diff --git a/src/StaticPHP/Util/System/WindowsUtil.php b/src/StaticPHP/Util/System/WindowsUtil.php
index a6df4156..9ed7a7b5 100644
--- a/src/StaticPHP/Util/System/WindowsUtil.php
+++ b/src/StaticPHP/Util/System/WindowsUtil.php
@@ -8,8 +8,10 @@ use StaticPHP\Util\FileSystem;
 
 class WindowsUtil
 {
+    private static array|false|null $vsCache = null;
+
     /**
-     * Find windows program using executable name.
+     * Find Windows program using executable name.
      *
      * @param  string      $name  command name (xxx.exe)
      * @param  array       $paths search path (default use env path)
@@ -39,6 +41,10 @@ class WindowsUtil
      */
     public static function findVisualStudio(): array|false
     {
+        if (self::$vsCache !== null) {
+            return self::$vsCache;
+        }
+
         // call vswhere (need VS and C++ tools installed), output is json
         $vswhere_exec = PKG_ROOT_PATH . DIRECTORY_SEPARATOR . 'bin' . DIRECTORY_SEPARATOR . 'vswhere.exe';
         $args = [
@@ -49,13 +55,13 @@ class WindowsUtil
         $cmd = escapeshellarg($vswhere_exec) . ' ' . implode(' ', $args);
         $result = f_exec($cmd, $out, $code);
         if ($code !== 0 || !$result) {
-            return false;
+            return self::$vsCache = false;
         }
         $json = json_decode(implode("\n", $out), true);
         if (!is_array($json) || count($json) === 0) {
-            return false;
+            return self::$vsCache = false;
         }
-        return [
+        return self::$vsCache = [
             'version' => $json[0]['installationVersion'],
             'major_version' => explode('.', $json[0]['installationVersion'])[0],
             'dir' => $json[0]['installationPath'],
@@ -89,6 +95,7 @@ class WindowsUtil
             $ldflags = '/nodefaultlib:msvcrt /nodefaultlib:msvcrtd /defaultlib:libcmt';
         }
         $buildroot = str_replace('\\', '\\\\', BUILD_ROOT_PATH);
+        $source = str_replace('\\', '/', SOURCE_PATH);
         $toolchain = <<<CMAKE
 set(CMAKE_SYSTEM_NAME Windows)
 SET(CMAKE_SYSTEM_PROCESSOR x64)
@@ -99,11 +106,50 @@ SET(CMAKE_CXX_FLAGS_DEBUG "{$cflags}")
 SET(CMAKE_EXE_LINKER_FLAGS "{$ldflags}")
 SET(CMAKE_FIND_ROOT_PATH "{$buildroot}")
 SET(CMAKE_MSVC_RUNTIME_LIBRARY MultiThreaded)
+list(PREPEND CMAKE_MODULE_PATH "{$source}/cmake-find")
 CMAKE;
         if (!is_dir(SOURCE_PATH)) {
             FileSystem::createDir(SOURCE_PATH);
         }
         FileSystem::writeFile(SOURCE_PATH . '\toolchain.cmake', $toolchain);
+        self::writeCmakeFindModules();
         return realpath(SOURCE_PATH . '\toolchain.cmake');
     }
+
+    /**
+     * Write cmake-find wrapper modules to source/cmake-find/.
+     * These override cmake's built-in Find*.cmake modules to inject
+     * Windows-specific static library dependencies (e.g. zlib into OpenSSL).
+     * Called both from makeCmakeToolchainFile() and from WindowsCMakeExecutor
+     * so the modules are always present even when the static toolchain.cmake
+     * file is used directly without regeneration.
+     */
+    public static function writeCmakeFindModules(): void
+    {
+        $cmake_find_dir = SOURCE_PATH . DIRECTORY_SEPARATOR . 'cmake-find';
+        if (!is_dir($cmake_find_dir)) {
+            FileSystem::createDir($cmake_find_dir);
+        }
+        FileSystem::writeFile($cmake_find_dir . DIRECTORY_SEPARATOR . 'FindOpenSSL.cmake', <<<'CMAKE'
+# Custom FindOpenSSL.cmake wrapper for static-php-cli Windows builds.
+
+if(WIN32 AND (OpenSSL_FOUND OR OPENSSL_FOUND))
+    list(GET CMAKE_FIND_ROOT_PATH 0 _spc_buildroot)
+    # Normalize to forward slashes — backslash paths cause 'Invalid character
+    # escape' errors when cmake parses them inside string arguments.
+    file(TO_CMAKE_PATH "${_spc_buildroot}" _spc_buildroot)
+    set(_spc_zlib "${_spc_buildroot}/lib/zlibstatic.lib")
+    if(EXISTS "${_spc_zlib}")
+        foreach(_spc_var OPENSSL_LIBRARIES OPENSSL_CRYPTO_LIBRARIES OPENSSL_SSL_LIBRARIES)
+            if(DEFINED ${_spc_var} AND NOT "${_spc_zlib}" IN_LIST ${_spc_var})
+                list(APPEND ${_spc_var} "${_spc_zlib}")
+            endif()
+        endforeach()
+    endif()
+    unset(_spc_buildroot)
+    unset(_spc_zlib)
+    unset(_spc_var)
+endif()
+CMAKE);
+    }
 }