diff --git a/proxy/http/client.go b/proxy/http/client.go
index 2115572a6..318ff3327 100644
--- a/proxy/http/client.go
+++ b/proxy/http/client.go
@@ -4,11 +4,13 @@ package http
 
 import (
 	"bufio"
-	"io"
 	"context"
 	"encoding/base64"
+	"io"
 	"net/http"
 	"strings"
+	"sync"
+	"time"
 
 	"v2ray.com/core"
 	"v2ray.com/core/common"
@@ -123,13 +125,8 @@ func (c *Client) Process(ctx context.Context, link *transport.Link, dialer inter
 	return nil
 }
 
-type tunnelConn struct {
-	internet.Connection
-	header *buf.Buffer
-}
-
 // setUpHTTPTunnel will create a socket tunnel via HTTP CONNECT method
-func setUpHTTPTunnel(conn internet.Connection, destination *net.Destination, user *protocol.MemoryUser) *tunnelConn {
+func setUpHTTPTunnel(conn internet.Connection, destination *net.Destination, user *protocol.MemoryUser) *tunConn {
 	var headers []string
 	destNetAddr := destination.NetAddr()
 	headers = append(headers, "CONNECT "+destNetAddr+" HTTP/1.1")
@@ -143,40 +140,59 @@ func setUpHTTPTunnel(conn internet.Connection, destination *net.Destination, use
 
 	b := buf.New()
 	b.WriteString(strings.Join(headers, "\r\n") + "\r\n\r\n")
-	return &tunnelConn {
-		Connection: conn,
-		header:     b,
-	}
+	return newTunConn(conn, b, 5 * time.Millisecond)
 }
 
-func (c *tunnelConn) Write(b []byte) (n int, err error) {
+// tunConn is a connection that writes header before content,
+// the header will be written during the next Write call or after
+// specified delay.
+type tunConn struct {
+	internet.Connection
+	header *buf.Buffer
+	once   sync.Once
+	timer  *time.Timer
+}
+
+func newTunConn(conn internet.Connection, header *buf.Buffer, delay time.Duration) *tunConn {
+	tc := &tunConn{
+		Connection: conn,
+		header:     header,
+	}
+	if delay > 0 {
+		tc.timer = time.AfterFunc(delay, func() {
+			tc.Write([]byte{})
+		})
+	}
+	return tc
+}
+
+func (c *tunConn) Write(b []byte) (n int, err error) {
+	// fallback to normal write if header is sent
 	if c.header == nil {
 		return c.Connection.Write(b)
 	}
-	buffer := c.header
-	lenheader := c.header.Len()
-	// Concate header and b
-	_, err = buffer.Write(b)
-	if err != nil {
-		c.header.Resize(0, lenheader)
-		return 0, err
-	}
-	// Write buffer
-	nc, err := io.Copy(c.Connection, buffer)
-	if int32(nc) < lenheader {
-		c.header.Resize(int32(nc), lenheader)
-		return 0, err
-	}
-	c.header.Release()
-	c.header = nil
-	n = int(nc) - int(lenheader)
-	if err != nil {
-		return n, err
-	}
-	// Write trailing bytes
-	if n < len(b) {
+	// Prevent timer and writer race condition
+	c.once.Do(func() {
+		if c.timer != nil {
+			c.timer.Stop()
+			c.timer = nil
+		}
+		lenheader := c.header.Len()
+		// Concate header and b
+		common.Must2(c.header.Write(b))
+		// Write buffer
+		var nc int64
+		nc, err = io.Copy(c.Connection, c.header)
+		c.header.Release()
+		c.header = nil
+		n = int(nc) - int(lenheader)
+		if n < 0 { n = 0 }
+		b = b[n:]
+	})
+	// Write Trailing bytes
+	if len(b) > 0 && err == nil {
 		var nw int
-		nw, err = c.Connection.Write(b[:n])
+		nw, err = c.Connection.Write(b)
 		n += nw
 	}
 	return n, err