package smtp2shoutrrr

import (
	"crypto/sha256"
	"crypto/subtle"
	"errors"
	"fmt"
	"io"
	"log/slog"
	"net/mail"
	"net/url"
	"slices"
	"strings"
	"sync"

	"github.com/containrrr/shoutrrr"
	"github.com/emersion/go-sasl"
	"github.com/emersion/go-smtp"
)

// errNoUsableTargets marks a configuration fault rather than a delivery one:
// the recipient matched, but there is nothing to notify. No retry can add
// targets to a configuration.
var errNoUsableTargets = errors.New("recipient has no usable targets")

var (
	// errUnreadableMessage rejects a message for good. Both causes — a
	// message that is not parseable as mail, and a Content-Type this server
	// cannot make sense of — fail identically on every redelivery.
	errUnreadableMessage = &smtp.SMTPError{
		Code:         550,
		EnhancedCode: smtp.EnhancedCode{5, 6, 0},
		Message:      "Message could not be parsed",
	}

	// errMisconfiguredRecipient is permanent for the same reason: the server
	// has nowhere to send this recipient's mail until its configuration
	// changes, which no amount of redelivery brings about.
	errMisconfiguredRecipient = &smtp.SMTPError{
		Code:         550,
		EnhancedCode: smtp.EnhancedCode{5, 3, 5},
		Message:      "Recipient has no notification targets configured",
	}

	// errForwardingFailed asks the sender to try again later. The 250 this
	// replaces told the client a message had been delivered when no target
	// had received it, so the client dropped a notification nobody ever saw.
	errForwardingFailed = &smtp.SMTPError{
		Code:         451,
		EnhancedCode: smtp.EnhancedCode{4, 3, 0},
		Message:      "Failed to forward message to notification targets",
	}
)

type Backend struct {
	config *Config
}

func (bkd *Backend) sendNotifications(recipient ConfigRecipient, email *ReceivedEmail) error {
	// Get all target URLs (handles merging and caching)
	targetURLs := recipient.GetTargetURLs()

	if len(targetURLs) == 0 {
		return fmt.Errorf("%w: %s", errNoUsableTargets,
			strings.Join(recipient.Addresses, ","))
	}

	// Prepare email body once (reuse for all targets)
	body, err := email.FormattedBody(recipient.Format)
	if err != nil {
		slog.Error("Error getting email body", slog.String("err", err.Error()))
		return fmt.Errorf("failed to get email body: %w", err)
	}

	slog.Debug("Prepared email body",
		slog.Int("body_length", len(body)),
		slog.String("format", string(recipient.Format)),
		slog.String("subject", email.Msg.Header.Get("Subject")),
		slog.String("content_type", email.Msg.Header.Get("Content-Type")))

	urlParams := url.Values{
		"title": {email.Msg.Header.Get("Subject")},
	}

	// Send to all targets, collect errors
	var errs []error
	for i, targetURL := range targetURLs {
		// Clone URL to avoid mutation
		destinationURL := *targetURL

		// Merge new params with existing query params
		existingParams := destinationURL.Query()
		for key, values := range urlParams {
			for _, value := range values {
				existingParams.Add(key, value)
			}
		}
		destinationURL.RawQuery = existingParams.Encode()

		if err := shoutrrr.Send(destinationURL.String(), body); err != nil {
			slog.Error("Error sending message to target",
				slog.Int("target_index", i),
				slog.String("target", targetURL.Host),
				slog.String("err", err.Error()))
			errs = append(errs, fmt.Errorf("target %d: %w", i, err))
			// Continue to next target even if this one fails
		} else {
			slog.Info("Successfully sent notification",
				slog.String("target", targetURL.Host),
				slog.String("recipient", strings.Join(recipient.Addresses, ",")))
		}
	}

	// Only a total failure is reported to the sender. A retry redelivers to
	// every target, so pushing back on a partial one would duplicate the
	// notification on the targets that already accepted it.
	if len(errs) == len(targetURLs) {
		return fmt.Errorf("no target accepted the notification: %w", errors.Join(errs...))
	}

	if len(errs) > 0 {
		slog.Warn("notification reached only some targets",
			slog.Int("failed", len(errs)),
			slog.Int("targets", len(targetURLs)),
			slog.String("recipient", strings.Join(recipient.Addresses, ",")))
	}

	return nil
}

func (bkd *Backend) NewSession(c *smtp.Conn) (smtp.Session, error) {
	return &Session{
		forwarderFunc: bkd.forwardEmail,
		config:        bkd.config,
	}, nil
}

func (bkd *Backend) forwardEmail(email *ReceivedEmail) error {
	slog.Info("forwading message", slog.String("to", strings.Join(email.Recipients, ",")))

	// Try to match configured recipients first
	matched := false
	for _, r := range bkd.config.Recipients {
		for _, a := range email.Recipients {
			if slices.Contains(r.Addresses, a) {
				if err := bkd.sendNotifications(r, email); err != nil {
					return err
				}
				matched = true
				break
			}
		}
		if matched {
			break
		}
	}

	// If no recipient matched and catch-all is configured, use it
	if !matched && bkd.config.CatchAll != nil {
		slog.Info("using catch-all recipient for unmatched email")
		if err := bkd.sendNotifications(*bkd.config.CatchAll, email); err != nil {
			return err
		}
	}

	return nil
}

type Session struct {
	// mu guards the transaction state below. go-smtp runs Data on its own
	// goroutine for a BDAT transfer and keeps serving commands on the
	// connection goroutine meanwhile, so an RSET can land in the middle of
	// one and reset the session from under it.
	mu sync.Mutex

	addresses []string

	// authenticated gates the mail transaction. go-smtp advertises AUTH but
	// never enforces it — that is the backend's job — so without this the
	// server relays for anyone who can open a connection.
	authenticated bool

	config *Config

	// forwarderFunc takes the message by pointer: the body is read from a
	// single-use stream and cached on it, so a copy would forward an empty
	// notification to every recipient after the first.
	forwarderFunc func(*ReceivedEmail) error
}

func (s *Session) isAuthenticated() bool {
	s.mu.Lock()
	defer s.mu.Unlock()

	return s.authenticated
}

// recipients copies the transaction's recipients so a concurrent Reset cannot
// empty the slice a forward in progress is still reading.
func (s *Session) recipients() []string {
	s.mu.Lock()
	defer s.mu.Unlock()

	return slices.Clone(s.addresses)
}

func (s *Session) AuthMechanisms() []string {
	return []string{sasl.Plain}
}

func (s *Session) Auth(mech string) (sasl.Server, error) {
	if mech != sasl.Plain {
		return nil, smtp.ErrAuthUnknownMechanism
	}

	return sasl.NewPlainServer(func(identity, username, password string) error {
		// PLAIN carries an authorization identity distinct from the
		// authenticating one (RFC 4616). There is nobody to act on behalf of
		// here, so only the empty and self-referential forms are accepted.
		if identity != "" && identity != username {
			return smtp.ErrAuthFailed
		}

		// Both comparisons run before either is acted on: short-circuiting on
		// the username would time-distinguish a wrong username from a right
		// one with a wrong password, handing an attacker the username.
		usernameMatches := credentialMatches(username, s.config.Username)
		passwordMatches := credentialMatches(password, s.config.Password)

		if !usernameMatches || !passwordMatches {
			// Logged without the attempted values: a misconfigured client
			// sends its password in the username field often enough that
			// recording them turns the log into a credential store.
			slog.Warn("rejected authentication attempt")
			return smtp.ErrAuthFailed
		}

		s.mu.Lock()
		s.authenticated = true
		s.mu.Unlock()

		return nil
	}), nil
}

// credentialMatches compares a supplied credential against the configured one
// in time independent of how much of it is right. Both sides are hashed first
// because subtle.ConstantTimeCompare returns early when the lengths differ,
// which would still leak the length of the configured credential.
func credentialMatches(supplied, configured string) bool {
	suppliedSum := sha256.Sum256([]byte(supplied))
	configuredSum := sha256.Sum256([]byte(configured))

	return subtle.ConstantTimeCompare(suppliedSum[:], configuredSum[:]) == 1
}

func (s *Session) Mail(from string, opts *smtp.MailOptions) error {
	if !s.isAuthenticated() {
		return smtp.ErrAuthRequired
	}

	slog.Debug("Mail from", slog.String("from", from))

	return nil
}

func (s *Session) Rcpt(to string, opts *smtp.RcptOptions) error {
	if !s.isAuthenticated() {
		return smtp.ErrAuthRequired
	}

	slog.Debug("Rcpt to", slog.String("to", to))

	s.mu.Lock()
	defer s.mu.Unlock()
	s.addresses = append(s.addresses, to)

	return nil
}

func (s *Session) Data(r io.Reader) error {
	if !s.isAuthenticated() {
		return smtp.ErrAuthRequired
	}

	// Taken before the message is read: an RSET arriving mid-transfer aborts
	// the read, and this is the transaction the recipients belong to either
	// way.
	recipients := s.recipients()

	msg, err := mail.ReadMessage(r)
	if err != nil {
		slog.Error("Error reading data", slog.String("err", err.Error()))
		return errUnreadableMessage
	}

	slog.Info("Received email", slog.String("destination", strings.Join(recipients, ",")))

	if err := s.forwarderFunc(&ReceivedEmail{
		Recipients: recipients,
		Msg:        msg,
	}); err != nil {
		slog.Error("Error forwarding email", slog.String("err", err.Error()))

		switch {
		case errors.Is(err, errMalformedMessage):
			return errUnreadableMessage
		case errors.Is(err, errNoUsableTargets):
			return errMisconfiguredRecipient
		default:
			return errForwardingFailed
		}
	}

	return nil
}

// Reset ends the current mail transaction. go-smtp calls it after every
// message, so the recipients have to go: leaving them would forward the next
// message on the connection to the previous one's targets as well.
// Authentication deliberately survives, as RFC 5321 scopes RSET to the
// transaction.
func (s *Session) Reset() {
	s.mu.Lock()
	defer s.mu.Unlock()
	s.addresses = nil
}

func (s *Session) Logout() error {
	return nil
}