diff --git a/service/history/replication/executable_task.go b/service/history/replication/executable_task.go
index 02dc6494728..ea0951f959b 100644
--- a/service/history/replication/executable_task.go
+++ b/service/history/replication/executable_task.go
@@ -32,6 +32,7 @@ import (
 
 	commonpb "go.temporal.io/api/common/v1"
 	"go.temporal.io/api/serviceerror"
+
 	"go.temporal.io/server/api/historyservice/v1"
 	"go.temporal.io/server/common"
 	"go.temporal.io/server/common/backoff"
@@ -234,7 +235,7 @@ func (e *ExecutableTaskImpl) Reschedule() {
 
 func (e *ExecutableTaskImpl) IsRetryableError(err error) bool {
 	switch err.(type) {
-	case *serviceerror.InvalidArgument:
+	case *serviceerror.InvalidArgument, *serviceerror.DataLoss:
 		return false
 	default:
 		return true
@@ -355,16 +356,30 @@ func (e *ExecutableTaskImpl) Resend(
 		//  c. attempt failed due to old workflow does not exist
 		//  d. return error to resend new workflow before the branching point
 
+		if resendErr.NamespaceId == retryErr.NamespaceId &&
+			resendErr.WorkflowId == retryErr.WorkflowId &&
+			resendErr.RunId == retryErr.RunId {
+			e.Logger.Error("error resend history on the same workflow run",
+				tag.WorkflowNamespaceID(retryErr.NamespaceId),
+				tag.WorkflowID(retryErr.WorkflowId),
+				tag.WorkflowRunID(retryErr.RunId),
+				tag.NewStringTag("first-resend-error", retryErr.Error()),
+				tag.NewStringTag("second-resend-error", resendErr.Error()),
+			)
+			return false, serviceerror.NewDataLoss("failed to get requested data while resending history")
+		}
 		// handle 2nd resend error, then 1st resend error
-		if _, err := e.Resend(ctx, remoteCluster, resendErr, remainingAttempt); err == nil {
+		_, err := e.Resend(ctx, remoteCluster, resendErr, remainingAttempt)
+		if err == nil {
 			return e.Resend(ctx, remoteCluster, retryErr, remainingAttempt)
 		}
-		e.Logger.Error("error resend history for history event",
-			tag.WorkflowNamespaceID(retryErr.NamespaceId),
-			tag.WorkflowID(retryErr.WorkflowId),
-			tag.WorkflowRunID(retryErr.RunId),
-			tag.Value(retryErr),
-			tag.Error(resendErr),
+		e.Logger.Error("error resend 2nd workflow history for history event",
+			tag.WorkflowNamespaceID(resendErr.NamespaceId),
+			tag.WorkflowID(resendErr.WorkflowId),
+			tag.WorkflowRunID(resendErr.RunId),
+			tag.NewStringTag("first-resend-error", retryErr.Error()),
+			tag.NewStringTag("second-resend-error", resendErr.Error()),
+			tag.Error(err),
 		)
 		return false, resendErr
 	default:
@@ -372,8 +387,8 @@ func (e *ExecutableTaskImpl) Resend(
 			tag.WorkflowNamespaceID(retryErr.NamespaceId),
 			tag.WorkflowID(retryErr.WorkflowId),
 			tag.WorkflowRunID(retryErr.RunId),
-			tag.Value(retryErr),
-			tag.Error(resendErr),
+			tag.NewStringTag("first-resend-error", retryErr.Error()),
+			tag.NewStringTag("second-resend-error", resendErr.Error()),
 		)
 		return false, resendErr
 	}
diff --git a/service/history/replication/executable_task_test.go b/service/history/replication/executable_task_test.go
index 2f7acb1cc5c..4a0c88104b9 100644
--- a/service/history/replication/executable_task_test.go
+++ b/service/history/replication/executable_task_test.go
@@ -37,6 +37,7 @@ import (
 	"github.com/stretchr/testify/suite"
 	commonpb "go.temporal.io/api/common/v1"
 	"go.temporal.io/api/serviceerror"
+
 	"go.temporal.io/server/common/dynamicconfig"
 	"go.temporal.io/server/service/history/configs"
 	"go.temporal.io/server/service/history/replication/eventhandler"
@@ -351,7 +352,7 @@ func (s *executableTaskSuite) TestResend_ResendError_Success() {
 	anotherResendErr := &serviceerrors.RetryReplication{
 		NamespaceId:       resendErr.NamespaceId,
 		WorkflowId:        resendErr.WorkflowId,
-		RunId:             resendErr.RunId,
+		RunId:             uuid.NewString(),
 		StartEventId:      rand.Int63(),
 		StartEventVersion: rand.Int63(),
 		EndEventId:        rand.Int63(),
@@ -414,7 +415,7 @@ func (s *executableTaskSuite) TestResend_ResendError_Error() {
 	anotherResendErr := &serviceerrors.RetryReplication{
 		NamespaceId:       resendErr.NamespaceId,
 		WorkflowId:        resendErr.WorkflowId,
-		RunId:             resendErr.RunId,
+		RunId:             uuid.NewString(),
 		StartEventId:      rand.Int63(),
 		StartEventVersion: rand.Int63(),
 		EndEventId:        rand.Int63(),
@@ -451,6 +452,46 @@ func (s *executableTaskSuite) TestResend_ResendError_Error() {
 	s.False(doContinue)
 }
 
+func (s *executableTaskSuite) TestResend_SecondResendError_SameWorkflowRun() {
+	remoteCluster := cluster.TestAlternativeClusterName
+	resendErr := &serviceerrors.RetryReplication{
+		NamespaceId:       uuid.NewString(),
+		WorkflowId:        uuid.NewString(),
+		RunId:             uuid.NewString(),
+		StartEventId:      rand.Int63(),
+		StartEventVersion: rand.Int63(),
+		EndEventId:        rand.Int63(),
+		EndEventVersion:   rand.Int63(),
+	}
+
+	anotherResendErr := &serviceerrors.RetryReplication{
+		NamespaceId:       resendErr.NamespaceId,
+		WorkflowId:        resendErr.WorkflowId,
+		RunId:             resendErr.RunId,
+		StartEventId:      rand.Int63(),
+		StartEventVersion: rand.Int63(),
+		EndEventId:        rand.Int63(),
+		EndEventVersion:   rand.Int63(),
+	}
+
+	s.ndcHistoryResender.EXPECT().SendSingleWorkflowHistory(
+		gomock.Any(),
+		remoteCluster,
+		namespace.ID(resendErr.NamespaceId),
+		resendErr.WorkflowId,
+		resendErr.RunId,
+		resendErr.StartEventId,
+		resendErr.StartEventVersion,
+		resendErr.EndEventId,
+		resendErr.EndEventVersion,
+	).Return(anotherResendErr)
+
+	doContinue, err := s.task.Resend(context.Background(), remoteCluster, resendErr, ResendAttempt)
+	var dataLossErr *serviceerror.DataLoss
+	s.ErrorAs(err, &dataLossErr)
+	s.False(doContinue)
+}
+
 func (s *executableTaskSuite) TestResend_Error() {
 	remoteCluster := cluster.TestAlternativeClusterName
 	resendErr := &serviceerrors.RetryReplication{