diff --git a/NEWS b/NEWS
index fa0a98a01c6..a021293adc1 100644
--- a/NEWS
+++ b/NEWS
@@ -36,6 +36,8 @@ PHP                                                                        NEWS
     (Girgias)
   . Implement #80495 (Enable to set padding in openssl_(sign|verify).
     (Jakub Zelenka)
+  . Implement #47728 (openssl_pkcs7_sign ignores new openssl flags).
+    (Jakub Zelenka)
 
 - PDO:
   . The "uri:" DSN scheme has been deprecated due to security concerns with
diff --git a/UPGRADING b/UPGRADING
index c95ed92f6da..1d5b2b8ede4 100644
--- a/UPGRADING
+++ b/UPGRADING
@@ -674,6 +674,10 @@ PHP 8.5 UPGRADE NOTES
 
 - OpenSSL:
   . OPENSSL_PKCS1_PSS_PADDING
+  . PKCS7_NOSMIMECAP
+  . PKCS7_CRLFEOL
+  . PKCS7_NOCRL
+  . PKCS7_NO_DUAL_CONTENT
 
 - POSIX:
   . POSIX_SC_OPEN_MAX.
diff --git a/ext/openssl/openssl.stub.php b/ext/openssl/openssl.stub.php
index a7d1a5cda6e..4950000c775 100644
--- a/ext/openssl/openssl.stub.php
+++ b/ext/openssl/openssl.stub.php
@@ -166,6 +166,26 @@ const PKCS7_NOSIGS = UNKNOWN;
  * @cvalue PKCS7_NOOLDMIMETYPE
  */
 const PKCS7_NOOLDMIMETYPE = UNKNOWN;
+/**
+ * @var int
+ * @cvalue PKCS7_NOSMIMECAP
+ */
+const PKCS7_NOSMIMECAP = UNKNOWN;
+/**
+ * @var int
+ * @cvalue PKCS7_CRLFEOL
+ */
+const PKCS7_CRLFEOL = UNKNOWN;
+/**
+ * @var int
+ * @cvalue PKCS7_NOCRL
+ */
+const PKCS7_NOCRL = UNKNOWN;
+/**
+ * @var int
+ * @cvalue PKCS7_NO_DUAL_CONTENT
+ */
+const PKCS7_NO_DUAL_CONTENT = UNKNOWN;
 
 /**
  * @var int
diff --git a/ext/openssl/openssl_arginfo.h b/ext/openssl/openssl_arginfo.h
index 22b4f10dfab..c032b7543a3 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: ff620528ee3035e295099637cc9f94b78a53416b */
+ * Stub hash: 03e511abb97901a4a8268276b809b3cf7afbfa29 */
 
 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)
@@ -586,6 +586,10 @@ static void register_openssl_symbols(int module_number)
 	REGISTER_LONG_CONSTANT("PKCS7_BINARY", PKCS7_BINARY, CONST_PERSISTENT);
 	REGISTER_LONG_CONSTANT("PKCS7_NOSIGS", PKCS7_NOSIGS, CONST_PERSISTENT);
 	REGISTER_LONG_CONSTANT("PKCS7_NOOLDMIMETYPE", PKCS7_NOOLDMIMETYPE, CONST_PERSISTENT);
+	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);
+	REGISTER_LONG_CONSTANT("PKCS7_NO_DUAL_CONTENT", PKCS7_NO_DUAL_CONTENT, CONST_PERSISTENT);
 	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);