diff --git a/backend/application/workflow/chatflow.go b/backend/application/workflow/chatflow.go
index ce308b164f..f33eccd752 100644
--- a/backend/application/workflow/chatflow.go
+++ b/backend/application/workflow/chatflow.go
@@ -52,7 +52,6 @@ import (
 	"github.com/coze-dev/coze-studio/backend/pkg/logs"
 	"github.com/coze-dev/coze-studio/backend/pkg/safego"
 	"github.com/coze-dev/coze-studio/backend/pkg/sonic"
-	"github.com/coze-dev/coze-studio/backend/pkg/taskgroup"
 	"github.com/coze-dev/coze-studio/backend/types/consts"
 	"github.com/coze-dev/coze-studio/backend/types/errno"
 )
@@ -642,6 +641,22 @@ func (w *ApplicationService) OpenAPIChatFlowRun(ctx context.Context, req *workfl
 		sectionID = sID
 	}
 
+	// 先处理历史消息（additional_messages 中除最后一条外的所有消息）
+	// 确保历史消息的 CreatedAt 早于当前用户消息，使 prefetchChatHistory 的跳过逻辑正确工作
+	messageClient := crossmessage.DefaultSVC()
+	historyMessages, err := makeChatFlowHistoryMessages(ctx, bizID, conversationID, userID, sectionID, connectorID, messages[:len(req.GetAdditionalMessages())-1])
+	if err != nil {
+		return nil, err
+	}
+
+	if len(historyMessages) > 0 {
+		_, err := messageClient.BatchCreate(ctx, historyMessages)
+		if err != nil {
+			return nil, err
+		}
+	}
+
+	// 再创建当前轮次的 runRecord 和用户消息
 	runRecord, err := crossagentrun.DefaultSVC().Create(ctx, &agententity.AgentRunMeta{
 		AgentID:        bizID,
 		ConversationID: conversationID,
@@ -660,7 +675,6 @@ func (w *ApplicationService) OpenAPIChatFlowRun(ctx context.Context, req *workfl
 		return nil, err
 	}
 
-	messageClient := crossmessage.DefaultSVC()
 	_, err = messageClient.Create(ctx, userMessage)
 	if err != nil {
 		return nil, err
@@ -743,28 +757,6 @@ func (w *ApplicationService) OpenAPIChatFlowRun(ctx context.Context, req *workfl
 		Cancellable: isDebug,
 	}
 
-	historyMessages, err := makeChatFlowHistoryMessages(ctx, bizID, conversationID, userID, sectionID, connectorID, messages[:len(req.GetAdditionalMessages())-1])
-	if err != nil {
-		return nil, err
-	}
-
-	if len(historyMessages) > 0 {
-		g := taskgroup.NewTaskGroup(ctx, len(historyMessages))
-		for _, hm := range historyMessages {
-			hMsg := hm
-			g.Go(func() error {
-				_, err := messageClient.Create(ctx, hMsg)
-				if err != nil {
-					return err
-				}
-				return nil
-			})
-		}
-		err = g.Wait()
-		if err != nil {
-			logs.CtxWarnf(ctx, "create history message failed, err=%v", err)
-		}
-	}
 	parameters[vo.UserInputKey], err = w.makeChatFlowUserInput(ctx, lastUserMessage)
 	if err != nil {
 		return nil, err
@@ -1226,8 +1218,9 @@ func makeChatFlowHistoryMessages(ctx context.Context, bizID, conversationID, use
 	)
 
 	historyMessages := make([]*message.Message, 0, len(messages))
+	baseTimestamp := time.Now().UnixMilli() - int64(len(messages)*1000)
 
-	for _, msg := range messages {
+	for i, msg := range messages {
 		if msg.Role == userRole {
 			runRecord, err = crossagentrun.DefaultSVC().Create(ctx, &agententity.AgentRunMeta{
 				AgentID:        bizID,
@@ -1253,6 +1246,7 @@ func makeChatFlowHistoryMessages(ctx context.Context, bizID, conversationID, use
 			return nil, err
 		}
 
+		m.CreatedAt = baseTimestamp + int64(i*100)
 		historyMessages = append(historyMessages, m)
 
 	}
@@ -1359,7 +1353,7 @@ func toConversationMessage(ctx context.Context, bizID, cid, userID, roundID, sec
 	}
 	if msg.ContentType == "text" {
 		return &message.Message{
-			Role:           schema.User,
+			Role:           schema.RoleType(msg.Role),
 			ConversationID: cid,
 			AgentID:        bizID,
 			RunID:          roundID,
@@ -1378,7 +1372,7 @@ func toConversationMessage(ctx context.Context, bizID, cid, userID, roundID, sec
 		}
 
 		m := &message.Message{
-			Role:           schema.User,
+			Role:           schema.RoleType(msg.Role),
 			MessageType:    messageType,
 			ConversationID: cid,
 			AgentID:        bizID,