diff --git a/NEWS b/NEWS
index a5605382424..c94a84b1911 100644
--- a/NEWS
+++ b/NEWS
@@ -23,6 +23,7 @@ PHP                                                                        NEWS
 - OpenSSL:
   . Fixed bug GH-21083 (Skip private_key_bits validation for EC/curve-based
     keys). (iliaal)
+  . Fix missing error propagation for BIO_printf() calls. (ndossche)
 
 - PCRE:
   . Fixed re-entrancy issue on php_pcre_match_impl, php_pcre_replace_impl,
diff --git a/ext/openssl/openssl.c b/ext/openssl/openssl.c
index 7e2b9568325..1c1073345a1 100644
--- a/ext/openssl/openssl.c
+++ b/ext/openssl/openssl.c
@@ -5900,16 +5900,21 @@ PHP_FUNCTION(openssl_pkcs7_encrypt)
 	/* tack on extra headers */
 	if (zheaders) {
 		ZEND_HASH_FOREACH_STR_KEY_VAL(Z_ARRVAL_P(zheaders), strindex, zcertval) {
+			int ret;
 			zend_string *str = zval_try_get_string(zcertval);
 			if (UNEXPECTED(!str)) {
 				goto clean_exit;
 			}
 			if (strindex) {
-				BIO_printf(outfile, "%s: %s\n", ZSTR_VAL(strindex), ZSTR_VAL(str));
+				ret = BIO_printf(outfile, "%s: %s\n", ZSTR_VAL(strindex), ZSTR_VAL(str));
 			} else {
-				BIO_printf(outfile, "%s\n", ZSTR_VAL(str));
+				ret = BIO_printf(outfile, "%s\n", ZSTR_VAL(str));
 			}
 			zend_string_release(str);
+			if (ret < 0) {
+				php_openssl_store_errors();
+				goto clean_exit;
+			}
 		} ZEND_HASH_FOREACH_END();
 	}
 
@@ -6128,6 +6133,7 @@ PHP_FUNCTION(openssl_pkcs7_sign)
 			zend_string_release(str);
 			if (ret < 0) {
 				php_openssl_store_errors();
+				goto clean_exit;
 			}
 		} ZEND_HASH_FOREACH_END();
 	}
@@ -6518,16 +6524,21 @@ PHP_FUNCTION(openssl_cms_encrypt)
 	/* tack on extra headers */
 	if (zheaders && encoding == ENCODING_SMIME) {
 		ZEND_HASH_FOREACH_STR_KEY_VAL(Z_ARRVAL_P(zheaders), strindex, zcertval) {
+			int ret;
 			zend_string *str = zval_try_get_string(zcertval);
 			if (UNEXPECTED(!str)) {
 				goto clean_exit;
 			}
 			if (strindex) {
-				BIO_printf(outfile, "%s: %s\n", ZSTR_VAL(strindex), ZSTR_VAL(str));
+				ret = BIO_printf(outfile, "%s: %s\n", ZSTR_VAL(strindex), ZSTR_VAL(str));
 			} else {
-				BIO_printf(outfile, "%s\n", ZSTR_VAL(str));
+				ret = BIO_printf(outfile, "%s\n", ZSTR_VAL(str));
 			}
 			zend_string_release(str);
+			if (ret < 0) {
+				php_openssl_store_errors();
+				goto clean_exit;
+			}
 		} ZEND_HASH_FOREACH_END();
 	}
 
@@ -6807,6 +6818,7 @@ PHP_FUNCTION(openssl_cms_sign)
 			zend_string_release(str);
 			if (ret < 0) {
 				php_openssl_store_errors();
+				goto clean_exit;
 			}
 		} ZEND_HASH_FOREACH_END();
 	}