diff --git a/cmd/tun2socks/main.go b/cmd/tun2socks/main.go
index 12d29782..645180ef 100644
--- a/cmd/tun2socks/main.go
+++ b/cmd/tun2socks/main.go
@@ -1,6 +1,7 @@
 package main
 
 import (
+	"bufio"
 	"flag"
 	"fmt"
 	"io"
@@ -75,7 +76,7 @@ func (a *CmdArgs) addFlag(f cmdFlag) {
 	if fn, found := flagCreaters[f]; found && fn != nil {
 		fn()
 	} else {
-		log.Fatalf("unsupported flag")
+		fatal("unsupported flag")
 	}
 }
 
@@ -85,6 +86,22 @@ const (
 	maxMTU = 65535
 )
 
+func fatal(err interface{}) {
+	if runtime.GOOS == "windows" {
+		// Escalated privileges in windows opens a new terminal, and if there is an
+		// error, it is impossible to see it. Thus we wait for user to press a button.
+		log.Errorf("%s, press enter to exit", err)
+		bufio.NewReader(os.Stdin).ReadBytes('\n')
+		os.Exit(1)
+	}
+	switch err := err.(type) {
+	case error:
+		log.Fatalf(err.Error())
+	case string:
+		log.Fatalf(err)
+	}
+}
+
 func main() {
 	// linux and darwin pick up the tun index automatically
 	// windows requires the exact tun name
@@ -116,6 +133,10 @@ func main() {
 		os.Exit(0)
 	}
 
+	if err := checkPermissions(); err != nil {
+		fatal(err)
+	}
+
 	if *args.TunMTU > maxMTU {
 		fmt.Printf("MTU exceeds %d\n", maxMTU)
 		os.Exit(1)
@@ -146,7 +167,7 @@ func main() {
 
 	err := run()
 	if err != nil {
-		log.Fatalf("%v", err)
+		fatal(err)
 	}
 }
 
diff --git a/cmd/tun2socks/root_others.go b/cmd/tun2socks/root_others.go
new file mode 100644
index 00000000..881c37f3
--- /dev/null
+++ b/cmd/tun2socks/root_others.go
@@ -0,0 +1,15 @@
+// +build !windows
+
+package main
+
+import (
+	"fmt"
+	"os"
+)
+
+func checkPermissions() error {
+	if uid := os.Getuid(); uid != 0 {
+		return fmt.Errorf("tun2socks needs to run as root")
+	}
+	return nil
+}
diff --git a/cmd/tun2socks/root_windows.go b/cmd/tun2socks/root_windows.go
new file mode 100644
index 00000000..9da0022d
--- /dev/null
+++ b/cmd/tun2socks/root_windows.go
@@ -0,0 +1,56 @@
+// +build windows
+
+package main
+
+import (
+	"fmt"
+	"os"
+	"path/filepath"
+
+	"golang.org/x/sys/windows"
+)
+
+const (
+	winTun     = "wintun.dll"
+	winTunSite = "https://www.wintun.net/"
+)
+
+func checkPermissions() error {
+	// https://github.com/golang/go/issues/28804#issuecomment-505326268
+	var sid *windows.SID
+
+	// https://docs.microsoft.com/en-us/windows/desktop/api/securitybaseapi/nf-securitybaseapi-checktokenmembership
+	err := windows.AllocateAndInitializeSid(
+		&windows.SECURITY_NT_AUTHORITY,
+		2,
+		windows.SECURITY_BUILTIN_DOMAIN_RID,
+		windows.DOMAIN_ALIAS_RID_ADMINS,
+		0, 0, 0, 0, 0, 0,
+		&sid)
+	if err != nil {
+		return fmt.Errorf("error while checking for elevated permissions: %s", err)
+	}
+
+	// We must free the sid to prevent security token leaks
+	defer windows.FreeSid(sid)
+	token := windows.Token(0)
+
+	member, err := token.IsMember(sid)
+	if err != nil {
+		return fmt.Errorf("error while checking for elevated permissions: %s", err)
+	}
+	if !member {
+		return fmt.Errorf("tun2socks needs to run with administrator permissions")
+	}
+
+	err = windows.NewLazyDLL(winTun).Load()
+	if err != nil {
+		dir, err := filepath.Abs(filepath.Dir(os.Args[0]))
+		if err != nil {
+			dir = "tun2socks"
+		}
+		return fmt.Errorf("the %s was not found, you can download it from %s and place it into the %q directory", winTun, winTunSite, dir)
+	}
+
+	return nil
+}
diff --git a/cmd/tun2socks/tun2socks.manifest b/cmd/tun2socks/tun2socks.manifest
new file mode 100644
index 00000000..20f793a6
--- /dev/null
+++ b/cmd/tun2socks/tun2socks.manifest
@@ -0,0 +1,16 @@
+<?xml version="1.0" encoding="UTF-8" standalone="yes"?>
+<assembly xmlns="urn:schemas-microsoft-com:asm.v1" manifestVersion="1.0">
+<assemblyIdentity
+    version="6.0.0.0"
+    name="org.eycorsican.tun2socks"
+    type="win32"
+/>
+<description>tun2socks requires Administrator privileges</description>
+<trustInfo xmlns="urn:schemas-microsoft-com:asm.v3">
+    <security>
+        <requestedPrivileges>
+            <requestedExecutionLevel level="requireAdministrator" uiAccess="false"/>
+        </requestedPrivileges>
+    </security>
+</trustInfo>
+</assembly>
diff --git a/cmd/tun2socks/tun2socks_windows.syso b/cmd/tun2socks/tun2socks_windows.syso
new file mode 100644
index 00000000..f310342d
Binary files /dev/null and b/cmd/tun2socks/tun2socks_windows.syso differ