diff --git a/cmd/commands/upgrade_win.go b/cmd/commands/upgrade_win.go
index 9c069b6c..c018d61c 100644
--- a/cmd/commands/upgrade_win.go
+++ b/cmd/commands/upgrade_win.go
@@ -20,6 +20,7 @@ package commands
 
 import (
 	"os"
+	"strings"
 	"syscall"
 	"unsafe"
 
@@ -58,11 +59,23 @@ func runAsAdmin() error {
 		return err
 	}
 
+	// Build arguments string from os.Args (skip the executable name)
+	// This ensures all flags like --debug are passed through
+	args := ""
+	if len(os.Args) > 1 {
+		// Join all arguments starting from index 1
+		quotedArgs := make([]string, 0, len(os.Args)-1)
+		for _, arg := range os.Args[1:] {
+			quotedArgs = append(quotedArgs, escapeArg(arg))
+		}
+		args = strings.Join(quotedArgs, " ")
+	}
+
 	verb := "runas"
 	cwd, _ := syscall.UTF16PtrFromString(".")
-	arg, _ := syscall.UTF16PtrFromString(SelfUpgradeName)
+	arg, _ := syscall.UTF16PtrFromString(args)
 	run := windows.NewLazySystemDLL("shell32.dll").NewProc("ShellExecuteW")
-	run.Call(
+	ret, _, _ := run.Call(
 		0,
 		uintptr(unsafe.Pointer(syscall.StringToUTF16Ptr(verb))),
 		uintptr(unsafe.Pointer(syscall.StringToUTF16Ptr(exePath))),
@@ -70,6 +83,55 @@ func runAsAdmin() error {
 		uintptr(unsafe.Pointer(cwd)),
 		1,
 	)
+	// ShellExecuteW returns a value > 32 on success
+	if ret <= 32 {
+		return syscall.Errno(ret)
+	}
+	// Exit the current process since we've successfully launched the elevated one
+	// This function never returns normally after successful elevation
 	os.Exit(0)
-	return nil
+	return nil // unreachable but required for compilation
+}
+
+// escapeArg escapes a command-line argument according to Windows rules.
+// Based on https://docs.microsoft.com/en-us/archive/blogs/twistylittlepassagesallalike/everyone-quotes-command-line-arguments-the-wrong-way
+func escapeArg(arg string) string {
+	// If the argument doesn't contain special characters, return as-is
+	if !strings.ContainsAny(arg, " \t\n\"") {
+		return arg
+	}
+
+	// Build the escaped argument
+	var b strings.Builder
+	b.WriteByte('"')
+
+	for i := 0; i < len(arg); {
+		// Count consecutive backslashes
+		backslashes := 0
+		for i < len(arg) && arg[i] == '\\' {
+			backslashes++
+			i++
+		}
+
+		if i >= len(arg) {
+			// Backslashes at the end need to be doubled (they precede the closing quote)
+			b.WriteString(strings.Repeat("\\", backslashes*2))
+			break
+		}
+
+		if arg[i] == '"' {
+			// Backslashes before a quote need to be doubled, and the quote needs to be escaped
+			b.WriteString(strings.Repeat("\\", backslashes*2))
+			b.WriteString("\\\"")
+			i++
+		} else {
+			// Regular backslashes (not before a quote) are literal
+			b.WriteString(strings.Repeat("\\", backslashes))
+			b.WriteByte(arg[i])
+			i++
+		}
+	}
+
+	b.WriteByte('"')
+	return b.String()
 }