diff --git a/common/net/sing.go b/common/net/sing.go
index 7eb92f03..aa6f6917 100644
--- a/common/net/sing.go
+++ b/common/net/sing.go
@@ -23,7 +23,7 @@ func NewDeadlineConn(conn net.Conn) ExtendedConn {
 	return deadline.NewFallbackConn(conn)
 }
 
-func NewDeadlinePacketConn(pc net.PacketConn) net.PacketConn {
+func NewDeadlinePacketConn(pc net.PacketConn) network.NetPacketConn {
 	return deadline.NewFallbackPacketConn(bufio.NewPacketConn(pc))
 }
 
diff --git a/listener/sing/sing.go b/listener/sing/sing.go
index 2ccdfe2d..4a86dc82 100644
--- a/listener/sing/sing.go
+++ b/listener/sing/sing.go
@@ -18,6 +18,7 @@ import (
 	mux "github.com/sagernet/sing-mux"
 	vmess "github.com/sagernet/sing-vmess"
 	"github.com/sagernet/sing/common/buf"
+	"github.com/sagernet/sing/common/bufio"
 	"github.com/sagernet/sing/common/bufio/deadline"
 	E "github.com/sagernet/sing/common/exceptions"
 	M "github.com/sagernet/sing/common/metadata"
@@ -104,6 +105,9 @@ func (h *ListenerHandler) NewPacketConnection(ctx context.Context, conn network.
 		additions = slices.Clone(additions)
 		additions = append(additions, ctxAdditions...)
 	}
+	if deadline.NeedAdditionalReadDeadline(conn) {
+		conn = N.NewDeadlinePacketConn(bufio.NewNetPacketConn(conn)) // conn from sing should check NeedAdditionalReadDeadline
+	}
 	defer func() { _ = conn.Close() }()
 	mutex := sync.Mutex{}
 	conn2 := conn // a new interface to set nil in defer