diff --git a/docs/development/test-vectors.rst b/docs/development/test-vectors.rst
index cb72181da..84fe83d48 100644
--- a/docs/development/test-vectors.rst
+++ b/docs/development/test-vectors.rst
@@ -189,6 +189,10 @@ Custom asymmetric vectors
   ``TEST(DSATest, NilpotentGenerator)``).
 * ``asymmetric/PKCS8/ec-invalid-private-scalar.pem`` - Contains a PKCS8 encoded
   PEM with a ``secp256r1`` OID and an invalid (very large) private scalar.
+* ``asymmetric/PKCS8/invalid-version.der`` - Contains a PKCS8 encoded DER with
+  an invalid version field.
+* ``asymmetric/PKCS8/unknown-oid.der`` - Contains a PKCS8 encoded DER with an
+  unknown OID.
 
 
 Key exchange
diff --git a/tests/hazmat/primitives/test_serialization.py b/tests/hazmat/primitives/test_serialization.py
index 32e0ded0e..2c6a39cbc 100644
--- a/tests/hazmat/primitives/test_serialization.py
+++ b/tests/hazmat/primitives/test_serialization.py
@@ -405,6 +405,25 @@ class TestDERSerialization:
         with pytest.raises(ValueError):
             load_der_parameters(param_data, backend)
 
+    @pytest.mark.xfail()
+    def test_load_pkcs8_private_key_invalid_version(self):
+        data = load_vectors_from_file(
+            os.path.join("asymmetric", "PKCS8", "invalid-version.der"),
+            lambda f: f.read(),
+            mode="rb",
+        )
+        with pytest.raises(ValueError):
+            load_der_private_key(data, password=None)
+
+    def test_load_pkcs8_private_key_unknown_oid(self):
+        data = load_vectors_from_file(
+            os.path.join("asymmetric", "PKCS8", "unknown-oid.der"),
+            lambda f: f.read(),
+            mode="rb",
+        )
+        with pytest.raises(ValueError):
+            load_der_private_key(data, password=None)
+
 
 class TestPEMSerialization:
     @pytest.mark.parametrize(
diff --git a/vectors/cryptography_vectors/asymmetric/PKCS8/invalid-version.der b/vectors/cryptography_vectors/asymmetric/PKCS8/invalid-version.der
new file mode 100644
index 000000000..f3612258e
Binary files /dev/null and b/vectors/cryptography_vectors/asymmetric/PKCS8/invalid-version.der differ
diff --git a/vectors/cryptography_vectors/asymmetric/PKCS8/unknown-oid.der b/vectors/cryptography_vectors/asymmetric/PKCS8/unknown-oid.der
new file mode 100644
index 000000000..3e276c1b0
Binary files /dev/null and b/vectors/cryptography_vectors/asymmetric/PKCS8/unknown-oid.der differ