pgpainless/pgpainless-sop/src/test/java/org/pgpainless/sop/EncryptDecryptRoundTripTest...

392 lines
19 KiB
Java

// SPDX-FileCopyrightText: 2021 Paul Schaub <vanitasvitae@fsfe.org>
//
// SPDX-License-Identifier: Apache-2.0
package org.pgpainless.sop;
import static org.junit.jupiter.api.Assertions.assertArrayEquals;
import static org.junit.jupiter.api.Assertions.assertEquals;
import static org.junit.jupiter.api.Assertions.assertThrows;
import static org.junit.jupiter.api.Assertions.assertTrue;
import java.io.ByteArrayOutputStream;
import java.io.IOException;
import java.nio.charset.StandardCharsets;
import org.bouncycastle.util.io.Streams;
import org.junit.jupiter.api.BeforeAll;
import org.junit.jupiter.api.Test;
import sop.ByteArrayAndResult;
import sop.DecryptionResult;
import sop.SOP;
import sop.SessionKey;
import sop.exception.SOPGPException;
public class EncryptDecryptRoundTripTest {
private static SOP sop;
private static byte[] aliceKey;
private static byte[] aliceCert;
private static byte[] bobKey;
private static byte[] bobCert;
private static byte[] message = "Hello, World!\n".getBytes(StandardCharsets.UTF_8);
@BeforeAll
public static void setup() throws IOException {
sop = new SOPImpl();
aliceKey = sop.generateKey()
.userId("Alice <alice@pgpainless.org>")
.generate()
.getBytes();
aliceCert = sop.extractCert()
.key(aliceKey)
.getBytes();
bobKey = sop.generateKey()
.userId("Bob <bob@pgpainless.org>")
.generate()
.getBytes();
bobCert = sop.extractCert()
.key(bobKey)
.getBytes();
}
@Test
public void basicRoundTripWithKey() throws IOException, SOPGPException.KeyCannotSign {
byte[] encrypted = sop.encrypt()
.signWith(aliceKey)
.withCert(aliceCert)
.withCert(bobCert)
.plaintext(message)
.getBytes();
ByteArrayAndResult<DecryptionResult> bytesAndResult = sop.decrypt()
.withKey(bobKey)
.verifyWithCert(aliceCert)
.ciphertext(encrypted)
.toByteArrayAndResult();
ByteArrayOutputStream decrypted = new ByteArrayOutputStream();
Streams.pipeAll(bytesAndResult.getInputStream(), decrypted);
assertArrayEquals(message, decrypted.toByteArray());
DecryptionResult result = bytesAndResult.getResult();
assertEquals(1, result.getVerifications().size());
}
@Test
public void basicRoundTripWithoutArmorUsingKey() throws IOException, SOPGPException.KeyCannotSign {
byte[] aliceKeyNoArmor = sop.generateKey()
.userId("Alice <alice@unarmored.org>")
.noArmor()
.generate()
.getBytes();
byte[] aliceCertNoArmor = sop.extractCert()
.noArmor()
.key(aliceKeyNoArmor)
.getBytes();
byte[] encrypted = sop.encrypt()
.signWith(aliceKeyNoArmor)
.withCert(aliceCertNoArmor)
.noArmor()
.plaintext(message)
.getBytes();
ByteArrayAndResult<DecryptionResult> bytesAndResult = sop.decrypt()
.withKey(aliceKeyNoArmor)
.verifyWithCert(aliceCertNoArmor)
.ciphertext(encrypted)
.toByteArrayAndResult();
byte[] decrypted = bytesAndResult.getBytes();
assertArrayEquals(message, decrypted);
DecryptionResult result = bytesAndResult.getResult();
assertEquals(1, result.getVerifications().size());
}
@Test
public void basicRoundTripWithPassword() throws IOException {
byte[] encrypted = sop.encrypt()
.withPassword("passphr4s3")
.plaintext(message)
.getBytes();
ByteArrayAndResult<DecryptionResult> bytesAndResult = sop.decrypt()
.withPassword("passphr4s3")
.ciphertext(encrypted)
.toByteArrayAndResult();
byte[] decrypted = bytesAndResult.getBytes();
assertArrayEquals(message, decrypted);
DecryptionResult result = bytesAndResult.getResult();
assertEquals(0, result.getVerifications().size());
}
@Test
public void roundTripWithDecryptionPasswordContainingWhitespace() throws IOException {
ByteArrayAndResult<DecryptionResult> bytesAndResult = sop.decrypt()
.withPassword("passphr4s3 ") // whitespace is removed
.ciphertext(
sop.encrypt()
.withPassword("passphr4s3")
.plaintext(message)
.getInputStream()
)
.toByteArrayAndResult();
byte[] decrypted = bytesAndResult.getBytes();
assertArrayEquals(message, decrypted);
DecryptionResult result = bytesAndResult.getResult();
assertEquals(0, result.getVerifications().size());
}
@Test
public void roundTripWithEncryptionPasswordContainingWhitespace() throws IOException {
byte[] encrypted = sop.encrypt()
.withPassword("passphr4s3 ")
.plaintext(message)
.getBytes();
ByteArrayAndResult<DecryptionResult> bytesAndResult = sop.decrypt()
.withPassword("passphr4s3 ")
.ciphertext(encrypted)
.toByteArrayAndResult();
byte[] decrypted = bytesAndResult.getBytes();
assertArrayEquals(message, decrypted);
DecryptionResult result = bytesAndResult.getResult();
assertEquals(0, result.getVerifications().size());
}
@Test
public void encrypt_decryptAndVerifyYieldsNoSignatureException() throws IOException {
byte[] encrypted = sop.encrypt()
.withCert(bobCert)
.plaintext(message)
.getBytes();
assertThrows(SOPGPException.NoSignature.class, () -> sop
.decrypt()
.withKey(bobKey)
.verifyWithCert(aliceCert)
.ciphertext(encrypted)
.toByteArrayAndResult());
}
@Test
public void encrypt_decryptWithoutKeyOrPassphraseYieldsMissingArgException() throws IOException {
byte[] encrypted = sop.encrypt()
.withCert(bobCert)
.plaintext(message)
.getBytes();
assertThrows(SOPGPException.MissingArg.class, () -> sop
.decrypt()
.ciphertext(encrypted)
.toByteArrayAndResult());
}
@Test
public void decrypt_withKeyWithPasswordProtectionFails() {
String passwordProtectedKey = "-----BEGIN PGP PRIVATE KEY BLOCK-----\n" +
"Version: PGPainless\n" +
"Comment: 1777 B08F B9FE 25B8 E32C E2E2 5974 2F3E DEC0 1772\n" +
"Comment: Protected <protected@pgpainless.org>\n" +
"\n" +
"lIYEYSztkRYJKwYBBAHaRw8BAQdAMAcay1YOujgMVAXQsAz/QwL2PHc8EBroTQpe\n" +
"Skizmyf+CQMC03aJCFqkseNgXBlZLknishdIO2iMz5YT2ptOjDkYLenEc71LqDTZ\n" +
"abhG9vjfaMtfUvfF6qZurbvVAC0QBr/cSVREuEqDCxpbmYKeFrMz6LQkUHJvdGVj\n" +
"dGVkIDxwcm90ZWN0ZWRAcGdwYWlubGVzcy5vcmc+iHgEExYKACAFAmEs7ZECGwEF\n" +
"FgIDAQAECwkIBwUVCgkICwIeAQIZAQAKCRBZdC8+3sAXcksuAP961t8IhIHK7cG9\n" +
"O7DjNNi35rEgvtHK6yC529gCzE5cBAEAjEgCHSu9UK4SQOSCiQNPKIJ4UUTuCWm8\n" +
"bla6dtuB1QSciwRhLO2REgorBgEEAZdVAQUBAQdAqVXssfkOprxE8weHZoa7T/5f\n" +
"kbGOA/6hmzLoYfWURhEDAQgH/gkDAtN2iQhapLHjYEJJ+kwyW2SnEFhMoWKZBG94\n" +
"RV+S+rwq+ITz/CV53Qc/XcveX6x4QmoXqK6ges7dDLYog/iJ/tFAMeV//LJHpow/\n" +
"U2SA6XGIdQQYFgoAHQUCYSztkQIbDAUWAgMBAAQLCQgHBRUKCQgLAh4BAAoJEFl0\n" +
"Lz7ewBdyWJkA/j8zj+6AhhAJOdlfqA2empI+eZfZQg8D1uB/QfKNh+5CAP9VYUUf\n" +
"EZMNtnSCXP6ERFy1/CJLW4eqLL19oVBJ/mvMDJyGBGEs7ZEWCSsGAQQB2kcPAQEH\n" +
"QMZgsx/zrhfULWNsjs0ZREzEwLsPRzSgh9zKn53U/zlY/gkDAtN2iQhapLHjYHe7\n" +
"hmEPgxR7lsOZJazPnBzJGP6uRs4ts6m7e4MfEF2gk0N+iaQPowkypZS98pN5rsDg\n" +
"t9Yby6+IgqSQkMZitZAxnfepOCOI1QQYFgoAfQUCYSztkQIbAgUWAgMBAAQLCQgH\n" +
"BRUKCQgLAh4BXyAEGRYKAAYFAmEs7ZEACgkQpHV13KorLUkL3gEAnNx1GARit/FL\n" +
"4OoL0dINsmTCF8hQKe2OGgNhhkN8v90A/i2RifktEqcmMW1ezSRGlmn5hx5bTWRc\n" +
"99Ts4FiwRLQJAAoJEFl0Lz7ewBdyaysA/jk61StphMpfuRsuQwznH7L7SddNcZ1k\n" +
"l1wHK5kRJXyCAP0WUgkpEcM2bpwb4sxkCDxrfk/ixc47hGa68MPWwOJkAQ==\n" +
"=MUYS\n" +
"-----END PGP PRIVATE KEY BLOCK-----";
assertThrows(SOPGPException.KeyIsProtected.class, () -> sop.decrypt()
.withKey(passwordProtectedKey.getBytes(StandardCharsets.UTF_8)));
}
@Test
public void verifyWith_noDataThrowsBadData() {
assertThrows(SOPGPException.BadData.class, () -> sop.decrypt()
.verifyWithCert(new byte[0]));
}
@Test
public void testPassphraseDecryptionYieldsSessionKey() throws IOException {
byte[] message = "Hello\nWorld\n".getBytes(StandardCharsets.UTF_8);
byte[] ciphertext = ("-----BEGIN PGP MESSAGE-----\n" +
"Version: PGPainless\n" +
"\n" +
"jA0ECQMCdFswArqHpj1g0j4BLDTkZhCC1crZf0EFq1xPIMUtnyRmfJJ7IzsdMJ5Y\n" +
"EhKbBc2h6wIX7B/GxUbyNj1xh5JRzt2ZX8KL2d6HAQ==\n" +
"=zZ0/\n" +
"-----END PGP MESSAGE-----").getBytes(StandardCharsets.UTF_8);
String passphrase = "sw0rdf1sh";
ByteArrayAndResult<DecryptionResult> bytesAndResult = sop.decrypt().withPassword(passphrase).ciphertext(ciphertext).toByteArrayAndResult();
assertArrayEquals(message, bytesAndResult.getBytes());
assertTrue(bytesAndResult.getResult().getSessionKey().isPresent());
assertEquals("9:7BCB7383D23E20D4BA8980B26D6C0813769056546C45B7E55F4612BFAD5B4B1C", bytesAndResult.getResult().getSessionKey().get().toString());
}
@Test
public void testPublicKeyDecryptionYieldsSessionKey() throws IOException {
byte[] key = ("-----BEGIN PGP PRIVATE KEY BLOCK-----\n" +
"Version: PGPainless\n" +
"Comment: D94A AA9C 5F73 48B2 5D81 72E7 F20C F71E 93FE 897F\n" +
"Comment: Alice\n" +
"\n" +
"lFgEYWlyaRYJKwYBBAHaRw8BAQdAJsJfjByLE+8HNVGbEKiIbSGXBYwR6L61bT5E\n" +
"Hhu642kAAP49D4TOaI+Z3G5ko4C4D1bOzLajLRpIuPLuwYHpF1xD0RHmtAVBbGlj\n" +
"ZYh4BBMWCgAgBQJhaXJpAhsBBRYCAwEABRUKCQgLBAsJCAcCHgECGQEACgkQ8gz3\n" +
"HpP+iX/c8AD9Hx0PUu97n8ZlrpuA6YuJL3rONPQnaXMz9eE+KHxJS6sBAM06X8Wm\n" +
"XRGUVURsoerwYTbUnXcUnqH/U/JhwlUerJAInF0EYWlyaRIKKwYBBAGXVQEFAQEH\n" +
"QJOHyxI5K8ZqX+v/AmTLHAIjWd8wHO8eGld4KHniCFx9AwEIBwAA/0zVZYYWsr3w\n" +
"GKkmqfIZlB+wIeJlWrho87kvXiNAe0LIEIGIdQQYFgoAHQUCYWlyaQIbDAUWAgMB\n" +
"AAUVCgkICwQLCQgHAh4BAAoJEPIM9x6T/ol/vggA/ilxi5UTjDYDR7sGrYyaGPRK\n" +
"Sg0KNn2SV4c5M5ZmZR7sAP4kKz6kQ4UtYmSmUmMBu+A3mMTN8VQY+6LSTdekvU0N\n" +
"ApxYBGFpcmkWCSsGAQQB2kcPAQEHQJiiZENQ52jyt8wBwX7fD1vQkvgTg5T3v1S1\n" +
"yzr1yI0RAAD+KOTcMdv8rz3U6K42PNE4b983KoMfyQ/hgjIWOi2BYBwP94jVBBgW\n" +
"CgB9BQJhaXJpAhsCBRYCAwEABRUKCQgLBAsJCAcCHgFfIAQZFgoABgUCYWlyaQAK\n" +
"CRDP7lemqmadIYLuAP9oAm+OFzyMNrmWRcvdHqH/DAfJTM2+ZmANSm44geZDEAD9\n" +
"HfeCHev1H1H1wOd0S3tW9gZwonrYFoqOBW/YTmf5XwYACgkQ8gz3HpP+iX+veQEA\n" +
"sWC+xDo+lc6oJr4q0mTJkxzYfgUBtQ0VjUWNcGyOdegBAL8hMzb9+e4wbP2F0tMb\n" +
"ZFA2MgHsvqGhXyAXi50arZYF\n" +
"=k66N\n" +
"-----END PGP PRIVATE KEY BLOCK-----\n").getBytes(StandardCharsets.UTF_8);
byte[] message = "Hello\nWorld\n".getBytes(StandardCharsets.UTF_8);
byte[] ciphertext = ("-----BEGIN PGP MESSAGE-----\n" +
"Version: PGPainless\n" +
"\n" +
"hF4DrJ3c2YF1IKUSAQdA9VL6OwIwOwB4GnE4yR5JJ5OjcC76WTpdm85I6WHvhD4w\n" +
"hqHpf6UGaDDQ7xAcSd7YnEGVMBOOBnJfD1PRuNWE5hwgqqsqpMDrvvMHjUsg3HNH\n" +
"0j4BriMU8XQ6MLdvCaFmeQqFwBD4mlI/x32wj0I9VyBIKysopA8HNV4ES2rOhGuW\n" +
"T/zFmI9Tm9eWvNwv0LUNhQ==\n" +
"=4Z+m\n" +
"-----END PGP MESSAGE-----\n").getBytes(StandardCharsets.UTF_8);
ByteArrayAndResult<DecryptionResult> bytesAndResult = sop.decrypt().withKey(key).ciphertext(ciphertext).toByteArrayAndResult();
DecryptionResult result = bytesAndResult.getResult();
assertArrayEquals(message, bytesAndResult.getBytes());
assertTrue(result.getSessionKey().isPresent());
assertEquals("9:63F741E7FB60247BE59C64158573308F727236482DB7653908C95839E4166AAE", result.getSessionKey().get().toString());
}
@Test
public void testDecryptionWithSessionKey() throws IOException {
byte[] message = "Hello\nWorld\n".getBytes(StandardCharsets.UTF_8);
byte[] ciphertext = ("-----BEGIN PGP MESSAGE-----\n" +
"Version: PGPainless\n" +
"\n" +
"hF4DrJ3c2YF1IKUSAQdA9VL6OwIwOwB4GnE4yR5JJ5OjcC76WTpdm85I6WHvhD4w\n" +
"hqHpf6UGaDDQ7xAcSd7YnEGVMBOOBnJfD1PRuNWE5hwgqqsqpMDrvvMHjUsg3HNH\n" +
"0j4BriMU8XQ6MLdvCaFmeQqFwBD4mlI/x32wj0I9VyBIKysopA8HNV4ES2rOhGuW\n" +
"T/zFmI9Tm9eWvNwv0LUNhQ==\n" +
"=4Z+m\n" +
"-----END PGP MESSAGE-----\n").getBytes(StandardCharsets.UTF_8);
SessionKey sessionKey = SessionKey.fromString("9:63F741E7FB60247BE59C64158573308F727236482DB7653908C95839E4166AAE");
ByteArrayAndResult<DecryptionResult> bytesAndResult = sop.decrypt().withSessionKey(sessionKey)
.ciphertext(ciphertext)
.toByteArrayAndResult();
DecryptionResult result = bytesAndResult.getResult();
assertTrue(result.getSessionKey().isPresent());
assertEquals(sessionKey, result.getSessionKey().get());
assertArrayEquals(message, bytesAndResult.getBytes());
}
@Test
public void testDecryptionWithSessionKey_VerificationWithCert() throws IOException {
byte[] plaintext = "This is a test message.\nSit back and relax.\n".getBytes(StandardCharsets.UTF_8);
byte[] key = ("-----BEGIN PGP PRIVATE KEY BLOCK-----\n" +
"Version: PGPainless\n" +
"Comment: 9C26 EFAB 1C65 00A2 28E8 A9C2 658E E420 C824 D191\n" +
"Comment: Alice\n" +
"\n" +
"lFgEYWl4ixYJKwYBBAHaRw8BAQdAv6+cd8R/ICS/z9hlT99g++wyquxVsO0FCb8F\n" +
"MSkTplUAAP9gPoBi8fxdfLaEyt6GWeIBTeYsVxsogbKzXXnjp3MbiRE/tAVBbGlj\n" +
"ZYh4BBMWCgAgBQJhaXiLAhsBBRYCAwEABRUKCQgLBAsJCAcCHgECGQEACgkQZY7k\n" +
"IMgk0ZEZuAEA3hWzfqCXGUjlv+miWey1AyWRu9eQvTdE9YqbIMuxIk4BAMtGlo6l\n" +
"d3E868q0zLOOktmsBxnzaE7knbd9nAlK3FUJnF0EYWl4ixIKKwYBBAGXVQEFAQEH\n" +
"QK8vS3T3Yf3Gpy9iWOTR0jdhV4XgtchcvKCpFMgc5uwFAwEIBwAA/1tNle5cT9kS\n" +
"8yzNxL16ElEREtEX+5kpkt6JZyTx0xfAEPGIdQQYFgoAHQUCYWl4iwIbDAUWAgMB\n" +
"AAUVCgkICwQLCQgHAh4BAAoJEGWO5CDIJNGRM80BANJ6EGKIkVNxYj7wOaEqyRh1\n" +
"Rtv3tLAnEzLl/b0mZx3WAQDADAPNCl5xnjTt5InyfrwV90kM4vDGcl4mQE8FD7dD\n" +
"B5xYBGFpeIsWCSsGAQQB2kcPAQEHQFuEaBKUllw+MfdkkSNE0CncJCeFGCbHvmsc\n" +
"Ma/DPgrpAAEAlsoxcTyTFfHxV2CayDCFvBSHYXOSOg6fyMdh0SxzjC0PVIjVBBgW\n" +
"CgB9BQJhaXiLAhsCBRYCAwEABRUKCQgLBAsJCAcCHgFfIAQZFgoABgUCYWl4iwAK\n" +
"CRBGMq3j1oKUXenjAP974AvBOAVIdNUkVAishoDL7ee7/eAU3Ni7V2Kn47cusQD/\n" +
"c8c9phtf2NIL23K4bvBdvsU3opV2DIVJwRutV4v6jgAACgkQZY7kIMgk0ZG1dwEA\n" +
"sFp1AuPcn3dGF05D6ohlqunoBwBWEcwZLjx+v5X27R8A/17V5nzC+eny3XjCF8Ib\n" +
"qw1VTfR84stki65Xhm2lxFAN\n" +
"=TQO7\n" +
"-----END PGP PRIVATE KEY BLOCK-----\n").getBytes(StandardCharsets.UTF_8);
byte[] cert = sop.extractCert().key(key).getBytes();
byte[] ciphertext = ("-----BEGIN PGP MESSAGE-----\n" +
"Version: PGPainless\n" +
"\n" +
"hF4DSjXDMRql2RASAQdAkhJyA9GX5ios8PNlti7v7BieggiiR9trqrKFQwomU2Aw\n" +
"elEFuDA3ugJO2rNiyQQH1riFFJuod6BiQuxFhdf/mmsFFDzHmJeUOx9pQeNemzST\n" +
"0sAdAQQYC+iXUNn2y15kTqbFQFgfOWObgsqspGY04V17fZdVI7bEORLM+YT6KoZA\n" +
"uq2WO49ze9jp2jdvTsjjNNseZDhmxtgOCfi1/Fi3IHPnBJW7M3UWaJCSLozWkO95\n" +
"FztCSWL22jDGPGIjgQ589hYW+WuJMvMv6ltTOo+l70S5dHSObijbcOqfNSmrxlpw\n" +
"hqZfkU0BA01I9Pf3lBPCNyMbCPZP0oaIiWACnm6svWp4oH5u5ClhS9BVJTptzwXv\n" +
"mMj+lTi5ahGQJ3Nr8krloTSsjpkssz6D2+FDnvjwu6E=\n" +
"=BYOB\n" +
"-----END PGP MESSAGE-----").getBytes(StandardCharsets.UTF_8);
String sessionKey = "9:87C0870598AD908ABEECCAE265DCEEA146CF557AAF698D097024404A00EBD072";
// Decrypt with public key
ByteArrayAndResult<DecryptionResult> bytesAndResult =
sop.decrypt().withKey(key).verifyWithCert(cert).ciphertext(ciphertext).toByteArrayAndResult();
assertEquals(sessionKey, bytesAndResult.getResult().getSessionKey().get().toString());
assertArrayEquals(plaintext, bytesAndResult.getBytes());
assertEquals(1, bytesAndResult.getResult().getVerifications().size());
// Decrypt with session key
bytesAndResult = sop.decrypt().withSessionKey(SessionKey.fromString(sessionKey))
.verifyWithCert(cert).ciphertext(ciphertext).toByteArrayAndResult();
assertEquals(sessionKey, bytesAndResult.getResult().getSessionKey().get().toString());
assertArrayEquals(plaintext, bytesAndResult.getBytes());
assertEquals(1, bytesAndResult.getResult().getVerifications().size());
}
@Test
public void decryptWithWrongSessionKey() {
byte[] ciphertext = ("-----BEGIN PGP MESSAGE-----\n" +
"Version: PGPainless\n" +
"\n" +
"hF4DSjXDMRql2RASAQdAkhJyA9GX5ios8PNlti7v7BieggiiR9trqrKFQwomU2Aw\n" +
"elEFuDA3ugJO2rNiyQQH1riFFJuod6BiQuxFhdf/mmsFFDzHmJeUOx9pQeNemzST\n" +
"0sAdAQQYC+iXUNn2y15kTqbFQFgfOWObgsqspGY04V17fZdVI7bEORLM+YT6KoZA\n" +
"uq2WO49ze9jp2jdvTsjjNNseZDhmxtgOCfi1/Fi3IHPnBJW7M3UWaJCSLozWkO95\n" +
"FztCSWL22jDGPGIjgQ589hYW+WuJMvMv6ltTOo+l70S5dHSObijbcOqfNSmrxlpw\n" +
"hqZfkU0BA01I9Pf3lBPCNyMbCPZP0oaIiWACnm6svWp4oH5u5ClhS9BVJTptzwXv\n" +
"mMj+lTi5ahGQJ3Nr8krloTSsjpkssz6D2+FDnvjwu6E=\n" +
"=BYOB\n" +
"-----END PGP MESSAGE-----").getBytes(StandardCharsets.UTF_8);
SessionKey wrongSessionKey = SessionKey.fromString("9:63F741E7FB60247BE59C64158573308F727236482DB7653908C95839E4166AAE");
assertThrows(SOPGPException.BadData.class, () ->
sop.decrypt().withSessionKey(wrongSessionKey).ciphertext(ciphertext));
}
}