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Diffstat (limited to 'tests/hazmat/primitives/test_pkcs7.py')
| -rw-r--r-- | tests/hazmat/primitives/test_pkcs7.py | 675 |
1 files changed, 675 insertions, 0 deletions
diff --git a/tests/hazmat/primitives/test_pkcs7.py b/tests/hazmat/primitives/test_pkcs7.py new file mode 100644 index 000000000..8b93cb633 --- /dev/null +++ b/tests/hazmat/primitives/test_pkcs7.py @@ -0,0 +1,675 @@ +# This file is dual licensed under the terms of the Apache License, Version +# 2.0, and the BSD License. See the LICENSE file in the root of this repository +# for complete details. + +from __future__ import absolute_import, division, print_function + +import os + +import pytest + +from cryptography import x509 +from cryptography.exceptions import _Reasons +from cryptography.hazmat.primitives import hashes, serialization +from cryptography.hazmat.primitives.asymmetric import ed25519 +from cryptography.hazmat.primitives.serialization import pkcs7 + +from .utils import load_vectors_from_file +from ...utils import raises_unsupported_algorithm + + +class TestPKCS7Loading(object): + def test_load_invalid_der_pkcs7(self): + with pytest.raises(ValueError): + pkcs7.load_der_pkcs7_certificates(b"nonsense") + + def test_load_invalid_pem_pkcs7(self): + with pytest.raises(ValueError): + pkcs7.load_pem_pkcs7_certificates(b"nonsense") + + def test_not_bytes_der(self): + with pytest.raises(TypeError): + pkcs7.load_der_pkcs7_certificates(38) + + def test_not_bytes_pem(self): + with pytest.raises(TypeError): + pkcs7.load_pem_pkcs7_certificates(38) + + def test_load_pkcs7_pem(self): + certs = load_vectors_from_file( + os.path.join("pkcs7", "isrg.pem"), + lambda pemfile: pkcs7.load_pem_pkcs7_certificates(pemfile.read()), + mode="rb", + ) + assert len(certs) == 1 + assert certs[0].subject.get_attributes_for_oid( + x509.oid.NameOID.COMMON_NAME + ) == [ + x509.NameAttribute(x509.oid.NameOID.COMMON_NAME, u"ISRG Root X1") + ] + + def test_load_pkcs7_der(self): + certs = load_vectors_from_file( + os.path.join("pkcs7", "amazon-roots.p7b"), + lambda derfile: pkcs7.load_der_pkcs7_certificates(derfile.read()), + mode="rb", + ) + assert len(certs) == 2 + assert certs[0].subject.get_attributes_for_oid( + x509.oid.NameOID.COMMON_NAME + ) == [ + x509.NameAttribute( + x509.oid.NameOID.COMMON_NAME, u"Amazon Root CA 3" + ) + ] + assert certs[1].subject.get_attributes_for_oid( + x509.oid.NameOID.COMMON_NAME + ) == [ + x509.NameAttribute( + x509.oid.NameOID.COMMON_NAME, u"Amazon Root CA 2" + ) + ] + + def test_load_pkcs7_unsupported_type(self): + with raises_unsupported_algorithm(_Reasons.UNSUPPORTED_SERIALIZATION): + load_vectors_from_file( + os.path.join("pkcs7", "enveloped.pem"), + lambda pemfile: pkcs7.load_pem_pkcs7_certificates( + pemfile.read() + ), + mode="rb", + ) + + +# We have no public verification API and won't be adding one until we get +# some requirements from users so this function exists to give us basic +# verification for the signing tests. +def _pkcs7_verify(encoding, sig, msg, certs, options, backend): + sig_bio = backend._bytes_to_bio(sig) + if encoding is serialization.Encoding.DER: + p7 = backend._lib.d2i_PKCS7_bio(sig_bio.bio, backend._ffi.NULL) + elif encoding is serialization.Encoding.PEM: + p7 = backend._lib.PEM_read_bio_PKCS7( + sig_bio.bio, + backend._ffi.NULL, + backend._ffi.NULL, + backend._ffi.NULL, + ) + else: + p7 = backend._lib.SMIME_read_PKCS7(sig_bio.bio, backend._ffi.NULL) + backend.openssl_assert(p7 != backend._ffi.NULL) + p7 = backend._ffi.gc(p7, backend._lib.PKCS7_free) + flags = 0 + for option in options: + if option is pkcs7.PKCS7Options.Text: + flags |= backend._lib.PKCS7_TEXT + store = backend._lib.X509_STORE_new() + backend.openssl_assert(store != backend._ffi.NULL) + store = backend._ffi.gc(store, backend._lib.X509_STORE_free) + for cert in certs: + res = backend._lib.X509_STORE_add_cert(store, cert._x509) + backend.openssl_assert(res == 1) + if msg is None: + res = backend._lib.PKCS7_verify( + p7, + backend._ffi.NULL, + store, + backend._ffi.NULL, + backend._ffi.NULL, + flags, + ) + else: + msg_bio = backend._bytes_to_bio(msg) + res = backend._lib.PKCS7_verify( + p7, backend._ffi.NULL, store, msg_bio.bio, backend._ffi.NULL, flags + ) + backend.openssl_assert(res == 1) + + +def _load_cert_key(): + key = load_vectors_from_file( + os.path.join("x509", "custom", "ca", "ca_key.pem"), + lambda pemfile: serialization.load_pem_private_key( + pemfile.read(), None + ), + mode="rb", + ) + cert = load_vectors_from_file( + os.path.join("x509", "custom", "ca", "ca.pem"), + loader=lambda pemfile: x509.load_pem_x509_certificate(pemfile.read()), + mode="rb", + ) + return cert, key + + +class TestPKCS7Builder(object): + def test_invalid_data(self): + builder = pkcs7.PKCS7SignatureBuilder() + with pytest.raises(TypeError): + builder.set_data(u"not bytes") + + def test_set_data_twice(self): + builder = pkcs7.PKCS7SignatureBuilder().set_data(b"test") + with pytest.raises(ValueError): + builder.set_data(b"test") + + def test_sign_no_signer(self): + builder = pkcs7.PKCS7SignatureBuilder().set_data(b"test") + with pytest.raises(ValueError): + builder.sign(serialization.Encoding.SMIME, []) + + def test_sign_no_data(self): + cert, key = _load_cert_key() + builder = pkcs7.PKCS7SignatureBuilder().add_signer( + cert, key, hashes.SHA256() + ) + with pytest.raises(ValueError): + builder.sign(serialization.Encoding.SMIME, []) + + def test_unsupported_hash_alg(self): + cert, key = _load_cert_key() + with pytest.raises(TypeError): + pkcs7.PKCS7SignatureBuilder().add_signer( + cert, key, hashes.SHA512_256() + ) + + def test_not_a_cert(self): + cert, key = _load_cert_key() + with pytest.raises(TypeError): + pkcs7.PKCS7SignatureBuilder().add_signer( + b"notacert", key, hashes.SHA256() + ) + + @pytest.mark.supported( + only_if=lambda backend: backend.ed25519_supported(), + skip_message="Does not support ed25519.", + ) + def test_unsupported_key_type(self, backend): + cert, _ = _load_cert_key() + key = ed25519.Ed25519PrivateKey.generate() + with pytest.raises(TypeError): + pkcs7.PKCS7SignatureBuilder().add_signer( + cert, key, hashes.SHA256() + ) + + def test_sign_invalid_options(self): + cert, key = _load_cert_key() + builder = ( + pkcs7.PKCS7SignatureBuilder() + .set_data(b"test") + .add_signer(cert, key, hashes.SHA256()) + ) + with pytest.raises(ValueError): + builder.sign(serialization.Encoding.SMIME, [b"invalid"]) + + def test_sign_invalid_encoding(self): + cert, key = _load_cert_key() + builder = ( + pkcs7.PKCS7SignatureBuilder() + .set_data(b"test") + .add_signer(cert, key, hashes.SHA256()) + ) + with pytest.raises(ValueError): + builder.sign(serialization.Encoding.Raw, []) + + def test_sign_invalid_options_text_no_detached(self): + cert, key = _load_cert_key() + builder = ( + pkcs7.PKCS7SignatureBuilder() + .set_data(b"test") + .add_signer(cert, key, hashes.SHA256()) + ) + options = [pkcs7.PKCS7Options.Text] + with pytest.raises(ValueError): + builder.sign(serialization.Encoding.SMIME, options) + + def test_sign_invalid_options_text_der_encoding(self): + cert, key = _load_cert_key() + builder = ( + pkcs7.PKCS7SignatureBuilder() + .set_data(b"test") + .add_signer(cert, key, hashes.SHA256()) + ) + options = [ + pkcs7.PKCS7Options.Text, + pkcs7.PKCS7Options.DetachedSignature, + ] + with pytest.raises(ValueError): + builder.sign(serialization.Encoding.DER, options) + + def test_sign_invalid_options_no_attrs_and_no_caps(self): + cert, key = _load_cert_key() + builder = ( + pkcs7.PKCS7SignatureBuilder() + .set_data(b"test") + .add_signer(cert, key, hashes.SHA256()) + ) + options = [ + pkcs7.PKCS7Options.NoAttributes, + pkcs7.PKCS7Options.NoCapabilities, + ] + with pytest.raises(ValueError): + builder.sign(serialization.Encoding.SMIME, options) + + def test_smime_sign_detached(self, backend): + data = b"hello world" + cert, key = _load_cert_key() + options = [pkcs7.PKCS7Options.DetachedSignature] + builder = ( + pkcs7.PKCS7SignatureBuilder() + .set_data(data) + .add_signer(cert, key, hashes.SHA256()) + ) + + sig = builder.sign(serialization.Encoding.SMIME, options) + sig_binary = builder.sign(serialization.Encoding.DER, options) + # We don't have a generic ASN.1 parser available to us so we instead + # will assert on specific byte sequences being present based on the + # parameters chosen above. + assert b"sha-256" in sig + # Detached signature means that the signed data is *not* embedded into + # the PKCS7 structure itself, but is present in the SMIME serialization + # as a separate section before the PKCS7 data. So we should expect to + # have data in sig but not in sig_binary + assert data in sig + _pkcs7_verify( + serialization.Encoding.SMIME, sig, data, [cert], options, backend + ) + assert data not in sig_binary + _pkcs7_verify( + serialization.Encoding.DER, + sig_binary, + data, + [cert], + options, + backend, + ) + + def test_sign_byteslike(self): + data = bytearray(b"hello world") + cert, key = _load_cert_key() + options = [pkcs7.PKCS7Options.DetachedSignature] + builder = ( + pkcs7.PKCS7SignatureBuilder() + .set_data(data) + .add_signer(cert, key, hashes.SHA256()) + ) + + sig = builder.sign(serialization.Encoding.SMIME, options) + assert bytes(data) in sig + + def test_sign_pem(self, backend): + data = b"hello world" + cert, key = _load_cert_key() + options = [] + builder = ( + pkcs7.PKCS7SignatureBuilder() + .set_data(data) + .add_signer(cert, key, hashes.SHA256()) + ) + + sig = builder.sign(serialization.Encoding.PEM, options) + _pkcs7_verify( + serialization.Encoding.PEM, + sig, + None, + [cert], + options, + backend, + ) + + @pytest.mark.parametrize( + ("hash_alg", "expected_value"), + [ + (hashes.SHA1(), b"\x06\x05+\x0e\x03\x02\x1a"), + (hashes.SHA256(), b"\x06\t`\x86H\x01e\x03\x04\x02\x01"), + (hashes.SHA384(), b"\x06\t`\x86H\x01e\x03\x04\x02\x02"), + (hashes.SHA512(), b"\x06\t`\x86H\x01e\x03\x04\x02\x03"), + ], + ) + def test_sign_alternate_digests_der( + self, hash_alg, expected_value, backend + ): + data = b"hello world" + cert, key = _load_cert_key() + builder = ( + pkcs7.PKCS7SignatureBuilder() + .set_data(data) + .add_signer(cert, key, hash_alg) + ) + options = [] + sig = builder.sign(serialization.Encoding.DER, options) + assert expected_value in sig + _pkcs7_verify( + serialization.Encoding.DER, sig, None, [cert], options, backend + ) + + @pytest.mark.parametrize( + ("hash_alg", "expected_value"), + [ + (hashes.SHA1(), b"sha1"), + (hashes.SHA256(), b"sha-256"), + (hashes.SHA384(), b"sha-384"), + (hashes.SHA512(), b"sha-512"), + ], + ) + def test_sign_alternate_digests_detached(self, hash_alg, expected_value): + data = b"hello world" + cert, key = _load_cert_key() + builder = ( + pkcs7.PKCS7SignatureBuilder() + .set_data(data) + .add_signer(cert, key, hash_alg) + ) + options = [pkcs7.PKCS7Options.DetachedSignature] + sig = builder.sign(serialization.Encoding.SMIME, options) + # When in detached signature mode the hash algorithm is stored as a + # byte string like "sha-384". + assert expected_value in sig + + def test_sign_attached(self, backend): + data = b"hello world" + cert, key = _load_cert_key() + options = [] + builder = ( + pkcs7.PKCS7SignatureBuilder() + .set_data(data) + .add_signer(cert, key, hashes.SHA256()) + ) + + sig_binary = builder.sign(serialization.Encoding.DER, options) + # When not passing detached signature the signed data is embedded into + # the PKCS7 structure itself + assert data in sig_binary + _pkcs7_verify( + serialization.Encoding.DER, + sig_binary, + None, + [cert], + options, + backend, + ) + + def test_sign_binary(self, backend): + data = b"hello\nworld" + cert, key = _load_cert_key() + builder = ( + pkcs7.PKCS7SignatureBuilder() + .set_data(data) + .add_signer(cert, key, hashes.SHA256()) + ) + options = [] + sig_no_binary = builder.sign(serialization.Encoding.DER, options) + sig_binary = builder.sign( + serialization.Encoding.DER, [pkcs7.PKCS7Options.Binary] + ) + # Binary prevents translation of LF to CR+LF (SMIME canonical form) + # so data should not be present in sig_no_binary, but should be present + # in sig_binary + assert data not in sig_no_binary + _pkcs7_verify( + serialization.Encoding.DER, + sig_no_binary, + None, + [cert], + options, + backend, + ) + assert data in sig_binary + _pkcs7_verify( + serialization.Encoding.DER, + sig_binary, + None, + [cert], + options, + backend, + ) + + def test_sign_smime_canonicalization(self, backend): + data = b"hello\nworld" + cert, key = _load_cert_key() + builder = ( + pkcs7.PKCS7SignatureBuilder() + .set_data(data) + .add_signer(cert, key, hashes.SHA256()) + ) + + options = [] + sig_binary = builder.sign(serialization.Encoding.DER, options) + # LF gets converted to CR+LF (SMIME canonical form) + # so data should not be present in the sig + assert data not in sig_binary + assert b"hello\r\nworld" in sig_binary + _pkcs7_verify( + serialization.Encoding.DER, + sig_binary, + None, + [cert], + options, + backend, + ) + + def test_sign_text(self, backend): + data = b"hello world" + cert, key = _load_cert_key() + builder = ( + pkcs7.PKCS7SignatureBuilder() + .set_data(data) + .add_signer(cert, key, hashes.SHA256()) + ) + + options = [ + pkcs7.PKCS7Options.Text, + pkcs7.PKCS7Options.DetachedSignature, + ] + sig_pem = builder.sign(serialization.Encoding.SMIME, options) + # The text option adds text/plain headers to the S/MIME message + # These headers are only relevant in SMIME mode, not binary, which is + # just the PKCS7 structure itself. + assert b"text/plain" in sig_pem + # When passing the Text option the header is prepended so the actual + # signed data is this. + signed_data = b"Content-Type: text/plain\r\n\r\nhello world" + _pkcs7_verify( + serialization.Encoding.SMIME, + sig_pem, + signed_data, + [cert], + options, + backend, + ) + + def test_sign_no_capabilities(self, backend): + data = b"hello world" + cert, key = _load_cert_key() + builder = ( + pkcs7.PKCS7SignatureBuilder() + .set_data(data) + .add_signer(cert, key, hashes.SHA256()) + ) + + options = [pkcs7.PKCS7Options.NoCapabilities] + sig_binary = builder.sign(serialization.Encoding.DER, options) + # NoCapabilities removes the SMIMECapabilities attribute from the + # PKCS7 structure. This is an ASN.1 sequence with the + # OID 1.2.840.113549.1.9.15. It does NOT remove all authenticated + # attributes, so we verify that by looking for the signingTime OID. + + # 1.2.840.113549.1.9.15 SMIMECapabilities as an ASN.1 DER encoded OID + assert b"\x06\t*\x86H\x86\xf7\r\x01\t\x0f" not in sig_binary + # 1.2.840.113549.1.9.5 signingTime as an ASN.1 DER encoded OID + assert b"\x06\t*\x86H\x86\xf7\r\x01\t\x05" in sig_binary + _pkcs7_verify( + serialization.Encoding.DER, + sig_binary, + None, + [cert], + options, + backend, + ) + + def test_sign_no_attributes(self, backend): + data = b"hello world" + cert, key = _load_cert_key() + builder = ( + pkcs7.PKCS7SignatureBuilder() + .set_data(data) + .add_signer(cert, key, hashes.SHA256()) + ) + + options = [pkcs7.PKCS7Options.NoAttributes] + sig_binary = builder.sign(serialization.Encoding.DER, options) + # NoAttributes removes all authenticated attributes, so we shouldn't + # find SMIMECapabilities or signingTime. + + # 1.2.840.113549.1.9.15 SMIMECapabilities as an ASN.1 DER encoded OID + assert b"\x06\t*\x86H\x86\xf7\r\x01\t\x0f" not in sig_binary + # 1.2.840.113549.1.9.5 signingTime as an ASN.1 DER encoded OID + assert b"\x06\t*\x86H\x86\xf7\r\x01\t\x05" not in sig_binary + _pkcs7_verify( + serialization.Encoding.DER, + sig_binary, + None, + [cert], + options, + backend, + ) + + def test_sign_no_certs(self, backend): + data = b"hello world" + cert, key = _load_cert_key() + builder = ( + pkcs7.PKCS7SignatureBuilder() + .set_data(data) + .add_signer(cert, key, hashes.SHA256()) + ) + + options = [] + sig = builder.sign(serialization.Encoding.DER, options) + assert sig.count(cert.public_bytes(serialization.Encoding.DER)) == 1 + + options = [pkcs7.PKCS7Options.NoCerts] + sig_no = builder.sign(serialization.Encoding.DER, options) + assert sig_no.count(cert.public_bytes(serialization.Encoding.DER)) == 0 + + def test_multiple_signers(self, backend): + data = b"hello world" + cert, key = _load_cert_key() + rsa_key = load_vectors_from_file( + os.path.join("x509", "custom", "ca", "rsa_key.pem"), + lambda pemfile: serialization.load_pem_private_key( + pemfile.read(), None + ), + mode="rb", + ) + rsa_cert = load_vectors_from_file( + os.path.join("x509", "custom", "ca", "rsa_ca.pem"), + loader=lambda pemfile: x509.load_pem_x509_certificate( + pemfile.read() + ), + mode="rb", + ) + builder = ( + pkcs7.PKCS7SignatureBuilder() + .set_data(data) + .add_signer(cert, key, hashes.SHA512()) + .add_signer(rsa_cert, rsa_key, hashes.SHA512()) + ) + options = [] + sig = builder.sign(serialization.Encoding.DER, options) + # There should be three SHA512 OIDs in this structure + assert sig.count(b"\x06\t`\x86H\x01e\x03\x04\x02\x03") == 3 + _pkcs7_verify( + serialization.Encoding.DER, + sig, + None, + [cert, rsa_cert], + options, + backend, + ) + + def test_multiple_signers_different_hash_algs(self, backend): + data = b"hello world" + cert, key = _load_cert_key() + rsa_key = load_vectors_from_file( + os.path.join("x509", "custom", "ca", "rsa_key.pem"), + lambda pemfile: serialization.load_pem_private_key( + pemfile.read(), None + ), + mode="rb", + ) + rsa_cert = load_vectors_from_file( + os.path.join("x509", "custom", "ca", "rsa_ca.pem"), + loader=lambda pemfile: x509.load_pem_x509_certificate( + pemfile.read() + ), + mode="rb", + ) + builder = ( + pkcs7.PKCS7SignatureBuilder() + .set_data(data) + .add_signer(cert, key, hashes.SHA384()) + .add_signer(rsa_cert, rsa_key, hashes.SHA512()) + ) + options = [] + sig = builder.sign(serialization.Encoding.DER, options) + # There should be two SHA384 and two SHA512 OIDs in this structure + assert sig.count(b"\x06\t`\x86H\x01e\x03\x04\x02\x02") == 2 + assert sig.count(b"\x06\t`\x86H\x01e\x03\x04\x02\x03") == 2 + _pkcs7_verify( + serialization.Encoding.DER, + sig, + None, + [cert, rsa_cert], + options, + backend, + ) + + def test_add_additional_cert_not_a_cert(self, backend): + with pytest.raises(TypeError): + pkcs7.PKCS7SignatureBuilder().add_certificate(b"notacert") + + def test_add_additional_cert(self, backend): + data = b"hello world" + cert, key = _load_cert_key() + rsa_cert = load_vectors_from_file( + os.path.join("x509", "custom", "ca", "rsa_ca.pem"), + loader=lambda pemfile: x509.load_pem_x509_certificate( + pemfile.read() + ), + mode="rb", + ) + builder = ( + pkcs7.PKCS7SignatureBuilder() + .set_data(data) + .add_signer(cert, key, hashes.SHA384()) + .add_certificate(rsa_cert) + ) + options = [] + sig = builder.sign(serialization.Encoding.DER, options) + assert ( + sig.count(rsa_cert.public_bytes(serialization.Encoding.DER)) == 1 + ) + + def test_add_multiple_additional_certs(self, backend): + data = b"hello world" + cert, key = _load_cert_key() + rsa_cert = load_vectors_from_file( + os.path.join("x509", "custom", "ca", "rsa_ca.pem"), + loader=lambda pemfile: x509.load_pem_x509_certificate( + pemfile.read() + ), + mode="rb", + ) + builder = ( + pkcs7.PKCS7SignatureBuilder() + .set_data(data) + .add_signer(cert, key, hashes.SHA384()) + .add_certificate(rsa_cert) + .add_certificate(rsa_cert) + ) + options = [] + sig = builder.sign(serialization.Encoding.DER, options) + assert ( + sig.count(rsa_cert.public_bytes(serialization.Encoding.DER)) == 2 + ) |