diff --git a/ext/openssl/ossl_x509cert.c b/ext/openssl/ossl_x509cert.c
index 996f184170..9443541645 100644
--- a/ext/openssl/ossl_x509cert.c
+++ b/ext/openssl/ossl_x509cert.c
@@ -642,12 +642,12 @@ ossl_x509_set_extensions(VALUE self, VALUE ary)
 	OSSL_Check_Kind(RARRAY_AREF(ary, i), cX509Ext);
     }
     GetX509(self, x509);
-    while ((ext = X509_delete_ext(x509, 0)))
-	X509_EXTENSION_free(ext);
+    for (i = X509_get_ext_count(x509); i > 0; i--)
+        X509_EXTENSION_free(X509_delete_ext(x509, 0));
     for (i=0; i<RARRAY_LEN(ary); i++) {
 	ext = GetX509ExtPtr(RARRAY_AREF(ary, i));
 	if (!X509_add_ext(x509, ext, -1)) { /* DUPs ext */
-	    ossl_raise(eX509CertError, NULL);
+	    ossl_raise(eX509CertError, "X509_add_ext");
 	}
     }
 
diff --git a/ext/openssl/ossl_x509crl.c b/ext/openssl/ossl_x509crl.c
index 863f0286c0..6c1d915370 100644
--- a/ext/openssl/ossl_x509crl.c
+++ b/ext/openssl/ossl_x509crl.c
@@ -474,12 +474,12 @@ ossl_x509crl_set_extensions(VALUE self, VALUE ary)
 	OSSL_Check_Kind(RARRAY_AREF(ary, i), cX509Ext);
     }
     GetX509CRL(self, crl);
-    while ((ext = X509_CRL_delete_ext(crl, 0)))
-	X509_EXTENSION_free(ext);
+    for (i = X509_CRL_get_ext_count(crl); i > 0; i--)
+        X509_EXTENSION_free(X509_CRL_delete_ext(crl, 0));
     for (i=0; i<RARRAY_LEN(ary); i++) {
 	ext = GetX509ExtPtr(RARRAY_AREF(ary, i)); /* NO NEED TO DUP */
 	if (!X509_CRL_add_ext(crl, ext, -1)) {
-	    ossl_raise(eX509CRLError, NULL);
+	    ossl_raise(eX509CRLError, "X509_CRL_add_ext");
 	}
     }
 
diff --git a/ext/openssl/ossl_x509req.c b/ext/openssl/ossl_x509req.c
index 6eb91e9c2f..77a7d3f2ff 100644
--- a/ext/openssl/ossl_x509req.c
+++ b/ext/openssl/ossl_x509req.c
@@ -380,13 +380,13 @@ ossl_x509req_set_attributes(VALUE self, VALUE ary)
 	OSSL_Check_Kind(RARRAY_AREF(ary, i), cX509Attr);
     }
     GetX509Req(self, req);
-    while ((attr = X509_REQ_delete_attr(req, 0)))
-	X509_ATTRIBUTE_free(attr);
+    for (i = X509_REQ_get_attr_count(req); i > 0; i--)
+        X509_ATTRIBUTE_free(X509_REQ_delete_attr(req, 0));
     for (i=0;i<RARRAY_LEN(ary); i++) {
 	item = RARRAY_AREF(ary, i);
 	attr = GetX509AttrPtr(item);
 	if (!X509_REQ_add1_attr(req, attr)) {
-	    ossl_raise(eX509ReqError, NULL);
+	    ossl_raise(eX509ReqError, "X509_REQ_add1_attr");
 	}
     }
     return ary;
diff --git a/ext/openssl/ossl_x509revoked.c b/ext/openssl/ossl_x509revoked.c
index 5fe6853430..10b8aa4ad6 100644
--- a/ext/openssl/ossl_x509revoked.c
+++ b/ext/openssl/ossl_x509revoked.c
@@ -223,13 +223,13 @@ ossl_x509revoked_set_extensions(VALUE self, VALUE ary)
 	OSSL_Check_Kind(RARRAY_AREF(ary, i), cX509Ext);
     }
     GetX509Rev(self, rev);
-    while ((ext = X509_REVOKED_delete_ext(rev, 0)))
-	X509_EXTENSION_free(ext);
+    for (i = X509_REVOKED_get_ext_count(rev); i > 0; i--)
+        X509_EXTENSION_free(X509_REVOKED_delete_ext(rev, 0));
     for (i=0; i<RARRAY_LEN(ary); i++) {
 	item = RARRAY_AREF(ary, i);
 	ext = GetX509ExtPtr(item);
 	if(!X509_REVOKED_add_ext(rev, ext, -1)) {
-	    ossl_raise(eX509RevError, NULL);
+	    ossl_raise(eX509RevError, "X509_REVOKED_add_ext");
 	}
     }