feat: PKCS#7 extension policies

nitneuqr · nitneuqr · commit 748700807989 · 2025-06-13T20:48:41.000+02:00
added tests accordingly

adapted the pkcs7 certificate

adapted EE policy

do not know if a CA policy is needed!

added SAN checking
diff --git a/docs/development/test-vectors.rst b/docs/development/test-vectors.rst
@@ -1003,6 +1003,14 @@ Custom PKCS7 Test Vectors
 * ``pkcs7/enveloped-no-content.der``- A DER encoded PKCS7 file with
   enveloped data, without encrypted content, with key encrypted under the
   public key of ``x509/custom/ca/rsa_ca.pem``.
+* ``pkcs7/ca.pem`` - A certificate adapted for S/MIME signature & verification. 
+  Its private key is ``pkcs7/ca_key.pem`` . 
+* ``pkcs7/ca.pem`` - A certificate adapted for S/MIME signature & verification. 
+  Its private key is ``pkcs7/ca_key.pem`` . 
+* ``pkcs7/ca_ascii_san.pem`` - An invalid certificate adapted for S/MIME signature 
+  & verification. It has an ASCII subject alternative name stored as `otherName`.
+* ``pkcs7/ca_non_ascii_san.pem`` - An invalid certificate adapted for S/MIME signature 
+  & verification. It has an non-ASCII subject alternative name  stored as `rfc822Name`.
 
 Custom OpenSSH Test Vectors
 ~~~~~~~~~~~~~~~~~~~~~~~~~~~
diff --git a/src/cryptography/hazmat/primitives/serialization/pkcs7.py b/src/cryptography/hazmat/primitives/serialization/pkcs7.py
@@ -21,6 +21,13 @@
     algorithms,
 )
 from cryptography.utils import _check_byteslike
+from cryptography.x509 import Certificate
+from cryptography.x509.oid import ExtendedKeyUsageOID
+from cryptography.x509.verification import (
+    Criticality,
+    ExtensionPolicy,
+    Policy,
+)
 
 load_pem_pkcs7_certificates = rust_pkcs7.load_pem_pkcs7_certificates
 
@@ -53,6 +60,111 @@ class PKCS7Options(utils.Enum):
     NoCerts = "Don't embed signer certificate"
 
 
+def pkcs7_x509_extension_policies() -> tuple[ExtensionPolicy, ExtensionPolicy]:
+    """
+    Gets the default X.509 extension policy for S/MIME. Some specifications
+    that differ from the standard ones:
+    - Certificates used as end entities (i.e., the cert used to sign
+      a PKCS#7/SMIME message) should not have ca=true in their basic
+      constraints extension.
+    - EKU_CLIENT_AUTH_OID is not required
+    - EKU_EMAIL_PROTECTION_OID is required
+    """
+
+    # CA policy - TODO: is default CA policy sufficient? Too much?
+    ca_policy = ExtensionPolicy.webpki_defaults_ca()
+
+    # EE policy
+    def _validate_basic_constraints(
+        policy: Policy, cert: Certificate, bc: x509.BasicConstraints | None
+    ) -> None:
+        if bc is not None and bc.ca:
+            raise ValueError("Basic Constraints CA must be False.")
+
+    def _validate_key_usage(
+        policy: Policy, cert: Certificate, ku: x509.KeyUsage | None
+    ) -> None:
+        if (
+            ku is not None
+            and not ku.digital_signature
+            and not ku.content_commitment
+        ):
+            raise ValueError(
+                "Key Usage, if specified, must have at least one of the "
+                "digital signature or content commitment (formerly non "
+                "repudiation) bits set."
+            )
+
+    def _validate_subject_alternative_name(
+        policy: Policy,
+        cert: Certificate,
+        san: x509.SubjectAlternativeName,
+    ) -> None:
+        """
+        For each general name in the SAN, for those which are email addresses:
+        - If it is an RFC822Name, general part must be ascii.
+        - If it is an OtherName, general part must be non-ascii.
+        """
+        for general_name in san:
+            if (
+                isinstance(general_name, x509.RFC822Name)
+                and "@" in general_name.value
+                and not general_name.value.split("@")[0].isascii()
+            ):
+                raise ValueError(
+                    f"RFC822Name {general_name.value} contains non-ASCII "
+                    "characters."
+                )
+            if (
+                isinstance(general_name, x509.OtherName)
+                and "@" in general_name.value.decode()
+                and general_name.value.decode().split("@")[0].isascii()
+            ):
+                raise ValueError(
+                    f"OtherName {general_name.value.decode()} is ASCII, "
+                    "so must be stored in RFC822Name."
+                )
+
+    def _validate_extended_key_usage(
+        policy: Policy, cert: Certificate, eku: x509.ExtendedKeyUsage | None
+    ) -> None:
+        if (
+            eku is not None
+            and ExtendedKeyUsageOID.EMAIL_PROTECTION not in eku
+            and ExtendedKeyUsageOID.ANY_EXTENDED_KEY_USAGE not in eku
+        ):
+            raise ValueError(
+                "Extended Key Usage, if specified, must include "
+                "emailProtection or anyExtendedKeyUsage."
+            )
+
+    ee_policy = (
+        ExtensionPolicy.webpki_defaults_ee()
+        .may_be_present(
+            x509.BasicConstraints,
+            Criticality.AGNOSTIC,
+            _validate_basic_constraints,
+        )
+        .may_be_present(
+            x509.KeyUsage,
+            Criticality.CRITICAL,
+            _validate_key_usage,
+        )
+        .require_present(
+            x509.SubjectAlternativeName,
+            Criticality.AGNOSTIC,
+            _validate_subject_alternative_name,
+        )
+        .may_be_present(
+            x509.ExtendedKeyUsage,
+            Criticality.AGNOSTIC,
+            _validate_extended_key_usage,
+        )
+    )
+
+    return ca_policy, ee_policy
+
+
 class PKCS7SignatureBuilder:
     def __init__(
         self,
diff --git a/tests/hazmat/primitives/test_pkcs7.py b/tests/hazmat/primitives/test_pkcs7.py
@@ -18,6 +18,16 @@
 from cryptography.hazmat.primitives.asymmetric import ed25519, padding, rsa
 from cryptography.hazmat.primitives.ciphers import algorithms
 from cryptography.hazmat.primitives.serialization import pkcs7
+from cryptography.x509.oid import (
+    ExtendedKeyUsageOID,
+    ExtensionOID,
+    ObjectIdentifier,
+)
+from cryptography.x509.verification import (
+    PolicyBuilder,
+    Store,
+    VerificationError,
+)
 from tests.x509.test_x509 import _generate_ca_and_leaf
 
 from ...hazmat.primitives.fixtures_rsa import (
@@ -125,20 +135,153 @@ def test_load_pkcs7_empty_certificates(self):
 
 def _load_cert_key():
     key = load_vectors_from_file(
-        os.path.join("x509", "custom", "ca", "ca_key.pem"),
+        os.path.join("pkcs7", "ca_key.pem"),
         lambda pemfile: serialization.load_pem_private_key(
             pemfile.read(), None, unsafe_skip_rsa_key_validation=True
         ),
         mode="rb",
     )
     cert = load_vectors_from_file(
-        os.path.join("x509", "custom", "ca", "ca.pem"),
+        os.path.join("pkcs7", "ca.pem"),
         loader=lambda pemfile: x509.load_pem_x509_certificate(pemfile.read()),
         mode="rb",
     )
     return cert, key
 
 
+class TestPKCS7VerifyCertificate:
+    @staticmethod
+    def build_pkcs7_certificate(
+        ca: bool = False,
+        digital_signature: bool = True,
+        usages: typing.Optional[typing.List[ObjectIdentifier]] = None,
+    ) -> x509.Certificate:
+        """
+        This static method is a helper to build certificates allowing us
+        to test all cases in PKCS#7 certificate verification.
+        """
+        # Load the standard certificate and private key
+        certificate, private_key = _load_cert_key()
+
+        # Basic certificate builder
+        certificate_builder = (
+            x509.CertificateBuilder()
+            .serial_number(certificate.serial_number)
+            .subject_name(certificate.subject)
+            .issuer_name(certificate.issuer)
+            .public_key(private_key.public_key())
+            .not_valid_before(certificate.not_valid_before)
+            .not_valid_after(certificate.not_valid_after)
+        )
+
+        # Add AuthorityKeyIdentifier extension
+        aki = certificate.extensions.get_extension_for_oid(
+            ExtensionOID.AUTHORITY_KEY_IDENTIFIER
+        )
+        certificate_builder = certificate_builder.add_extension(
+            aki.value, critical=False
+        )
+
+        # Add SubjectAlternativeName extension
+        san = certificate.extensions.get_extension_for_oid(
+            ExtensionOID.SUBJECT_ALTERNATIVE_NAME
+        )
+        certificate_builder = certificate_builder.add_extension(
+            san.value, critical=True
+        )
+
+        # Add BasicConstraints extension
+        bc_extension = x509.BasicConstraints(ca=ca, path_length=None)
+        certificate_builder = certificate_builder.add_extension(
+            bc_extension, False
+        )
+
+        # Add KeyUsage extension
+        ku_extension = x509.KeyUsage(
+            digital_signature=digital_signature,
+            content_commitment=False,
+            key_encipherment=True,
+            data_encipherment=True,
+            key_agreement=True,
+            key_cert_sign=True,
+            crl_sign=True,
+            encipher_only=False,
+            decipher_only=False,
+        )
+        certificate_builder = certificate_builder.add_extension(
+            ku_extension, True
+        )
+
+        # Add valid ExtendedKeyUsage extension
+        usages = usages or [ExtendedKeyUsageOID.EMAIL_PROTECTION]
+        certificate_builder = certificate_builder.add_extension(
+            x509.ExtendedKeyUsage(usages), True
+        )
+
+        # Build the certificate
+        return certificate_builder.sign(
+            private_key, certificate.signature_hash_algorithm, None
+        )
+
+    def test_verify_pkcs7_certificate(self):
+        # Prepare the parameters
+        certificate = self.build_pkcs7_certificate()
+        ca_policy, ee_policy = pkcs7.pkcs7_x509_extension_policies()
+
+        # Verify the certificate
+        verifier = (
+            PolicyBuilder()
+            .store(Store([certificate]))
+            .extension_policies(ca_policy=ca_policy, ee_policy=ee_policy)
+            .build_client_verifier()
+        )
+        verifier.verify(certificate, [])
+
+    @pytest.mark.parametrize(
+        "arguments",
+        [
+            {"ca": True},
+            {"digital_signature": False},
+            {"usages": [ExtendedKeyUsageOID.CLIENT_AUTH]},
+        ],
+    )
+    def test_verify_invalid_pkcs7_certificate(self, arguments: dict):
+        # Prepare the parameters
+        certificate = self.build_pkcs7_certificate(**arguments)
+
+        # Verify the certificate
+        self.verify_invalid_pkcs7_certificate(certificate)
+
+    @staticmethod
+    def verify_invalid_pkcs7_certificate(certificate: x509.Certificate):
+        ca_policy, ee_policy = pkcs7.pkcs7_x509_extension_policies()
+        verifier = (
+            PolicyBuilder()
+            .store(Store([certificate]))
+            .extension_policies(ca_policy=ca_policy, ee_policy=ee_policy)
+            .build_client_verifier()
+        )
+
+        with pytest.raises(VerificationError):
+            verifier.verify(certificate, [])
+
+    @pytest.mark.parametrize(
+        "filename", ["ca_non_ascii_san.pem", "ca_ascii_san.pem"]
+    )
+    def test_verify_pkcs7_certificate_wrong_san(self, filename):
+        # Read a certificate with an invalid SAN
+        pkcs7_certificate = load_vectors_from_file(
+            os.path.join("pkcs7", filename),
+            loader=lambda pemfile: x509.load_pem_x509_certificate(
+                pemfile.read()
+            ),
+            mode="rb",
+        )
+
+        # Verify the certificate
+        self.verify_invalid_pkcs7_certificate(pkcs7_certificate)
+
+
 @pytest.mark.supported(
     only_if=lambda backend: backend.pkcs7_supported(),
     skip_message="Requires OpenSSL with PKCS7 support",
diff --git a/vectors/cryptography_vectors/pkcs7/ca.pem b/vectors/cryptography_vectors/pkcs7/ca.pem
@@ -0,0 +1,11 @@
+-----BEGIN CERTIFICATE-----
+MIIBhjCCASygAwIBAgICAwkwCgYIKoZIzj0EAwIwJzELMAkGA1UEBhMCVVMxGDAW
+BgNVBAMMD2NyeXB0b2dyYXBoeSBDQTAgFw0xNzAxMDEwMTAwMDBaGA8yMTAwMDEw
+MTAwMDAwMFowJzELMAkGA1UEBhMCVVMxGDAWBgNVBAMMD2NyeXB0b2dyYXBoeSBD
+QTBZMBMGByqGSM49AgEGCCqGSM49AwEHA0IABBj/z7v5Obj13cPuwECLBnUGq0/N
+2CxSJE4f4BBGZ7VfFblivTvPDG++Gve0oQ+0uctuhrNQ+WxRv8GC177F+QWjRjBE
+MCEGA1UdEQEB/wQXMBWBE2V4YW1wbGVAZXhhbXBsZS5jb20wHwYDVR0jBBgwFoAU
+/Ou02BLyyT2Zwzxn9H03feYT7fowCgYIKoZIzj0EAwIDSAAwRQIgUwIdC0Emkd6f
+17DeOXTlmTAhwSDJ2FTuyHESwei7wJcCIQCnr9NpBxbtJfEzxHGGyd7PxgpOLi5u
+rk+8QfzGMmg/fw==
+-----END CERTIFICATE-----
diff --git a/vectors/cryptography_vectors/pkcs7/ca_ascii_san.pem b/vectors/cryptography_vectors/pkcs7/ca_ascii_san.pem
@@ -0,0 +1,23 @@
+-----BEGIN CERTIFICATE-----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+-----END CERTIFICATE-----
diff --git a/vectors/cryptography_vectors/pkcs7/ca_key.pem b/vectors/cryptography_vectors/pkcs7/ca_key.pem
@@ -0,0 +1,5 @@
+-----BEGIN PRIVATE KEY-----
+MIGHAgEAMBMGByqGSM49AgEGCCqGSM49AwEHBG0wawIBAQQgA8Zqz5vLeR0ePZUe
+jBfdyMmnnI4U5uAJApWTsMn/RuWhRANCAAQY/8+7+Tm49d3D7sBAiwZ1BqtPzdgs
+UiROH+AQRme1XxW5Yr07zwxvvhr3tKEPtLnLboazUPlsUb/Bgte+xfkF
+-----END PRIVATE KEY-----
diff --git a/vectors/cryptography_vectors/pkcs7/ca_non_ascii_san.pem b/vectors/cryptography_vectors/pkcs7/ca_non_ascii_san.pem
@@ -0,0 +1,23 @@
+-----BEGIN CERTIFICATE-----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+-----END CERTIFICATE-----
