diff --git a/CHANGELOG.rst b/CHANGELOG.rst
index f727bb9e479d..e4b674120644 100644
--- a/CHANGELOG.rst
+++ b/CHANGELOG.rst
@@ -22,6 +22,11 @@ Changelog
   :func:`~cryptography.hazmat.primitives.serialization.load_der_public_key`,
   and :meth:`~cryptography.x509.Certificate.public_key` when called on
   certificates with unsupported public key algorithms.
+* **BACKWARDS INCOMPATIBLE:** When parsing elliptic curve private keys, we now
+  reject keys that incorrectly encode a private key of the wrong length because
+  such keys are impossible to process in a constant-time manner. We do not
+  believe keys with this problem are in wide use, however we may revert this
+  change based on the feedback we receive.
 * Updated the minimum supported Rust version (MSRV) to 1.83.0, from 1.74.0.
 * Added support for loading elliptic curve keys that contain explicit encodings
   of the curves ``secp256r1``, ``secp384r1``, and ``secp521r1``.
diff --git a/docs/development/test-vectors.rst b/docs/development/test-vectors.rst
index 5730c6432b87..75ff9680de67 100644
--- a/docs/development/test-vectors.rst
+++ b/docs/development/test-vectors.rst
@@ -295,8 +295,10 @@ Custom asymmetric vectors
   encrypted with a 20 byte salt with the password ``password``.
 * ``asymmetric/PKCS8/wrong-pem-delimiter-rsa.pem`` - A PKCS8 encoded RSA key
   with the wrong PEM delimiter.
-* ``asymmetric/EC/high-bit-set.pem`` - A PKCS#1 encoded EC key the private key
-  value has its high bit set.
+* ``asymmetric/EC/high-bit-set.pem`` - A PKCS#1 encoded EC key where the
+  private key value has its high bit set.
+* ``asymmetric/EC/truncated-private-key.der`` - A PKCS#1 encoded EC key where
+  the private key value is not encoded to the order's length.
 
 Key exchange
 ~~~~~~~~~~~~
diff --git a/src/rust/cryptography-key-parsing/src/ec.rs b/src/rust/cryptography-key-parsing/src/ec.rs
index f92f67ff029d..be0186657e7e 100644
--- a/src/rust/cryptography-key-parsing/src/ec.rs
+++ b/src/rust/cryptography-key-parsing/src/ec.rs
@@ -171,6 +171,10 @@ pub fn parse_pkcs1_private_key(
         (None, None) => return Err(crate::KeyParsingError::InvalidKey),
     };
 
+    if ec_private_key.private_key.len() != group.order_bits().div_ceil(8).try_into().unwrap() {
+        return Err(crate::KeyParsingError::TruncatedEcPrivateKey);
+    }
+
     let private_number = openssl::bn::BigNum::from_slice(ec_private_key.private_key)?;
     let mut bn_ctx = openssl::bn::BigNumContext::new()?;
     let public_point = if let Some(point_bytes) = ec_private_key.public_key {
diff --git a/src/rust/cryptography-key-parsing/src/lib.rs b/src/rust/cryptography-key-parsing/src/lib.rs
index 7d19bebea39e..77191745c563 100644
--- a/src/rust/cryptography-key-parsing/src/lib.rs
+++ b/src/rust/cryptography-key-parsing/src/lib.rs
@@ -27,6 +27,7 @@ pub enum KeyParsingError {
     UnsupportedEncryptionAlgorithm(asn1::ObjectIdentifier),
     EncryptedKeyWithoutPassword,
     IncorrectPassword,
+    TruncatedEcPrivateKey,
     // PEM encryption errors
     PemMissingDekInfo,
     PemInvalidDekInfo,
diff --git a/src/rust/src/error.rs b/src/rust/src/error.rs
index 868cd5aadeda..dccf10943481 100644
--- a/src/rust/src/error.rs
+++ b/src/rust/src/error.rs
@@ -103,6 +103,11 @@ impl From<cryptography_key_parsing::KeyParsingError> for CryptographyError {
                     "Incorrect password, could not decrypt key",
                 ))
             }
+            cryptography_key_parsing::KeyParsingError::TruncatedEcPrivateKey => {
+                CryptographyError::Py(pyo3::exceptions::PyValueError::new_err(
+                    "EC private key is not encoded properly: private key value is too short. Please file an issue at https://github.com/pyca/cryptography/issues explaining how your private key was created.",
+                ))
+            }
             cryptography_key_parsing::KeyParsingError::PemMissingDekInfo => {
                 CryptographyError::Py(pyo3::exceptions::PyValueError::new_err(
                     "Encrypted PEM doesn't have a DEK-Info header.",
diff --git a/tests/hazmat/primitives/test_ec.py b/tests/hazmat/primitives/test_ec.py
index a11cd64a8b89..40d19ac1ec43 100644
--- a/tests/hazmat/primitives/test_ec.py
+++ b/tests/hazmat/primitives/test_ec.py
@@ -1274,6 +1274,16 @@ def test_private_bytes_small_key(self):
         # length.
         assert (b"\x00" * 31 + b"\x01") in der
 
+    def test_load_private_key_short_key_warngs(self):
+        data = load_vectors_from_file(
+            os.path.join("asymmetric", "EC", "truncated-private-key.der"),
+            lambda f: f.read(),
+            mode="rb",
+        )
+
+        with pytest.raises(ValueError, match="private key value is too short"):
+            serialization.load_der_private_key(data, password=None)
+
 
 class TestEllipticCurvePEMPublicKeySerialization:
     @pytest.mark.parametrize(
diff --git a/vectors/cryptography_vectors/asymmetric/EC/truncated-private-key.der b/vectors/cryptography_vectors/asymmetric/EC/truncated-private-key.der
new file mode 100644
index 000000000000..2a1731d4a939
Binary files /dev/null and b/vectors/cryptography_vectors/asymmetric/EC/truncated-private-key.der differ