diff --git a/listener/sing_tun/server.go b/listener/sing_tun/server.go
index f948320a..44824b75 100644
--- a/listener/sing_tun/server.go
+++ b/listener/sing_tun/server.go
@@ -182,7 +182,7 @@ func New(options config.Tun, tcpIn chan<- C.ConnContext, udpIn chan<- *inbound.P
 		err = E.Cause(err, "build android rules")
 		return
 	}
-	tunIf, err := tun.Open(tunOptions)
+	tunIf, err := tunOpen(tunOptions)
 	if err != nil {
 		err = E.Cause(err, "configure tun interface")
 		return
diff --git a/listener/sing_tun/server_other.go b/listener/sing_tun/server_notandroid.go
similarity index 100%
rename from listener/sing_tun/server_other.go
rename to listener/sing_tun/server_notandroid.go
diff --git a/listener/sing_tun/server_notwindows.go b/listener/sing_tun/server_notwindows.go
new file mode 100644
index 00000000..27872d8e
--- /dev/null
+++ b/listener/sing_tun/server_notwindows.go
@@ -0,0 +1,11 @@
+//go:build !windows
+
+package sing_tun
+
+import (
+	tun "github.com/sagernet/sing-tun"
+)
+
+func tunOpen(options tun.Options) (tun.Tun, error) {
+	return tun.Open(options)
+}
diff --git a/listener/sing_tun/server_windows.go b/listener/sing_tun/server_windows.go
index 33f3ff19..20fc7031 100644
--- a/listener/sing_tun/server_windows.go
+++ b/listener/sing_tun/server_windows.go
@@ -1,6 +1,29 @@
 package sing_tun
 
-import tun "github.com/sagernet/sing-tun"
+import (
+	"time"
+
+	"github.com/Dreamacro/clash/log"
+
+	tun "github.com/sagernet/sing-tun"
+)
+
+func tunOpen(options tun.Options) (tunIf tun.Tun, err error) {
+	maxRetry := 3
+	for i := 0; i < maxRetry; i++ {
+		timeBegin := time.Now()
+		tunIf, err = tun.Open(options)
+		if err == nil {
+			return
+		}
+		timeEnd := time.Now()
+		if timeEnd.Sub(timeBegin) < 1*time.Second { // retrying for "Cannot create a file when that file already exists."
+			return
+		}
+		log.Warnln("Start Tun interface timeout: %s [retrying %d/%d]", err, i+1, maxRetry)
+	}
+	return
+}
 
 func init() {
 	tun.TunnelType = InterfaceName