worker/internal/sender/email_context_test.go

package sender

import (
	"bufio"
	"context"
	"crypto/hmac"
	"crypto/md5" //nolint:gosec // CRAM-MD5 is an SMTP protocol requirement.
	"crypto/rand"
	"crypto/rsa"
	"crypto/tls"
	"crypto/x509"
	"crypto/x509/pkix"
	"encoding/base64"
	"encoding/pem"
	"errors"
	"math/big"
	"net"
	"strings"
	"testing"
	"time"

	"github.com/stretchr/testify/require"

	"rocketgit.ru/rsmon/worker/internal/wire"
)

type fakeSMTPServer struct {
	listener net.Listener
	done     chan error
	tls      *tls.Config
}

func newFakeSMTPServer(t *testing.T, implicitTLS, startTLS, blockEHLO bool, auth string) *fakeSMTPServer {
	t.Helper()
	listener, err := net.Listen("tcp", "127.0.0.1:0")
	require.NoError(t, err)
	server := &fakeSMTPServer{listener: listener, done: make(chan error, 1), tls: fakeSMTPTLSConfig(t)}
	go func() { server.done <- server.serve(implicitTLS, startTLS, blockEHLO, auth) }()
	t.Cleanup(func() {
		_ = listener.Close()
		select {
		case err := <-server.done:
			require.NoError(t, err)
		case <-time.After(time.Second):
			t.Error("fake SMTP server did not exit")
		}
	})
	return server
}

func (s *fakeSMTPServer) serve(implicitTLS, startTLS, blockEHLO bool, auth string) error {
	conn, err := s.listener.Accept()
	if err != nil {
		return nil
	}
	defer conn.Close() //nolint:errcheck
	if implicitTLS {
		conn = tls.Server(conn, s.tls)
		if err := conn.(*tls.Conn).Handshake(); err != nil {
			return err
		}
	}
	reader := bufio.NewReader(conn)
	writer := bufio.NewWriter(conn)
	if err := smtpReply(writer, "220 fake smtp"); err != nil {
		return err
	}
	line, err := smtpCommand(reader)
	if err != nil {
		return err
	}
	if !strings.HasPrefix(line, "EHLO ") {
		return errors.New("expected EHLO")
	}
	if blockEHLO {
		_, _ = reader.ReadByte()
		return nil
	}
	capabilities := []string{"250-fake"}
	if startTLS {
		capabilities = append(capabilities, "250-STARTTLS")
	}
	if auth != "" {
		capabilities = append(capabilities, "250-AUTH "+auth)
	}
	capabilities = append(capabilities, "250 OK")
	if err := smtpReplies(writer, capabilities...); err != nil {
		return err
	}
	if startTLS {
		if line, err = smtpCommand(reader); err != nil || line != "STARTTLS" {
			return errors.New("expected STARTTLS")
		}
		if err := smtpReply(writer, "220 ready for TLS"); err != nil {
			return err
		}
		conn = tls.Server(conn, s.tls)
		if err := conn.(*tls.Conn).Handshake(); err != nil {
			return err
		}
		reader, writer = bufio.NewReader(conn), bufio.NewWriter(conn)
		if line, err = smtpCommand(reader); err != nil || !strings.HasPrefix(line, "EHLO ") {
			return errors.New("expected EHLO after STARTTLS")
		}
		capabilities = []string{"250-fake"}
		if auth != "" {
			capabilities = append(capabilities, "250-AUTH "+auth)
		}
		capabilities = append(capabilities, "250 OK")
		if err := smtpReplies(writer, capabilities...); err != nil {
			return err
		}
	}
	if err := smtpAuthenticate(reader, writer, auth); err != nil {
		return err
	}
	if line, err = smtpCommand(reader); err != nil || !strings.HasPrefix(line, "MAIL FROM:<sender@example.test>") {
		return errors.New("expected MAIL FROM")
	}
	if err := smtpReply(writer, "250 sender ok"); err != nil {
		return err
	}
	if line, err = smtpCommand(reader); err != nil || !strings.HasPrefix(line, "RCPT TO:<recipient@example.test>") {
		return errors.New("expected RCPT TO")
	}
	if err := smtpReply(writer, "250 recipient ok"); err != nil {
		return err
	}
	if line, err = smtpCommand(reader); err != nil || line != "DATA" {
		return errors.New("expected DATA")
	}
	if err := smtpReply(writer, "354 send data"); err != nil {
		return err
	}
	dataLines := 0
	for {
		line, err = smtpCommand(reader)
		if err != nil {
			return err
		}
		if line == "." {
			break
		}
		dataLines++
	}
	if dataLines == 0 {
		return errors.New("expected non-empty DATA payload")
	}
	if err := smtpReply(writer, "250 queued"); err != nil {
		return err
	}
	line, err = smtpCommand(reader)
	if err != nil || line != "QUIT" {
		return errors.New("expected QUIT")
	}
	return smtpReply(writer, "221 bye")
}

func smtpAuthenticate(reader *bufio.Reader, writer *bufio.Writer, auth string) error {
	if auth == "" {
		return nil
	}
	line, err := smtpCommand(reader)
	if err != nil {
		return err
	}
	if strings.Contains(auth, "CRAM-MD5") {
		if line != "AUTH CRAM-MD5" {
			return errors.New("expected capability-selected CRAM-MD5 authentication")
		}
		challenge := []byte("fake-cram-challenge")
		if err := smtpReply(writer, "334 "+base64.StdEncoding.EncodeToString(challenge)); err != nil {
			return err
		}
		response, err := smtpCommand(reader)
		if err != nil {
			return err
		}
		decoded, err := base64.StdEncoding.DecodeString(response)
		if err != nil {
			return err
		}
		mac := hmac.New(md5.New, []byte("password")) //nolint:gosec // CRAM-MD5 is an SMTP protocol requirement.
		_, _ = mac.Write(challenge)
		if string(decoded) != "user "+fmtHex(mac.Sum(nil)) {
			return errors.New("invalid CRAM-MD5 response")
		}
		return smtpReply(writer, "235 authenticated")
	}
	if line != "AUTH LOGIN" {
		return errors.New("expected capability-selected LOGIN authentication")
	}
	if err := smtpReply(writer, "334 VXNlcm5hbWU6"); err != nil {
		return err
	}
	if line, err = smtpCommand(reader); err != nil || line != base64.StdEncoding.EncodeToString([]byte("user")) {
		return errors.New("invalid LOGIN username")
	}
	if err := smtpReply(writer, "334 UGFzc3dvcmQ6"); err != nil {
		return err
	}
	if line, err = smtpCommand(reader); err != nil || line != base64.StdEncoding.EncodeToString([]byte("password")) {
		return errors.New("invalid LOGIN password")
	}
	return smtpReply(writer, "235 authenticated")
}

func TestSendEmailWithCredentialContextImplicitTLS(t *testing.T) {
	server := newFakeSMTPServer(t, true, false, false, "CRAM-MD5 PLAIN")
	cred := fakeSMTPCredential(t, server.listener.Addr().String())
	require.NoError(t, sendEmailWithCredentialContext(context.Background(), "recipient@example.test", "subject", "body", "<b>body</b>", cred, true))
}

func TestSendEmailWithCredentialContextSTARTTLSAndLogin(t *testing.T) {
	server := newFakeSMTPServer(t, false, true, false, "LOGIN PLAIN")
	cred := fakeSMTPCredential(t, server.listener.Addr().String())
	require.NoError(t, SendEmailWithCredentialContext(context.Background(), "recipient@example.test", "subject", "body", "<b>body</b>", cred))
}

func TestSendEmailWithCredentialContextDeadlineInterruptsSMTPCommand(t *testing.T) {
	server := newFakeSMTPServer(t, false, false, true, "")
	cred := fakeSMTPCredential(t, server.listener.Addr().String())
	ctx, cancel := context.WithTimeout(context.Background(), 25*time.Millisecond)
	defer cancel()
	err := SendEmailWithCredentialContext(ctx, "recipient@example.test", "subject", "body", "<b>body</b>", cred)
	require.ErrorIs(t, err, context.DeadlineExceeded)
}

func fakeSMTPCredential(t *testing.T, address string) *wire.SMTPCredential {
	t.Helper()
	host, port, err := net.SplitHostPort(address)
	require.NoError(t, err)
	portNumber, err := net.LookupPort("tcp", port)
	require.NoError(t, err)
	return &wire.SMTPCredential{Server: host, Port: portNumber, Login: "user", Password: "password", FromAddress: "sender@example.test", InsecureSkipVerify: true}
}

func fakeSMTPTLSConfig(t *testing.T) *tls.Config {
	t.Helper()
	key, err := rsa.GenerateKey(rand.Reader, 2048)
	require.NoError(t, err)
	template := x509.Certificate{SerialNumber: big.NewInt(1), Subject: pkix.Name{CommonName: "fake smtp"}, NotBefore: time.Now().Add(-time.Hour), NotAfter: time.Now().Add(time.Hour)}
	der, err := x509.CreateCertificate(rand.Reader, &template, &template, &key.PublicKey, key)
	require.NoError(t, err)
	certificate, err := tls.X509KeyPair(pem.EncodeToMemory(&pem.Block{Type: "CERTIFICATE", Bytes: der}), pem.EncodeToMemory(&pem.Block{Type: "RSA PRIVATE KEY", Bytes: x509.MarshalPKCS1PrivateKey(key)}))
	require.NoError(t, err)
	return &tls.Config{Certificates: []tls.Certificate{certificate}}
}

func smtpCommand(reader *bufio.Reader) (string, error) {
	line, err := reader.ReadString('\n')
	return strings.TrimRight(line, "\r\n"), err
}

func smtpReply(writer *bufio.Writer, line string) error { return smtpReplies(writer, line) }

func smtpReplies(writer *bufio.Writer, lines ...string) error {
	for _, line := range lines {
		if _, err := writer.WriteString(line + "\r\n"); err != nil {
			return err
		}
	}
	return writer.Flush()
}

func fmtHex(value []byte) string {
	const hex = "0123456789abcdef"
	result := make([]byte, len(value)*2)
	for i, b := range value {
		result[i*2], result[i*2+1] = hex[b>>4], hex[b&0x0f]
	}
	return string(result)
}