diff --git a/stack_system.go b/stack_system.go
index 62bc9a7..9f32abc 100644
--- a/stack_system.go
+++ b/stack_system.go
@@ -120,8 +120,15 @@ func (s *System) start() error {
 			return nil
 		})
 	}
+	var tcpListener net.Listener
 	if s.inet4Address.IsValid() {
-		tcpListener, err := listener.Listen(s.ctx, "tcp4", net.JoinHostPort(s.inet4ServerAddress.String(), "0"))
+		for i := 0; i < 3; i++ {
+			tcpListener, err = listener.Listen(s.ctx, "tcp4", net.JoinHostPort(s.inet4ServerAddress.String(), "0"))
+			if !retryableListenError(err) {
+				break
+			}
+			time.Sleep(time.Second)
+		}
 		if err != nil {
 			return err
 		}
@@ -130,7 +137,13 @@ func (s *System) start() error {
 		go s.acceptLoop(tcpListener)
 	}
 	if s.inet6Address.IsValid() {
-		tcpListener, err := listener.Listen(s.ctx, "tcp6", net.JoinHostPort(s.inet6ServerAddress.String(), "0"))
+		for i := 0; i < 3; i++ {
+			tcpListener, err = listener.Listen(s.ctx, "tcp6", net.JoinHostPort(s.inet6ServerAddress.String(), "0"))
+			if !retryableListenError(err) {
+				break
+			}
+			time.Sleep(time.Second)
+		}
 		if err != nil {
 			return err
 		}
diff --git a/stack_system_nonwindows.go b/stack_system_nonwindows.go
index 15b8741..822e509 100644
--- a/stack_system_nonwindows.go
+++ b/stack_system_nonwindows.go
@@ -2,6 +2,16 @@
 
 package tun
 
+import (
+	"errors"
+
+	"golang.org/x/sys/unix"
+)
+
 func fixWindowsFirewall() error {
 	return nil
 }
+
+func retryableListenError(err error) bool {
+	return errors.Is(err, unix.EADDRNOTAVAIL)
+}
diff --git a/stack_system_windows.go b/stack_system_windows.go
index 39f1877..ffa2a09 100644
--- a/stack_system_windows.go
+++ b/stack_system_windows.go
@@ -1,10 +1,13 @@
 package tun
 
 import (
+	"errors"
 	"os"
 	"path/filepath"
 
 	"github.com/sagernet/sing-tun/internal/winfw"
+
+	"golang.org/x/sys/windows"
 )
 
 func fixWindowsFirewall() error {
@@ -23,3 +26,7 @@ func fixWindowsFirewall() error {
 	_, err = winfw.FirewallRuleAddAdvanced(rule)
 	return err
 }
+
+func retryableListenError(err error) bool {
+	return errors.Is(err, windows.WSAEADDRNOTAVAIL)
+}