/* * Copyright (c) 2003, 2016, 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. */ import com.sun.net.httpserver.*; import java.io.ByteArrayOutputStream; import java.io.File; import java.io.IOException; import java.io.InputStream; import java.io.OutputStream; import java.math.BigInteger; import java.net.InetSocketAddress; import java.nio.file.Files; import java.nio.file.Paths; import java.security.KeyStore; import java.security.PrivateKey; import java.security.Signature; import java.security.cert.Certificate; import java.security.cert.X509Certificate; import java.util.ArrayList; import java.util.Arrays; import java.util.Calendar; import java.util.List; import java.util.jar.JarEntry; import java.util.jar.JarFile; import jdk.testlibrary.*; import jdk.testlibrary.JarUtils; import sun.security.pkcs.ContentInfo; import sun.security.pkcs.PKCS7; import sun.security.pkcs.PKCS9Attribute; import sun.security.pkcs.SignerInfo; import sun.security.timestamp.TimestampToken; import sun.security.util.DerOutputStream; import sun.security.util.DerValue; import sun.security.util.ObjectIdentifier; import sun.security.x509.AlgorithmId; import sun.security.x509.X500Name; /* * @test * @bug 6543842 6543440 6939248 8009636 8024302 8163304 8169911 * @summary checking response of timestamp * @modules java.base/sun.security.pkcs * java.base/sun.security.timestamp * java.base/sun.security.x509 * java.base/sun.security.util * java.base/sun.security.tools.keytool * @library /lib/testlibrary * @run main/timeout=600 TimestampCheck */ public class TimestampCheck { static final String defaultPolicyId = "2.3.4"; static String host = null; static class Handler implements HttpHandler, AutoCloseable { private final HttpServer httpServer; private final String keystore; @Override public void handle(HttpExchange t) throws IOException { int len = 0; for (String h: t.getRequestHeaders().keySet()) { if (h.equalsIgnoreCase("Content-length")) { len = Integer.valueOf(t.getRequestHeaders().get(h).get(0)); } } byte[] input = new byte[len]; t.getRequestBody().read(input); try { String path = t.getRequestURI().getPath().substring(1); byte[] output = sign(input, path); Headers out = t.getResponseHeaders(); out.set("Content-Type", "application/timestamp-reply"); t.sendResponseHeaders(200, output.length); OutputStream os = t.getResponseBody(); os.write(output); } catch (Exception e) { e.printStackTrace(); t.sendResponseHeaders(500, 0); } t.close(); } /** * @param input The data to sign * @param path different cases to simulate, impl on URL path * @returns the signed */ byte[] sign(byte[] input, String path) throws Exception { DerValue value = new DerValue(input); System.err.println("\nIncoming Request\n==================="); System.err.println("Version: " + value.data.getInteger()); DerValue messageImprint = value.data.getDerValue(); AlgorithmId aid = AlgorithmId.parse( messageImprint.data.getDerValue()); System.err.println("AlgorithmId: " + aid); ObjectIdentifier policyId = new ObjectIdentifier(defaultPolicyId); BigInteger nonce = null; while (value.data.available() > 0) { DerValue v = value.data.getDerValue(); if (v.tag == DerValue.tag_Integer) { nonce = v.getBigInteger(); System.err.println("nonce: " + nonce); } else if (v.tag == DerValue.tag_Boolean) { System.err.println("certReq: " + v.getBoolean()); } else if (v.tag == DerValue.tag_ObjectId) { policyId = v.getOID(); System.err.println("PolicyID: " + policyId); } } System.err.println("\nResponse\n==================="); KeyStore ks = KeyStore.getInstance( new File(keystore), "changeit".toCharArray()); String alias = "ts"; if (path.startsWith("bad") || path.equals("weak")) { alias = "ts" + path; } if (path.equals("diffpolicy")) { policyId = new ObjectIdentifier(defaultPolicyId); } DerOutputStream statusInfo = new DerOutputStream(); statusInfo.putInteger(0); AlgorithmId[] algorithms = {aid}; Certificate[] chain = ks.getCertificateChain(alias); X509Certificate[] signerCertificateChain; X509Certificate signer = (X509Certificate)chain[0]; if (path.equals("fullchain")) { // Only case 5 uses full chain signerCertificateChain = new X509Certificate[chain.length]; for (int i=0; i<chain.length; i++) { signerCertificateChain[i] = (X509Certificate)chain[i]; } } else if (path.equals("nocert")) { signerCertificateChain = new X509Certificate[0]; } else { signerCertificateChain = new X509Certificate[1]; signerCertificateChain[0] = (X509Certificate)chain[0]; } DerOutputStream tst = new DerOutputStream(); tst.putInteger(1); tst.putOID(policyId); if (!path.equals("baddigest") && !path.equals("diffalg")) { tst.putDerValue(messageImprint); } else { byte[] data = messageImprint.toByteArray(); if (path.equals("diffalg")) { data[6] = (byte)0x01; } else { data[data.length-1] = (byte)0x01; data[data.length-2] = (byte)0x02; data[data.length-3] = (byte)0x03; } tst.write(data); } tst.putInteger(1); Calendar cal = Calendar.getInstance(); tst.putGeneralizedTime(cal.getTime()); if (path.equals("diffnonce")) { tst.putInteger(1234); } else if (path.equals("nononce")) { // no noce } else { tst.putInteger(nonce); } DerOutputStream tstInfo = new DerOutputStream(); tstInfo.write(DerValue.tag_Sequence, tst); DerOutputStream tstInfo2 = new DerOutputStream(); tstInfo2.putOctetString(tstInfo.toByteArray()); // Always use the same algorithm at timestamp signing // so it is different from the hash algorithm. Signature sig = Signature.getInstance("SHA1withRSA"); sig.initSign((PrivateKey)(ks.getKey( alias, "changeit".toCharArray()))); sig.update(tstInfo.toByteArray()); ContentInfo contentInfo = new ContentInfo(new ObjectIdentifier( "1.2.840.113549.1.9.16.1.4"), new DerValue(tstInfo2.toByteArray())); System.err.println("Signing..."); System.err.println(new X500Name(signer .getIssuerX500Principal().getName())); System.err.println(signer.getSerialNumber()); SignerInfo signerInfo = new SignerInfo( new X500Name(signer.getIssuerX500Principal().getName()), signer.getSerialNumber(), AlgorithmId.get("SHA-1"), AlgorithmId.get("RSA"), sig.sign()); SignerInfo[] signerInfos = {signerInfo}; PKCS7 p7 = new PKCS7(algorithms, contentInfo, signerCertificateChain, signerInfos); ByteArrayOutputStream p7out = new ByteArrayOutputStream(); p7.encodeSignedData(p7out); DerOutputStream response = new DerOutputStream(); response.write(DerValue.tag_Sequence, statusInfo); response.putDerValue(new DerValue(p7out.toByteArray())); DerOutputStream out = new DerOutputStream(); out.write(DerValue.tag_Sequence, response); return out.toByteArray(); } private Handler(HttpServer httpServer, String keystore) { this.httpServer = httpServer; this.keystore = keystore; } /** * Initialize TSA instance. * * Extended Key Info extension of certificate that is used for * signing TSA responses should contain timeStamping value. */ static Handler init(int port, String keystore) throws IOException { HttpServer httpServer = HttpServer.create( new InetSocketAddress(port), 0); Handler tsa = new Handler(httpServer, keystore); httpServer.createContext("/", tsa); return tsa; } /** * Start TSA service. */ void start() { httpServer.start(); } /** * Stop TSA service. */ void stop() { httpServer.stop(0); } /** * Return server port number. */ int getPort() { return httpServer.getAddress().getPort(); } @Override public void close() throws Exception { stop(); } } public static void main(String[] args) throws Throwable { prepare(); try (Handler tsa = Handler.init(0, "tsks");) { tsa.start(); int port = tsa.getPort(); host = "http://localhost:" + port + "/"; if (args.length == 0) { // Run this test sign("none") .shouldContain("is not timestamped") .shouldHaveExitValue(0); sign("badku") .shouldHaveExitValue(0); checkBadKU("badku.jar"); sign("normal") .shouldNotContain("is not timestamped") .shouldHaveExitValue(0); sign("nononce") .shouldHaveExitValue(1); sign("diffnonce") .shouldHaveExitValue(1); sign("baddigest") .shouldHaveExitValue(1); sign("diffalg") .shouldHaveExitValue(1); sign("fullchain") .shouldHaveExitValue(0); // Success, 6543440 solved. sign("bad1") .shouldHaveExitValue(1); sign("bad2") .shouldHaveExitValue(1); sign("bad3") .shouldHaveExitValue(1); sign("nocert") .shouldHaveExitValue(1); sign("policy", "-tsapolicyid", "1.2.3") .shouldHaveExitValue(0); checkTimestamp("policy.jar", "1.2.3", "SHA-256"); sign("diffpolicy", "-tsapolicyid", "1.2.3") .shouldHaveExitValue(1); sign("tsaalg", "-tsadigestalg", "SHA") .shouldHaveExitValue(0); checkTimestamp("tsaalg.jar", defaultPolicyId, "SHA-1"); sign("weak", "-digestalg", "MD5", "-sigalg", "MD5withRSA", "-tsadigestalg", "MD5") .shouldHaveExitValue(0) .shouldMatch("MD5.*-digestalg.*risk") .shouldMatch("MD5.*-tsadigestalg.*risk") .shouldMatch("MD5withRSA.*-sigalg.*risk"); checkWeak("weak.jar"); signWithAliasAndTsa("halfWeak", "old.jar", "old", "-digestalg", "MD5") .shouldHaveExitValue(0); checkHalfWeak("halfWeak.jar"); // sign with DSA key signWithAliasAndTsa("sign1", "old.jar", "dsakey") .shouldHaveExitValue(0); // sign with RSAkeysize < 1024 signWithAliasAndTsa("sign2", "sign1.jar", "weakkeysize") .shouldHaveExitValue(0); checkMultiple("sign2.jar"); // When .SF or .RSA is missing or invalid checkMissingOrInvalidFiles("normal.jar"); } else { // Run as a standalone server System.err.println("Press Enter to quit server"); System.in.read(); } } } private static void checkMissingOrInvalidFiles(String s) throws Throwable { JarUtils.updateJar(s, "1.jar", "-", "META-INF/OLD.SF"); verify("1.jar", "-verbose") .shouldHaveExitValue(0) .shouldContain("treated as unsigned") .shouldContain("Missing signature-related file META-INF/OLD.SF"); JarUtils.updateJar(s, "2.jar", "-", "META-INF/OLD.RSA"); verify("2.jar", "-verbose") .shouldHaveExitValue(0) .shouldContain("treated as unsigned") .shouldContain("Missing block file for signature-related file META-INF/OLD.SF"); JarUtils.updateJar(s, "3.jar", "META-INF/OLD.SF"); verify("3.jar", "-verbose") .shouldHaveExitValue(0) .shouldContain("treated as unsigned") .shouldContain("Unparsable signature-related file META-INF/OLD.SF"); JarUtils.updateJar(s, "4.jar", "META-INF/OLD.RSA"); verify("4.jar", "-verbose") .shouldHaveExitValue(0) .shouldContain("treated as unsigned") .shouldContain("Unparsable signature-related file META-INF/OLD.RSA"); } static OutputAnalyzer jarsigner(List<String> extra) throws Throwable { JDKToolLauncher launcher = JDKToolLauncher.createUsingTestJDK("jarsigner") .addVMArg("-Duser.language=en") .addVMArg("-Duser.country=US") .addToolArg("-keystore") .addToolArg("tsks") .addToolArg("-storepass") .addToolArg("changeit"); for (String s : extra) { if (s.startsWith("-J")) { launcher.addVMArg(s.substring(2)); } else { launcher.addToolArg(s); } } return ProcessTools.executeCommand(launcher.getCommand()); } static OutputAnalyzer verify(String file, String... extra) throws Throwable { List<String> args = new ArrayList<>(); args.add("-verify"); args.add(file); args.addAll(Arrays.asList(extra)); return jarsigner(args); } static void checkBadKU(String file) throws Throwable { verify(file) .shouldHaveExitValue(0) .shouldContain("treated as unsigned") .shouldContain("re-run jarsigner with debug enabled"); verify(file, "-verbose") .shouldHaveExitValue(0) .shouldContain("Signed by") .shouldContain("treated as unsigned") .shouldContain("re-run jarsigner with debug enabled"); verify(file, "-J-Djava.security.debug=jar") .shouldHaveExitValue(0) .shouldContain("SignatureException: Key usage restricted") .shouldContain("treated as unsigned") .shouldContain("re-run jarsigner with debug enabled"); } static void checkWeak(String file) throws Throwable { verify(file) .shouldHaveExitValue(0) .shouldContain("treated as unsigned") .shouldMatch("weak algorithm that is now disabled.") .shouldMatch("Re-run jarsigner with the -verbose option for more details"); verify(file, "-verbose") .shouldHaveExitValue(0) .shouldContain("treated as unsigned") .shouldMatch("weak algorithm that is now disabled by") .shouldMatch("Digest algorithm: .*weak") .shouldMatch("Signature algorithm: .*weak") .shouldMatch("Timestamp digest algorithm: .*weak") .shouldNotMatch("Timestamp signature algorithm: .*weak.*weak") .shouldMatch("Timestamp signature algorithm: .*key.*weak"); verify(file, "-J-Djava.security.debug=jar") .shouldHaveExitValue(0) .shouldMatch("SignatureException:.*Disabled"); } static void checkHalfWeak(String file) throws Throwable { verify(file) .shouldHaveExitValue(0) .shouldContain("treated as unsigned") .shouldMatch("weak algorithm that is now disabled.") .shouldMatch("Re-run jarsigner with the -verbose option for more details"); verify(file, "-verbose") .shouldHaveExitValue(0) .shouldContain("treated as unsigned") .shouldMatch("weak algorithm that is now disabled by") .shouldMatch("Digest algorithm: .*weak") .shouldNotMatch("Signature algorithm: .*weak") .shouldNotMatch("Timestamp digest algorithm: .*weak") .shouldNotMatch("Timestamp signature algorithm: .*weak.*weak") .shouldNotMatch("Timestamp signature algorithm: .*key.*weak"); } static void checkMultiple(String file) throws Throwable { verify(file) .shouldHaveExitValue(0) .shouldContain("jar verified"); verify(file, "-verbose", "-certs") .shouldHaveExitValue(0) .shouldContain("jar verified") .shouldMatch("X.509.*CN=dsakey") .shouldNotMatch("X.509.*CN=weakkeysize") .shouldMatch("Signed by .*CN=dsakey") .shouldMatch("Signed by .*CN=weakkeysize") .shouldMatch("Signature algorithm: .*key.*weak"); } static void checkTimestamp(String file, String policyId, String digestAlg) throws Exception { try (JarFile jf = new JarFile(file)) { JarEntry je = jf.getJarEntry("META-INF/OLD.RSA"); try (InputStream is = jf.getInputStream(je)) { byte[] content = is.readAllBytes(); PKCS7 p7 = new PKCS7(content); SignerInfo[] si = p7.getSignerInfos(); if (si == null || si.length == 0) { throw new Exception("Not signed"); } PKCS9Attribute p9 = si[0].getUnauthenticatedAttributes() .getAttribute(PKCS9Attribute.SIGNATURE_TIMESTAMP_TOKEN_OID); PKCS7 tsToken = new PKCS7((byte[]) p9.getValue()); TimestampToken tt = new TimestampToken(tsToken.getContentInfo().getData()); if (!tt.getHashAlgorithm().toString().equals(digestAlg)) { throw new Exception("Digest alg different"); } if (!tt.getPolicyID().equals(policyId)) { throw new Exception("policyId different"); } } } } static int which = 0; /** * @param extra more args given to jarsigner */ static OutputAnalyzer sign(String path, String... extra) throws Throwable { String alias = path.equals("badku") ? "badku" : "old"; return signWithAliasAndTsa(path, "old.jar", alias, extra); } static OutputAnalyzer signWithAliasAndTsa (String path, String jar, String alias, String...extra) throws Throwable { which++; System.err.println("\n>> Test #" + which + ": " + Arrays.toString(extra)); List<String> args = List.of("-J-Djava.security.egd=file:/dev/./urandom", "-debug", "-signedjar", path + ".jar", jar, alias); args = new ArrayList<>(args); if (!path.equals("none") && !path.equals("badku")) { args.add("-tsa"); args.add(host + path); } args.addAll(Arrays.asList(extra)); return jarsigner(args); } static void prepare() throws Exception { jdk.testlibrary.JarUtils.createJar("old.jar", "A"); Files.deleteIfExists(Paths.get("tsks")); keytool("-alias ca -genkeypair -ext bc -dname CN=CA"); keytool("-alias old -genkeypair -dname CN=old"); keytool("-alias dsakey -genkeypair -keyalg DSA -dname CN=dsakey"); keytool("-alias weakkeysize -genkeypair -keysize 512 -dname CN=weakkeysize"); keytool("-alias badku -genkeypair -dname CN=badku"); keytool("-alias ts -genkeypair -dname CN=ts"); keytool("-alias tsweak -genkeypair -keysize 512 -dname CN=tsbad1"); keytool("-alias tsbad1 -genkeypair -dname CN=tsbad1"); keytool("-alias tsbad2 -genkeypair -dname CN=tsbad2"); keytool("-alias tsbad3 -genkeypair -dname CN=tsbad3"); gencert("old"); gencert("dsakey"); gencert("weakkeysize"); gencert("badku", "-ext ku:critical=keyAgreement"); gencert("ts", "-ext eku:critical=ts"); gencert("tsweak", "-ext eku:critical=ts"); gencert("tsbad1"); gencert("tsbad2", "-ext eku=ts"); gencert("tsbad3", "-ext eku:critical=cs"); } static void gencert(String alias, String... extra) throws Exception { keytool("-alias " + alias + " -certreq -file " + alias + ".req"); String genCmd = "-gencert -alias ca -infile " + alias + ".req -outfile " + alias + ".cert"; for (String s : extra) { genCmd += " " + s; } keytool(genCmd); keytool("-alias " + alias + " -importcert -file " + alias + ".cert"); } static void keytool(String cmd) throws Exception { cmd = "-keystore tsks -storepass changeit -keypass changeit " + "-keyalg rsa -validity 200 " + cmd; sun.security.tools.keytool.Main.main(cmd.split(" ")); } }