RenewCMS/test/smtp_mailer_test.go

package test

import (
	"RenewCMS/internal/infrastructure/config"
	"RenewCMS/internal/infrastructure/mailer"
	"RenewCMS/internal/infrastructure/useCases"
	"io"
	"mime"
	"mime/quotedprintable"
	"net/mail"
	"strings"
	"testing"
	"time"
)

var smtpMailerClock = time.Date(2026, time.March, 1, 12, 0, 0, 0, time.UTC)

func smtpMailerFor(server *fakeSMTPServer, settings config.SmtpSettings) *mailer.MailRepository {
	if settings.Host == "" {
		settings.Host = "127.0.0.1"
	}
	settings.Port = server.port()
	if settings.Sender == "" {
		settings.Sender = "notify@example.com"
	}
	return mailer.NewMailRepository(settings, mailer.WithTLSConfig(server.clientTLS()), mailer.WithClock(func() time.Time { return smtpMailerClock }))
}

func verificationData() useCases.MailValidationData {
	return useCases.MailValidationData{Host: "https://cms.example.com", VerificationCode: "abc123"}
}

func parseDeliveredMail(t *testing.T, raw string) (*mail.Message, string) {
	t.Helper()
	message, err := mail.ReadMessage(strings.NewReader(raw))
	if err != nil {
		t.Fatalf("delivered data is not a valid message: %v\n%s", err, raw)
	}
	decoded, err := io.ReadAll(quotedprintable.NewReader(message.Body))
	if err != nil {
		t.Fatalf("body is not valid quoted-printable: %v", err)
	}
	return message, string(decoded)
}

func TestSMTPMailerDelivery(t *testing.T) {
	t.Run("Delivers a well-formed HTML message to a plain local server", func(t *testing.T) {
		server := newFakeSMTPServer(t, fakeSMTPOptions{})

		err := smtpMailerFor(server, config.SmtpSettings{}).Send("reader@example.org", "verification", verificationData())

		if err != nil {
			t.Fatalf("send failed: %v", err)
		}
		sessions := server.received()
		if len(sessions) != 1 || sessions[0].from != "notify@example.com" || sessions[0].to != "reader@example.org" {
			t.Fatalf("unexpected envelope %+v", sessions)
		}
		message, body := parseDeliveredMail(t, sessions[0].data)
		if got := message.Header.Get("From"); got != `"RenewCMS" <notify@example.com>` {
			t.Errorf("unexpected From %q", got)
		}
		if got := message.Header.Get("To"); got != "<reader@example.org>" {
			t.Errorf("unexpected To %q", got)
		}
		subject, _ := new(mime.WordDecoder).DecodeHeader(message.Header.Get("Subject"))
		if subject != "Verify your RenewCMS account" {
			t.Errorf("unexpected Subject %q", subject)
		}
		if got := message.Header.Get("Content-Type"); got != "text/html; charset=UTF-8" {
			t.Errorf("unexpected Content-Type %q", got)
		}
		if got := message.Header.Get("MIME-Version"); got != "1.0" {
			t.Errorf("unexpected MIME-Version %q", got)
		}
		if !strings.Contains(body, "https://cms.example.com/register/validate?c=abc123") {
			t.Errorf("verification link missing from body %q", body)
		}
	})

	t.Run("Stamps a Date from the clock and a unique Message-ID on the sender's domain", func(t *testing.T) {
		server := newFakeSMTPServer(t, fakeSMTPOptions{})
		repo := smtpMailerFor(server, config.SmtpSettings{})

		_ = repo.Send("a@example.org", "verification", verificationData())
		_ = repo.Send("a@example.org", "verification", verificationData())

		sessions := server.received()
		first, _ := parseDeliveredMail(t, sessions[0].data)
		second, _ := parseDeliveredMail(t, sessions[1].data)
		date, err := first.Header.Date()
		if err != nil || !date.Equal(smtpMailerClock) {
			t.Errorf("expected Date %v, got %v (%v)", smtpMailerClock, date, err)
		}
		id := first.Header.Get("Message-ID")
		if !strings.HasPrefix(id, "<") || !strings.HasSuffix(id, "@example.com>") {
			t.Errorf("unexpected Message-ID %q", id)
		}
		if id == second.Header.Get("Message-ID") {
			t.Error("Message-IDs must be unique")
		}
	})

	t.Run("Encodes a non-ASCII subject and body without corrupting them", func(t *testing.T) {
		server := newFakeSMTPServer(t, fakeSMTPOptions{})
		repo := smtpMailerFor(server, config.SmtpSettings{})

		err := repo.Send("reader@example.org", "verification", verificationData())

		if err != nil {
			t.Fatal(err)
		}
		raw := server.received()[0].data
		headerBlock, _, _ := strings.Cut(raw, "\r\n\r\n")
		for _, r := range headerBlock {
			if r > 127 {
				t.Fatalf("header contains a raw non-ASCII rune %q", r)
			}
		}
	})

	t.Run("Authenticates with PLAIN over STARTTLS", func(t *testing.T) {
		server := newFakeSMTPServer(t, fakeSMTPOptions{startTLS: true, authMechanisms: "PLAIN LOGIN"})
		settings := config.SmtpSettings{Login: "user@example.com", Password: "s3cret"}

		err := smtpMailerFor(server, settings).Send("reader@example.org", "verification", verificationData())

		if err != nil {
			t.Fatalf("send failed: %v", err)
		}
		session := server.received()[0]
		if !session.usedTLS || session.username != "user@example.com" || session.password != "s3cret" {
			t.Errorf("unexpected session %+v", session)
		}
	})

	t.Run("Falls back to LOGIN when PLAIN is not offered", func(t *testing.T) {
		server := newFakeSMTPServer(t, fakeSMTPOptions{startTLS: true, authMechanisms: "LOGIN"})
		settings := config.SmtpSettings{Login: "user@example.com", Password: "s3cret"}

		err := smtpMailerFor(server, settings).Send("reader@example.org", "verification", verificationData())

		if err != nil {
			t.Fatalf("send failed: %v", err)
		}
		session := server.received()[0]
		if session.username != "user@example.com" || session.password != "s3cret" {
			t.Errorf("unexpected credentials %+v", session)
		}
	})

	t.Run("Skips authentication when no login is configured", func(t *testing.T) {
		server := newFakeSMTPServer(t, fakeSMTPOptions{authMechanisms: "PLAIN"})

		err := smtpMailerFor(server, config.SmtpSettings{}).Send("reader@example.org", "verification", verificationData())

		if err != nil {
			t.Fatal(err)
		}
		for _, command := range server.received()[0].commands {
			if strings.HasPrefix(strings.ToUpper(command), "AUTH") {
				t.Errorf("unexpected %q", command)
			}
		}
	})

	for _, mechanisms := range []string{"PLAIN", "LOGIN"} {
		t.Run("Refuses to send "+mechanisms+" credentials in clear text to a non-loopback server", func(t *testing.T) {
			server := newFakeSMTPServer(t, fakeSMTPOptions{authMechanisms: mechanisms, listenAddress: "127.0.0.2:0"})
			settings := config.SmtpSettings{Login: "user@example.com", Password: "s3cret", Host: "127.0.0.2"}

			err := smtpMailerFor(server, settings).Send("reader@example.org", "verification", verificationData())

			if err == nil {
				t.Fatal("expected an error")
			}
			if session := server.received()[0]; session.password != "" || session.data != "" {
				t.Errorf("credentials or data leaked: %+v", session)
			}
		})
	}

	t.Run("Fails when credentials are configured but the server offers no AUTH", func(t *testing.T) {
		server := newFakeSMTPServer(t, fakeSMTPOptions{})
		settings := config.SmtpSettings{Login: "user@example.com", Password: "s3cret"}

		err := smtpMailerFor(server, settings).Send("reader@example.org", "verification", verificationData())

		if err == nil {
			t.Fatal("expected an error")
		}
		if len(server.received()[0].data) != 0 {
			t.Error("no message may be delivered")
		}
	})

	t.Run("Fails the STARTTLS handshake against an untrusted certificate", func(t *testing.T) {
		server := newFakeSMTPServer(t, fakeSMTPOptions{startTLS: true})
		repo := mailer.NewMailRepository(config.SmtpSettings{Host: "127.0.0.1", Port: server.port(), Sender: "notify@example.com"})

		err := repo.Send("reader@example.org", "verification", verificationData())

		if err == nil {
			t.Fatal("expected a certificate error")
		}
		if len(server.received()[0].data) != 0 {
			t.Error("no message may be delivered")
		}
	})

	t.Run("Uses implicit TLS on port 465", func(t *testing.T) {
		server := newFakeSMTPServer(t, fakeSMTPOptions{implicitTLS: true, listenAddress: "127.0.0.1:465"})
		repo := mailer.NewMailRepository(config.SmtpSettings{Host: "127.0.0.1", Port: 465, Sender: "notify@example.com"}, mailer.WithTLSConfig(server.clientTLS()))

		err := repo.Send("reader@example.org", "verification", verificationData())

		if err != nil {
			t.Fatalf("send failed: %v", err)
		}
		if !server.received()[0].usedTLS {
			t.Error("expected a TLS session")
		}
	})

	t.Run("Surfaces a rejected recipient", func(t *testing.T) {
		server := newFakeSMTPServer(t, fakeSMTPOptions{rejectRcpt: true})

		err := smtpMailerFor(server, config.SmtpSettings{}).Send("reader@example.org", "verification", verificationData())

		if err == nil {
			t.Fatal("expected an error")
		}
	})

	t.Run("Surfaces a rejected DATA command", func(t *testing.T) {
		server := newFakeSMTPServer(t, fakeSMTPOptions{rejectData: true})

		err := smtpMailerFor(server, config.SmtpSettings{}).Send("reader@example.org", "verification", verificationData())

		if err == nil {
			t.Fatal("expected an error")
		}
	})

	t.Run("Surfaces an unreachable server", func(t *testing.T) {
		server := newFakeSMTPServer(t, fakeSMTPOptions{})
		repo := smtpMailerFor(server, config.SmtpSettings{})
		_ = server.listener.Close()

		if err := repo.Send("reader@example.org", "verification", verificationData()); err == nil {
			t.Fatal("expected an error")
		}
	})
}

func TestSMTPMailerRejectsUnsafeInput(t *testing.T) {
	cases := map[string]struct {
		sender   string
		receiver string
		template string
	}{
		"receiver with an injected header": {"notify@example.com", "a@example.org\r\nBcc: evil@example.net", "verification"},
		"receiver that is not an address":  {"notify@example.com", "not-an-address", "verification"},
		"empty receiver":                   {"notify@example.com", "", "verification"},
		"sender that is not an address":    {"nope", "a@example.org", "verification"},
		"unknown template":                 {"notify@example.com", "a@example.org", "does-not-exist"},
	}

	for name, tc := range cases {
		t.Run("Rejects a "+name+" before opening a connection", func(t *testing.T) {
			server := newFakeSMTPServer(t, fakeSMTPOptions{})
			repo := smtpMailerFor(server, config.SmtpSettings{Sender: tc.sender})

			err := repo.Send(tc.receiver, tc.template, verificationData())

			if err == nil {
				t.Fatal("expected an error")
			}
			if len(server.received()) != 0 {
				t.Errorf("no connection may be made, got %d", len(server.received()))
			}
		})
	}
}