// Package email is the platform's shared transactional-mail transport: a
// small Sender interface with an SMTP implementation (implicit TLS, STARTTLS
// and plain relays; PLAIN/LOGIN auth) and a dev-only log sender. It was
// extracted from go-cart-actor's pkg/order (where the order, ledger and
// newsletter paths use it) so a second consumer — go-auth's forgot-password
// and invite mail — reuses the same transport contract instead of
// duplicating it.
//
// Pure stdlib (net/smtp, crypto/tls, mime, net/mail): no external SDK, so it
// stays usable from the stdlib-only services. The MailerSend API sender is
// intentionally not here — services that need it keep their own client.
package email

import (
	"bytes"
	"context"
	"crypto/tls"
	"fmt"
	"log/slog"
	"mime"
	"mime/quotedprintable"
	"net"
	"net/mail"
	"net/smtp"
	"strings"
	"time"
)

// Message is a rendered mail payload a sender delivers. HTMLBody is optional
// (a text-only message is fine); when both are set the SMTP sender emits a
// multipart/alternative body.
type Message struct {
	From     mail.Address
	To       []mail.Address
	Subject  string
	TextBody string
	HTMLBody string
	// Headers holds optional extra RFC 5322 headers (e.g. List-Unsubscribe).
	// Reserved headers (From/To/Subject/Date/MIME-*) are skipped, and CR/LF
	// injection is rejected.
	Headers map[string]string
}

// Sender delivers an already-rendered mail and exposes its default sender
// address (used when the caller has no From of its own).
type Sender interface {
	Send(ctx context.Context, msg Message) error
	DefaultFrom() mail.Address
}

// LogSender logs each rendered message via slog instead of delivering it —
// the dev default for compose stacks without SMTP credentials, so mail flows
// (forgot-password, invites) can be exercised end-to-end while the content
// shows up in the service logs. It never sends.
type LogSender struct {
	logger *slog.Logger
	from   mail.Address
}

// NewLogSender builds a sender that prints mail to logger.
func NewLogSender(logger *slog.Logger, from mail.Address) *LogSender {
	return &LogSender{logger: logger, from: from}
}

// DefaultFrom returns the configured sender address.
func (s *LogSender) DefaultFrom() mail.Address { return s.from }

// Send logs the message (recipients + subject only — never the body).
func (s *LogSender) Send(_ context.Context, msg Message) error {
	if s.logger == nil {
		return nil
	}
	attrs := []any{
		"from", msg.From.Address,
		"recipients", len(msg.To),
		"subject", msg.Subject,
	}
	if len(msg.To) == 1 {
		attrs = append(attrs, "to", msg.To[0].Address)
	}
	s.logger.Info("email (log sender — not delivered)", attrs...)
	return nil
}

// SMTPConfig configures the SMTP mail transport.
//
// Transport selection: SSL=true uses implicit TLS from the first byte
// (typical port 465); SSL=false connects in plain text and upgrades via
// STARTTLS when the server offers it, unless DisableSTARTTLS is set for
// relays that have no TLS at all (e.g. an internal k8s relay).
type SMTPConfig struct {
	Host     string
	Port     int
	Username string
	Password string
	SSL      bool // implicit TLS connection (typically port 465)
	// DisableSTARTTLS skips the opportunistic STARTTLS upgrade on plain
	// connections so unencrypted internal relays keep working.
	DisableSTARTTLS bool
	DefaultFrom     mail.Address
	Timeout         time.Duration
}

type smtpSender struct {
	host        string
	addr        string
	ssl         bool
	noStartTLS  bool
	username    string
	password    string
	defaultFrom mail.Address
	timeout     time.Duration
}

// loginAuth implements the SASL LOGIN mechanism — many internal relays only
// advertise LOGIN (and Go's net/smtp only ships PLAIN/CRAM-MD5).
type loginAuth struct {
	username, password string
}

func (a *loginAuth) Start(*smtp.ServerInfo) (string, []byte, error) {
	return "LOGIN", nil, nil
}

func (a *loginAuth) Next(fromServer []byte, more bool) ([]byte, error) {
	if !more {
		return nil, nil
	}
	switch strings.ToLower(strings.TrimRight(string(fromServer), ":")) {
	case "username":
		return []byte(a.username), nil
	case "password":
		return []byte(a.password), nil
	}
	return nil, fmt.Errorf("smtp sender: unexpected LOGIN challenge %q", fromServer)
}

// plainAuth implements SASL PLAIN without net/smtp's cleartext refusal.
// PlainAuth refuses to send credentials over an unencrypted connection to a
// non-local host, but internal k8s relays (port 25, STARTTLS disabled) often
// advertise only PLAIN — the operator explicitly opts into cleartext auth for
// those (see SMTPConfig.DisableSTARTTLS).
type plainAuth struct {
	username, password string
}

func (a *plainAuth) Start(*smtp.ServerInfo) (string, []byte, error) {
	resp := []byte("\x00" + a.username + "\x00" + a.password)
	return "PLAIN", resp, nil
}

func (a *plainAuth) Next(fromServer []byte, more bool) ([]byte, error) {
	if more {
		return nil, fmt.Errorf("smtp sender: unexpected server challenge during PLAIN auth")
	}
	return nil, nil
}

// NewSMTP returns an SMTP-backed sender supporting implicit-TLS, STARTTLS
// and plain transports with PLAIN or LOGIN authentication.
func NewSMTP(cfg SMTPConfig) (Sender, error) {
	if strings.TrimSpace(cfg.Host) == "" {
		return nil, fmt.Errorf("smtp sender: missing host")
	}
	if cfg.Port <= 0 {
		return nil, fmt.Errorf("smtp sender: invalid port %d", cfg.Port)
	}
	if cfg.Timeout <= 0 {
		cfg.Timeout = 10 * time.Second
	}
	if strings.TrimSpace(cfg.DefaultFrom.Address) == "" {
		return nil, fmt.Errorf("smtp sender: missing default from address")
	}
	return &smtpSender{
		host:        cfg.Host,
		addr:        net.JoinHostPort(cfg.Host, fmt.Sprintf("%d", cfg.Port)),
		ssl:         cfg.SSL,
		noStartTLS:  cfg.DisableSTARTTLS,
		username:    strings.TrimSpace(cfg.Username),
		password:    cfg.Password,
		defaultFrom: cfg.DefaultFrom,
		timeout:     cfg.Timeout,
	}, nil
}

// DefaultFrom returns the configured sender address.
func (s *smtpSender) DefaultFrom() mail.Address { return s.defaultFrom }

// authenticate negotiates AUTH with the best mechanism both sides support:
// PLAIN on encrypted (or localhost) connections, LOGIN otherwise — net/smtp's
// PlainAuth refuses to send credentials over an unencrypted connection to a
// non-local host, so plain internal relays need LOGIN.
func (s *smtpSender) authenticate(client *smtp.Client) error {
	ok, mechs := client.Extension("AUTH")
	if !ok {
		return fmt.Errorf("smtp sender: server does not support auth")
	}
	advertised := make(map[string]bool)
	for _, mech := range strings.Fields(mechs) {
		advertised[strings.ToUpper(mech)] = true
	}
	_, encrypted := client.TLSConnectionState()
	encrypted = encrypted || s.ssl || s.host == "localhost" || s.host == "127.0.0.1"
	var auth smtp.Auth
	switch {
	case advertised["PLAIN"] && encrypted:
		auth = smtp.PlainAuth("", s.username, s.password, s.host)
	case advertised["LOGIN"]:
		auth = &loginAuth{username: s.username, password: s.password}
	case advertised["PLAIN"]:
		// Unencrypted PLAIN-only relay: stdlib PlainAuth would refuse to send
		// credentials in the clear, so use the cleartext-capable implementation.
		auth = &plainAuth{username: s.username, password: s.password}
	default:
		return fmt.Errorf("smtp sender: server does not support a known auth mechanism (advertised: %s)", mechs)
	}
	if err := client.Auth(auth); err != nil {
		return fmt.Errorf("smtp sender: auth (%T): %w", auth, err)
	}
	return nil
}

// Send delivers msg over SMTP. The envelope From/To are the address parts of
// msg.From/msg.To (display names stay in the headers).
func (s *smtpSender) Send(ctx context.Context, msg Message) error {
	if strings.TrimSpace(msg.From.Address) == "" {
		return fmt.Errorf("smtp sender: missing from address")
	}
	if len(msg.To) == 0 {
		return fmt.Errorf("smtp sender: missing recipients")
	}
	if strings.TrimSpace(msg.Subject) == "" {
		return fmt.Errorf("smtp sender: missing subject")
	}
	body, err := buildMessage(msg)
	if err != nil {
		return err
	}

	var conn net.Conn
	if s.ssl {
		d := &net.Dialer{Timeout: s.timeout}
		conn, err = tls.DialWithDialer(d, "tcp", s.addr, &tls.Config{ServerName: s.host, MinVersion: tls.VersionTLS12})
	} else {
		conn, err = (&net.Dialer{Timeout: s.timeout}).DialContext(ctx, "tcp", s.addr)
	}
	if err != nil {
		return fmt.Errorf("smtp sender: dial %s: %w", s.addr, err)
	}
	defer conn.Close()
	_ = conn.SetDeadline(time.Now().Add(s.timeout))

	client, err := smtp.NewClient(conn, s.host)
	if err != nil {
		return fmt.Errorf("smtp sender: create client: %w", err)
	}
	defer client.Close()

	if !s.ssl && !s.noStartTLS {
		if ok, _ := client.Extension("STARTTLS"); ok {
			if err := client.StartTLS(&tls.Config{ServerName: s.host, MinVersion: tls.VersionTLS12}); err != nil {
				return fmt.Errorf("smtp sender: starttls: %w", err)
			}
		}
	}
	if s.username != "" {
		if err := s.authenticate(client); err != nil {
			return err
		}
	}
	if err := client.Mail(msg.From.Address); err != nil {
		return fmt.Errorf("smtp sender: mail from %s: %w", msg.From.Address, err)
	}
	for _, rcpt := range msg.To {
		if err := client.Rcpt(rcpt.Address); err != nil {
			return fmt.Errorf("smtp sender: rcpt to %s: %w", rcpt.Address, err)
		}
	}
	w, err := client.Data()
	if err != nil {
		return fmt.Errorf("smtp sender: data: %w", err)
	}
	if _, err := w.Write(body); err != nil {
		_ = w.Close()
		return fmt.Errorf("smtp sender: write body: %w", err)
	}
	if err := w.Close(); err != nil {
		return fmt.Errorf("smtp sender: close body: %w", err)
	}
	if err := client.Quit(); err != nil {
		return fmt.Errorf("smtp sender: quit: %w", err)
	}
	return nil
}

// buildMessage renders the RFC 5322 wire message: headers (From/To/Subject
// Q-encoded/Date/custom), then a multipart/alternative body when both text
// and HTML are present, else a single quoted-printable part.
func buildMessage(msg Message) ([]byte, error) {
	if strings.TrimSpace(msg.TextBody) == "" && strings.TrimSpace(msg.HTMLBody) == "" {
		return nil, fmt.Errorf("email: missing body")
	}

	var buf bytes.Buffer
	writeHeader := func(name, value string) {
		buf.WriteString(name)
		buf.WriteString(": ")
		buf.WriteString(value)
		buf.WriteString("\r\n")
	}
	writeHeader("From", msg.From.String())
	toList := make([]string, 0, len(msg.To))
	for _, rcpt := range msg.To {
		toList = append(toList, rcpt.String())
	}
	writeHeader("To", strings.Join(toList, ", "))
	writeHeader("Subject", mime.QEncoding.Encode("utf-8", msg.Subject))
	writeHeader("Date", time.Now().Format(time.RFC1123Z))
	// Custom headers — reserved headers are skipped to avoid clobbering the
	// ones written above; CR/LF injection is rejected.
	for name, value := range msg.Headers {
		switch strings.ToLower(strings.TrimSpace(name)) {
		case "from", "to", "subject", "date", "mime-version", "content-type", "content-transfer-encoding":
			continue
		}
		if strings.ContainsAny(name, "\r\n") || strings.ContainsAny(value, "\r\n") {
			continue
		}
		writeHeader(name, value)
	}
	writeHeader("MIME-Version", "1.0")

	switch {
	case msg.TextBody != "" && msg.HTMLBody != "":
		boundary := fmt.Sprintf("alt-%d", time.Now().UnixNano())
		writeHeader("Content-Type", fmt.Sprintf(`multipart/alternative; boundary="%s"`, boundary))
		buf.WriteString("\r\n")
		writeMIMEPart(&buf, boundary, "text/plain; charset=utf-8", msg.TextBody)
		writeMIMEPart(&buf, boundary, "text/html; charset=utf-8", msg.HTMLBody)
		buf.WriteString("--")
		buf.WriteString(boundary)
		buf.WriteString("--\r\n")
	case msg.HTMLBody != "":
		writeHeader("Content-Type", `text/html; charset=utf-8`)
		writeHeader("Content-Transfer-Encoding", "quoted-printable")
		buf.WriteString("\r\n")
		if err := writeQuotedPrintable(&buf, msg.HTMLBody); err != nil {
			return nil, fmt.Errorf("email: encode html body: %w", err)
		}
	default:
		writeHeader("Content-Type", `text/plain; charset=utf-8`)
		writeHeader("Content-Transfer-Encoding", "quoted-printable")
		buf.WriteString("\r\n")
		if err := writeQuotedPrintable(&buf, msg.TextBody); err != nil {
			return nil, fmt.Errorf("email: encode text body: %w", err)
		}
	}
	return buf.Bytes(), nil
}

func writeMIMEPart(buf *bytes.Buffer, boundary, contentType, body string) {
	buf.WriteString("--")
	buf.WriteString(boundary)
	buf.WriteString("\r\n")
	buf.WriteString("Content-Type: ")
	buf.WriteString(contentType)
	buf.WriteString("\r\n")
	buf.WriteString("Content-Transfer-Encoding: quoted-printable\r\n\r\n")
	_ = writeQuotedPrintable(buf, body)
	buf.WriteString("\r\n")
}

func writeQuotedPrintable(buf *bytes.Buffer, body string) error {
	w := quotedprintable.NewWriter(buf)
	if _, err := w.Write([]byte(strings.ReplaceAll(body, "\n", "\r\n"))); err != nil {
		return err
	}
	return w.Close()
}