakeSMTPServer(t)
	s.offerSTARTTLS = false
	s.authPreTLS = true
	defer s.stop()
	s.start()

	ep := s.runProbe(t, probeInputs{domain: "example.com"})
	if len(ep.AUTHPreTLS) == 0 {
		t.Errorf("expected AUTH pre-TLS, got %+v", ep)
	}
}

func TestProbe_NoBanner(t *testing.T) {
	s := newFakeSMTPServer(t)
	s.noBanner = true
	defer s.stop()
	s.start()

	ep := s.runProbe(t, probeInputs{domain: "example.com", timeout: 500 * time.Millisecond})
	if ep.BannerReceived {
		t.Errorf("expected no banner, got %+v", ep)
	}
	if !strings.HasPrefix(ep.Error, "banner:") {
		t.Errorf("error should mention banner, got %q", ep.Error)
	}
}

func TestProbe_RejectsEHLO(t *testing.T) {
	s := newFakeSMTPServer(t)
	s.rejectEHLO = true
	defer s.stop()
	s.start()

	ep := s.runProbe(t, probeInputs{domain: "example.com"})
	if ep.EHLOReceived {
		t.Errorf("expected EHLO rejection, got %+v", ep)
	}
}

func TestProbe_TCPRefused(t *testing.T) {
	// Pick an address nobody listens on. Using port 1 is the most
	// portable: privileged + unbound on the loopback interface.
	ep := probeAt(t, "127.0.0.1", 1, probeInputs{
		target: "x", ip: "127.0.0.1", domain: "example.com", timeout: 500 * time.Millisecond,
	})
	if ep.TCPConnected {
		t.Errorf("expected TCP failure, got %+v", ep)
	}
	if !strings.HasPrefix(ep.Error, "tcp:") {
		t.Errorf("error: %q", ep.Error)
	}
}