sgmail-skill/internal/service/service.go

package service

import (
	"context"
	"crypto/sha256"
	"database/sql"
	"encoding/hex"
	"encoding/json"
	"errors"
	"fmt"
	"os"
	"path/filepath"
	"regexp"
	"sort"
	"strings"
	"time"

	"internal-mail-skill/internal/db"
	"internal-mail-skill/internal/model"
	"internal-mail-skill/internal/parser"
	mailsmtp "internal-mail-skill/internal/smtp"
)

type POP3Source interface {
	Fetch(ctx context.Context) ([]model.FetchedMessage, error)
}

type MailSender interface {
	Send(ctx context.Context, req mailsmtp.SendRequest) (mailsmtp.SendResult, error)
}

type Service struct {
	store         *db.Store
	pop3          POP3Source
	mailer        MailSender
	accountID     string
	rawDir        string
	attachmentDir string
	fromAddress   string
	fromName      string
}

type Options struct {
	RawDir        string
	AttachmentDir string
	FromAddress   string
	FromName      string
}

func New(store *db.Store, pop3 POP3Source, mailer MailSender, accountID string) *Service {
	return NewWithOptions(store, pop3, mailer, accountID, Options{})
}

func NewWithOptions(store *db.Store, pop3 POP3Source, mailer MailSender, accountID string, opts Options) *Service {
	if accountID == "" {
		accountID = "default"
	}
	return &Service{
		store:         store,
		pop3:          pop3,
		mailer:        mailer,
		accountID:     accountID,
		rawDir:        opts.RawDir,
		attachmentDir: opts.AttachmentDir,
		fromAddress:   opts.FromAddress,
		fromName:      opts.FromName,
	}
}

type SaveEmailInput struct {
	POP3UID string
	Raw     []byte
	Parsed  model.ParsedEmail
}

type SearchFilters struct {
	Q             string
	From          string
	To            string
	After         string
	Before        string
	HasAttachment *bool
	Read          *bool
	Processed     *bool
	Archived      *bool
	Replied       *bool
	Limit         int
	Offset        int
}

type MarkInput struct {
	Read      *bool `json:"read"`
	Processed *bool `json:"processed"`
	Archived  *bool `json:"archived"`
	Deleted   *bool `json:"deleted"`
	Replied   *bool `json:"replied"`
}

type DraftInput struct {
	To             []string `json:"to"`
	Cc             []string `json:"cc"`
	Bcc            []string `json:"bcc"`
	Subject        string   `json:"subject"`
	Body           string   `json:"body"`
	ReplyToEmailID *int64   `json:"reply_to_email_id,omitempty"`
}

type SyncResult struct {
	Total   int         `json:"total"`
	Stored  int         `json:"stored"`
	Skipped int         `json:"skipped"`
	Errors  []SyncError `json:"errors"`
}

type SyncError struct {
	UID      string `json:"uid,omitempty"`
	ServerID int    `json:"server_id,omitempty"`
	Error    string `json:"error"`
}

type SendOutcome struct {
	SentMessage model.SentMessage `json:"sent_message"`
	Draft       *model.Draft      `json:"draft,omitempty"`
}

func (s *Service) Health(ctx context.Context) string {
	if err := s.store.Ping(ctx); err != nil {
		return "down"
	}
	return "ok"
}

func (s *Service) Sync(ctx context.Context) (SyncResult, error) {
	if s.pop3 == nil {
		return SyncResult{}, fmt.Errorf("POP3 client is not configured")
	}
	messages, err := s.pop3.Fetch(ctx)
	if err != nil {
		return SyncResult{}, err
	}
	result := SyncResult{Total: len(messages)}
	for _, fetched := range messages {
		if fetched.Error != "" {
			result.Errors = append(result.Errors, SyncError{UID: fetched.UID, ServerID: fetched.ServerID, Error: fetched.Error})
			continue
		}
		exists, err := s.hasPOP3UID(ctx, fetched.UID)
		if err != nil {
			result.Errors = append(result.Errors, SyncError{UID: fetched.UID, ServerID: fetched.ServerID, Error: err.Error()})
			continue
		}
		if exists {
			result.Skipped++
			continue
		}
		parsed, err := parser.Parse(fetched.Raw)
		if err != nil {
			result.Errors = append(result.Errors, SyncError{UID: fetched.UID, ServerID: fetched.ServerID, Error: err.Error()})
			continue
		}
		if _, err := s.SaveParsedEmail(ctx, SaveEmailInput{POP3UID: fetched.UID, Raw: fetched.Raw, Parsed: parsed}); err != nil {
			result.Errors = append(result.Errors, SyncError{UID: fetched.UID, ServerID: fetched.ServerID, Error: err.Error()})
			continue
		}
		result.Stored++
	}
	return result, nil
}

func (s *Service) SaveParsedEmail(ctx context.Context, input SaveEmailInput) (int64, error) {
	if input.POP3UID == "" {
		input.POP3UID = "local-" + hashBytes([]byte(input.Parsed.MessageIDHeader+input.Parsed.Subject+time.Now().String()))
	}
	if id, ok, err := s.findByPOP3UID(ctx, input.POP3UID); err != nil {
		return 0, err
	} else if ok {
		return id, nil
	}

	now := time.Now().UTC()
	rawPath := ""
	if len(input.Raw) > 0 && s.rawDir != "" {
		rawPath = filepath.Join(s.rawDir, s.accountID+"_"+hashBytes([]byte(input.POP3UID))+".eml")
	}

	toJSON, err := marshalJSON(input.Parsed.To)
	if err != nil {
		return 0, err
	}
	ccJSON, err := marshalJSON(input.Parsed.Cc)
	if err != nil {
		return 0, err
	}
	sentAt := timePtrString(input.Parsed.SentAt)

	tx, err := s.store.DB.BeginTx(ctx, nil)
	if err != nil {
		return 0, err
	}
	var writtenFiles []string
	committed := false
	defer func() {
		if !committed {
			_ = tx.Rollback()
			for _, path := range writtenFiles {
				_ = os.Remove(path)
			}
		}
	}()

	res, err := tx.ExecContext(ctx, `
		INSERT INTO mail_messages (
			account_id, pop3_uid, message_id_header, in_reply_to, references_header,
			subject, sender_name, sender_email, to_json, cc_json, date_header,
			sent_at, received_at, body_text, body_html, raw_eml_path, has_attachment,
			created_at, updated_at
		) VALUES (?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?)`,
		s.accountID,
		input.POP3UID,
		input.Parsed.MessageIDHeader,
		input.Parsed.InReplyTo,
		input.Parsed.References,
		input.Parsed.Subject,
		input.Parsed.SenderName,
		input.Parsed.SenderEmail,
		toJSON,
		ccJSON,
		input.Parsed.DateHeader,
		sentAt,
		formatTime(now),
		input.Parsed.BodyText,
		input.Parsed.BodyHTML,
		rawPath,
		boolInt(len(input.Parsed.Attachments) > 0),
		formatTime(now),
		formatTime(now),
	)
	if err != nil {
		return 0, fmt.Errorf("insert mail message: %w", err)
	}
	id, err := res.LastInsertId()
	if err != nil {
		return 0, err
	}
	if rawPath != "" {
		if err := os.MkdirAll(s.rawDir, 0750); err != nil {
			return 0, fmt.Errorf("create raw mail dir: %w", err)
		}
		if err := os.WriteFile(rawPath, input.Raw, 0600); err != nil {
			return 0, fmt.Errorf("write raw eml: %w", err)
		}
		writtenFiles = append(writtenFiles, rawPath)
	}
	if err := s.saveAttachments(ctx, tx, id, input.Parsed.Attachments, now, &writtenFiles); err != nil {
		return 0, err
	}
	if err := tx.Commit(); err != nil {
		return 0, err
	}
	committed = true
	return id, nil
}

func (s *Service) SearchEmails(ctx context.Context, filters SearchFilters) ([]model.EmailSummary, error) {
	where := []string{"account_id = ?"}
	args := []any{s.accountID}
	if filters.Q != "" {
		where = append(where, "(subject LIKE ? OR sender_email LIKE ? OR body_text LIKE ? OR body_html LIKE ?)")
		like := "%" + filters.Q + "%"
		args = append(args, like, like, like, like)
	}
	if filters.From != "" {
		where = append(where, "(sender_email LIKE ? OR sender_name LIKE ?)")
		like := "%" + filters.From + "%"
		args = append(args, like, like)
	}
	if filters.To != "" {
		where = append(where, "to_json LIKE ?")
		args = append(args, "%"+filters.To+"%")
	}
	if after := normalizeDateFilter(filters.After, false); after != "" {
		where = append(where, "sent_at >= ?")
		args = append(args, after)
	}
	if before := normalizeDateFilter(filters.Before, true); before != "" {
		where = append(where, "sent_at <= ?")
		args = append(args, before)
	}
	addBoolFilter := func(name string, val *bool) {
		if val != nil {
			where = append(where, name+" = ?")
			args = append(args, boolInt(*val))
		}
	}
	addBoolFilter("has_attachment", filters.HasAttachment)
	addBoolFilter("local_read", filters.Read)
	addBoolFilter("local_processed", filters.Processed)
	addBoolFilter("local_archived", filters.Archived)
	addBoolFilter("local_replied", filters.Replied)
	limit := filters.Limit
	if limit <= 0 || limit > 100 {
		limit = 50
	}
	offset := filters.Offset
	if offset < 0 {
		offset = 0
	}
	args = append(args, limit, offset)

	query := `
		SELECT id, subject, sender_name, sender_email, to_json, cc_json, date_header,
		       sent_at, received_at, body_text, has_attachment, local_read,
		       local_processed, local_archived, local_deleted, local_replied,
		       (SELECT COUNT(*) FROM attachments WHERE message_id = mail_messages.id)
		FROM mail_messages
		WHERE ` + strings.Join(where, " AND ") + `
		ORDER BY COALESCE(sent_at, received_at) DESC, id DESC
		LIMIT ? OFFSET ?`
	rows, err := s.store.DB.QueryContext(ctx, query, args...)
	if err != nil {
		return nil, err
	}
	defer rows.Close()

	var out []model.EmailSummary
	for rows.Next() {
		summary, err := scanSummary(rows)
		if err != nil {
			return nil, err
		}
		out = append(out, summary)
	}
	if err := rows.Err(); err != nil {
		return nil, err
	}
	for i := range out {
		out[i].Labels = s.labelsForMessage(ctx, out[i].ID)
	}
	return out, nil
}

func (s *Service) GetEmail(ctx context.Context, id int64) (model.EmailDetail, error) {
	row := s.store.DB.QueryRowContext(ctx, `
		SELECT id, message_id_header, in_reply_to, references_header, subject,
		       sender_name, sender_email, to_json, cc_json, date_header, sent_at,
		       received_at, body_text, body_html, local_read, local_processed,
		       local_archived, local_deleted, local_replied
		FROM mail_messages WHERE account_id = ? AND id = ?`, s.accountID, id)
	detail, err := scanDetail(row)
	if err != nil {
		if errors.Is(err, sql.ErrNoRows) {
			return model.EmailDetail{}, ErrNotFound
		}
		return model.EmailDetail{}, err
	}
	detail.Attachments = s.attachmentsForMessage(ctx, id)
	detail.Labels = s.labelsForMessage(ctx, id)
	return detail, nil
}

func (s *Service) GetThread(ctx context.Context, id int64) ([]model.EmailSummary, error) {
	candidates, err := s.threadCandidates(ctx)
	if err != nil {
		return nil, err
	}
	if _, ok := candidates[id]; !ok {
		return nil, ErrNotFound
	}
	selected := map[int64]bool{id: true}
	changed := true
	for changed {
		changed = false
		for candidateID, candidate := range candidates {
			if selected[candidateID] {
				continue
			}
			for selectedID := range selected {
				if linked(candidate, candidates[selectedID]) {
					selected[candidateID] = true
					changed = true
					break
				}
			}
		}
	}
	out := make([]model.EmailSummary, 0, len(selected))
	for selectedID := range selected {
		summary := candidates[selectedID].summary
		summary.Labels = s.labelsForMessage(ctx, selectedID)
		out = append(out, summary)
	}
	sort.Slice(out, func(i, j int) bool {
		ti := summaryTime(out[i])
		tj := summaryTime(out[j])
		if ti.Equal(tj) {
			return out[i].ID < out[j].ID
		}
		return ti.Before(tj)
	})
	return out, nil
}

func (s *Service) MarkEmail(ctx context.Context, id int64, input MarkInput) error {
	sets := []string{}
	args := []any{}
	add := func(field string, value *bool) {
		if value != nil {
			sets = append(sets, field+" = ?")
			args = append(args, boolInt(*value))
		}
	}
	add("local_read", input.Read)
	add("local_processed", input.Processed)
	add("local_archived", input.Archived)
	add("local_deleted", input.Deleted)
	add("local_replied", input.Replied)
	if len(sets) == 0 {
		return nil
	}
	sets = append(sets, "updated_at = ?")
	args = append(args, formatTime(time.Now().UTC()), s.accountID, id)
	res, err := s.store.DB.ExecContext(ctx, "UPDATE mail_messages SET "+strings.Join(sets, ", ")+" WHERE account_id = ? AND id = ?", args...)
	if err != nil {
		return err
	}
	return requireAffected(res)
}

func (s *Service) CreateLabel(ctx context.Context, name, color string) (model.Label, error) {
	name = strings.TrimSpace(name)
	if name == "" {
		return model.Label{}, fmt.Errorf("label name is required")
	}
	now := formatTime(time.Now().UTC())
	_, err := s.store.DB.ExecContext(ctx, `
		INSERT INTO labels(name, color, created_at, updated_at)
		VALUES (?, ?, ?, ?)
		ON CONFLICT(name) DO UPDATE SET color = excluded.color, updated_at = excluded.updated_at`,
		name, color, now, now)
	if err != nil {
		return model.Label{}, err
	}
	var label model.Label
	if err := s.store.DB.QueryRowContext(ctx, "SELECT id, name, color FROM labels WHERE name = ?", name).Scan(&label.ID, &label.Name, &label.Color); err != nil {
		return model.Label{}, err
	}
	return label, nil
}

func (s *Service) ApplyLabels(ctx context.Context, emailIDs, labelIDs []int64, op string) error {
	if len(emailIDs) == 0 || len(labelIDs) == 0 {
		return fmt.Errorf("email_ids and label_ids are required")
	}
	op = strings.ToLower(strings.TrimSpace(op))
	if op != "add" && op != "remove" {
		return fmt.Errorf("op must be add or remove")
	}
	now := formatTime(time.Now().UTC())
	for _, emailID := range emailIDs {
		for _, labelID := range labelIDs {
			if op == "add" {
				if _, err := s.store.DB.ExecContext(ctx, `
					INSERT OR IGNORE INTO message_labels(message_id, label_id, created_at)
					VALUES (?, ?, ?)`, emailID, labelID, now); err != nil {
					return err
				}
			} else {
				if _, err := s.store.DB.ExecContext(ctx, `DELETE FROM message_labels WHERE message_id = ? AND label_id = ?`, emailID, labelID); err != nil {
					return err
				}
			}
		}
	}
	return nil
}

func (s *Service) CreateDraft(ctx context.Context, input DraftInput) (model.Draft, error) {
	now := formatTime(time.Now().UTC())
	toJSON, _ := marshalJSON(input.To)
	ccJSON, _ := marshalJSON(input.Cc)
	bccJSON, _ := marshalJSON(input.Bcc)
	res, err := s.store.DB.ExecContext(ctx, `
		INSERT INTO drafts(to_json, cc_json, bcc_json, subject, body, reply_to_email_id, status, created_at, updated_at)
		VALUES (?, ?, ?, ?, ?, ?, 'draft', ?, ?)`,
		toJSON, ccJSON, bccJSON, input.Subject, input.Body, input.ReplyToEmailID, now, now)
	if err != nil {
		return model.Draft{}, err
	}
	id, err := res.LastInsertId()
	if err != nil {
		return model.Draft{}, err
	}
	return s.GetDraft(ctx, id)
}

func (s *Service) ListDrafts(ctx context.Context) ([]model.Draft, error) {
	rows, err := s.store.DB.QueryContext(ctx, `
		SELECT id, to_json, cc_json, bcc_json, subject, body, reply_to_email_id,
		       status, last_error, sent_message_id, created_at, updated_at
		FROM drafts ORDER BY updated_at DESC, id DESC`)
	if err != nil {
		return nil, err
	}
	defer rows.Close()
	var drafts []model.Draft
	for rows.Next() {
		draft, err := scanDraft(rows)
		if err != nil {
			return nil, err
		}
		drafts = append(drafts, draft)
	}
	return drafts, rows.Err()
}

func (s *Service) GetDraft(ctx context.Context, id int64) (model.Draft, error) {
	row := s.store.DB.QueryRowContext(ctx, `
		SELECT id, to_json, cc_json, bcc_json, subject, body, reply_to_email_id,
		       status, last_error, sent_message_id, created_at, updated_at
		FROM drafts WHERE id = ?`, id)
	draft, err := scanDraft(row)
	if err != nil {
		if errors.Is(err, sql.ErrNoRows) {
			return model.Draft{}, ErrNotFound
		}
		return model.Draft{}, err
	}
	return draft, nil
}

func (s *Service) UpdateDraft(ctx context.Context, id int64, input DraftInput) (model.Draft, error) {
	toJSON, _ := marshalJSON(input.To)
	ccJSON, _ := marshalJSON(input.Cc)
	bccJSON, _ := marshalJSON(input.Bcc)
	res, err := s.store.DB.ExecContext(ctx, `
		UPDATE drafts SET to_json = ?, cc_json = ?, bcc_json = ?, subject = ?,
			body = ?, reply_to_email_id = ?, updated_at = ?
		WHERE id = ? AND status != 'sent'`,
		toJSON, ccJSON, bccJSON, input.Subject, input.Body, input.ReplyToEmailID, formatTime(time.Now().UTC()), id)
	if err != nil {
		return model.Draft{}, err
	}
	if err := requireAffected(res); err != nil {
		return model.Draft{}, err
	}
	return s.GetDraft(ctx, id)
}

func (s *Service) SendDraft(ctx context.Context, id int64) (SendOutcome, error) {
	draft, err := s.GetDraft(ctx, id)
	if err != nil {
		return SendOutcome{}, err
	}
	if draft.Status == "sent" {
		if draft.SentMessageID == nil {
			return SendOutcome{}, ErrDraftAlreadySent
		}
		sent, err := s.getSentMessage(ctx, *draft.SentMessageID)
		if err != nil {
			return SendOutcome{}, err
		}
		return SendOutcome{SentMessage: sent, Draft: &draft}, nil
	}
	req := mailsmtp.SendRequest{
		FromAddress: s.fromAddress,
		FromName:    s.fromName,
		To:          draft.To,
		Cc:          draft.Cc,
		Bcc:         draft.Bcc,
		Subject:     draft.Subject,
		Body:        draft.Body,
	}
	if draft.ReplyToEmailID != nil {
		original, err := s.GetEmail(ctx, *draft.ReplyToEmailID)
		if err != nil {
			return SendOutcome{}, err
		}
		req.InReplyTo = original.MessageIDHeader
		req.References = buildReplyReferences(original)
	}
	var result mailsmtp.SendResult
	if s.mailer == nil {
		err = fmt.Errorf("SMTP client is not configured")
	} else {
		result, err = s.mailer.Send(ctx, req)
	}
	if err != nil {
		sent, recordErr := s.recordSentMessage(ctx, &id, draft, req, "failed", "", err.Error(), nil)
		if recordErr != nil {
			return SendOutcome{}, recordErr
		}
		_, _ = s.store.DB.ExecContext(ctx, "UPDATE drafts SET last_error = ?, updated_at = ? WHERE id = ?", err.Error(), formatTime(time.Now().UTC()), id)
		return SendOutcome{SentMessage: sent, Draft: &draft}, err
	}
	sentAt := result.SentAt
	sent, err := s.recordSentMessage(ctx, &id, draft, req, "sent", result.MessageIDHeader, "", &sentAt)
	if err != nil {
		return SendOutcome{}, err
	}
	_, err = s.store.DB.ExecContext(ctx, `
		UPDATE drafts SET status = 'sent', last_error = NULL, sent_message_id = ?, updated_at = ?
		WHERE id = ?`, sent.ID, formatTime(time.Now().UTC()), id)
	if err != nil {
		return SendOutcome{}, err
	}
	if draft.ReplyToEmailID != nil {
		_ = s.MarkEmail(ctx, *draft.ReplyToEmailID, MarkInput{Replied: ptrBool(true)})
	}
	updated, _ := s.GetDraft(ctx, id)
	return SendOutcome{SentMessage: sent, Draft: &updated}, nil
}

func (s *Service) SendDirect(ctx context.Context, input DraftInput) (SendOutcome, error) {
	draft, err := s.CreateDraft(ctx, input)
	if err != nil {
		return SendOutcome{}, err
	}
	return s.SendDraft(ctx, draft.ID)
}

type ForwardInput struct {
	To                 []string `json:"to"`
	Cc                 []string `json:"cc"`
	Bcc                []string `json:"bcc"`
	Subject            string   `json:"subject"`
	Body               string   `json:"body"`
	IncludeAttachments bool     `json:"include_attachments"`
}

func (s *Service) ForwardEmail(ctx context.Context, emailID int64, input ForwardInput) (SendOutcome, error) {
	if input.IncludeAttachments {
		return SendOutcome{}, ErrAttachmentsForwardUnsupported
	}
	original, err := s.GetEmail(ctx, emailID)
	if err != nil {
		return SendOutcome{}, err
	}
	subject := input.Subject
	if strings.TrimSpace(subject) == "" {
		subject = "Fwd: " + original.Subject
	}
	body := input.Body
	if strings.TrimSpace(body) != "" {
		body += "\n\n"
	}
	body += "---------- Forwarded message ----------\n"
	body += "From: " + original.SenderEmail + "\n"
	body += "Date: " + original.DateHeader + "\n"
	body += "Subject: " + original.Subject + "\n\n"
	if strings.TrimSpace(original.BodyText) != "" {
		body += original.BodyText
	} else {
		body += original.BodyHTML
	}
	return s.SendDirect(ctx, DraftInput{To: input.To, Cc: input.Cc, Bcc: input.Bcc, Subject: subject, Body: body})
}

func (s *Service) hasPOP3UID(ctx context.Context, uid string) (bool, error) {
	_, ok, err := s.findByPOP3UID(ctx, uid)
	return ok, err
}

func (s *Service) findByPOP3UID(ctx context.Context, uid string) (int64, bool, error) {
	var id int64
	err := s.store.DB.QueryRowContext(ctx, `SELECT id FROM mail_messages WHERE account_id = ? AND pop3_uid = ?`, s.accountID, uid).Scan(&id)
	if errors.Is(err, sql.ErrNoRows) {
		return 0, false, nil
	}
	if err != nil {
		return 0, false, err
	}
	return id, true, nil
}

func (s *Service) saveAttachments(ctx context.Context, execer interface {
	ExecContext(context.Context, string, ...any) (sql.Result, error)
}, messageID int64, attachments []model.ParsedAttachment, now time.Time, writtenFiles *[]string) error {
	if len(attachments) == 0 {
		return nil
	}
	if s.attachmentDir == "" {
		for _, attachment := range attachments {
			if _, err := execer.ExecContext(ctx, `
				INSERT INTO attachments(message_id, file_name, content_type, content_id, size_bytes, storage_path, created_at)
				VALUES (?, ?, ?, ?, ?, ?, ?)`,
				messageID, attachment.Filename, attachment.ContentType, attachment.ContentID, attachment.SizeBytes, "", formatTime(now)); err != nil {
				return err
			}
		}
		return nil
	}
	dir := filepath.Join(s.attachmentDir, fmt.Sprintf("%d", messageID))
	if err := os.MkdirAll(dir, 0750); err != nil {
		return fmt.Errorf("create attachment dir: %w", err)
	}
	for i, attachment := range attachments {
		filename := fmt.Sprintf("%03d_%s", i+1, attachment.Filename)
		path := filepath.Join(dir, filename)
		if err := os.WriteFile(path, attachment.Data, 0600); err != nil {
			return fmt.Errorf("write attachment: %w", err)
		}
		*writtenFiles = append(*writtenFiles, path)
		if _, err := execer.ExecContext(ctx, `
			INSERT INTO attachments(message_id, file_name, content_type, content_id, size_bytes, storage_path, created_at)
			VALUES (?, ?, ?, ?, ?, ?, ?)`,
			messageID, attachment.Filename, attachment.ContentType, attachment.ContentID, attachment.SizeBytes, path, formatTime(now)); err != nil {
			return err
		}
	}
	return nil
}

func (s *Service) recordSentMessage(ctx context.Context, draftID *int64, draft model.Draft, req mailsmtp.SendRequest, status, messageID, errorMessage string, sentAt *time.Time) (model.SentMessage, error) {
	toJSON, _ := marshalJSON(draft.To)
	ccJSON, _ := marshalJSON(draft.Cc)
	bccJSON, _ := marshalJSON(draft.Bcc)
	sentAtValue := timePtrString(sentAt)
	res, err := s.store.DB.ExecContext(ctx, `
		INSERT INTO sent_messages(draft_id, to_json, cc_json, bcc_json, subject, body,
			message_id_header, in_reply_to, references_header, smtp_from, status,
			error_message, sent_at, created_at)
		VALUES (?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?)`,
		draftID, toJSON, ccJSON, bccJSON, draft.Subject, draft.Body,
		messageID, req.InReplyTo, req.References, req.FromAddress, status,
		errorMessage, sentAtValue, formatTime(time.Now().UTC()))
	if err != nil {
		return model.SentMessage{}, err
	}
	id, err := res.LastInsertId()
	if err != nil {
		return model.SentMessage{}, err
	}
	return model.SentMessage{
		ID:              id,
		DraftID:         draftID,
		Subject:         draft.Subject,
		MessageIDHeader: messageID,
		Status:          status,
		ErrorMessage:    errorMessage,
		SentAt:          sentAt,
	}, nil
}

func (s *Service) getSentMessage(ctx context.Context, id int64) (model.SentMessage, error) {
	var sent model.SentMessage
	var draftID sql.NullInt64
	var sentAt, errorMessage sql.NullString
	err := s.store.DB.QueryRowContext(ctx, `
		SELECT id, draft_id, subject, message_id_header, status, error_message, sent_at
		FROM sent_messages WHERE id = ?`, id).Scan(
		&sent.ID,
		&draftID,
		&sent.Subject,
		&sent.MessageIDHeader,
		&sent.Status,
		&errorMessage,
		&sentAt,
	)
	if err != nil {
		if errors.Is(err, sql.ErrNoRows) {
			return model.SentMessage{}, ErrNotFound
		}
		return model.SentMessage{}, err
	}
	if draftID.Valid {
		sent.DraftID = &draftID.Int64
	}
	if errorMessage.Valid {
		sent.ErrorMessage = errorMessage.String
	}
	if sentAt.Valid {
		sent.SentAt = parseStoredTime(sentAt.String)
	}
	return sent, nil
}

func scanSummary(rows interface{ Scan(dest ...any) error }) (model.EmailSummary, error) {
	var toJSON, ccJSON, sentAt, receivedAt, body string
	var hasAttachment, read, processed, archived, deleted, replied int
	var summary model.EmailSummary
	err := rows.Scan(
		&summary.ID,
		&summary.Subject,
		&summary.SenderName,
		&summary.SenderEmail,
		&toJSON,
		&ccJSON,
		&summary.DateHeader,
		&sentAt,
		&receivedAt,
		&body,
		&hasAttachment,
		&read,
		&processed,
		&archived,
		&deleted,
		&replied,
		&summary.AttachmentCount,
	)
	if err != nil {
		return model.EmailSummary{}, err
	}
	summary.To = decodeAddresses(toJSON)
	summary.Cc = decodeAddresses(ccJSON)
	summary.SentAt = parseStoredTime(sentAt)
	summary.ReceivedAt = parseStoredTime(receivedAt)
	summary.Snippet = snippet(body)
	summary.HasAttachment = hasAttachment == 1
	summary.LocalStatus = model.LocalStatus{Read: read == 1, Processed: processed == 1, Archived: archived == 1, Deleted: deleted == 1, Replied: replied == 1}
	return summary, nil
}

func scanDetail(row interface{ Scan(dest ...any) error }) (model.EmailDetail, error) {
	var toJSON, ccJSON, sentAt, receivedAt string
	var read, processed, archived, deleted, replied int
	var detail model.EmailDetail
	err := row.Scan(
		&detail.ID,
		&detail.MessageIDHeader,
		&detail.InReplyTo,
		&detail.References,
		&detail.Subject,
		&detail.SenderName,
		&detail.SenderEmail,
		&toJSON,
		&ccJSON,
		&detail.DateHeader,
		&sentAt,
		&receivedAt,
		&detail.BodyText,
		&detail.BodyHTML,
		&read,
		&processed,
		&archived,
		&deleted,
		&replied,
	)
	if err != nil {
		return model.EmailDetail{}, err
	}
	detail.To = decodeAddresses(toJSON)
	detail.Cc = decodeAddresses(ccJSON)
	detail.SentAt = parseStoredTime(sentAt)
	detail.ReceivedAt = parseStoredTime(receivedAt)
	detail.LocalStatus = model.LocalStatus{Read: read == 1, Processed: processed == 1, Archived: archived == 1, Deleted: deleted == 1, Replied: replied == 1}
	return detail, nil
}

func scanDraft(row interface{ Scan(dest ...any) error }) (model.Draft, error) {
	var draft model.Draft
	var toJSON, ccJSON, bccJSON string
	var replyTo, sentMessage sql.NullInt64
	var lastError sql.NullString
	var createdAt, updatedAt string
	err := row.Scan(
		&draft.ID,
		&toJSON,
		&ccJSON,
		&bccJSON,
		&draft.Subject,
		&draft.Body,
		&replyTo,
		&draft.Status,
		&lastError,
		&sentMessage,
		&createdAt,
		&updatedAt,
	)
	if err != nil {
		return model.Draft{}, err
	}
	draft.To = decodeStrings(toJSON)
	draft.Cc = decodeStrings(ccJSON)
	draft.Bcc = decodeStrings(bccJSON)
	if replyTo.Valid {
		draft.ReplyToEmailID = &replyTo.Int64
	}
	if sentMessage.Valid {
		draft.SentMessageID = &sentMessage.Int64
	}
	if lastError.Valid {
		draft.LastError = lastError.String
	}
	draft.CreatedAt = parseStoredTime(createdAt)
	draft.UpdatedAt = parseStoredTime(updatedAt)
	return draft, nil
}

type threadCandidate struct {
	summary    model.EmailSummary
	messageID  string
	inReplyTo  string
	references string
}

func (s *Service) threadCandidates(ctx context.Context) (map[int64]threadCandidate, error) {
	rows, err := s.store.DB.QueryContext(ctx, `
		SELECT id, subject, sender_name, sender_email, to_json, cc_json, date_header,
		       sent_at, received_at, body_text, has_attachment, local_read,
		       local_processed, local_archived, local_deleted, local_replied,
		       (SELECT COUNT(*) FROM attachments WHERE message_id = mail_messages.id)
		FROM mail_messages WHERE account_id = ?`, s.accountID)
	if err != nil {
		return nil, err
	}
	defer rows.Close()
	out := map[int64]threadCandidate{}
	for rows.Next() {
		summary, err := scanSummary(rows)
		if err != nil {
			return nil, err
		}
		out[summary.ID] = threadCandidate{summary: summary}
	}
	if err := rows.Err(); err != nil {
		return nil, err
	}
	refRows, err := s.store.DB.QueryContext(ctx, `SELECT id, message_id_header, in_reply_to, references_header FROM mail_messages WHERE account_id = ?`, s.accountID)
	if err != nil {
		return nil, err
	}
	defer refRows.Close()
	for refRows.Next() {
		var id int64
		var messageID, inReplyTo, refs string
		if err := refRows.Scan(&id, &messageID, &inReplyTo, &refs); err != nil {
			return nil, err
		}
		c := out[id]
		c.messageID = messageID
		c.inReplyTo = inReplyTo
		c.references = refs
		out[id] = c
	}
	return out, refRows.Err()
}

func (s *Service) attachmentsForMessage(ctx context.Context, messageID int64) []model.Attachment {
	rows, err := s.store.DB.QueryContext(ctx, `SELECT id, message_id, file_name, content_type, content_id, size_bytes FROM attachments WHERE message_id = ? ORDER BY id`, messageID)
	if err != nil {
		return nil
	}
	defer rows.Close()
	var out []model.Attachment
	for rows.Next() {
		var item model.Attachment
		if err := rows.Scan(&item.ID, &item.MessageID, &item.Filename, &item.ContentType, &item.ContentID, &item.SizeBytes); err == nil {
			out = append(out, item)
		}
	}
	return out
}

func (s *Service) labelsForMessage(ctx context.Context, messageID int64) []model.Label {
	rows, err := s.store.DB.QueryContext(ctx, `
		SELECT labels.id, labels.name, labels.color
		FROM labels
		JOIN message_labels ON message_labels.label_id = labels.id
		WHERE message_labels.message_id = ?
		ORDER BY labels.name`, messageID)
	if err != nil {
		return nil
	}
	defer rows.Close()
	var out []model.Label
	for rows.Next() {
		var label model.Label
		if err := rows.Scan(&label.ID, &label.Name, &label.Color); err == nil {
			out = append(out, label)
		}
	}
	return out
}

var messageIDPattern = regexp.MustCompile(`<[^>]+>`)

func linked(a, b threadCandidate) bool {
	if a.messageID == "" || b.messageID == "" {
		return false
	}
	return refsContain(a.inReplyTo+" "+a.references, b.messageID) || refsContain(b.inReplyTo+" "+b.references, a.messageID)
}

func refsContain(refs, messageID string) bool {
	for _, ref := range extractMessageIDs(refs) {
		if ref == messageID {
			return true
		}
	}
	return false
}

func extractMessageIDs(value string) []string {
	matches := messageIDPattern.FindAllString(value, -1)
	if len(matches) > 0 {
		return matches
	}
	return strings.Fields(value)
}

func buildReplyReferences(original model.EmailDetail) string {
	refs := strings.TrimSpace(original.References)
	if original.MessageIDHeader == "" {
		return refs
	}
	if refs == "" {
		return original.MessageIDHeader
	}
	if refsContain(refs, original.MessageIDHeader) {
		return refs
	}
	return refs + " " + original.MessageIDHeader
}

func normalizeDateFilter(value string, endOfDay bool) string {
	value = strings.TrimSpace(value)
	if value == "" {
		return ""
	}
	if t, err := time.Parse(time.RFC3339Nano, value); err == nil {
		return formatTime(t.UTC())
	}
	if t, err := time.Parse("2006-01-02", value); err == nil {
		if endOfDay {
			t = t.Add(24*time.Hour - time.Nanosecond)
		}
		return formatTime(t.UTC())
	}
	return value
}

func marshalJSON(v any) (string, error) {
	data, err := json.Marshal(v)
	if err != nil {
		return "", err
	}
	return string(data), nil
}

func decodeAddresses(value string) []model.Address {
	var out []model.Address
	if err := json.Unmarshal([]byte(value), &out); err != nil {
		return nil
	}
	return out
}

func decodeStrings(value string) []string {
	var out []string
	if err := json.Unmarshal([]byte(value), &out); err != nil {
		return nil
	}
	return out
}

func boolInt(v bool) int {
	if v {
		return 1
	}
	return 0
}

func ptrBool(v bool) *bool {
	return &v
}

func formatTime(t time.Time) string {
	return t.UTC().Format(time.RFC3339Nano)
}

func timePtrString(t *time.Time) string {
	if t == nil {
		return ""
	}
	return formatTime(*t)
}

func parseStoredTime(value string) *time.Time {
	if value == "" {
		return nil
	}
	t, err := time.Parse(time.RFC3339Nano, value)
	if err != nil {
		return nil
	}
	return &t
}

func snippet(value string) string {
	value = strings.Join(strings.Fields(value), " ")
	if len(value) <= 160 {
		return value
	}
	return value[:160]
}

func hashBytes(data []byte) string {
	sum := sha256.Sum256(data)
	return hex.EncodeToString(sum[:16])
}

func requireAffected(res sql.Result) error {
	affected, err := res.RowsAffected()
	if err != nil {
		return err
	}
	if affected == 0 {
		return ErrNotFound
	}
	return nil
}

func summaryTime(summary model.EmailSummary) time.Time {
	if summary.SentAt != nil {
		return *summary.SentAt
	}
	if summary.ReceivedAt != nil {
		return *summary.ReceivedAt
	}
	return time.Unix(0, summary.ID)
}

var (
	ErrNotFound                      = errors.New("not found")
	ErrAttachmentsForwardUnsupported = errors.New("forwarding attachments is not supported in MVP")
	ErrDraftAlreadySent              = errors.New("draft is already sent")
)