openssl 2.2.1 → 3.2.0

data/ext/openssl/ossl_ssl_session.c

@@ -4,6 +4,7 @@
 
 #include "ossl.h"
 
+#ifndef OPENSSL_NO_SOCK
 VALUE cSSLSession;
 static VALUE eSSLSession;
 
@@ -18,7 +19,7 @@ const rb_data_type_t ossl_ssl_session_type = {
     {
 	0, ossl_ssl_session_free,
     },
-    0, 0, RUBY_TYPED_FREE_IMMEDIATELY,
+    0, 0, RUBY_TYPED_FREE_IMMEDIATELY | RUBY_TYPED_WB_PROTECTED,
 };
 
 static VALUE ossl_ssl_session_alloc(VALUE klass)
@@ -34,43 +35,38 @@ static VALUE ossl_ssl_session_alloc(VALUE klass)
  * Creates a new Session object from an instance of SSLSocket or DER/PEM encoded
  * String.
  */
-static VALUE ossl_ssl_session_initialize(VALUE self, VALUE arg1)
+static VALUE
+ossl_ssl_session_initialize(VALUE self, VALUE arg1)
 {
-	SSL_SESSION *ctx = NULL;
-
-	if (RDATA(self)->data)
-		ossl_raise(eSSLSession, "SSL Session already initialized");
-
-	if (rb_obj_is_instance_of(arg1, cSSLSocket)) {
-		SSL *ssl;
-
-		GetSSL(arg1, ssl);
-
-		if ((ctx = SSL_get1_session(ssl)) == NULL)
-			ossl_raise(eSSLSession, "no session available");
-	} else {
-		BIO *in = ossl_obj2bio(&arg1);
+    SSL_SESSION *ctx;
 
-		ctx = PEM_read_bio_SSL_SESSION(in, NULL, NULL, NULL);
+    if (RTYPEDDATA_DATA(self))
+        ossl_raise(eSSLSession, "SSL Session already initialized");
 
-		if (!ctx) {
-		        OSSL_BIO_reset(in);
-			ctx = d2i_SSL_SESSION_bio(in, NULL);
-		}
+    if (rb_obj_is_instance_of(arg1, cSSLSocket)) {
+        SSL *ssl;
 
-		BIO_free(in);
+        GetSSL(arg1, ssl);
 
-		if (!ctx)
-			ossl_raise(rb_eArgError, "unknown type");
-	}
+        if ((ctx = SSL_get1_session(ssl)) == NULL)
+            ossl_raise(eSSLSession, "no session available");
+    }
+    else {
+        BIO *in = ossl_obj2bio(&arg1);
 
-	/* should not happen */
-	if (ctx == NULL)
-		ossl_raise(eSSLSession, "ctx not set - internal error");
+        ctx = d2i_SSL_SESSION_bio(in, NULL);
+        if (!ctx) {
+            OSSL_BIO_reset(in);
+            ctx = PEM_read_bio_SSL_SESSION(in, NULL, NULL, NULL);
+        }
+        BIO_free(in);
+        if (!ctx)
+            ossl_raise(rb_eArgError, "unknown type");
+    }
 
-	RDATA(self)->data = ctx;
+    RTYPEDDATA_DATA(self) = ctx;
 
-	return self;
+    return self;
 }
 
 static VALUE
@@ -304,6 +300,7 @@ static VALUE ossl_ssl_session_to_text(VALUE self)
 	return ossl_membio2str(out);
 }
 
+#endif /* !defined(OPENSSL_NO_SOCK) */
 
 void Init_ossl_ssl_session(void)
 {
@@ -312,6 +309,7 @@ void Init_ossl_ssl_session(void)
     mSSL = rb_define_module_under(mOSSL, "SSL");
     eOSSLError = rb_define_class_under(mOSSL, "OpenSSLError", rb_eStandardError);
 #endif
+#ifndef OPENSSL_NO_SOCK
 	cSSLSession = rb_define_class_under(mSSL, "Session", rb_cObject);
 	eSSLSession = rb_define_class_under(cSSLSession, "SessionError", eOSSLError);
 
@@ -329,4 +327,5 @@ void Init_ossl_ssl_session(void)
 	rb_define_method(cSSLSession, "to_der", ossl_ssl_session_to_der, 0);
 	rb_define_method(cSSLSession, "to_pem", ossl_ssl_session_to_pem, 0);
 	rb_define_method(cSSLSession, "to_text", ossl_ssl_session_to_text, 0);
+#endif /* !defined(OPENSSL_NO_SOCK) */
 }

data/ext/openssl/ossl_ts.c

@@ -83,7 +83,7 @@ static const rb_data_type_t ossl_ts_req_type = {
     {
         0, ossl_ts_req_free,
     },
-    0, 0, RUBY_TYPED_FREE_IMMEDIATELY,
+    0, 0, RUBY_TYPED_FREE_IMMEDIATELY | RUBY_TYPED_WB_PROTECTED,
 };
 
 static void
@@ -97,7 +97,7 @@ static  const rb_data_type_t ossl_ts_resp_type = {
     {
         0, ossl_ts_resp_free,
     },
-    0, 0, RUBY_TYPED_FREE_IMMEDIATELY,
+    0, 0, RUBY_TYPED_FREE_IMMEDIATELY | RUBY_TYPED_WB_PROTECTED,
 };
 
 static void
@@ -111,7 +111,7 @@ static const rb_data_type_t ossl_ts_token_info_type = {
     {
         0, ossl_ts_token_info_free,
     },
-    0, 0, RUBY_TYPED_FREE_IMMEDIATELY,
+    0, 0, RUBY_TYPED_FREE_IMMEDIATELY | RUBY_TYPED_WB_PROTECTED,
 };
 
 static VALUE
@@ -145,6 +145,12 @@ obj_to_asn1obj(VALUE obj)
     return a1obj;
 }
 
+static VALUE
+obj_to_asn1obj_i(VALUE obj)
+{
+    return (VALUE)obj_to_asn1obj(obj);
+}
+
 static VALUE
 get_asn1obj(ASN1_OBJECT *obj)
 {
@@ -820,17 +826,14 @@ ossl_ts_resp_verify(int argc, VALUE *argv, VALUE self)
         X509_up_ref(cert);
     }
 
-    TS_VERIFY_CTS_set_certs(ctx, x509inter);
+    TS_VERIFY_CTX_set_certs(ctx, x509inter);
     TS_VERIFY_CTX_add_flags(ctx, TS_VFY_SIGNATURE);
     TS_VERIFY_CTX_set_store(ctx, x509st);
 
     ok = TS_RESP_verify_response(ctx, resp);
-
-    /* WORKAROUND:
-     *   X509_STORE can count references, but X509_STORE_free() doesn't check
-     *   this. To prevent our X509_STORE from being freed with our
-     *   TS_VERIFY_CTX we set the store to NULL first.
-     *   Fixed in OpenSSL 1.0.2; bff9ce4db38b (master), 5b4b9ce976fc (1.0.2)
+    /*
+     * TS_VERIFY_CTX_set_store() call above does not increment the reference
+     * counter, so it must be unset before TS_VERIFY_CTX_free() is called.
      */
     TS_VERIFY_CTX_set_store(ctx, NULL);
     TS_VERIFY_CTX_free(ctx);
@@ -1091,6 +1094,18 @@ ossl_tsfac_time_cb(struct TS_resp_ctx *ctx, void *data, time_t *sec, long *usec)
     return 1;
 }
 
+static VALUE
+ossl_evp_get_digestbyname_i(VALUE arg)
+{
+    return (VALUE)ossl_evp_get_digestbyname(arg);
+}
+
+static VALUE
+ossl_obj2bio_i(VALUE arg)
+{
+    return (VALUE)ossl_obj2bio((VALUE *)arg);
+}
+
 /*
  * Creates a Response with the help of an OpenSSL::PKey, an
  * OpenSSL::X509::Certificate and a Request.
@@ -1159,7 +1174,7 @@ ossl_tsfac_create_ts(VALUE self, VALUE key, VALUE certificate, VALUE request)
         goto end;
     }
     if (!NIL_P(def_policy_id) && !TS_REQ_get_policy_id(req)) {
-        def_policy_id_obj = (ASN1_OBJECT*)rb_protect((VALUE (*)(VALUE))obj_to_asn1obj, (VALUE)def_policy_id, &status);
+        def_policy_id_obj = (ASN1_OBJECT*)rb_protect(obj_to_asn1obj_i, (VALUE)def_policy_id, &status);
         if (status)
             goto end;
     }
@@ -1201,7 +1216,7 @@ ossl_tsfac_create_ts(VALUE self, VALUE key, VALUE certificate, VALUE request)
 
         for (i = 0; i < RARRAY_LEN(allowed_digests); i++) {
             rbmd = rb_ary_entry(allowed_digests, i);
-            md = (const EVP_MD *)rb_protect((VALUE (*)(VALUE))ossl_evp_get_digestbyname, rbmd, &status);
+            md = (const EVP_MD *)rb_protect(ossl_evp_get_digestbyname_i, rbmd, &status);
             if (status)
                 goto end;
             TS_RESP_CTX_add_md(ctx, md);
@@ -1212,7 +1227,7 @@ ossl_tsfac_create_ts(VALUE self, VALUE key, VALUE certificate, VALUE request)
     if (status)
         goto end;
 
-    req_bio = (BIO*)rb_protect((VALUE (*)(VALUE))ossl_obj2bio, (VALUE)&str, &status);
+    req_bio = (BIO*)rb_protect(ossl_obj2bio_i, (VALUE)&str, &status);
     if (status)
         goto end;
 
@@ -1236,7 +1251,7 @@ end:
     ASN1_OBJECT_free(def_policy_id_obj);
     TS_RESP_CTX_free(ctx);
     if (err_msg)
-        ossl_raise(eTimestampError, err_msg);
+        rb_exc_raise(ossl_make_error(eTimestampError, rb_str_new_cstr(err_msg)));
     if (status)
         rb_jump_tag(status);
     return ret;
@@ -1290,7 +1305,7 @@ Init_ossl_ts(void)
      * ===Create a Response:
      *      #Assumes ts.p12 is a PKCS#12-compatible file with a private key
      *      #and a certificate that has an extended key usage of 'timeStamping'
-     *      p12 = OpenSSL::PKCS12.new(File.open('ts.p12', 'rb'), 'pwd')
+     *      p12 = OpenSSL::PKCS12.new(File.binread('ts.p12'), 'pwd')
      *      md = OpenSSL::Digest.new('SHA1')
      *      hash = md.digest(data) #some binary data to be timestamped
      *      req = OpenSSL::Timestamp::Request.new
@@ -1305,16 +1320,16 @@ Init_ossl_ts(void)
      *
      * ===Verify a timestamp response:
      *      #Assume we have a timestamp token in a file called ts.der
-     *      ts = OpenSSL::Timestamp::Response.new(File.open('ts.der', 'rb')
+     *      ts = OpenSSL::Timestamp::Response.new(File.binread('ts.der'))
      *      #Assume we have the Request for this token in a file called req.der
-     *      req = OpenSSL::Timestamp::Request.new(File.open('req.der', 'rb')
+     *      req = OpenSSL::Timestamp::Request.new(File.binread('req.der'))
      *      # Assume the associated root CA certificate is contained in a
      *      # DER-encoded file named root.cer
-     *      root = OpenSSL::X509::Certificate.new(File.open('root.cer', 'rb')
+     *      root = OpenSSL::X509::Certificate.new(File.binread('root.cer'))
      *      # get the necessary intermediate certificates, available in
      *      # DER-encoded form in inter1.cer and inter2.cer
-     *      inter1 = OpenSSL::X509::Certificate.new(File.open('inter1.cer', 'rb')
-     *      inter2 = OpenSSL::X509::Certificate.new(File.open('inter2.cer', 'rb')
+     *      inter1 = OpenSSL::X509::Certificate.new(File.binread('inter1.cer'))
+     *      inter2 = OpenSSL::X509::Certificate.new(File.binread('inter2.cer'))
      *      ts.verify(req, root, inter1, inter2) -> ts or raises an exception if validation fails
      *
      */
@@ -1447,9 +1462,9 @@ Init_ossl_ts(void)
      * timestamping certificate.
      *
      *      req = OpenSSL::Timestamp::Request.new(raw_bytes)
-     *      p12 = OpenSSL::PKCS12.new(File.open('ts.p12', 'rb'), 'pwd')
-     *      inter1 = OpenSSL::X509::Certificate.new(File.open('inter1.cer', 'rb')
-     *      inter2 = OpenSSL::X509::Certificate.new(File.open('inter2.cer', 'rb')
+     *      p12 = OpenSSL::PKCS12.new(File.binread('ts.p12'), 'pwd')
+     *      inter1 = OpenSSL::X509::Certificate.new(File.binread('inter1.cer'))
+     *      inter2 = OpenSSL::X509::Certificate.new(File.binread('inter2.cer'))
      *      fac = OpenSSL::Timestamp::Factory.new
      *      fac.gen_time = Time.now
      *      fac.serial_number = 1

data/ext/openssl/ossl_x509.c

@@ -115,11 +115,9 @@ Init_ossl_x509(void)
     DefX509Const(V_ERR_SUITE_B_LOS_NOT_ALLOWED);
     DefX509Const(V_ERR_SUITE_B_CANNOT_SIGN_P_384_WITH_P_256);
 #endif
-#if defined(X509_V_ERR_HOSTNAME_MISMATCH)
     DefX509Const(V_ERR_HOSTNAME_MISMATCH);
     DefX509Const(V_ERR_EMAIL_MISMATCH);
     DefX509Const(V_ERR_IP_ADDRESS_MISMATCH);
-#endif
 #if defined(X509_V_ERR_DANE_NO_MATCH)
     DefX509Const(V_ERR_DANE_NO_MATCH);
 #endif
@@ -187,12 +185,10 @@ Init_ossl_x509(void)
     /* Set by Store#flags= and StoreContext#flags=. Enables checking of the
      * signature of the root self-signed CA. */
     DefX509Const(V_FLAG_CHECK_SS_SIGNATURE);
-#if defined(X509_V_FLAG_TRUSTED_FIRST)
     /* Set by Store#flags= and StoreContext#flags=. When constructing a
      * certificate chain, search the Store first for the issuer certificate.
      * Enabled by default in OpenSSL >= 1.1.0. */
     DefX509Const(V_FLAG_TRUSTED_FIRST);
-#endif
 #if defined(X509_V_FLAG_SUITEB_128_LOS_ONLY)
     /* Set by Store#flags= and StoreContext#flags=.
      * Enables Suite B 128 bit only mode. */
@@ -208,11 +204,9 @@ Init_ossl_x509(void)
      * Enables Suite B 128 bit mode allowing 192 bit algorithms. */
     DefX509Const(V_FLAG_SUITEB_128_LOS);
 #endif
-#if defined(X509_V_FLAG_PARTIAL_CHAIN)
     /* Set by Store#flags= and StoreContext#flags=.
      * Allows partial chains if at least one certificate is in trusted store. */
     DefX509Const(V_FLAG_PARTIAL_CHAIN);
-#endif
 #if defined(X509_V_FLAG_NO_ALT_CHAINS)
     /* Set by Store#flags= and StoreContext#flags=. Suppresses searching for
      * a alternative chain. No effect in OpenSSL >= 1.1.0. */

data/ext/openssl/ossl_x509attr.c

@@ -41,7 +41,7 @@ static const rb_data_type_t ossl_x509attr_type = {
     {
 	0, ossl_x509attr_free,
     },
-    0, 0, RUBY_TYPED_FREE_IMMEDIATELY,
+    0, 0, RUBY_TYPED_FREE_IMMEDIATELY | RUBY_TYPED_WB_PROTECTED,
 };
 
 /*

data/ext/openssl/ossl_x509cert.c

@@ -41,7 +41,7 @@ static const rb_data_type_t ossl_x509_type = {
     {
 	0, ossl_x509_free,
     },
-    0, 0, RUBY_TYPED_FREE_IMMEDIATELY,
+    0, 0, RUBY_TYPED_FREE_IMMEDIATELY | RUBY_TYPED_WB_PROTECTED,
 };
 
 /*
@@ -115,24 +115,27 @@ static VALUE
 ossl_x509_initialize(int argc, VALUE *argv, VALUE self)
 {
     BIO *in;
-    X509 *x509, *x = DATA_PTR(self);
+    X509 *x509, *x509_orig = RTYPEDDATA_DATA(self);
     VALUE arg;
 
+    rb_check_frozen(self);
     if (rb_scan_args(argc, argv, "01", &arg) == 0) {
 	/* create just empty X509Cert */
 	return self;
     }
     arg = ossl_to_der_if_possible(arg);
     in = ossl_obj2bio(&arg);
-    x509 = PEM_read_bio_X509(in, &x, NULL, NULL);
-    DATA_PTR(self) = x;
+    x509 = d2i_X509_bio(in, NULL);
     if (!x509) {
-	OSSL_BIO_reset(in);
-	x509 = d2i_X509_bio(in, &x);
-	DATA_PTR(self) = x;
+        OSSL_BIO_reset(in);
+        x509 = PEM_read_bio_X509(in, NULL, NULL, NULL);
     }
     BIO_free(in);
-    if (!x509) ossl_raise(eX509CertError, NULL);
+    if (!x509)
+        ossl_raise(eX509CertError, "PEM_read_bio_X509");
+
+    RTYPEDDATA_DATA(self) = x509;
+    X509_free(x509_orig);
 
     return self;
 }
@@ -639,12 +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");
 	}
     }
 
@@ -704,6 +707,157 @@ ossl_x509_eq(VALUE self, VALUE other)
     return !X509_cmp(a, b) ? Qtrue : Qfalse;
 }
 
+struct load_chained_certificates_arguments {
+    VALUE certificates;
+    X509 *certificate;
+};
+
+static VALUE
+load_chained_certificates_append_push(VALUE _arguments) {
+    struct load_chained_certificates_arguments *arguments = (struct load_chained_certificates_arguments*)_arguments;
+
+    if (arguments->certificates == Qnil) {
+        arguments->certificates = rb_ary_new();
+    }
+
+    rb_ary_push(arguments->certificates, ossl_x509_new(arguments->certificate));
+
+    return Qnil;
+}
+
+static VALUE
+load_chained_certificate_append_ensure(VALUE _arguments) {
+    struct load_chained_certificates_arguments *arguments = (struct load_chained_certificates_arguments*)_arguments;
+
+    X509_free(arguments->certificate);
+
+    return Qnil;
+}
+
+inline static VALUE
+load_chained_certificates_append(VALUE certificates, X509 *certificate) {
+    struct load_chained_certificates_arguments arguments;
+    arguments.certificates = certificates;
+    arguments.certificate = certificate;
+
+    rb_ensure(load_chained_certificates_append_push, (VALUE)&arguments, load_chained_certificate_append_ensure, (VALUE)&arguments);
+
+    return arguments.certificates;
+}
+
+static VALUE
+load_chained_certificates_PEM(BIO *in) {
+    VALUE certificates = Qnil;
+    X509 *certificate = PEM_read_bio_X509(in, NULL, NULL, NULL);
+
+    /* If we cannot read even one certificate: */
+    if (certificate == NULL) {
+        /* If we cannot read one certificate because we could not read the PEM encoding: */
+        if (ERR_GET_REASON(ERR_peek_last_error()) == PEM_R_NO_START_LINE) {
+            ossl_clear_error();
+        }
+
+        if (ERR_peek_last_error())
+            ossl_raise(eX509CertError, NULL);
+        else
+            return Qnil;
+    }
+
+    certificates = load_chained_certificates_append(Qnil, certificate);
+
+    while ((certificate = PEM_read_bio_X509(in, NULL, NULL, NULL))) {
+      load_chained_certificates_append(certificates, certificate);
+    }
+
+    /* We tried to read one more certificate but could not read start line: */
+    if (ERR_GET_REASON(ERR_peek_last_error()) == PEM_R_NO_START_LINE) {
+        /* This is not an error, it means we are finished: */
+        ossl_clear_error();
+
+        return certificates;
+    }
+
+    /* Alternatively, if we reached the end of the file and there was no error: */
+    if (BIO_eof(in) && !ERR_peek_last_error()) {
+        return certificates;
+    } else {
+        /* Otherwise, we tried to read a certificate but failed somewhere: */
+        ossl_raise(eX509CertError, NULL);
+    }
+}
+
+static VALUE
+load_chained_certificates_DER(BIO *in) {
+    X509 *certificate = d2i_X509_bio(in, NULL);
+
+    /* If we cannot read one certificate: */
+    if (certificate == NULL) {
+        /* Ignore error. We could not load. */
+        ossl_clear_error();
+
+        return Qnil;
+    }
+
+    return load_chained_certificates_append(Qnil, certificate);
+}
+
+static VALUE
+load_chained_certificates(VALUE _io) {
+    BIO *in = (BIO*)_io;
+    VALUE certificates = Qnil;
+
+    /*
+      DER is a binary format and it may contain octets within it that look like
+      PEM encoded certificates. So we need to check DER first.
+    */
+    certificates = load_chained_certificates_DER(in);
+
+    if (certificates != Qnil)
+        return certificates;
+
+    OSSL_BIO_reset(in);
+
+    certificates = load_chained_certificates_PEM(in);
+
+    if (certificates != Qnil)
+        return certificates;
+
+    /* Otherwise we couldn't read the output correctly so fail: */
+    ossl_raise(eX509CertError, "Could not detect format of certificate data!");
+}
+
+static VALUE
+load_chained_certificates_ensure(VALUE _io) {
+    BIO *in = (BIO*)_io;
+
+    BIO_free(in);
+
+    return Qnil;
+}
+
+/*
+ * call-seq:
+ *    OpenSSL::X509::Certificate.load(string) -> [certs...]
+ *    OpenSSL::X509::Certificate.load(file) -> [certs...]
+ *
+ * Read the chained certificates from the given input. Supports both PEM
+ * and DER encoded certificates.
+ *
+ * PEM is a text format and supports more than one certificate.
+ *
+ * DER is a binary format and only supports one certificate.
+ *
+ * If the file is empty, or contains only unrelated data, an
+ * +OpenSSL::X509::CertificateError+ exception will be raised.
+ */
+static VALUE
+ossl_x509_load(VALUE klass, VALUE buffer)
+{
+    BIO *in = ossl_obj2bio(&buffer);
+
+    return rb_ensure(load_chained_certificates, (VALUE)in, load_chained_certificates_ensure, (VALUE)in);
+}
+
 /*
  * INIT
  */
@@ -730,7 +884,7 @@ Init_ossl_x509cert(void)
      * Certificate is capable of handling DER-encoded certificates and
      * certificates encoded in OpenSSL's PEM format.
      *
-     *   raw = File.read "cert.cer" # DER- or PEM-encoded
+     *   raw = File.binread "cert.cer" # DER- or PEM-encoded
      *   certificate = OpenSSL::X509::Certificate.new raw
      *
      * === Saving a certificate to a file
@@ -812,6 +966,8 @@ Init_ossl_x509cert(void)
      */
     cX509Cert = rb_define_class_under(mX509, "Certificate", rb_cObject);
 
+    rb_define_singleton_method(cX509Cert, "load", ossl_x509_load, 1);
+
     rb_define_alloc_func(cX509Cert, ossl_x509_alloc);
     rb_define_method(cX509Cert, "initialize", ossl_x509_initialize, -1);
     rb_define_method(cX509Cert, "initialize_copy", ossl_x509_copy, 1);

data/ext/openssl/ossl_x509crl.c

@@ -41,7 +41,7 @@ static const rb_data_type_t ossl_x509crl_type = {
     {
 	0, ossl_x509crl_free,
     },
-    0, 0, RUBY_TYPED_FREE_IMMEDIATELY,
+    0, 0, RUBY_TYPED_FREE_IMMEDIATELY | RUBY_TYPED_WB_PROTECTED,
 };
 
 /*
@@ -93,23 +93,26 @@ static VALUE
 ossl_x509crl_initialize(int argc, VALUE *argv, VALUE self)
 {
     BIO *in;
-    X509_CRL *crl, *x = DATA_PTR(self);
+    X509_CRL *crl, *crl_orig = RTYPEDDATA_DATA(self);
     VALUE arg;
 
+    rb_check_frozen(self);
     if (rb_scan_args(argc, argv, "01", &arg) == 0) {
 	return self;
     }
     arg = ossl_to_der_if_possible(arg);
     in = ossl_obj2bio(&arg);
-    crl = PEM_read_bio_X509_CRL(in, &x, NULL, NULL);
-    DATA_PTR(self) = x;
+    crl = d2i_X509_CRL_bio(in, NULL);
     if (!crl) {
-	OSSL_BIO_reset(in);
-	crl = d2i_X509_CRL_bio(in, &x);
-	DATA_PTR(self) = x;
+        OSSL_BIO_reset(in);
+        crl = PEM_read_bio_X509_CRL(in, NULL, NULL, NULL);
     }
     BIO_free(in);
-    if (!crl) ossl_raise(eX509CRLError, NULL);
+    if (!crl)
+        ossl_raise(eX509CRLError, "PEM_read_bio_X509_CRL");
+
+    RTYPEDDATA_DATA(self) = crl;
+    X509_CRL_free(crl_orig);
 
     return self;
 }
@@ -471,12 +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");
 	}
     }
 

data/ext/openssl/ossl_x509ext.c

@@ -55,7 +55,7 @@ static const rb_data_type_t ossl_x509ext_type = {
     {
 	0, ossl_x509ext_free,
     },
-    0, 0, RUBY_TYPED_FREE_IMMEDIATELY,
+    0, 0, RUBY_TYPED_FREE_IMMEDIATELY | RUBY_TYPED_WB_PROTECTED,
 };
 
 /*
@@ -108,7 +108,7 @@ static const rb_data_type_t ossl_x509extfactory_type = {
     {
 	0, ossl_x509extfactory_free,
     },
-    0, 0, RUBY_TYPED_FREE_IMMEDIATELY,
+    0, 0, RUBY_TYPED_FREE_IMMEDIATELY | RUBY_TYPED_WB_PROTECTED,
 };
 
 static VALUE
@@ -209,15 +209,16 @@ ossl_x509extfactory_create_ext(int argc, VALUE *argv, VALUE self)
     int nid;
     VALUE rconf;
     CONF *conf;
+    const char *oid_cstr = NULL;
 
     rb_scan_args(argc, argv, "21", &oid, &value, &critical);
-    StringValueCStr(oid);
     StringValue(value);
     if(NIL_P(critical)) critical = Qfalse;
 
-    nid = OBJ_ln2nid(RSTRING_PTR(oid));
-    if(!nid) nid = OBJ_sn2nid(RSTRING_PTR(oid));
-    if(!nid) ossl_raise(eX509ExtError, "unknown OID `%"PRIsVALUE"'", oid);
+    oid_cstr = StringValueCStr(oid);
+    nid = OBJ_ln2nid(oid_cstr);
+    if (nid != NID_undef)
+      oid_cstr = OBJ_nid2sn(nid);
 
     valstr = rb_str_new2(RTEST(critical) ? "critical," : "");
     rb_str_append(valstr, value);
@@ -226,11 +227,15 @@ ossl_x509extfactory_create_ext(int argc, VALUE *argv, VALUE self)
     GetX509ExtFactory(self, ctx);
     obj = NewX509Ext(cX509Ext);
     rconf = rb_iv_get(self, "@config");
-    conf = NIL_P(rconf) ? NULL : DupConfigPtr(rconf);
+    conf = NIL_P(rconf) ? NULL : GetConfig(rconf);
     X509V3_set_nconf(ctx, conf);
-    ext = X509V3_EXT_nconf_nid(conf, ctx, nid, RSTRING_PTR(valstr));
+
+#if OSSL_OPENSSL_PREREQ(1, 1, 0) || OSSL_IS_LIBRESSL
+    ext = X509V3_EXT_nconf(conf, ctx, oid_cstr, RSTRING_PTR(valstr));
+#else
+    ext = X509V3_EXT_nconf(conf, ctx, (char *)oid_cstr, RSTRING_PTR(valstr));
+#endif
     X509V3_set_ctx_nodb(ctx);
-    NCONF_free(conf);
     if (!ext){
 	ossl_raise(eX509ExtError, "%"PRIsVALUE" = %"PRIsVALUE, oid, valstr);
     }