diff --git a/ext/openssl/openssl.c b/ext/openssl/openssl.c
index 4b4a8d7f35667..6c55e573b89fc 100644
--- a/ext/openssl/openssl.c
+++ b/ext/openssl/openssl.c
@@ -1495,7 +1495,7 @@ PHP_FUNCTION(openssl_x509_export_to_file)
 	}
 
 	if (!php_openssl_check_path(filename, filename_len, file_path, 2)) {
-		return;
+		goto exit_cleanup_cert;
 	}
 
 	bio_out = BIO_new_file(file_path, PHP_OPENSSL_BIO_MODE_W(PKCS7_BINARY));
@@ -1513,13 +1513,14 @@ PHP_FUNCTION(openssl_x509_export_to_file)
 		php_error_docref(NULL, E_WARNING, "Error opening file %s", file_path);
 	}
 
-	if (cert_str) {
-		X509_free(cert);
-	}
-
 	if (!BIO_free(bio_out)) {
 		php_openssl_store_errors();
 	}
+
+exit_cleanup_cert:
+	if (cert_str) {
+		X509_free(cert);
+	}
 }
 /* }}} */
 
@@ -3064,7 +3065,7 @@ PHP_FUNCTION(openssl_csr_export_to_file)
 	}
 
 	if (!php_openssl_check_path(filename, filename_len, file_path, 2)) {
-		return;
+		goto exit_cleanup;
 	}
 
 	bio_out = BIO_new_file(file_path, PHP_OPENSSL_BIO_MODE_W(PKCS7_BINARY));
@@ -3084,6 +3085,7 @@ PHP_FUNCTION(openssl_csr_export_to_file)
 		php_error_docref(NULL, E_WARNING, "Error opening file %s", file_path);
 	}
 
+exit_cleanup:
 	if (csr_str) {
 		X509_REQ_free(csr);
 	}
@@ -4555,7 +4557,7 @@ PHP_FUNCTION(openssl_pkey_export_to_file)
 	}
 
 	if (!php_openssl_check_path(filename, filename_len, file_path, 2)) {
-		RETURN_FALSE;
+		goto clean_exit_key;
 	}
 
 	PHP_SSL_REQ_INIT(&req);
@@ -4591,8 +4593,9 @@ PHP_FUNCTION(openssl_pkey_export_to_file)
 
 clean_exit:
 	PHP_SSL_REQ_DISPOSE(&req);
-	EVP_PKEY_free(key);
 	BIO_free(bio_out);
+clean_exit_key:
+	EVP_PKEY_free(key);
 }
 /* }}} */
 
diff --git a/ext/openssl/tests/openssl_csr_export_to_file_leak.phpt b/ext/openssl/tests/openssl_csr_export_to_file_leak.phpt
new file mode 100644
index 0000000000000..e6ce373d355b1
--- /dev/null
+++ b/ext/openssl/tests/openssl_csr_export_to_file_leak.phpt
@@ -0,0 +1,14 @@
+--TEST--
+openssl_csr_export_to_file memory leak
+--EXTENSIONS--
+openssl
+--FILE--
+<?php
+
+$path = "file://" . __DIR__ . "/cert.csr";
+var_dump(openssl_csr_export_to_file($path, str_repeat("a", 10000)));
+
+?>
+--EXPECTF--
+Warning: openssl_csr_export_to_file(output_filename): must be a valid file path %s
+bool(false)
diff --git a/ext/openssl/tests/openssl_pkey_export_to_file_leak.phpt b/ext/openssl/tests/openssl_pkey_export_to_file_leak.phpt
new file mode 100644
index 0000000000000..5e2bdff6b48fc
--- /dev/null
+++ b/ext/openssl/tests/openssl_pkey_export_to_file_leak.phpt
@@ -0,0 +1,15 @@
+--TEST--
+openssl_pkey_export_to_file memory leak
+--EXTENSIONS--
+openssl
+--FILE--
+<?php
+
+$path = "file://" . __DIR__ . "/private_rsa_1024.key";
+$key = [$path, ""];
+var_dump(openssl_pkey_export_to_file($key, str_repeat("a", 10000), passphrase: ""));
+
+?>
+--EXPECTF--
+Warning: openssl_pkey_export_to_file(output_filename): must be a valid file path %s
+bool(false)
diff --git a/ext/openssl/tests/openssl_x509_export_to_file_leak.phpt b/ext/openssl/tests/openssl_x509_export_to_file_leak.phpt
new file mode 100644
index 0000000000000..5775c2597c3e0
--- /dev/null
+++ b/ext/openssl/tests/openssl_x509_export_to_file_leak.phpt
@@ -0,0 +1,14 @@
+--TEST--
+openssl_x509_export_to_file memory leak
+--EXTENSIONS--
+openssl
+--FILE--
+<?php
+
+$path = "file://" . __DIR__ . "/sni_server_ca.pem";
+var_dump(openssl_x509_export_to_file($path, str_repeat("a", 10000)));
+
+?>
+--EXPECTF--
+Warning: openssl_x509_export_to_file(output_filename): must be a valid file path %s
+bool(false)