diff --git a/ext/openssl/openssl.stub.php b/ext/openssl/openssl.stub.php
index 94902a4acf0da..c8c6cb2efc728 100644
--- a/ext/openssl/openssl.stub.php
+++ b/ext/openssl/openssl.stub.php
@@ -181,12 +181,13 @@
  * @cvalue PKCS7_NOCRL
  */
 const PKCS7_NOCRL = UNKNOWN;
+#ifndef OPENSSL_NO_RMD160
 /**
  * @var int
  * @cvalue PKCS7_NO_DUAL_CONTENT
  */
 const PKCS7_NO_DUAL_CONTENT = UNKNOWN;
-
+#endif
 /**
  * @var int
  * @cvalue CMS_DETACHED
diff --git a/ext/openssl/openssl_arginfo.h b/ext/openssl/openssl_arginfo.h
index 796582c185bb6..44410a42b8dc2 100644
--- a/ext/openssl/openssl_arginfo.h
+++ b/ext/openssl/openssl_arginfo.h
@@ -1,5 +1,5 @@
 /* This is a generated file, edit the .stub.php file instead.
- * Stub hash: 8233a8abc8ab7145d905d0fa51478edfe1e55a06 */
+ * Stub hash: ce5290d366b1e0710386453c27539333df270c96 */
 
 ZEND_BEGIN_ARG_WITH_RETURN_TYPE_INFO_EX(arginfo_openssl_x509_export_to_file, 0, 2, _IS_BOOL, 0)
 	ZEND_ARG_OBJ_TYPE_MASK(0, certificate, OpenSSLCertificate, MAY_BE_STRING, NULL)
@@ -589,7 +589,9 @@ static void register_openssl_symbols(int module_number)
 	REGISTER_LONG_CONSTANT("PKCS7_NOSMIMECAP", PKCS7_NOSMIMECAP, CONST_PERSISTENT);
 	REGISTER_LONG_CONSTANT("PKCS7_CRLFEOL", PKCS7_CRLFEOL, CONST_PERSISTENT);
 	REGISTER_LONG_CONSTANT("PKCS7_NOCRL", PKCS7_NOCRL, CONST_PERSISTENT);
+#if !defined(OPENSSL_NO_RMD160)
 	REGISTER_LONG_CONSTANT("PKCS7_NO_DUAL_CONTENT", PKCS7_NO_DUAL_CONTENT, CONST_PERSISTENT);
+#endif
 	REGISTER_LONG_CONSTANT("OPENSSL_CMS_DETACHED", CMS_DETACHED, CONST_PERSISTENT);
 	REGISTER_LONG_CONSTANT("OPENSSL_CMS_TEXT", CMS_TEXT, CONST_PERSISTENT);
 	REGISTER_LONG_CONSTANT("OPENSSL_CMS_NOINTERN", CMS_NOINTERN, CONST_PERSISTENT);
diff --git a/ext/openssl/openssl_backend_v1.c b/ext/openssl/openssl_backend_v1.c
index 81c327dbfe34b..ee5ac85239902 100644
--- a/ext/openssl/openssl_backend_v1.c
+++ b/ext/openssl/openssl_backend_v1.c
@@ -51,8 +51,10 @@ void php_openssl_backend_shutdown(void)
 	/* prevent accessing locking callback from unloaded extension */
 	CRYPTO_set_locking_callback(NULL);
 
+#ifdef HAVE_ENGINE_CLEANUP
 	/* Free engine list initialized by OPENSSL_config */
 	ENGINE_cleanup();
+#endif
 
 	/* free allocated error strings */
 	ERR_free_strings();
diff --git a/ext/standard/config.m4 b/ext/standard/config.m4
index ef6b3c5a01018..896b743bbc5a7 100644
--- a/ext/standard/config.m4
+++ b/ext/standard/config.m4
@@ -383,6 +383,21 @@ AS_VAR_IF([php_cv_func_getifaddrs], [yes],
   [AC_DEFINE([HAVE_GETIFADDRS], [1],
     [Define to 1 if you have the 'getifaddrs' function.])])
 
+dnl Check whether ENGINE_cleanup() exists in the OpenSSL/LibreSSL we build against
+AC_CHECK_HEADERS([openssl/engine.h])
+
+AC_CHECK_FUNCS([ENGINE_cleanup], [], [
+  AC_MSG_CHECKING([for ENGINE_cleanup in libcrypto])
+  AC_LINK_IFELSE(
+    [AC_LANG_PROGRAM(
+      [[#include <openssl/engine.h>]],
+      [[ENGINE_cleanup();]]
+    )],
+    [AC_MSG_RESULT([yes]); AC_DEFINE([HAVE_ENGINE_CLEANUP], [1], [Define if ENGINE_cleanup is available])],
+    [AC_MSG_RESULT([no])]
+  )
+])
+
 dnl
 dnl Setup extension sources
 dnl
diff --git a/ext/standard/config.w32 b/ext/standard/config.w32
index c7c14b8705ca2..af2636a338193 100644
--- a/ext/standard/config.w32
+++ b/ext/standard/config.w32
@@ -19,6 +19,13 @@ ARG_WITH("config-file-scan-dir", "Dir to check for additional php ini files", ""
 AC_DEFINE("PHP_CONFIG_FILE_SCAN_DIR", PHP_CONFIG_FILE_SCAN_DIR);
 AC_DEFINE("PHP_USE_PHP_CRYPT_R", 1, "Define to 1 if PHP uses its own crypt_r, and to 0 if using the external crypt library.");
 
+/* Check whether ENGINE_cleanup() exists in the OpenSSL */
+if (CHECK_HEADER_ADD_INCLUDE("openssl/engine.h", "CFLAGS")) {
+    if (CHECK_FUNC_IN_HEADER("openssl/engine.h", "ENGINE_cleanup", null, "CFLAGS")) {
+        AC_DEFINE("HAVE_ENGINE_CLEANUP", 1, "Define to 1 if ENGINE_cleanup is available.");
+    }
+}
+
 CHECK_HEADER_ADD_INCLUDE("timelib_config.h", "CFLAGS_STANDARD", "ext/date/lib");
 
 ADD_FLAG("LIBS_STANDARD", "iphlpapi.lib");