diff --git a/ping/ping.go b/ping/ping.go
index 069cc18..c9fdc52 100644
--- a/ping/ping.go
+++ b/ping/ping.go
@@ -59,28 +59,27 @@ func (c *Conn) isLinuxUnprivileged() bool {
 func (c *Conn) ReadIP(buffer *buf.Buffer) error {
 	if c.destination.Is6() || c.isLinuxUnprivileged() {
 		var readMsg func(b, oob []byte) (n, oobn int, addr netip.Addr, err error)
-		switch conn := c.conn.(type) {
-		case *net.IPConn:
+		if ipConn, isIPConn := common.Cast[*net.IPConn](c.conn); isIPConn {
 			readMsg = func(b, oob []byte) (n, oobn int, addr netip.Addr, err error) {
 				var ipAddr *net.IPAddr
-				n, oobn, _, ipAddr, err = conn.ReadMsgIP(b, oob)
+				n, oobn, _, ipAddr, err = ipConn.ReadMsgIP(b, oob)
 				if err == nil {
 					addr = M.AddrFromNet(ipAddr)
 				}
 				return
 			}
-		case *net.UDPConn:
+		} else if udpConn, isUDPConn := common.Cast[*net.UDPConn](c.conn); isUDPConn {
 			readMsg = func(b, oob []byte) (n, oobn int, addr netip.Addr, err error) {
 				var addrPort netip.AddrPort
-				n, oobn, _, addrPort, err = conn.ReadMsgUDPAddrPort(b, oob)
+				n, oobn, _, addrPort, err = udpConn.ReadMsgUDPAddrPort(b, oob)
 				if err == nil {
 					addr = addrPort.Addr()
 				}
 				return
 			}
-		case *UnprivilegedConn:
-			readMsg = conn.ReadMsg
-		default:
+		} else if unprivilegedConn, isUnprivilegedConn := c.conn.(*UnprivilegedConn); isUnprivilegedConn {
+			readMsg = unprivilegedConn.ReadMsg
+		} else {
 			return E.New("unsupported conn type: ", reflect.TypeOf(c.conn))
 		}
 		if !c.destination.Is6() {
diff --git a/ping/socket_unix.go b/ping/socket_unix.go
index 3e9bc99..1eec10a 100644
--- a/ping/socket_unix.go
+++ b/ping/socket_unix.go
@@ -9,6 +9,7 @@ import (
 	"runtime"
 	"syscall"
 
+	"github.com/sagernet/sing/common/bufio"
 	"github.com/sagernet/sing/common/control"
 	E "github.com/sagernet/sing/common/exceptions"
 	M "github.com/sagernet/sing/common/metadata"
@@ -76,23 +77,34 @@ func connect(privileged bool, controlFunc control.Func, destination netip.Addr)
 
 	var bindAddress netip.Addr
 	if !destination.Is6() {
-		bindAddress = netip.AddrFrom4([4]byte{0, 0, 0, 0})
+		bindAddress = netip.AddrFrom4([4]byte{})
 	} else {
 		bindAddress = netip.AddrFrom16([16]byte{})
 	}
+
 	err = unix.Bind(fd, M.AddrPortToSockaddr(netip.AddrPortFrom(bindAddress, 0)))
 	if err != nil {
 		return nil, err
 	}
 
-	err = unix.Connect(fd, M.AddrPortToSockaddr(netip.AddrPortFrom(destination, 0)))
-	if err != nil {
-		return nil, E.Cause(err, "connect()")
+	if runtime.GOOS == "darwin" && !privileged {
+		// When running in NetworkExtension on macOS, write to connected socket results in EPIPE.
+		var packetConn net.PacketConn
+		packetConn, err = net.FilePacketConn(file)
+		if err != nil {
+			return nil, err
+		}
+		return bufio.NewBindPacketConn(packetConn, M.SocksaddrFrom(destination, 0).UDPAddr()), nil
+	} else {
+		err = unix.Connect(fd, M.AddrPortToSockaddr(netip.AddrPortFrom(destination, 0)))
+		if err != nil {
+			return nil, err
+		}
+		var conn net.Conn
+		conn, err = net.FileConn(file)
+		if err != nil {
+			return nil, err
+		}
+		return conn, nil
 	}
-
-	conn, err := net.FileConn(file)
-	if err != nil {
-		return nil, err
-	}
-	return conn, nil
 }