diff --git a/transport/vless/conn.go b/transport/vless/conn.go
index 0f4d3bf7..aceda463 100644
--- a/transport/vless/conn.go
+++ b/transport/vless/conn.go
@@ -57,9 +57,14 @@ func (vc *Conn) Write(p []byte) (int, error) {
 	select {
 	case <-vc.handshake:
 	default:
-		err := vc.sendRequest(p)
-		if err != nil {
-			return 0, err
+		if vc.sendRequest(p) {
+			if vc.err != nil {
+				return 0, vc.err
+			}
+			return len(p), vc.err
+		}
+		if vc.err != nil {
+			return 0, vc.err
 		}
 	}
 	return vc.ExtendedConn.Write(p)
@@ -69,21 +74,25 @@ func (vc *Conn) WriteBuffer(buffer *buf.Buffer) error {
 	select {
 	case <-vc.handshake:
 	default:
-		err := vc.sendRequest(buffer.Bytes())
-		if err != nil {
-			return err
+		if vc.sendRequest(buffer.Bytes()) {
+			return vc.err
+		}
+		if vc.err != nil {
+			return vc.err
 		}
 	}
 	return vc.ExtendedConn.WriteBuffer(buffer)
 }
 
-func (vc *Conn) sendRequest(p []byte) (err error) {
+func (vc *Conn) sendRequest(p []byte) bool {
 	vc.handshakeMutex.Lock()
 	defer vc.handshakeMutex.Unlock()
 
 	select {
 	case <-vc.handshake:
-		return vc.err
+		// The handshake has been completed before.
+		// So return false to remind the caller.
+		return false
 	default:
 	}
 	defer close(vc.handshake)
@@ -93,9 +102,9 @@ func (vc *Conn) sendRequest(p []byte) (err error) {
 	requestLen += 1  // addons length
 	var addonsBytes []byte
 	if vc.addons != nil {
-		addonsBytes, err = proto.Marshal(vc.addons)
-		if err != nil {
-			return err
+		addonsBytes, vc.err = proto.Marshal(vc.addons)
+		if vc.err != nil {
+			return true
 		}
 	}
 	requestLen += len(addonsBytes)
@@ -137,8 +146,8 @@ func (vc *Conn) sendRequest(p []byte) (err error) {
 
 	buf.Must(buf.Error(buffer.Write(p)))
 
-	_, err = vc.ExtendedConn.Write(buffer.Bytes())
-	return
+	_, vc.err = vc.ExtendedConn.Write(buffer.Bytes())
+	return true
 }
 
 func (vc *Conn) recvResponse() error {
@@ -203,7 +212,7 @@ func newConn(conn net.Conn, client *Client, dst *DstAddr) (*Conn, error) {
 		select {
 		case <-c.handshake:
 		case <-time.After(200 * time.Millisecond):
-			_ = c.sendRequest(nil)
+			c.sendRequest(nil)
 		}
 	}()
 	return c, nil