/* * Copyright (c) 2025, Oracle and/or its affiliates. All rights reserved. * DO NOT ALTER OR REMOVE COPYRIGHT NOTICES OR THIS FILE HEADER. * * This code is free software; you can redistribute it and/or modify it * under the terms of the GNU General Public License version 2 only, as * published by the Free Software Foundation. * * This code is distributed in the hope that it will be useful, but WITHOUT * ANY WARRANTY; without even the implied warranty of MERCHANTABILITY or * FITNESS FOR A PARTICULAR PURPOSE. See the GNU General Public License * version 2 for more details (a copy is included in the LICENSE file that * accompanied this code). * * You should have received a copy of the GNU General Public License version * 2 along with this work; if not, write to the Free Software Foundation, * Inc., 51 Franklin St, Fifth Floor, Boston, MA 02110-1301 USA. * * Please contact Oracle, 500 Oracle Parkway, Redwood Shores, CA 94065 USA * or visit www.oracle.com if you need additional information or have any * questions. */ /* * @test * @bug 8350807 * @summary Certificates using MD5 algorithm that are disabled by default are * incorrectly allowed in TLSv1.3 when re-enabled. * @modules java.base/sun.security.x509 * java.base/sun.security.util * @library /javax/net/ssl/templates * /test/lib * @run main/othervm MD5NotAllowedInTLS13CertificateSignature */ import static jdk.test.lib.Asserts.assertTrue; import static jdk.test.lib.Utils.runAndCheckException; import java.io.IOException; import java.math.BigInteger; import java.security.KeyPair; import java.security.KeyPairGenerator; import java.security.KeyStore; import java.security.PrivateKey; import java.security.PublicKey; import java.security.SecureRandom; import java.security.cert.Certificate; import java.security.cert.CertificateException; import java.security.cert.X509Certificate; import java.time.Instant; import java.time.temporal.ChronoUnit; import java.util.Date; import java.util.List; import javax.net.ssl.KeyManagerFactory; import javax.net.ssl.SSLContext; import javax.net.ssl.SSLHandshakeException; import javax.net.ssl.TrustManagerFactory; import jdk.test.lib.security.CertificateBuilder; import jdk.test.lib.security.SecurityUtils; import sun.security.x509.AuthorityKeyIdentifierExtension; import sun.security.x509.GeneralName; import sun.security.x509.GeneralNames; import sun.security.x509.KeyIdentifier; import sun.security.x509.SerialNumber; import sun.security.x509.X500Name; public class MD5NotAllowedInTLS13CertificateSignature extends SSLSocketTemplate { private final String protocol; private X509Certificate trustedCert; private X509Certificate serverCert; private X509Certificate clientCert; private KeyPair serverKeys; private KeyPair clientKeys; protected MD5NotAllowedInTLS13CertificateSignature(String protocol) throws Exception { super(); this.protocol = protocol; setupCertificates(); } public static void main(String[] args) throws Exception { // MD5 is disabled by default in java.security config file, // re-enable it for our test. SecurityUtils.removeFromDisabledAlgs( "jdk.certpath.disabledAlgorithms", List.of("MD5")); SecurityUtils.removeFromDisabledAlgs( "jdk.tls.disabledAlgorithms", List.of("MD5withRSA")); // Should fail on TLSv1.3 and up. runAndCheckException( // The conditions to reproduce the bug being fixed only met when // 'TLS' is specified, i.e. when older versions of protocol are // supported besides TLSv1.3. () -> new MD5NotAllowedInTLS13CertificateSignature("TLS").run(), serverEx -> { Throwable clientEx = serverEx.getSuppressed()[0]; assertTrue(clientEx instanceof SSLHandshakeException); assertTrue(clientEx.getMessage().startsWith( "(bad_certificate)" + " PKIX path validation failed: " + "java.security.cert.CertPathValidatorException:" + " Algorithm constraints check failed on " + "MD5withRSA signature and RSA key")); }); // Should run fine on TLSv1.2. new MD5NotAllowedInTLS13CertificateSignature("TLSv1.2").run(); } @Override public SSLContext createServerSSLContext() throws Exception { return getSSLContext( trustedCert, serverCert, serverKeys.getPrivate(), protocol); } @Override public SSLContext createClientSSLContext() throws Exception { return getSSLContext( trustedCert, clientCert, clientKeys.getPrivate(), protocol); } private static SSLContext getSSLContext( X509Certificate trustedCertificate, X509Certificate keyCertificate, PrivateKey privateKey, String protocol) throws Exception { // create a key store KeyStore ks = KeyStore.getInstance("PKCS12"); ks.load(null, null); // import the trusted cert ks.setCertificateEntry("TLS Signer", trustedCertificate); // generate certificate chain Certificate[] chain = new Certificate[2]; chain[0] = keyCertificate; chain[1] = trustedCertificate; // import the key entry. final char[] passphrase = "passphrase".toCharArray(); ks.setKeyEntry("Whatever", privateKey, passphrase, chain); // Using PKIX TrustManager - this is where MD5 signature check is done. TrustManagerFactory tmf = TrustManagerFactory.getInstance("PKIX"); tmf.init(ks); // create SSL context SSLContext ctx = SSLContext.getInstance(protocol); // Disable KeyManager's algorithm constraints checking, // so we check against local supported signature // algorithms which constitutes the fix being tested. System.setProperty( "jdk.tls.SunX509KeyManager.certChecking", "false"); KeyManagerFactory kmf = KeyManagerFactory.getInstance("SunX509"); kmf.init(ks, passphrase); ctx.init(kmf.getKeyManagers(), tmf.getTrustManagers(), null); return ctx; } // Certificate-building helper methods. // Certificates are signed with signature using MD5WithRSA algorithm. private void setupCertificates() throws Exception { KeyPairGenerator kpg = KeyPairGenerator.getInstance("RSA"); KeyPair caKeys = kpg.generateKeyPair(); this.serverKeys = kpg.generateKeyPair(); this.clientKeys = kpg.generateKeyPair(); this.trustedCert = createTrustedCert(caKeys); this.serverCert = customCertificateBuilder( "O=Some-Org, L=Some-City, ST=Some-State, C=US", serverKeys.getPublic(), caKeys.getPublic()) .addBasicConstraintsExt(false, false, -1) .build(trustedCert, caKeys.getPrivate(), "MD5WithRSA"); this.clientCert = customCertificateBuilder( "CN=localhost, OU=SSL-Client, O=Some-Org, L=Some-City, ST=Some-State, C=US", clientKeys.getPublic(), caKeys.getPublic()) .addBasicConstraintsExt(false, false, -1) .build(trustedCert, caKeys.getPrivate(), "MD5WithRSA"); } private static X509Certificate createTrustedCert(KeyPair caKeys) throws Exception { SecureRandom random = new SecureRandom(); KeyIdentifier kid = new KeyIdentifier(caKeys.getPublic()); GeneralNames gns = new GeneralNames(); GeneralName name = new GeneralName(new X500Name( "O=Some-Org, L=Some-City, ST=Some-State, C=US")); gns.add(name); BigInteger serialNumber = BigInteger.valueOf( random.nextLong(1000000) + 1); return customCertificateBuilder( "O=Some-Org, L=Some-City, ST=Some-State, C=US", caKeys.getPublic(), caKeys.getPublic()) .setSerialNumber(serialNumber) .addExtension(new AuthorityKeyIdentifierExtension(kid, gns, new SerialNumber(serialNumber))) .addBasicConstraintsExt(true, true, -1) .build(null, caKeys.getPrivate(), "MD5WithRSA"); } private static CertificateBuilder customCertificateBuilder( String subjectName, PublicKey publicKey, PublicKey caKey) throws CertificateException, IOException { SecureRandom random = new SecureRandom(); CertificateBuilder builder = new CertificateBuilder() .setSubjectName(subjectName) .setPublicKey(publicKey) .setNotBefore( Date.from(Instant.now().minus(1, ChronoUnit.HOURS))) .setNotAfter(Date.from(Instant.now().plus(1, ChronoUnit.HOURS))) .setSerialNumber( BigInteger.valueOf(random.nextLong(1000000) + 1)) .addSubjectKeyIdExt(publicKey) .addAuthorityKeyIdExt(caKey); builder.addKeyUsageExt( new boolean[]{true, true, true, true, true, true}); return builder; } }