mailgoserver/internal/smtpserver/mailbox_alias_test.go

package smtpserver

import (
	"net/smtp"
	"strings"
	"testing"

	"mailgoserver/internal/db"
)

// createAlias mirrors createMailboxFor in webui's multitenant tests, for aliases.
func createAlias(t *testing.T, backend *Backend, mailboxID, domainID int64, email string, canSendAs bool) {
	t.Helper()
	if _, err := backend.DB.CreateAlias(mailboxID, email, domainID, canSendAs); err != nil {
		t.Fatal(err)
	}
}

func TestLocalDeliveryToAliasLandsInOwningMailbox(t *testing.T) {
	backend, mailboxID := newTestBackendWithMailbox(t)
	createAlias(t, backend, mailboxID, 1, "alias@example.com", false)
	addr := startTestServer(t, backend)

	c, err := smtp.Dial(addr)
	if err != nil {
		t.Fatal(err)
	}
	defer c.Close()

	if err := c.Auth(smtp.PlainAuth("", "test@example.com", "testpass123", "127.0.0.1")); err != nil {
		t.Fatalf("auth: %v", err)
	}
	if err := c.Mail("test@example.com"); err != nil {
		t.Fatalf("MAIL FROM: %v", err)
	}
	if err := c.Rcpt("alias@example.com"); err != nil {
		t.Fatalf("expected RCPT to a receive-only alias to succeed, got: %v", err)
	}
	w, err := c.Data()
	if err != nil {
		t.Fatal(err)
	}
	w.Write([]byte("Subject: via alias\r\n\r\nhi"))
	if err := w.Close(); err != nil {
		t.Fatalf("expected DATA to succeed delivering to an alias, got: %v", err)
	}

	mbox, err := backend.DB.GetMailboxByID(mailboxID)
	if err != nil {
		t.Fatal(err)
	}
	if mbox.UsedBytes == 0 {
		t.Fatal("expected mail delivered to an alias to land in the owning mailbox")
	}
}

func TestMailboxAppPasswordCanSendAsPrimaryButNotArbitraryAddress(t *testing.T) {
	backend, mailboxID := newTestBackendWithMailbox(t)
	appPassword := "a-long-enough-app-password-123456"
	hash, err := db.HashPassword(appPassword)
	if err != nil {
		t.Fatal(err)
	}
	if _, err := backend.DB.CreateAppPassword(mailboxID, "test", hash, nil); err != nil {
		t.Fatal(err)
	}
	addr := startTestServer(t, backend)

	c, err := smtp.Dial(addr)
	if err != nil {
		t.Fatal(err)
	}
	defer c.Close()

	if err := c.Auth(smtp.PlainAuth("", "inbox@example.com", appPassword, "127.0.0.1")); err != nil {
		t.Fatalf("expected app-password auth to succeed, got: %v", err)
	}
	if err := c.Mail("inbox@example.com"); err != nil {
		t.Fatalf("expected MAIL FROM as own primary address to succeed, got: %v", err)
	}

	c2, err := smtp.Dial(addr)
	if err != nil {
		t.Fatal(err)
	}
	defer c2.Close()
	if err := c2.Auth(smtp.PlainAuth("", "inbox@example.com", appPassword, "127.0.0.1")); err != nil {
		t.Fatalf("auth: %v", err)
	}
	err = c2.Mail("someoneelse@example.com")
	if err == nil {
		t.Fatal("expected MAIL FROM as an address with no alias relationship to be rejected")
	}
	if !strings.Contains(err.Error(), "550") {
		t.Fatalf("expected 550, got: %v", err)
	}
}

func TestMailboxAppPasswordCanSendAsEnabledAlias(t *testing.T) {
	backend, mailboxID := newTestBackendWithMailbox(t)
	createAlias(t, backend, mailboxID, 1, "sendalias@example.com", true)
	appPassword := "another-long-enough-app-password-9"
	hash, err := db.HashPassword(appPassword)
	if err != nil {
		t.Fatal(err)
	}
	if _, err := backend.DB.CreateAppPassword(mailboxID, "test", hash, nil); err != nil {
		t.Fatal(err)
	}
	addr := startTestServer(t, backend)

	c, err := smtp.Dial(addr)
	if err != nil {
		t.Fatal(err)
	}
	defer c.Close()

	if err := c.Auth(smtp.PlainAuth("", "inbox@example.com", appPassword, "127.0.0.1")); err != nil {
		t.Fatalf("auth: %v", err)
	}
	if err := c.Mail("sendalias@example.com"); err != nil {
		t.Fatalf("expected MAIL FROM as a send-as-enabled alias to succeed, got: %v", err)
	}
}

func TestMailboxAppPasswordCannotSendAsReceiveOnlyAlias(t *testing.T) {
	backend, mailboxID := newTestBackendWithMailbox(t)
	createAlias(t, backend, mailboxID, 1, "receivealias@example.com", false)
	appPassword := "yet-another-long-enough-app-pass1"
	hash, err := db.HashPassword(appPassword)
	if err != nil {
		t.Fatal(err)
	}
	if _, err := backend.DB.CreateAppPassword(mailboxID, "test", hash, nil); err != nil {
		t.Fatal(err)
	}
	addr := startTestServer(t, backend)

	c, err := smtp.Dial(addr)
	if err != nil {
		t.Fatal(err)
	}
	defer c.Close()

	if err := c.Auth(smtp.PlainAuth("", "inbox@example.com", appPassword, "127.0.0.1")); err != nil {
		t.Fatalf("auth: %v", err)
	}
	err = c.Mail("receivealias@example.com")
	if err == nil {
		t.Fatal("expected MAIL FROM as a receive-only alias to be rejected")
	}
	if !strings.Contains(err.Error(), "550") {
		t.Fatalf("expected 550, got: %v", err)
	}
}