diff --git a/network/lwip2transport/udp.go b/network/lwip2transport/udp.go
index 3666d18f..40a48923 100644
--- a/network/lwip2transport/udp.go
+++ b/network/lwip2transport/udp.go
@@ -17,6 +17,7 @@ package lwip2transport
 import (
 	"net"
 	"sync"
+	"sync/atomic"
 
 	"github.com/Jigsaw-Code/outline-internal-sdk/network"
 	lwip "github.com/eycorsican/go-tun2socks/core"
@@ -69,7 +70,10 @@ func (h *udpHandler) ReceiveTo(tunConn lwip.UDPConn, data []byte, destAddr *net.
 // newSession creates a new PacketRequestSender related to conn. The caller needs to put the new PacketRequestSender
 // to the h.senders map.
 func (h *udpHandler) newSession(conn lwip.UDPConn) (network.PacketRequestSender, error) {
-	respWriter := &udpConnResponseWriter{conn, h}
+	respWriter := &udpConnResponseWriter{
+		conn: conn,
+		h:    h,
+	}
 	reqSender, err := h.proxy.NewSession(respWriter)
 	if err != nil {
 		respWriter.Close()
@@ -93,12 +97,17 @@ func (h *udpHandler) closeSession(conn lwip.UDPConn) error {
 
 // The PacketResponseWriter that will write responses to the lwip network stack.
 type udpConnResponseWriter struct {
-	conn lwip.UDPConn
-	h    *udpHandler
+	closed atomic.Bool
+	conn   lwip.UDPConn
+	h      *udpHandler
 }
 
 // Write relays packets from the proxy to the lwIP TUN device.
 func (r *udpConnResponseWriter) WriteFrom(p []byte, source net.Addr) (int, error) {
+	if r.closed.Load() {
+		return 0, network.ErrClosed
+	}
+
 	// net.Addr -> *net.UDPAddr, because r.conn.WriteFrom requires *net.UDPAddr
 	// and this is more reliable than type assertion
 	// also the source address host will be an IP address, no actual resolution will be done
@@ -106,10 +115,14 @@ func (r *udpConnResponseWriter) WriteFrom(p []byte, source net.Addr) (int, error
 	if err != nil {
 		return 0, err
 	}
+
 	return r.conn.WriteFrom(p, srcAddr)
 }
 
 // Close informs the udpHandler to close the UDPConn and clean up the UDP session.
 func (r *udpConnResponseWriter) Close() error {
-	return r.h.closeSession(r.conn)
+	if r.closed.CompareAndSwap(false, true) {
+		return r.h.closeSession(r.conn)
+	}
+	return network.ErrClosed
 }
diff --git a/network/lwip2transport/udp_test.go b/network/lwip2transport/udp_test.go
new file mode 100644
index 00000000..5450f4e8
--- /dev/null
+++ b/network/lwip2transport/udp_test.go
@@ -0,0 +1,87 @@
+// Copyright 2023 Jigsaw Operations LLC
+//
+// Licensed under the Apache License, Version 2.0 (the "License");
+// you may not use this file except in compliance with the License.
+// You may obtain a copy of the License at
+//
+//     https://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing, software
+// distributed under the License is distributed on an "AS IS" BASIS,
+// WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+// See the License for the specific language governing permissions and
+// limitations under the License.
+
+package lwip2transport
+
+import (
+	"errors"
+	"net"
+	"net/netip"
+	"testing"
+
+	"github.com/Jigsaw-Code/outline-internal-sdk/network"
+	"github.com/stretchr/testify/require"
+)
+
+// Make sure we can successfully Close the request sender and response receiver wihout deadlock
+func TestUDPResponseWriterCloseNoDeadlock(t *testing.T) {
+	proxy := &noopSingleSessionPacketProxy{}
+	h := newUDPHandler(proxy)
+
+	// Create one and only one session in the proxy
+	localAddr := net.UDPAddrFromAddrPort(netip.MustParseAddrPort("127.0.0.1:60127"))
+	destAddr := net.UDPAddrFromAddrPort(netip.MustParseAddrPort("1.2.3.4:4321"))
+	err := h.ReceiveTo(&noopLwIPUDPConn{localAddr}, []byte{}, destAddr)
+	require.NoError(t, err)
+
+	// Close this single session (i.e. the request sender), it will close proxy.respWriter
+	// udpHandler must make sure only one `Close()` is called, and there should be no deadlocks
+	err = proxy.respWriter.Close()
+	require.NoError(t, err)
+	require.Exactly(t, 1, proxy.closeCnt)
+}
+
+/********** Test Utilities **********/
+
+type noopSingleSessionPacketProxy struct {
+	closeCnt   int
+	respWriter network.PacketResponseReceiver
+}
+
+func (p *noopSingleSessionPacketProxy) NewSession(respWriter network.PacketResponseReceiver) (network.PacketRequestSender, error) {
+	if p.respWriter != nil {
+		return nil, errors.New("don't support multiple sessions in this proxy")
+	}
+	p.respWriter = respWriter
+	return p, nil
+}
+
+func (p *noopSingleSessionPacketProxy) Close() error {
+	p.closeCnt++
+	return p.respWriter.Close()
+}
+
+func (p *noopSingleSessionPacketProxy) WriteTo([]byte, netip.AddrPort) (int, error) {
+	return 0, nil
+}
+
+type noopLwIPUDPConn struct {
+	localAddr *net.UDPAddr
+}
+
+func (*noopLwIPUDPConn) Close() error {
+	return nil
+}
+
+func (conn *noopLwIPUDPConn) LocalAddr() *net.UDPAddr {
+	return conn.localAddr
+}
+
+func (*noopLwIPUDPConn) ReceiveTo(data []byte, addr *net.UDPAddr) error {
+	return nil
+}
+
+func (*noopLwIPUDPConn) WriteFrom(data []byte, addr *net.UDPAddr) (int, error) {
+	return 0, nil
+}