Initial RFC 5280 test cases

harness/gocryptox509/main.go

@@ -128,11 +128,12 @@ func evaluateTestcase(testcase Testcase) (testcaseResult, error) {
 		ts, err = time.Parse(time.RFC3339, *testcase.ValidationTime)
 
 		if err != nil {
+			fmt.Printf("%s\n", err)
 			return testcaseSkipped, errors.Wrap(err, "unable to parse testcase time as RFC3339")
 		}
 	}
 
-	expectSuccess := testcase.ExpectedResult == testcasePassed
+	expectSuccess := testcaseResult(testcase.ExpectedResult.(string)) == testcasePassed
 
 	// TODO: Support testcases that constrain signature algorthms.
 	if len(testcase.SignatureAlgorithms) != 0 {

limbo/_assets/cryptography.io.pem

@@ -0,0 +1,91 @@
+-----BEGIN CERTIFICATE-----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+-----END CERTIFICATE-----
+-----BEGIN CERTIFICATE-----
+MIIFFjCCAv6gAwIBAgIRAJErCErPDBinU/bWLiWnX1owDQYJKoZIhvcNAQELBQAw
+TzELMAkGA1UEBhMCVVMxKTAnBgNVBAoTIEludGVybmV0IFNlY3VyaXR5IFJlc2Vh
+cmNoIEdyb3VwMRUwEwYDVQQDEwxJU1JHIFJvb3QgWDEwHhcNMjAwOTA0MDAwMDAw
+WhcNMjUwOTE1MTYwMDAwWjAyMQswCQYDVQQGEwJVUzEWMBQGA1UEChMNTGV0J3Mg
+RW5jcnlwdDELMAkGA1UEAxMCUjMwggEiMA0GCSqGSIb3DQEBAQUAA4IBDwAwggEK
+AoIBAQC7AhUozPaglNMPEuyNVZLD+ILxmaZ6QoinXSaqtSu5xUyxr45r+XXIo9cP
+R5QUVTVXjJ6oojkZ9YI8QqlObvU7wy7bjcCwXPNZOOftz2nwWgsbvsCUJCWH+jdx
+sxPnHKzhm+/b5DtFUkWWqcFTzjTIUu61ru2P3mBw4qVUq7ZtDpelQDRrK9O8Zutm
+NHz6a4uPVymZ+DAXXbpyb/uBxa3Shlg9F8fnCbvxK/eG3MHacV3URuPMrSXBiLxg
+Z3Vms/EY96Jc5lP/Ooi2R6X/ExjqmAl3P51T+c8B5fWmcBcUr2Ok/5mzk53cU6cG
+/kiFHaFpriV1uxPMUgP17VGhi9sVAgMBAAGjggEIMIIBBDAOBgNVHQ8BAf8EBAMC
+AYYwHQYDVR0lBBYwFAYIKwYBBQUHAwIGCCsGAQUFBwMBMBIGA1UdEwEB/wQIMAYB
+Af8CAQAwHQYDVR0OBBYEFBQusxe3WFbLrlAJQOYfr52LFMLGMB8GA1UdIwQYMBaA
+FHm0WeZ7tuXkAXOACIjIGlj26ZtuMDIGCCsGAQUFBwEBBCYwJDAiBggrBgEFBQcw
+AoYWaHR0cDovL3gxLmkubGVuY3Iub3JnLzAnBgNVHR8EIDAeMBygGqAYhhZodHRw
+Oi8veDEuYy5sZW5jci5vcmcvMCIGA1UdIAQbMBkwCAYGZ4EMAQIBMA0GCysGAQQB
+gt8TAQEBMA0GCSqGSIb3DQEBCwUAA4ICAQCFyk5HPqP3hUSFvNVneLKYY611TR6W
+PTNlclQtgaDqw+34IL9fzLdwALduO/ZelN7kIJ+m74uyA+eitRY8kc607TkC53wl
+ikfmZW4/RvTZ8M6UK+5UzhK8jCdLuMGYL6KvzXGRSgi3yLgjewQtCPkIVz6D2QQz
+CkcheAmCJ8MqyJu5zlzyZMjAvnnAT45tRAxekrsu94sQ4egdRCnbWSDtY7kh+BIm
+lJNXoB1lBMEKIq4QDUOXoRgffuDghje1WrG9ML+Hbisq/yFOGwXD9RiX8F6sw6W4
+avAuvDszue5L3sz85K+EC4Y/wFVDNvZo4TYXao6Z0f+lQKc0t8DQYzk1OXVu8rp2
+yJMC6alLbBfODALZvYH7n7do1AZls4I9d1P4jnkDrQoxB3UqQ9hVl3LEKQ73xF1O
+yK5GhDDX8oVfGKF5u+decIsH4YaTw7mP3GFxJSqv3+0lUFJoi5Lc5da149p90Ids
+hCExroL1+7mryIkXPeFM5TgO9r0rvZaBFOvV2z0gp35Z0+L4WPlbuEjN/lxPFin+
+HlUjr8gRsI3qfJOQFy/9rKIJR0Y/8Omwt/8oTWgy1mdeHmmjk7j1nYsvC9JSQ6Zv
+MldlTTKB3zhThV1+XWYp6rjd5JW1zbVWEkLNxE7GJThEUG3szgBVGP7pSWTUTsqX
+nLRbwHOoq7hHwg==
+-----END CERTIFICATE-----
+-----BEGIN CERTIFICATE-----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=
+-----END CERTIFICATE-----

limbo/assets.py

@@ -8,27 +8,43 @@
 import logging
 from dataclasses import dataclass
 from functools import cache, cached_property
+from importlib import resources
+from typing import Generic, TypeVar
 
 from cryptography import x509
 from cryptography.hazmat.primitives import hashes, serialization
 from cryptography.hazmat.primitives.asymmetric import rsa
 from cryptography.hazmat.primitives.asymmetric.types import PrivateKeyTypes
-from cryptography.x509 import NameOID
+from cryptography.x509 import ExtensionType, NameOID, SubjectAlternativeName
 
 _EPOCH = datetime.datetime.fromtimestamp(0)
 _ONE_THOUSAND_YEARS_OF_TORMENT = _EPOCH + datetime.timedelta(days=365 * 1000)
+_ASSETS_PATH = resources.files("limbo._assets")
+_ExtensionType = TypeVar("_ExtensionType", bound=ExtensionType)
 
 
 logger = logging.getLogger(__name__)
 
 
 @dataclass(frozen=True)
-class CertificatePair:
+class Certificate:
     """
-    An X.509 certificate and its associated private key.
+    An X.509 certificate.
     """
 
     cert: x509.Certificate
+
+    @cached_property
+    def cert_pem(self) -> str:
+        return self.cert.public_bytes(encoding=serialization.Encoding.PEM).decode()
+
+
+@dataclass(frozen=True)
+class CertificatePair(Certificate):
+    """
+    An X.509 certificate and its associated private key.
+    """
+
     key: PrivateKeyTypes
 
     @cached_property
@@ -39,135 +55,31 @@ def key_pem(self) -> str:
             encryption_algorithm=serialization.NoEncryption(),
         ).decode()
 
-    @cached_property
-    def cert_pem(self) -> str:
-        return self.cert.public_bytes(encoding=serialization.Encoding.PEM).decode()
-
 
-@cache
-def v3_root_ca(*, aki: bool = True, ski: bool = True) -> CertificatePair:
+@dataclass(frozen=True)
+class _Extension(Generic[_ExtensionType]):
     """
-    A (configurable) X.509v3 root CA.
+    An X.509 extension and its criticality.
     """
-    key = rsa.generate_private_key(public_exponent=65537, key_size=4096)
 
-    builder = x509.CertificateBuilder()
-    builder = builder.subject_name(
-        x509.Name(
-            [
-                x509.NameAttribute(NameOID.COMMON_NAME, "x509-limbo-root"),
-            ]
-        )
-    )
-    builder = builder.issuer_name(
-        x509.Name(
-            [
-                x509.NameAttribute(NameOID.COMMON_NAME, "x509-limbo-root"),
-            ]
-        )
-    )
-    builder = builder.not_valid_before(_EPOCH)
-    builder = builder.not_valid_after(_ONE_THOUSAND_YEARS_OF_TORMENT)
-    builder = builder.serial_number(x509.random_serial_number())
-    builder = builder.public_key(key.public_key())
-    builder = builder.add_extension(
-        x509.SubjectKeyIdentifier.from_public_key(key.public_key()),
-        critical=False,
-    )
-    builder = builder.add_extension(
-        x509.BasicConstraints(ca=True, path_length=None),
-        critical=True,
-    )
-    builder = builder.add_extension(
-        x509.KeyUsage(
-            digital_signature=False,
-            key_cert_sign=True,
-            content_commitment=False,
-            key_encipherment=False,
-            data_encipherment=False,
-            key_agreement=False,
-            crl_sign=False,
-            encipher_only=False,
-            decipher_only=False,
-        ),
-        critical=False,
-    )
-    certificate = builder.sign(
-        private_key=key,
-        algorithm=hashes.SHA256(),
-    )
+    ext: _ExtensionType
+    critical: bool
 
-    return CertificatePair(certificate, key)
 
-
-@cache
-def intermediate_ca_pathlen_n(parent: CertificatePair, pathlen: int) -> CertificatePair:
+def ext(extension: _ExtensionType, *, critical: bool) -> _Extension[_ExtensionType]:
     """
-    An intermediate CA chained up to a root CA.
-
-    The intermediate CA has a `pathlen:N` constraint, where `N` varies.
-
-    These intermediates can be used to assert various behaviors, including:
-
-    * That `pathlen:N` constraints are properly honored;
-    * That certificates are correctly uniqued by both their key **and** their
-      subject (as each intermediate generated here shares the same key)
+    Constructs a new _Extension to pass into certificate builder helpers.
     """
-    key = rsa.generate_private_key(public_exponent=65537, key_size=2048)
-
-    builder = x509.CertificateBuilder()
-    builder = builder.subject_name(
-        x509.Name(
-            [
-                x509.NameAttribute(
-                    NameOID.COMMON_NAME, f"x509-limbo-intermediate-pathlen-{pathlen}"
-                ),
-            ]
-        )
-    )
-    builder = builder.issuer_name(parent.cert.subject)
-    builder = builder.not_valid_before(_EPOCH)
-    builder = builder.not_valid_after(_ONE_THOUSAND_YEARS_OF_TORMENT)
-    builder = builder.serial_number(x509.random_serial_number())
-    builder = builder.public_key(key.public_key())
-    builder = builder.add_extension(
-        x509.SubjectKeyIdentifier.from_public_key(key.public_key()),
-        critical=False,
-    )
-    builder = builder.add_extension(
-        x509.AuthorityKeyIdentifier.from_issuer_public_key(
-            parent.key.public_key()  # type: ignore[arg-type]
-        ),
-        critical=False,
-    )
-    builder = builder.add_extension(
-        x509.BasicConstraints(ca=True, path_length=pathlen),
-        critical=True,
-    )
-    builder = builder.add_extension(
-        x509.KeyUsage(
-            digital_signature=False,
-            key_cert_sign=True,
-            content_commitment=False,
-            key_encipherment=False,
-            data_encipherment=False,
-            key_agreement=False,
-            crl_sign=False,
-            encipher_only=False,
-            decipher_only=False,
-        ),
-        critical=False,
-    )
-    certificate = builder.sign(
-        private_key=parent.key,  # type: ignore[arg-type]
-        algorithm=hashes.SHA256(),
-    )
-
-    return CertificatePair(certificate, key)
+    return _Extension(extension, critical)
 
 
 @cache
-def ee_cert(parent: CertificatePair) -> CertificatePair:
+def ee_cert(
+    parent: CertificatePair,
+    subject_alternative_name: _Extension[SubjectAlternativeName] | None = None,
+    *,
+    extra_extension: _Extension | None = None,
+) -> CertificatePair:
     """
     Produces an end-entity (EE) certificate, signed by the given `parent`'s
     key.
@@ -200,7 +112,7 @@ def ee_cert(parent: CertificatePair) -> CertificatePair:
     )
     builder = builder.add_extension(
         x509.BasicConstraints(ca=False, path_length=None),
-        critical=True,
+        critical=False,
     )
     builder = builder.add_extension(
         x509.KeyUsage(
@@ -216,6 +128,13 @@ def ee_cert(parent: CertificatePair) -> CertificatePair:
         ),
         critical=False,
     )
+    if subject_alternative_name is not None:
+        builder = builder.add_extension(
+            subject_alternative_name.ext, subject_alternative_name.critical
+        )
+    if extra_extension is not None:
+        builder = builder.add_extension(extra_extension.ext, extra_extension.critical)
+
     certificate = builder.sign(
         private_key=parent.key,  # type: ignore[arg-type]
         algorithm=hashes.SHA256(),

limbo/testcases/__init__.py

@@ -5,6 +5,8 @@
 from limbo.testcases._core import registry
 
 from .pathlen import *  # noqa: F403
+from .rfc5280 import *  # noqa: F403
+from .webpki import *  # noqa: F403
 
 __all__ = [
     "registry",