package service

import (
	"context"
	"crypto/sha256"
	"encoding/json"
	"errors"
	"fmt"
	"strconv"
	"strings"
	"time"

	"github.com/gochat/gochat/internal/channel"
	"github.com/gochat/gochat/internal/llm"
	"github.com/gochat/gochat/internal/model"
	"github.com/gochat/gochat/internal/repository"
	"github.com/gochat/gochat/internal/search"
	"github.com/gochat/gochat/internal/worker"
	"github.com/gochat/gochat/internal/wsevent"
	applogger "github.com/gochat/gochat/pkg/logger"
	pkgvalidator "github.com/gochat/gochat/pkg/validator"

	"gorm.io/datatypes"
	"gorm.io/gorm"
	"gorm.io/gorm/clause"
)

// MessageService implements business logic for Message operations.
// Reference: Chatwoot app/controllers/api/v1/messages_controller.rb
type MessageService struct {
	repo          *repository.MessageRepo
	dispatcher    *channel.Dispatcher
	searchIndexer SearchIndexer
	llmProvider   llm.Provider
	worker        *worker.WorkerPool
	realtime      *wsevent.BridgeListener
}

// NewMessageService creates a new Message service.
func NewMessageService(repo *repository.MessageRepo, dispatcher *channel.Dispatcher, llmProvider llm.Provider) *MessageService {
	return &MessageService{repo: repo, dispatcher: dispatcher, llmProvider: llmProvider}
}

func (s *MessageService) SetSearchIndexer(indexer SearchIndexer) {
	s.searchIndexer = indexer
	RegisterMessageDeliverySearchIndexer(s.worker, s.repo.DB(), s.dispatcher, indexer)
}

func (s *MessageService) SetWorkerPool(wp *worker.WorkerPool) {
	s.worker = wp
	RegisterMessageDeliverySearchIndexer(wp, s.repo.DB(), s.dispatcher, s.searchIndexer)
}

func (s *MessageService) SetRealtimeEventBridge(bridge *wsevent.BridgeListener) {
	s.realtime = bridge
}

func (s *MessageService) DB() *gorm.DB {
	if s == nil || s.repo == nil {
		return nil
	}
	return s.repo.DB()
}

func (s *MessageService) indexMessage(ctx context.Context, message *model.Message) {
	if s.searchIndexer != nil {
		logSearchIndexError("message", message.ID, s.searchIndexer.IndexMessage(ctx, message))
	}
}

func (s *MessageService) deleteMessageIndex(ctx context.Context, accountID uint, id uint) {
	if s.searchIndexer != nil {
		logSearchIndexError("message", id, s.searchIndexer.DeleteMessage(ctx, accountID, id))
	}
}

// dispatchMessageEvent is a helper to build and dispatch a message event.
func (s *MessageService) dispatchMessageEvent(ctx context.Context, eventType channel.EventType, message *model.Message) error {
	event, err := s.buildMessageEvent(ctx, s.repo.DB(), eventType, message)
	if err != nil {
		return err
	}
	return s.dispatchPreparedMessageEvent(ctx, event, message.ID)
}

func (s *MessageService) buildMessageEvent(ctx context.Context, db *gorm.DB, eventType channel.EventType, message *model.Message) (*channel.ChannelEvent, error) {
	event := channel.NewChannelEvent(eventType, channel.ChannelAPI, message.AccountID, message.InboxID)
	event.ConversationID = message.ConversationID
	if message.SenderID != nil {
		event.UserID = *message.SenderID
	}
	event.Data["message"] = message
	if eventType == channel.EventMessageCreated || eventType == channel.EventMessageUpdated || eventType == channel.EventMessageDeleted {
		if err := s.addMessageEventContext(ctx, db, event, message); err != nil {
			return nil, fmt.Errorf("build %s event for message %d: %w", eventType, message.ID, err)
		}
	}
	return event, nil
}

func (s *MessageService) dispatchPreparedMessageEvent(ctx context.Context, event *channel.ChannelEvent, messageID uint) error {
	applogger.L().Infof("dispatching event %s for message %d", event.Type, messageID)
	if err := s.dispatcher.Dispatch(ctx, event); err != nil {
		return fmt.Errorf("dispatch event %s for message %d: %w", event.Type, messageID, err)
	}
	return nil
}

func (s *MessageService) addMessageEventContext(ctx context.Context, db *gorm.DB, event *channel.ChannelEvent, message *model.Message) error {
	var inbox model.Inbox
	if err := db.WithContext(ctx).Where("id = ? AND account_id = ?", message.InboxID, message.AccountID).First(&inbox).Error; err != nil {
		return fmt.Errorf("load inbox %d: %w", message.InboxID, err)
	}
	event.Data["inbox"] = &inbox
	isWebWidget := strings.EqualFold(strings.TrimSpace(inbox.ChannelType), string(channel.ChannelWebWidget)) ||
		strings.EqualFold(strings.TrimSpace(inbox.ChannelType), string(model.InboxChannelTypeWebWidget))
	if isWebWidget {
		event.Channel = channel.ChannelWebWidget
	}

	var conversation model.Conversation
	if err := db.WithContext(ctx).Where("id = ? AND account_id = ?", message.ConversationID, message.AccountID).First(&conversation).Error; err != nil {
		return fmt.Errorf("load conversation %d: %w", message.ConversationID, err)
	}
	event.ContactID = conversation.ContactID
	event.Data["conversation"] = &conversation
	widgetVisible := isWebWidget && !message.Private && message.MessageType != string(model.MessageTypeActivity)

	var contact model.Contact
	if err := db.WithContext(ctx).Where("id = ? AND account_id = ?", conversation.ContactID, message.AccountID).First(&contact).Error; err != nil {
		return fmt.Errorf("load contact %d: %w", conversation.ContactID, err)
	}
	event.Data["contact"] = &contact
	if message.SenderID != nil {
		switch strings.ToLower(strings.TrimSpace(message.SenderType)) {
		case "user":
			var sender model.User
			if err := db.WithContext(ctx).First(&sender, *message.SenderID).Error; err != nil {
				if widgetVisible {
					return fmt.Errorf("load user sender %d: %w", *message.SenderID, err)
				}
				break
			}
			event.Data["sender"] = &sender
		case "agentbot", "agent_bot":
			var sender model.AgentBot
			if err := db.WithContext(ctx).Where("id = ? AND (account_id IS NULL OR account_id = ?)", *message.SenderID, message.AccountID).First(&sender).Error; err != nil {
				return fmt.Errorf("load agent bot sender %d: %w", *message.SenderID, err)
			}
			event.Data["sender"] = &sender
		case "captain::assistant", "captainassistant", "captain_assistant":
			var sender model.CaptainAssistant
			if err := db.WithContext(ctx).Where("id = ? AND account_id = ?", *message.SenderID, message.AccountID).First(&sender).Error; err != nil {
				return fmt.Errorf("load captain sender %d: %w", *message.SenderID, err)
			}
			event.Data["sender"] = &sender
		}
	}
	if !widgetVisible {
		return nil
	}
	if conversation.ContactInboxID == nil {
		return fmt.Errorf("web widget conversation %d has no contact inbox", conversation.ID)
	}
	var contactInbox model.ContactInbox
	if err := db.WithContext(ctx).Select("pubsub_token").Where(
		"id = ? AND contact_id = ? AND inbox_id = ?", *conversation.ContactInboxID, conversation.ContactID, conversation.InboxID,
	).First(&contactInbox).Error; err != nil {
		return fmt.Errorf("load contact inbox %d: %w", *conversation.ContactInboxID, err)
	}
	if strings.TrimSpace(contactInbox.PubsubToken) == "" {
		return fmt.Errorf("contact inbox %d has no pubsub token", *conversation.ContactInboxID)
	}
	event.Data["widget_token"] = contactInbox.PubsubToken
	return nil
}

// ListByConversation retrieves all messages for a conversation.
func (s *MessageService) ListByConversation(ctx context.Context, conversationID uint, offset, limit int) ([]model.Message, int64, error) {
	return s.repo.FindByConversation(ctx, conversationID, offset, limit)
}

// ResolveConversationForRoute resolves Chatwoot message route IDs exclusively as account-scoped display IDs.
func (s *MessageService) ResolveConversationForRoute(ctx context.Context, accountID, displayID uint) (*model.Conversation, error) {
	var conversation model.Conversation
	if err := s.repo.DB().WithContext(ctx).Where("account_id = ? AND display_id = ?", accountID, displayID).First(&conversation).Error; err != nil {
		return nil, err
	}
	return &conversation, nil
}

// GetByID retrieves a single message.
func (s *MessageService) GetByID(ctx context.Context, id uint) (*model.Message, error) {
	return s.repo.FindByID(ctx, id)
}

// GetByAccountAndID retrieves a message scoped to an account.
func (s *MessageService) GetByAccountAndID(ctx context.Context, accountID, id uint) (*model.Message, error) {
	return s.repo.FindByAccountAndID(ctx, accountID, id)
}

// GetByConversationAndID retrieves a message scoped to a conversation.
func (s *MessageService) GetByConversationAndID(ctx context.Context, conversationID, id uint) (*model.Message, error) {
	return s.repo.FindByConversationAndID(ctx, conversationID, id)
}

// GetByAccountConversationAndID retrieves a message scoped to an account and conversation.
func (s *MessageService) GetByAccountConversationAndID(ctx context.Context, accountID, conversationID, id uint) (*model.Message, error) {
	return s.repo.FindByAccountConversationAndID(ctx, accountID, conversationID, id)
}

// Search searches messages by content within an account.
func (s *MessageService) Search(ctx context.Context, accountID uint, query string, offset, limit int, searchMode search.SearchMode) ([]model.Message, int64, error) {
	return s.repo.Search(ctx, accountID, query, offset, limit, searchMode)
}

// CreateMessageRequest is the DTO for creating a message.
// Reference: Chatwoot app/controllers/api/v1/accounts/conversations/messages_controller.rb #create
type CreateMessageRequest struct {
	ConversationID            uint                     `json:"conversation_id" validate:"required"`
	Content                   string                   `json:"content"`
	MessageType               string                   `json:"message_type,omitempty"`
	ContentType               string                   `json:"content_type,omitempty"`
	Private                   bool                     `json:"private,omitempty"`
	SenderID                  uint                     `json:"sender_id,omitempty"`
	SenderType                string                   `json:"sender_type,omitempty"`
	SourceID                  string                   `json:"source_id,omitempty"`
	EchoID                    string                   `json:"echo_id,omitempty"`
	ExternalCreatedAt         string                   `json:"external_created_at,omitempty"`
	External                  bool                     `json:"external,omitempty"`
	ContentAttributes         datatypes.JSON           `json:"content_attributes,omitempty"`
	AdditionalAttributes      datatypes.JSON           `json:"additional_attributes,omitempty"`
	ExternalSourceIDs         datatypes.JSON           `json:"external_source_ids,omitempty"`
	EmailHTMLContent          string                   `json:"email_html_content,omitempty"`
	CCEmails                  string                   `json:"cc_emails,omitempty"`
	BCCEmails                 string                   `json:"bcc_emails,omitempty"`
	ToEmails                  string                   `json:"to_emails,omitempty"`
	CampaignID                any                      `json:"campaign_id,omitempty"`
	TemplateParams            datatypes.JSON           `json:"template_params,omitempty"`
	IsVoiceMessage            bool                     `json:"is_voice_message,omitempty"`
	Attachments               []MessageAttachmentInput `json:"-"`
	ExpectedAITakeoverVersion uint                     `json:"-"`
}

type MessageAttachmentInput struct {
	FileName    string
	FileSize    int
	ContentType string
	SHA256      string
}

var ErrMessageIdempotencyConflict = errors.New("idempotency key is already associated with a different message payload")

// Create creates a new message.
func (s *MessageService) Create(ctx context.Context, accountID uint, userID uint, req CreateMessageRequest) (*model.Message, error) {
	req.MessageType = normalizeMessageType(req.MessageType)
	if req.ContentType == "" {
		req.ContentType = "text"
	}
	if !validMessageType(req.MessageType) {
		return nil, fmt.Errorf("invalid message_type")
	}
	if !validContentType(req.ContentType) {
		return nil, fmt.Errorf("invalid content_type")
	}
	if err := pkgvalidator.ValidateStruct(req); err != nil {
		return nil, err
	}
	if strings.TrimSpace(req.Content) == "" && len(req.Attachments) == 0 && !contentTypeAllowsEmptyContent(req.ContentType, req.ContentAttributes) {
		return nil, fmt.Errorf("content is required")
	}

	var conversation model.Conversation
	if err := s.repo.DB().WithContext(ctx).Where("account_id = ? AND id = ?", accountID, req.ConversationID).First(&conversation).Error; err != nil {
		return nil, err
	}
	var inbox *model.Inbox
	loadInbox := func() *model.Inbox {
		if inbox != nil {
			return inbox
		}
		var loaded model.Inbox
		if err := s.repo.DB().WithContext(ctx).Select("id", "channel_type").Where("id = ?", conversation.InboxID).First(&loaded).Error; err == nil {
			inbox = &loaded
			if strings.TrimSpace(conversation.ChannelType) == "" {
				conversation.ChannelType = loaded.ChannelType
			}
		}
		return inbox
	}
	if req.MessageType == "incoming" && !messageCreateAllowedIncoming(conversation.ChannelType) {
		if loaded := loadInbox(); loaded != nil {
			conversation.ChannelType = loaded.ChannelType
		}
		if !messageCreateAllowedIncoming(conversation.ChannelType) {
			return nil, fmt.Errorf("Incoming messages are only allowed in Api inboxes")
		}
	}
	loadedInbox := loadInbox()
	requestHash, err := shangwutongMessageRequestHash(req)
	if err != nil {
		return nil, err
	}
	if requestHash != "" {
		if existing, found, err := s.findShangwutongMessageReplay(ctx, conversation.InboxID, req.SourceID, requestHash); err != nil {
			return nil, err
		} else if found {
			return existing, nil
		}
	}

	contentAttributes := messageContentAttributes(req.ContentAttributes)
	contentAttributes = mergeMessageContentAttributes(contentAttributes, map[string]any{
		"external_created_at": strings.TrimSpace(req.ExternalCreatedAt),
	})
	contentAttributes = s.resolveInReplyToContentAttributes(ctx, req.ConversationID, contentAttributes)
	if messageCreateEmailInbox(conversation.ChannelType) || (loadInbox() != nil && messageCreateEmailInbox(inbox.ChannelType)) {
		contentAttributes = mergeMessageContentAttributes(contentAttributes, map[string]any{
			"cc_emails":  parseEmailList(req.CCEmails),
			"bcc_emails": parseEmailList(req.BCCEmails),
			"to_emails":  parseEmailList(req.ToEmails),
		})
		if !req.Private && strings.TrimSpace(req.Content) != "" {
			contentAttributes = mergeEmailContentAttributes(contentAttributes, req.Content, req.EmailHTMLContent)
		}
	}
	var senderID *uint
	senderType := ""
	if req.External {
		if req.MessageType == "incoming" && conversation.ContactID != 0 {
			contactID := conversation.ContactID
			senderID, senderType = &contactID, string(model.SenderTypeContact)
		}
	} else {
		id := userID
		senderID, senderType = &id, "user"
	}
	if !req.External && strings.TrimSpace(req.SenderType) == string(model.SenderTypeAgentBot) && req.SenderID != 0 {
		var bot model.AgentBot
		if err := s.repo.DB().WithContext(ctx).
			Where("id = ? AND (account_id IS NULL OR account_id = ?)", req.SenderID, accountID).
			First(&bot).Error; err != nil {
			return nil, errors.New("agent bot not found")
		}
		if conversation.AssigneeAgentBotID == nil || *conversation.AssigneeAgentBotID != bot.ID {
			return nil, errors.New("agent bot is not assigned to this conversation")
		}
		id := bot.ID
		senderID = &id
		senderType = string(model.SenderTypeAgentBot)
	}
	if !req.External && strings.TrimSpace(req.SenderType) == "Captain::Assistant" && req.SenderID != 0 {
		var assistant model.CaptainAssistant
		if err := s.repo.DB().WithContext(ctx).Where("id = ? AND account_id = ?", req.SenderID, accountID).First(&assistant).Error; err == nil {
			id := assistant.ID
			senderID = &id
			senderType = "Captain::Assistant"
		}
	}
	externalSourceIDs := messageContentAttributes(req.ExternalSourceIDs)
	additionalAttributes := messageContentAttributes(req.AdditionalAttributes)
	additionalAttributes = mergeMessageContentAttributes(additionalAttributes, map[string]any{
		"campaign_id": req.CampaignID, "template_params": req.TemplateParams,
	})
	queueShangwutong := loadedInbox != nil && loadedInbox.ChannelType == "shangwutong" && !req.External &&
		(req.MessageType == "outgoing" || req.MessageType == "template") && !req.Private
	status := string(model.MessageStatusSent)
	if queueShangwutong {
		status = string(model.MessageStatusProgress)
	}

	message := &model.Message{
		AccountID:            accountID,
		ConversationID:       req.ConversationID,
		InboxID:              conversation.InboxID,
		Content:              req.Content,
		MessageType:          req.MessageType,
		ContentType:          req.ContentType,
		SenderID:             senderID,
		SenderType:           senderType,
		Private:              req.Private,
		SourceID:             req.SourceID,
		EchoID:               req.EchoID,
		Status:               status,
		External:             req.External,
		ContentAttributes:    contentAttributes,
		AdditionalAttributes: additionalAttributes,
		ExternalSourceIDs:    externalSourceIDs,
		ExternalRequestHash:  requestHash,
	}

	// Chatwoot: when message_type is "private_note", force Private=true and ContentType="private_note"
	if req.MessageType == "private_note" {
		message.Private = true
		if message.ContentType == "text" {
			message.ContentType = "private_note"
		}
	}

	var deliveryJob *model.BackgroundJob
	var deliveryCreated bool
	var realtimeJobs []*model.BackgroundJob
	var messageCreatedEvent *channel.ChannelEvent
	if err := s.repo.DB().WithContext(ctx).Transaction(func(tx *gorm.DB) error {
		if req.ExpectedAITakeoverVersion != 0 {
			var active model.Conversation
			if err := tx.Clauses(clause.Locking{Strength: "UPDATE"}).
				Where("id = ? AND account_id = ? AND status = ? AND assignee_agent_bot_id IS NOT NULL AND ai_takeover_version = ?", message.ConversationID, accountID, model.ConversationStatusPending, req.ExpectedAITakeoverVersion).
				First(&active).Error; err != nil {
				if errors.Is(err, gorm.ErrRecordNotFound) {
					return errAITakeoverEnded
				}
				return err
			}
			if active.ID == 0 {
				return errAITakeoverEnded
			}
		}
		humanOutgoing := !req.External && !message.Private &&
			(message.MessageType == string(model.MessageTypeOutgoing) || message.MessageType == string(model.MessageTypeTemplate)) &&
			message.SenderType != string(model.SenderTypeAgentBot) && message.SenderType != "Captain::Assistant"
		if humanOutgoing {
			result := tx.Model(&model.Conversation{}).
				Where("id = ? AND account_id = ? AND assignee_agent_bot_id IS NOT NULL", message.ConversationID, accountID).
				Updates(map[string]any{
					"assignee_agent_bot_id": nil,
					"status":                gorm.Expr("CASE WHEN status = ? THEN ? ELSE status END", model.ConversationStatusPending, model.ConversationStatusOpen),
					"ai_takeover_version":   gorm.Expr("ai_takeover_version + 1"),
				})
			if result.Error != nil {
				return result.Error
			}
			message.AITakeoverExited = result.RowsAffected > 0
		}
		if err := tx.Create(message).Error; err != nil {
			return err
		}
		messageTimestamp := message.CreatedAt.Unix()
		conversationUpdates := map[string]any{
			"last_activity_at": messageTimestamp,
			"last_message_at":  messageTimestamp,
		}
		if message.MessageType != "activity" {
			conversationUpdates["last_non_sys_msg_at"] = messageTimestamp
		}
		if err := tx.Model(&model.Conversation{}).
			Where("id = ? AND account_id = ?", message.ConversationID, accountID).
			Updates(conversationUpdates).Error; err != nil {
			return fmt.Errorf("update conversation message timestamps: %w", err)
		}
		if message.AITakeoverExited {
			if err := tx.Where("id = ? AND account_id = ?", message.ConversationID, accountID).First(&conversation).Error; err != nil {
				return err
			}
		}
		for _, input := range req.Attachments {
			fileType := attachmentFileType(input.ContentType)
			attachment := &model.Attachment{
				MessageID: message.ID,
				AccountID: accountID,
				FileType:  fileType,
				FileURL:   attachmentDataURL(message.ID, input.FileName),
				ThumbURL:  attachmentThumbURL(input.ContentType, message.ID, input.FileName),
				FileSize:  input.FileSize,
				FileName:  input.FileName,
			}
			if req.IsVoiceMessage && fileType == "audio" {
				attachment.Metadata = `{"is_voice_message":true}`
			}
			createAttachment := tx
			if attachment.Metadata == "" {
				createAttachment = tx.Omit("Metadata")
			}
			if err := createAttachment.Create(attachment).Error; err != nil {
				return err
			}
			message.Attachments = append(message.Attachments, *attachment)
		}
		if queueShangwutong && s.worker != nil {
			var err error
			deliveryJob, deliveryCreated, err = s.worker.EnqueueInTransaction(
				ctx, tx, TaskTypeShangwutongWebhookDelivery, newShangwutongMessageJob("message_created", message, 0),
				worker.WithMaxAttempts(10), worker.WithIdempotencyKey(fmt.Sprintf("api-inbox-message:%d:created", message.ID)),
			)
			if err != nil {
				return err
			}
		}
		if s.realtime != nil {
			messageCreatedEvent, err = s.buildMessageEvent(ctx, tx, channel.EventMessageCreated, message)
			if err != nil {
				return err
			}
			realtimeJobs, err = s.realtime.EnqueueInTransaction(ctx, tx, messageCreatedEvent)
			if err != nil {
				return err
			}
		}
		return nil
	}); err != nil {
		if errors.Is(err, errAITakeoverEnded) {
			return nil, nil
		}
		if requestHash != "" {
			if existing, found, replayErr := s.findShangwutongMessageReplay(ctx, conversation.InboxID, req.SourceID, requestHash); replayErr == nil && found {
				return existing, nil
			}
		}
		applogger.L().Errorf("Failed to create message: %v", err)
		return nil, err
	}
	if deliveryCreated {
		s.worker.Publish(ctx, deliveryJob)
	}
	if s.realtime != nil {
		s.realtime.PublishEnqueued(ctx, realtimeJobs)
	}

	if message.AITakeoverExited {
		event := channel.NewChannelEvent(channel.EventConversationUpdated, channel.ChannelType(conversation.ChannelType), conversation.AccountID, conversation.InboxID)
		event.ConversationID = conversation.ID
		event.ContactID = conversation.ContactID
		event.Data["conversation"] = &conversation
		if err := s.dispatcher.Dispatch(ctx, event); err != nil {
			applogger.L().Errorf("failed to dispatch event %s for conversation %d: %v", channel.EventConversationUpdated, conversation.ID, err)
		}
	}

	// Dispatch EventMessageCreated
	var dispatchErr error
	if messageCreatedEvent != nil {
		dispatchErr = s.dispatchPreparedMessageEvent(ctx, messageCreatedEvent, message.ID)
	} else {
		dispatchErr = s.dispatchMessageEvent(ctx, channel.EventMessageCreated, message)
	}
	if dispatchErr != nil {
		return message, dispatchErr
	}
	s.indexMessage(ctx, message)

	// Dispatch additional event based on message type
	if req.MessageType == "incoming" {
		if err := s.dispatchMessageEvent(ctx, channel.EventMessageIncoming, message); err != nil {
			return message, err
		}
		if s.worker != nil {
			if _, err := EnqueueCaptainConversationResponseForMessage(ctx, s.worker, s.repo.DB(), message.ID); err != nil {
				return message, err
			}
		}
	} else if req.MessageType == "outgoing" || req.MessageType == "template" {
		if req.External || queueShangwutong {
			// Imported messages and Shangwutong messages use their dedicated external flow.
		} else if s.worker != nil {
			if _, err := EnqueueSendReply(ctx, s.worker, message.ID); err != nil {
				return message, err
			}
		} else {
			if err := s.dispatchMessageEvent(ctx, channel.EventMessageOutgoing, message); err != nil {
				return message, err
			}
		}
	}

	return message, nil
}

var errAITakeoverEnded = errors.New("AI takeover ended")

func messageCreateAllowedIncoming(channelType string) bool {
	return channel.IsAPIInboxLike(channelType)
}

func messageCreateEmailInbox(channelType string) bool {
	switch strings.TrimSpace(channelType) {
	case "email", string(model.InboxChannelTypeEmail):
		return true
	default:
		return false
	}
}

func messageContentAttributes(raw datatypes.JSON) datatypes.JSON {
	if len(raw) == 0 || string(raw) == "null" {
		return nil
	}
	attrs := map[string]any{}
	if err := json.Unmarshal(raw, &attrs); err != nil {
		var encoded string
		if stringErr := json.Unmarshal(raw, &encoded); stringErr != nil || strings.TrimSpace(encoded) == "" {
			return nil
		}
		if err := json.Unmarshal([]byte(encoded), &attrs); err != nil {
			return nil
		}
	}
	if len(attrs) == 0 {
		return nil
	}
	encoded, err := json.Marshal(attrs)
	if err != nil {
		return nil
	}
	return datatypes.JSON(encoded)
}

func mergeMessageContentAttributes(raw datatypes.JSON, values map[string]any) datatypes.JSON {
	attrs := map[string]any{}
	if len(raw) > 0 && string(raw) != "null" {
		_ = json.Unmarshal(raw, &attrs)
	}
	for key, value := range values {
		if list, ok := value.([]string); ok && len(list) == 0 {
			continue
		}
		attrs[key] = value
	}
	if len(attrs) == 0 {
		return nil
	}
	encoded, err := json.Marshal(attrs)
	if err != nil {
		return nil
	}
	return datatypes.JSON(encoded)
}

func mergeEmailContentAttributes(raw datatypes.JSON, content string, htmlContent string) datatypes.JSON {
	attrs := map[string]any{}
	if len(raw) > 0 && string(raw) != "null" {
		_ = json.Unmarshal(raw, &attrs)
	}
	emailAttrs := map[string]any{}
	if existing, ok := attrs["email"].(map[string]any); ok {
		emailAttrs = existing
	}
	textAttrs := map[string]any{}
	if existing, ok := emailAttrs["text_content"].(map[string]any); ok {
		textAttrs = existing
	}
	textAttrs["full"] = content
	textAttrs["reply"] = content
	emailAttrs["text_content"] = textAttrs

	renderedHTML := strings.TrimSpace(htmlContent)
	if renderedHTML == "" {
		renderedHTML = content
	}
	htmlAttrs := map[string]any{}
	if existing, ok := emailAttrs["html_content"].(map[string]any); ok {
		htmlAttrs = existing
	}
	htmlAttrs["full"] = renderedHTML
	htmlAttrs["reply"] = renderedHTML
	emailAttrs["html_content"] = htmlAttrs
	attrs["email"] = emailAttrs

	encoded, err := json.Marshal(attrs)
	if err != nil {
		return raw
	}
	return datatypes.JSON(encoded)
}

func (s *MessageService) resolveInReplyToContentAttributes(ctx context.Context, conversationID uint, raw datatypes.JSON) datatypes.JSON {
	attrs := map[string]any{}
	if len(raw) > 0 && string(raw) != "null" {
		_ = json.Unmarshal(raw, &attrs)
	}
	if _, hasReplyID := attrs["in_reply_to"]; !hasReplyID {
		if _, hasExternalID := attrs["in_reply_to_external_id"]; !hasExternalID {
			return raw
		}
	}

	var replyMessage model.Message
	found := false
	if replyID, ok := uintFromAny(attrs["in_reply_to"]); ok && replyID != 0 {
		if err := s.repo.DB().WithContext(ctx).Where("conversation_id = ? AND id = ?", conversationID, replyID).First(&replyMessage).Error; err == nil {
			found = true
		}
	}
	if !found {
		if externalID, ok := stringFromAny(attrs["in_reply_to_external_id"]); ok && strings.TrimSpace(externalID) != "" {
			if err := s.repo.DB().WithContext(ctx).Where("conversation_id = ? AND source_id = ?", conversationID, strings.TrimSpace(externalID)).First(&replyMessage).Error; err == nil {
				found = true
			}
		}
	}

	if found {
		attrs["in_reply_to"] = replyMessage.ID
		attrs["in_reply_to_external_id"] = replyMessage.SourceID
	} else {
		attrs["in_reply_to"] = nil
		attrs["in_reply_to_external_id"] = nil
	}
	encoded, err := json.Marshal(attrs)
	if err != nil {
		return raw
	}
	return datatypes.JSON(encoded)
}

func uintFromAny(value any) (uint, bool) {
	switch typed := value.(type) {
	case float64:
		if typed > 0 && typed == float64(uint(typed)) {
			return uint(typed), true
		}
	case int:
		if typed > 0 {
			return uint(typed), true
		}
	case uint:
		if typed > 0 {
			return typed, true
		}
	case string:
		parsed, err := strconv.ParseUint(strings.TrimSpace(typed), 10, 64)
		if err == nil && parsed > 0 {
			return uint(parsed), true
		}
	}
	return 0, false
}

func stringFromAny(value any) (string, bool) {
	if value == nil {
		return "", false
	}
	if typed, ok := value.(string); ok {
		return typed, true
	}
	return fmt.Sprint(value), true
}

func parseEmailList(value string) []string {
	if strings.TrimSpace(value) == "" {
		return nil
	}
	parts := strings.Split(strings.ReplaceAll(value, " ", ""), ",")
	emails := make([]string, 0, len(parts))
	for _, part := range parts {
		if part != "" {
			emails = append(emails, part)
		}
	}
	return emails
}

func shangwutongMessageRequestHash(req CreateMessageRequest) (string, error) {
	if !strings.HasPrefix(strings.TrimSpace(req.SourceID), "swt:") {
		return "", nil
	}
	contentAttributes, err := canonicalJSONValue(req.ContentAttributes)
	if err != nil {
		return "", fmt.Errorf("invalid content_attributes: %w", err)
	}
	additionalAttributes, err := canonicalJSONValue(req.AdditionalAttributes)
	if err != nil {
		return "", fmt.Errorf("invalid additional_attributes: %w", err)
	}
	externalSourceIDs, err := canonicalJSONValue(req.ExternalSourceIDs)
	if err != nil {
		return "", fmt.Errorf("invalid external_source_ids: %w", err)
	}
	attachments := make([]map[string]any, 0, len(req.Attachments))
	for _, attachment := range req.Attachments {
		attachments = append(attachments, map[string]any{
			"content_type": strings.TrimSpace(attachment.ContentType),
			"file_name":    strings.TrimSpace(attachment.FileName),
			"file_size":    attachment.FileSize,
			"sha256":       strings.ToLower(strings.TrimSpace(attachment.SHA256)),
		})
	}
	payload := struct {
		MessageType          string           `json:"message_type"`
		ContentType          string           `json:"content_type"`
		Content              string           `json:"content"`
		Private              bool             `json:"private"`
		SourceID             string           `json:"source_id"`
		External             bool             `json:"external"`
		ExternalCreatedAt    string           `json:"external_created_at"`
		ExternalSourceIDs    any              `json:"external_source_ids"`
		ContentAttributes    any              `json:"content_attributes"`
		AdditionalAttributes any              `json:"additional_attributes"`
		Attachments          []map[string]any `json:"attachments"`
	}{
		MessageType: req.MessageType, ContentType: req.ContentType, Content: req.Content,
		Private: req.Private, SourceID: strings.TrimSpace(req.SourceID), External: req.External,
		ExternalCreatedAt: strings.TrimSpace(req.ExternalCreatedAt), ExternalSourceIDs: externalSourceIDs,
		ContentAttributes: contentAttributes, AdditionalAttributes: additionalAttributes, Attachments: attachments,
	}
	encoded, err := json.Marshal(payload)
	if err != nil {
		return "", err
	}
	hash := sha256.Sum256(encoded)
	return fmt.Sprintf("%x", hash[:]), nil
}

func canonicalJSONValue(raw datatypes.JSON) (any, error) {
	if len(raw) == 0 || string(raw) == "null" || strings.TrimSpace(string(raw)) == "" {
		return nil, nil
	}
	var value any
	if err := json.Unmarshal(raw, &value); err != nil {
		return nil, err
	}
	if encoded, ok := value.(string); ok {
		if err := json.Unmarshal([]byte(encoded), &value); err != nil {
			return nil, err
		}
	}
	if value == nil {
		return nil, nil
	}
	if _, ok := value.(map[string]any); !ok {
		return nil, errors.New("must be a JSON object")
	}
	return value, nil
}

func (s *MessageService) findShangwutongMessageReplay(ctx context.Context, inboxID uint, sourceID, requestHash string) (*model.Message, bool, error) {
	var existing model.Message
	err := s.repo.DB().WithContext(ctx).Where("inbox_id = ? AND source_id = ?", inboxID, sourceID).First(&existing).Error
	if errors.Is(err, gorm.ErrRecordNotFound) {
		return nil, false, nil
	}
	if err != nil {
		return nil, false, err
	}
	if existing.ExternalRequestHash == "" || existing.ExternalRequestHash != requestHash {
		return nil, false, ErrMessageIdempotencyConflict
	}
	existing.IdempotentReplay = true
	return &existing, true, nil
}

func normalizeMessageType(value string) string {
	switch strings.ToLower(strings.TrimSpace(value)) {
	case "", "1", "outgoing":
		return "outgoing"
	case "0", "incoming":
		return "incoming"
	case "2", "activity":
		return "activity"
	case "3", "template":
		return "template"
	case "private_note":
		return "private_note"
	default:
		return value
	}
}

func validMessageType(value string) bool {
	switch value {
	case "incoming", "outgoing", "activity", "template", "private_note":
		return true
	default:
		return false
	}
}

func validContentType(value string) bool {
	switch value {
	case "text", "input_text", "input_textarea", "input_email", "input_select", "cards", "form", "article", "incoming_email", "input_csat", "integrations", "sticker", "voice_call", "input_phone", "select", "card", "private_note", "file", "image", "audio", "video":
		return true
	default:
		return false
	}
}

func contentTypeAllowsEmptyContent(contentType string, contentAttributes datatypes.JSON) bool {
	switch contentType {
	case "input_text", "input_textarea", "input_email", "input_select", "cards", "form", "article", "input_csat", "integrations", "sticker", "voice_call", "select", "card":
		return len(messageContentAttributes(contentAttributes)) > 0
	default:
		return false
	}
}

// UpdateMessageRequest is the DTO for updating a message.
type UpdateMessageRequest struct {
	Status        string `json:"status,omitempty"`
	ExternalError string `json:"external_error,omitempty"`
}

// Update modifies an existing message.
func (s *MessageService) Update(ctx context.Context, accountID, id uint, req UpdateMessageRequest) (*model.Message, error) {
	return s.UpdateInConversation(ctx, accountID, 0, id, req)
}

// UpdateInConversation modifies a message scoped to a conversation route.
func (s *MessageService) UpdateInConversation(ctx context.Context, accountID, conversationID, id uint, req UpdateMessageRequest) (*model.Message, error) {
	if err := pkgvalidator.ValidateStruct(req); err != nil {
		return nil, err
	}

	message, err := s.findMessageForConversationRoute(ctx, accountID, conversationID, id)
	if err != nil {
		return nil, err
	}

	if !s.messageInboxIsAPI(ctx, message.InboxID) {
		return nil, fmt.Errorf("Message status update is only allowed for API inboxes")
	}
	if req.Status != "" {
		if !validMessageStatus(req.Status) {
			return nil, fmt.Errorf("invalid status")
		}
		if !(message.Status == "read" && req.Status == "delivered") {
			message.Status = req.Status
			message.ContentAttributes = setMessageExternalError(message.ContentAttributes, req.Status, req.ExternalError)
		}
	}

	if err := s.repo.Update(ctx, message); err != nil {
		return nil, err
	}

	// Dispatch EventMessageUpdated
	if err := s.dispatchMessageEvent(ctx, channel.EventMessageUpdated, message); err != nil {
		return message, err
	}
	s.indexMessage(ctx, message)

	return message, nil
}

func (s *MessageService) messageInboxIsAPI(ctx context.Context, inboxID uint) bool {
	var inbox model.Inbox
	if err := s.repo.DB().WithContext(ctx).First(&inbox, inboxID).Error; err != nil {
		return false
	}
	return channel.IsAPIInboxLike(inbox.ChannelType)
}

// Delete marks a message deleted using Chatwoot's visible tombstone payload.
func (s *MessageService) Delete(ctx context.Context, accountID, id uint) (*model.Message, error) {
	return s.DeleteInConversation(ctx, accountID, 0, id)
}

// DeleteInConversation marks a message deleted using Chatwoot's conversation-scoped lookup.
func (s *MessageService) DeleteInConversation(ctx context.Context, accountID, conversationID, id uint) (*model.Message, error) {
	message, err := s.findMessageForConversationRoute(ctx, accountID, conversationID, id)
	if err != nil {
		return nil, err
	}

	message.Content = "This message was deleted"
	message.ContentType = "text"
	message.ContentAttributes = datatypes.JSON([]byte(`{"deleted":true}`))

	if err := s.repo.DB().WithContext(ctx).Transaction(func(tx *gorm.DB) error {
		if err := tx.Save(message).Error; err != nil {
			return err
		}
		if err := tx.Where("message_id = ?", message.ID).Delete(&model.Attachment{}).Error; err != nil {
			return err
		}
		return nil
	}); err != nil {
		return nil, err
	}

	// Dispatch EventMessageDeleted
	if err := s.dispatchMessageEvent(ctx, channel.EventMessageDeleted, message); err != nil {
		return message, err
	}
	s.deleteMessageIndex(ctx, accountID, message.ID)

	return message, nil
}

// UpdateStatus updates the delivery status of a message and dispatches EventMessageStatusUpdated.
func (s *MessageService) UpdateStatus(ctx context.Context, id uint, status string) (*model.Message, error) {
	message, err := s.repo.FindByID(ctx, id)
	if err != nil {
		return nil, err
	}

	message.Status = status

	if err := s.repo.Update(ctx, message); err != nil {
		return nil, err
	}

	s.dispatchMessageStatus(ctx, message, status)
	s.indexMessage(ctx, message)

	return message, nil
}

type ShangwutongMessageResult struct {
	ResultVersion int64
	Status        string
	ExternalID    *string
	ExternalIDs   []string
	ErrorCode     *string
	ErrorMessage  *string
	OccurredAt    time.Time
}

var (
	ErrShangwutongMessageResultConflict = errors.New("shangwutong message result conflicts with the stored result")
	ErrShangwutongMessageNotEligible    = errors.New("message is not eligible for shangwutong result updates")
)

func (s *MessageService) ApplyShangwutongMessageResult(ctx context.Context, accountID, inboxID, messageID uint, result ShangwutongMessageResult) (*model.Message, bool, error) {
	hash, err := shangwutongResultHash(result)
	if err != nil {
		return nil, false, err
	}
	var message model.Message
	applied := false
	err = s.repo.DB().WithContext(ctx).Transaction(func(tx *gorm.DB) error {
		if err := tx.Clauses(clause.Locking{Strength: "UPDATE"}).Where(
			"id = ? AND account_id = ? AND inbox_id = ?", messageID, accountID, inboxID,
		).First(&message).Error; err != nil {
			return err
		}
		if message.External || message.Private || (message.MessageType != "outgoing" && message.MessageType != "template") {
			return ErrShangwutongMessageNotEligible
		}
		attrs := webhookJSONObject(message.ContentAttributes)
		delivery, _ := attrs["swt_delivery"].(map[string]any)
		if delivery == nil {
			delivery = map[string]any{}
		}
		currentVersion := int64ValueFromJSON(delivery["result_version"])
		if result.ResultVersion < currentVersion {
			return nil
		}
		if result.ResultVersion == currentVersion && currentVersion > 0 {
			if storedHash, _ := delivery["request_hash"].(string); storedHash != hash {
				return ErrShangwutongMessageResultConflict
			}
			return nil
		}
		previousCode, _ := delivery["error_code"].(string)
		if message.Status == string(model.MessageStatusSent) && result.Status != string(model.MessageStatusSent) {
			return ErrShangwutongMessageResultConflict
		}
		if message.Status == string(model.MessageStatusFailed) && result.Status == string(model.MessageStatusSent) && previousCode != "uncertain_timeout" {
			return ErrShangwutongMessageResultConflict
		}

		delivery = map[string]any{
			"result_version": result.ResultVersion, "request_hash": hash, "status": result.Status,
			"occurred_at": result.OccurredAt.UTC().Format(time.RFC3339Nano),
		}
		if result.ErrorCode != nil {
			delivery["error_code"] = strings.TrimSpace(*result.ErrorCode)
		}
		if result.ErrorMessage != nil {
			delivery["error_message"] = strings.TrimSpace(*result.ErrorMessage)
		}
		attrs["swt_delivery"] = delivery
		switch result.Status {
		case string(model.MessageStatusSent):
			if message.Status != string(model.MessageStatusDelivered) && message.Status != string(model.MessageStatusRead) {
				message.Status = string(model.MessageStatusSent)
			}
			delete(attrs, "external_error")
			delete(attrs, "external_delivery_state")
		case string(model.MessageStatusFailed):
			message.Status = string(model.MessageStatusFailed)
			errorText := "shangwutong delivery failed"
			if result.ErrorMessage != nil && strings.TrimSpace(*result.ErrorMessage) != "" {
				errorText = strings.TrimSpace(*result.ErrorMessage)
			} else if result.ErrorCode != nil && strings.TrimSpace(*result.ErrorCode) != "" {
				errorText = strings.TrimSpace(*result.ErrorCode)
			}
			attrs["external_error"] = errorText
			delete(attrs, "external_delivery_state")
		case "uncertain":
			message.Status = string(model.MessageStatusProgress)
			attrs["external_delivery_state"] = "uncertain"
			delete(attrs, "external_error")
		default:
			return errors.New("invalid shangwutong result status")
		}
		if result.ExternalID != nil {
			externalIDs := webhookJSONObject(message.ExternalSourceIDs)
			externalIDs["shangwutong"] = mergeShangwutongExternalID(
				externalIDs["shangwutong"], strings.TrimSpace(*result.ExternalID),
			)
			message.ExternalSourceIDs, _ = json.Marshal(externalIDs)
		}
		if len(result.ExternalIDs) > 0 {
			externalIDs := webhookJSONObject(message.ExternalSourceIDs)
			for _, externalID := range result.ExternalIDs {
				externalIDs["shangwutong"] = mergeShangwutongExternalID(
					externalIDs["shangwutong"], strings.TrimSpace(externalID),
				)
			}
			message.ExternalSourceIDs, _ = json.Marshal(externalIDs)
		}
		message.ContentAttributes, _ = json.Marshal(attrs)
		if err := tx.Save(&message).Error; err != nil {
			return err
		}
		applied = true
		return nil
	})
	if err != nil {
		return nil, false, err
	}
	if applied {
		s.dispatchMessageStatus(ctx, &message, message.Status)
		s.indexMessage(ctx, &message)
	}
	return &message, applied, nil
}

func mergeShangwutongExternalID(current any, externalID string) any {
	if externalID == "" {
		return current
	}
	values := make([]string, 0, 2)
	appendUnique := func(value string) {
		value = strings.TrimSpace(value)
		if value == "" {
			return
		}
		for _, existing := range values {
			if existing == value {
				return
			}
		}
		values = append(values, value)
	}
	switch typed := current.(type) {
	case string:
		appendUnique(typed)
	case []any:
		for _, value := range typed {
			if text, ok := value.(string); ok {
				appendUnique(text)
			}
		}
	case []string:
		for _, value := range typed {
			appendUnique(value)
		}
	}
	appendUnique(externalID)
	if len(values) == 1 {
		return values[0]
	}
	return values
}

func shangwutongResultHash(result ShangwutongMessageResult) (string, error) {
	payload := struct {
		ResultVersion int64    `json:"result_version"`
		Status        string   `json:"status"`
		ExternalID    *string  `json:"external_id"`
		ExternalIDs   []string `json:"external_ids,omitempty"`
		ErrorCode     *string  `json:"error_code"`
		ErrorMessage  *string  `json:"error_message"`
		OccurredAt    string   `json:"occurred_at"`
	}{
		ResultVersion: result.ResultVersion, Status: result.Status, ExternalID: result.ExternalID,
		ExternalIDs: result.ExternalIDs,
		ErrorCode:   result.ErrorCode, ErrorMessage: result.ErrorMessage, OccurredAt: result.OccurredAt.UTC().Format(time.RFC3339Nano),
	}
	encoded, err := json.Marshal(payload)
	if err != nil {
		return "", err
	}
	hash := sha256.Sum256(encoded)
	return fmt.Sprintf("%x", hash[:]), nil
}

func (s *MessageService) dispatchMessageStatus(ctx context.Context, message *model.Message, status string) {
	event := channel.NewChannelEvent(channel.EventMessageStatusUpdated, channel.ChannelAPI, message.AccountID, message.InboxID)
	event.ConversationID = message.ConversationID
	if message.SenderID != nil {
		event.UserID = *message.SenderID
	}
	event.Data["message_id"] = message.ID
	event.Data["status"] = status
	applogger.L().Infof("dispatching event %s for message %d, status=%s", channel.EventMessageStatusUpdated, message.ID, status)
	if err := s.dispatcher.Dispatch(ctx, event); err != nil {
		applogger.L().Errorf("failed to dispatch event %s for message %d: %v", channel.EventMessageStatusUpdated, message.ID, err)
	}
}

func (s *MessageService) ListByConversationFinder(ctx context.Context, conversationID uint, after, before uint, filterInternal bool) ([]model.Message, int64, error) {
	return s.repo.FindByConversationFinder(ctx, conversationID, after, before, filterInternal)
}

func validMessageStatus(value string) bool {
	switch value {
	case "progress", "sent", "delivered", "read", "failed":
		return true
	default:
		return false
	}
}

func setMessageExternalError(attrs datatypes.JSON, status, externalError string) datatypes.JSON {
	obj := map[string]any{}
	if len(attrs) > 0 {
		_ = json.Unmarshal(attrs, &obj)
	}
	if status == "failed" && strings.TrimSpace(externalError) != "" {
		obj["external_error"] = externalError
	} else {
		delete(obj, "external_error")
	}
	bytes, _ := json.Marshal(obj)
	return datatypes.JSON(bytes)
}

func attachmentFileType(contentType string) string {
	contentType = strings.ToLower(contentType)
	switch {
	case strings.HasPrefix(contentType, "image/"):
		return "image"
	case strings.HasPrefix(contentType, "audio/"):
		return "audio"
	case strings.HasPrefix(contentType, "video/"):
		return "video"
	default:
		return "file"
	}
}

func attachmentDataURL(messageID uint, fileName string) string {
	fileName = strings.TrimSpace(fileName)
	if fileName == "" {
		return ""
	}
	return fmt.Sprintf("/uploads/messages/%d/%s", messageID, fileName)
}

func attachmentThumbURL(contentType string, messageID uint, fileName string) string {
	if strings.HasPrefix(strings.ToLower(contentType), "image/") {
		return attachmentDataURL(messageID, fileName)
	}
	return ""
}

// Retry retries a failed message by resetting its delivery status.
// Reference: Chatwoot MessagesController#retry sets status to sent, clears
// content_attributes, and queues SendReplyJob.
func (s *MessageService) Retry(ctx context.Context, accountID, id uint) (*model.Message, error) {
	return s.RetryInConversation(ctx, accountID, 0, id)
}

// RetryInConversation retries a failed message scoped to a conversation route.
func (s *MessageService) RetryInConversation(ctx context.Context, accountID, conversationID, id uint) (*model.Message, error) {
	message, err := s.findMessageForConversationRoute(ctx, accountID, conversationID, id)
	if err != nil {
		return nil, err
	}
	var inbox model.Inbox
	if err := s.repo.DB().WithContext(ctx).Select("id", "channel_type").First(&inbox, message.InboxID).Error; err != nil {
		return nil, err
	}
	if strings.EqualFold(inbox.ChannelType, "shangwutong") {
		return s.retryShangwutongMessage(ctx, message)
	}

	message.Status = "sent"
	message.ContentAttributes = datatypes.JSON([]byte(`{}`))

	if err := s.repo.Update(ctx, message); err != nil {
		return nil, err
	}
	if s.worker != nil {
		if _, err := EnqueueSendReply(ctx, s.worker, message.ID); err != nil {
			return nil, err
		}
	}

	event := channel.NewChannelEvent(channel.EventMessageStatusUpdated, channel.ChannelAPI, message.AccountID, message.InboxID)
	event.ConversationID = message.ConversationID
	if message.SenderID != nil {
		event.UserID = *message.SenderID
	}
	event.Data["message_id"] = message.ID
	event.Data["status"] = "sent"
	applogger.L().Infof("dispatching retry event for message %d", message.ID)
	if err := s.dispatcher.Dispatch(ctx, event); err != nil {
		applogger.L().Errorf("failed to dispatch retry event for message %d: %v", message.ID, err)
	}
	s.indexMessage(ctx, message)

	return message, nil
}

func (s *MessageService) retryShangwutongMessage(ctx context.Context, message *model.Message) (*model.Message, error) {
	if message.Status != string(model.MessageStatusFailed) || message.External || message.Private ||
		(message.MessageType != "outgoing" && message.MessageType != "template") {
		return nil, errors.New("only failed non-external shangwutong outgoing messages can be retried")
	}
	attrs := webhookJSONObject(message.ContentAttributes)
	retryVersion := int64ValueFromJSON(attrs["external_retry_version"]) + 1
	attrs["external_retry_version"] = retryVersion
	delete(attrs, "external_error")
	delete(attrs, "external_delivery_state")
	encoded, _ := json.Marshal(attrs)
	message.Status = string(model.MessageStatusProgress)
	message.ContentAttributes = datatypes.JSON(encoded)
	var job *model.BackgroundJob
	var created bool
	err := s.repo.DB().WithContext(ctx).Transaction(func(tx *gorm.DB) error {
		if err := tx.Save(message).Error; err != nil {
			return err
		}
		if s.worker == nil {
			return errors.New("shangwutong webhook worker is unavailable")
		}
		var err error
		job, created, err = s.worker.EnqueueInTransaction(
			ctx, tx, TaskTypeShangwutongWebhookDelivery, newShangwutongMessageJob("message_retry_requested", message, retryVersion),
			worker.WithMaxAttempts(10), worker.WithIdempotencyKey(fmt.Sprintf("api-inbox-message:%d:retry:%d", message.ID, retryVersion)),
		)
		return err
	})
	if err != nil {
		return nil, err
	}
	if created {
		s.worker.Publish(ctx, job)
	}
	s.dispatchMessageStatus(ctx, message, message.Status)
	s.indexMessage(ctx, message)
	return message, nil
}

func int64ValueFromJSON(value any) int64 {
	switch typed := value.(type) {
	case float64:
		return int64(typed)
	case int64:
		return typed
	case int:
		return int64(typed)
	case json.Number:
		result, _ := typed.Int64()
		return result
	default:
		return 0
	}
}

func (s *MessageService) findMessageForConversationRoute(ctx context.Context, accountID, conversationID, id uint) (*model.Message, error) {
	if conversationID == 0 {
		return s.repo.FindByAccountAndID(ctx, accountID, id)
	}
	return s.repo.FindByAccountConversationAndID(ctx, accountID, conversationID, id)
}

// CountByConversation returns the total message count in a conversation.
func (s *MessageService) CountByConversation(ctx context.Context, conversationID uint) (int64, error) {
	return s.repo.CountByConversation(ctx, conversationID)
}

// TranslateMessageRequest is the DTO for translating a message.
type TranslateMessageRequest struct {
	TargetLanguage string `json:"target_language" validate:"required"`
}

// TranslateMessageResult holds the translated message content.
type TranslateMessageResult struct {
	ID                uint   `json:"id"`
	OriginalContent   string `json:"original_content"`
	TranslatedContent string `json:"translated_content"`
	SourceLanguage    string `json:"source_language,omitempty"`
	TargetLanguage    string `json:"target_language"`
	AlreadyTranslated bool   `json:"-"`
}

// Translate translates a message's content to the target language using LLM.
func (s *MessageService) Translate(ctx context.Context, accountID, id uint, req TranslateMessageRequest) (*TranslateMessageResult, error) {
	return s.TranslateInConversation(ctx, accountID, 0, id, req)
}

// TranslateInConversation translates a message scoped to a conversation route and caches the result.
func (s *MessageService) TranslateInConversation(ctx context.Context, accountID, conversationID, id uint, req TranslateMessageRequest) (*TranslateMessageResult, error) {
	ctx = llm.WithAccountFeature(ctx, accountID, "copilot")
	if err := pkgvalidator.ValidateStruct(req); err != nil {
		return nil, err
	}

	message, err := s.findMessageForConversationRoute(ctx, accountID, conversationID, id)
	if err != nil {
		return nil, err
	}
	if translated, ok := messageTranslationForLanguage(message.ContentAttributes, req.TargetLanguage); ok {
		return &TranslateMessageResult{
			ID:                message.ID,
			OriginalContent:   message.Content,
			TranslatedContent: translated,
			TargetLanguage:    req.TargetLanguage,
			AlreadyTranslated: true,
		}, nil
	}

	llmResp, err := s.llmProvider.ChatCompletion(ctx, llm.ChatRequest{
		Messages: []llm.ChatMessage{
			{Role: "system", Content: fmt.Sprintf("You are a translator. Translate the user's message to %s. Return only the translated text, nothing else.", req.TargetLanguage)},
			{Role: "user", Content: message.Content},
		},
	})
	if err != nil {
		applogger.L().Errorf("Translate message LLM: %v", err)
		return nil, fmt.Errorf("translate message: %w", err)
	}

	translated := ""
	if len(llmResp.Choices) > 0 {
		translated = llmResp.Choices[0].Message.Content
	}
	if strings.TrimSpace(translated) != "" {
		message.ContentAttributes = setMessageTranslation(message.ContentAttributes, req.TargetLanguage, translated)
		if err := s.repo.Update(ctx, message); err != nil {
			return nil, err
		}
		s.indexMessage(ctx, message)
	}

	return &TranslateMessageResult{
		ID:                message.ID,
		OriginalContent:   message.Content,
		TranslatedContent: translated,
		TargetLanguage:    req.TargetLanguage,
	}, nil
}

func messageTranslationForLanguage(attrs datatypes.JSON, language string) (string, bool) {
	language = strings.TrimSpace(language)
	if language == "" {
		return "", false
	}
	obj := map[string]any{}
	if len(attrs) == 0 || string(attrs) == "null" {
		return "", false
	}
	if err := json.Unmarshal(attrs, &obj); err != nil {
		return "", false
	}
	translations, ok := obj["translations"].(map[string]any)
	if !ok {
		return "", false
	}
	value, ok := translations[language].(string)
	return value, ok && strings.TrimSpace(value) != ""
}

func setMessageTranslation(attrs datatypes.JSON, language string, translated string) datatypes.JSON {
	obj := map[string]any{}
	if len(attrs) > 0 && string(attrs) != "null" {
		_ = json.Unmarshal(attrs, &obj)
	}
	translations := map[string]any{}
	if existing, ok := obj["translations"].(map[string]any); ok {
		translations = existing
	}
	translations[strings.TrimSpace(language)] = translated
	obj["translations"] = translations
	encoded, err := json.Marshal(obj)
	if err != nil {
		return attrs
	}
	return datatypes.JSON(encoded)
}

// ListAttachments returns paginated attachments for all messages in a conversation.
// Reference: Chatwoot conversations_controller.rb #attachments (member route)
func (s *MessageService) ListAttachments(ctx context.Context, accountID, conversationID uint, offset, limit int) ([]model.Attachment, int64, error) {
	var attachments []model.Attachment
	var total int64

	db := s.repo.DB()
	scope := db.WithContext(ctx).
		Where("account_id = ? AND message_id IN (SELECT id FROM messages WHERE conversation_id = ?)", accountID, conversationID)
	if err := scope.Model(&model.Attachment{}).Count(&total).Error; err != nil {
		return nil, 0, err
	}
	if limit <= 0 {
		limit = 100
	}
	if err := scope.
		Preload("Message").
		Order("created_at DESC, id DESC").
		Offset(offset).
		Limit(limit).
		Find(&attachments).Error; err != nil {
		return nil, 0, err
	}

	return attachments, total, nil
}