// SPDX-FileCopyrightText: 2022 Paul Schaub // // SPDX-License-Identifier: Apache-2.0 package org.pgpainless.decryption_verification; import static org.junit.jupiter.api.Assertions.assertFalse; import static org.junit.jupiter.api.Assertions.assertNotNull; import static org.junit.jupiter.api.Assertions.assertNull; import static org.junit.jupiter.api.Assertions.assertThrows; import static org.junit.jupiter.api.Assertions.assertTrue; import java.io.ByteArrayInputStream; import java.io.ByteArrayOutputStream; import java.io.IOException; import java.nio.charset.StandardCharsets; import java.security.InvalidAlgorithmParameterException; import java.security.NoSuchAlgorithmException; import org.bouncycastle.openpgp.PGPException; import org.bouncycastle.openpgp.PGPPublicKeyRing; import org.bouncycastle.openpgp.PGPSecretKeyRing; import org.bouncycastle.util.io.Streams; import org.junit.jupiter.api.BeforeAll; import org.junit.jupiter.api.Test; import org.pgpainless.PGPainless; import org.pgpainless.algorithm.DocumentSignatureType; import org.pgpainless.algorithm.EncryptionPurpose; import org.pgpainless.encryption_signing.EncryptionOptions; import org.pgpainless.encryption_signing.EncryptionStream; import org.pgpainless.encryption_signing.ProducerOptions; import org.pgpainless.encryption_signing.SigningOptions; import org.pgpainless.exception.KeyException; import org.pgpainless.exception.MissingDecryptionMethodException; import org.pgpainless.key.info.KeyRingInfo; import org.pgpainless.key.protection.SecretKeyRingProtector; import org.pgpainless.key.util.KeyRingUtils; public class CertificateWithMissingSecretKeyTest { private static final String MISSING_SIGNING_SECKEY = "" + "-----BEGIN PGP PRIVATE KEY BLOCK-----\n" + "Version: PGPainless\n" + "Comment: E97B 15E6 52FA 8BAE 2311 DDCB A5BD 9DC4 4415 C987\n" + "Comment: Missing Signing Subkey \n" + "\n" + "lFgEYjCuERYJKwYBBAHaRw8BAQdAaqeTdbyb/D+UXd2aXsP58+k+tvt22DnL6bC0\n" + "7p2tJacAAP0fEmwUY7rSPugQakzsA8nV4Nv3PYlKa6meqEePT+8s8BFitC9NaXNz\n" + "aW5nIFNpZ25pbmcgU3Via2V5IDxtaXNzaW5nQHNpZ25pbmcuc3Via2V5PoiPBBMW\n" + "CgBBBQJiMK4RCRClvZ3ERBXJhxYhBOl7FeZS+ouuIxHdy6W9ncREFcmHAp4BApsB\n" + "BRYCAwEABAsJCAcFFQoJCAsCmQEAAN0HAPkB7IphgTM94s/VpyV5+hvYbxesnji5\n" + "RNzqs3nRhS8DBgEA/+gCpAkgznB3T/uNtWIoTf7Kuib5mIJ+SW0l+htuEgacXQRi\n" + "MK4REgorBgEEAZdVAQUBAQdAlaQH44c7PdKkjaVVXvg86i+thKV121C/nH75Krhh\n" + "QxYDAQgHAAD/aWJt9M85Al+57lPqS5ppzrIoCoTZ6JCwuJUSNEAg4BgQ6Ih1BBgW\n" + "CgAdBQJiMK4RAp4BApsMBRYCAwEABAsJCAcFFQoJCAsACgkQpb2dxEQVyYdzuAD9\n" + "GEkU7NfugHw8alQT7IJbUobVyZzeXQyzPqSKUw/Vp54BAJXZj8NzQrrM4Q5C3+Mf\n" + "uznN+ryRovDXhf8T5PUXHloDuDMEYjCuERYJKwYBBAHaRw8BAQdAVeBpPurrwAU3\n" + "ns+1C2c6wJ8iTZ1eWEP2qgBAlokx5N+I1QQYFgoAfQUCYjCuEQKeAQKbAgUWAgMB\n" + "AAQLCQgHBRUKCQgLXyAEGRYKAAYFAmIwrhEACgkQld4KwYO6xR4YEwEA942iduoW\n" + "1ANEmwCwnYwMAa3HlXsMs5bdIUGnxuo7MBEA/1YYeAu45O2Z8kTdrDZM/1emoxt1\n" + "j6EzybnaJ+2XGX4AAAoJEKW9ncREFcmHLXsBAITCIwGtaCvZdWCQlJeYak1NTuBp\n" + "bmOEFga0sLmRI/zYAP97U2oc8dqV55S1b4yNkfENK2MD6Ow0nv8CL6+S0UaCBw==\n" + "=eTh7\n" + "-----END PGP PRIVATE KEY BLOCK-----"; private static final long signingSubkeyId = -7647663290973502178L; private static PGPSecretKeyRing missingSigningSecKey; private static long encryptionSubkeyId; private static PGPSecretKeyRing missingDecryptionSecKey; private static final SecretKeyRingProtector protector = SecretKeyRingProtector.unprotectedKeys(); @BeforeAll public static void prepare() throws IOException, PGPException, InvalidAlgorithmParameterException, NoSuchAlgorithmException { // missing signing sec key we read from bytes missingSigningSecKey = PGPainless.readKeyRing().secretKeyRing(MISSING_SIGNING_SECKEY); // missing encryption sec key we generate on the fly PGPSecretKeyRing secretKeys = PGPainless.generateKeyRing() .modernKeyRing("Missing Decryption Key ", null); encryptionSubkeyId = PGPainless.inspectKeyRing(secretKeys) .getEncryptionSubkeys(EncryptionPurpose.ANY).get(0).getKeyID(); // remove the encryption/decryption secret key missingDecryptionSecKey = KeyRingUtils.removeSecretKey(secretKeys, encryptionSubkeyId); } @Test public void assureMissingSigningSecKeyOnlyContainSigningPubKey() { assertNotNull(missingSigningSecKey.getPublicKey(signingSubkeyId)); assertNull(missingSigningSecKey.getSecretKey(signingSubkeyId)); KeyRingInfo info = PGPainless.inspectKeyRing(missingSigningSecKey); assertFalse(info.getSigningSubkeys().isEmpty()); // This method only tests for pub keys. } @Test public void assureMissingDecryptionSecKeyOnlyContainsEncryptionPubKey() { assertNotNull(missingDecryptionSecKey.getPublicKey(encryptionSubkeyId)); assertNull(missingDecryptionSecKey.getSecretKey(encryptionSubkeyId)); KeyRingInfo info = PGPainless.inspectKeyRing(missingDecryptionSecKey); assertFalse(info.getEncryptionSubkeys(EncryptionPurpose.ANY).isEmpty()); // pub key is still there } @Test public void testSignWithMissingSigningSecKey() { SigningOptions signingOptions = SigningOptions.get(); assertThrows(KeyException.MissingSecretKeyException.class, () -> signingOptions.addInlineSignature(protector, missingSigningSecKey, DocumentSignatureType.CANONICAL_TEXT_DOCUMENT)); assertThrows(KeyException.MissingSecretKeyException.class, () -> signingOptions.addDetachedSignature(protector, missingSigningSecKey, DocumentSignatureType.CANONICAL_TEXT_DOCUMENT)); } @Test public void testEncryptDecryptWithMissingDecryptionKey() throws PGPException, IOException { ByteArrayInputStream in = new ByteArrayInputStream("Hello, World!\n".getBytes(StandardCharsets.UTF_8)); ByteArrayOutputStream out = new ByteArrayOutputStream(); PGPPublicKeyRing certificate = PGPainless.extractCertificate(missingDecryptionSecKey); ProducerOptions producerOptions = ProducerOptions.encrypt( EncryptionOptions.encryptCommunications() .addRecipient(certificate)); // we can still encrypt, since the pub key is still there EncryptionStream encryptionStream = PGPainless.encryptAndOrSign() .onOutputStream(out) .withOptions(producerOptions); Streams.pipeAll(in, encryptionStream); encryptionStream.close(); assertTrue(encryptionStream.getResult().isEncryptedFor(certificate)); // Test decryption ByteArrayInputStream cipherIn = new ByteArrayInputStream(out.toByteArray()); ConsumerOptions consumerOptions = new ConsumerOptions() .addDecryptionKey(missingDecryptionSecKey); assertThrows(MissingDecryptionMethodException.class, () -> PGPainless.decryptAndOrVerify() .onInputStream(cipherIn) .withOptions(consumerOptions)); // <- cannot find decryption key } }