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_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_invalid_options_text_no_detached(self, backend):
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_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: typing.List[pkcs7.PKCS7Options] = []
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_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",
)
assert isinstance(rsa_key, rsa.RSAPrivateKey)
builder = (pkcs7.PKCS7SignatureBuilder().set_data(data).add_signer(
cert, key, hashes.SHA384()).add_signer(rsa_cert, rsa_key,
hashes.SHA512()))
options: typing.List[pkcs7.PKCS7Options] = []
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_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_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_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_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_not_a_cert(self, backend):
cert, key = _load_cert_key()
with pytest.raises(TypeError):
pkcs7.PKCS7SignatureBuilder().add_signer(
b"notacert",
key,
hashes.SHA256() # type: ignore[arg-type]
)
def test_unsupported_hash_alg(self, backend):
cert, key = _load_cert_key()
with pytest.raises(TypeError):
pkcs7.PKCS7SignatureBuilder().add_signer(
cert,
key,
hashes.SHA512_256() # type: ignore[arg-type]
)
def test_sign_invalid_options(self, backend):
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"], # type: ignore[list-item]
)
def test_sign_byteslike(self, backend):
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_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_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 _sign_payload(self, temp_dir: str, cert: str, key: str) -> bytes:
""" signs the payload with one signer """
sb = pkcs7.PKCS7SignatureBuilder(Path(temp_dir, self.PAYLOAD_FILENAME).read_bytes())\
.add_signer(certs.decode_certificate(cert),
keys.decode_key(key),
hashes.SHA512())
return sb.sign(serialization.Encoding.DER, [
pkcs7.PKCS7Options.NoCerts, pkcs7.PKCS7Options.NoCapabilities,
pkcs7.PKCS7Options.Binary
])
def test_sign_invalid_options_no_attrs_and_no_caps(self, backend):
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_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: typing.List[pkcs7.PKCS7Options] = []
sig = builder.sign(serialization.Encoding.DER, options)
assert expected_value in sig
_pkcs7_verify(serialization.Encoding.DER, sig, 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: typing.List[pkcs7.PKCS7Options] = []
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_sign_alternate_digests_detached(self, hash_alg, expected_value,
backend):
if isinstance(hash_alg, hashes.SHA1) and backend._fips_enabled:
pytest.skip("SHA1 not supported in FIPS mode")
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_alternate_digests_der(self, hash_alg, expected_value,
backend):
if isinstance(hash_alg, hashes.SHA1) and backend._fips_enabled:
pytest.skip("SHA1 not supported in FIPS mode")
data = b"hello world"
cert, key = _load_cert_key()
builder = (pkcs7.PKCS7SignatureBuilder().set_data(data).add_signer(
cert, key, hash_alg))
options: typing.List[pkcs7.PKCS7Options] = []
sig = builder.sign(serialization.Encoding.DER, options)
assert expected_value in sig
_pkcs7_verify(serialization.Encoding.DER, sig, None, [cert], options,
backend)
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: typing.List[pkcs7.PKCS7Options] = []
sig = builder.sign(serialization.Encoding.DER, options)
assert (sig.count(rsa_cert.public_bytes(
serialization.Encoding.DER)) == 1)
def sign_data(data: str) -> str:
with open(config.mobileconfig_key(), "rb") as private_key_file:
private_key = serialization.load_pem_private_key(
private_key_file.read(), password=None, backend=None)
with open(config.mobileconfig_cert(), "rb") as public_cert_file:
public_cert = x509.load_pem_x509_certificate(public_cert_file.read())
with open(config.mobileconfig_ca(), "rb") as public_ca_file:
ca_cert = x509.load_pem_x509_certificate(public_ca_file.read())
return pkcs7.PKCS7SignatureBuilder().set_data(data).add_signer(
public_cert, private_key,
hashes.SHA256()).add_certificate(ca_cert).sign(
serialization.Encoding.DER, [])
def test_sign_pem(self, backend):
data = b"hello world"
cert, key = _load_cert_key()
options: typing.List[pkcs7.PKCS7Options] = []
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,
)
def test_sign_attached(self, backend):
data = b"hello world"
cert, key = _load_cert_key()
options: typing.List[pkcs7.PKCS7Options] = []
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_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: typing.List[pkcs7.PKCS7Options] = []
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 sign_payload(payload):
api_settings = settings["api"]
tls_privkey = api_settings.get("tls_privkey")
if not tls_privkey:
logger.error("Could not sign payload: missing tls privkey")
return payload
tls_fullchain = api_settings.get("tls_fullchain")
if not tls_fullchain:
logger.error("Could not sign payload: missing tls fullchain")
return payload
certificates = []
key = serialization.load_pem_private_key(
api_settings["tls_privkey"].encode("utf-8"), None)
head = "-----BEGIN CERTIFICATE-----"
for tail in api_settings["tls_fullchain"].split(head)[1:]:
cert_data = (head + tail).encode("utf-8")
certificates.append(x509.load_pem_x509_certificate(cert_data))
signature_builder = pkcs7.PKCS7SignatureBuilder().set_data(
payload).add_signer(certificates.pop(0), key, hashes.SHA256())
for certificate in certificates:
signature_builder = signature_builder.add_certificate(certificate)
return signature_builder.sign(serialization.Encoding.DER,
[pkcs7.PKCS7Options.Binary])
def test_add_additional_cert_not_a_cert(self, backend):
with pytest.raises(TypeError):
pkcs7.PKCS7SignatureBuilder().add_certificate(
b"notacert" # type: ignore[arg-type]
)
def test_set_data_twice(self, backend):
builder = pkcs7.PKCS7SignatureBuilder().set_data(b"test")
with pytest.raises(ValueError):
builder.set_data(b"test")
def test_sign_no_signer(self, backend):
builder = pkcs7.PKCS7SignatureBuilder().set_data(b"test")
with pytest.raises(ValueError):
builder.sign(serialization.Encoding.SMIME, [])
