@pairling/runtime-darwin-arm64 0.2.0 → 0.2.2

package/python/lib/python3.12/site-packages/cryptography/hazmat/primitives/serialization/ssh.py

@@ -0,0 +1,1619 @@
+# This file is dual licensed under the terms of the Apache License, Version
+# 2.0, and the BSD License. See the LICENSE file in the root of this repository
+# for complete details.
+
+from __future__ import annotations
+
+import binascii
+import enum
+import os
+import re
+import typing
+import warnings
+from base64 import encodebytes as _base64_encode
+from dataclasses import dataclass
+
+from cryptography import utils
+from cryptography.exceptions import UnsupportedAlgorithm
+from cryptography.hazmat.primitives import hashes
+from cryptography.hazmat.primitives.asymmetric import (
+    dsa,
+    ec,
+    ed25519,
+    padding,
+    rsa,
+)
+from cryptography.hazmat.primitives.asymmetric import utils as asym_utils
+from cryptography.hazmat.primitives.ciphers import (
+    AEADDecryptionContext,
+    Cipher,
+    algorithms,
+    modes,
+)
+from cryptography.hazmat.primitives.serialization import (
+    Encoding,
+    KeySerializationEncryption,
+    NoEncryption,
+    PrivateFormat,
+    PublicFormat,
+    _KeySerializationEncryption,
+)
+
+try:
+    from bcrypt import kdf as _bcrypt_kdf
+
+    _bcrypt_supported = True
+except ImportError:
+    _bcrypt_supported = False
+
+    def _bcrypt_kdf(
+        password: bytes,
+        salt: bytes,
+        desired_key_bytes: int,
+        rounds: int,
+        ignore_few_rounds: bool = False,
+    ) -> bytes:
+        raise UnsupportedAlgorithm("Need bcrypt module")
+
+
+_SSH_ED25519 = b"ssh-ed25519"
+_SSH_RSA = b"ssh-rsa"
+_SSH_DSA = b"ssh-dss"
+_ECDSA_NISTP256 = b"ecdsa-sha2-nistp256"
+_ECDSA_NISTP384 = b"ecdsa-sha2-nistp384"
+_ECDSA_NISTP521 = b"ecdsa-sha2-nistp521"
+_CERT_SUFFIX = b"-cert-v01@openssh.com"
+
+# U2F application string suffixed pubkey
+_SK_SSH_ED25519 = b"sk-ssh-ed25519@openssh.com"
+_SK_SSH_ECDSA_NISTP256 = b"sk-ecdsa-sha2-nistp256@openssh.com"
+
+# These are not key types, only algorithms, so they cannot appear
+# as a public key type
+_SSH_RSA_SHA256 = b"rsa-sha2-256"
+_SSH_RSA_SHA512 = b"rsa-sha2-512"
+
+_SSH_PUBKEY_RC = re.compile(rb"\A(\S+)[ \t]+(\S+)")
+_SK_MAGIC = b"openssh-key-v1\0"
+_SK_START = b"-----BEGIN OPENSSH PRIVATE KEY-----"
+_SK_END = b"-----END OPENSSH PRIVATE KEY-----"
+_BCRYPT = b"bcrypt"
+_NONE = b"none"
+_DEFAULT_CIPHER = b"aes256-ctr"
+_DEFAULT_ROUNDS = 16
+
+# re is only way to work on bytes-like data
+_PEM_RC = re.compile(_SK_START + b"(.*?)" + _SK_END, re.DOTALL)
+
+# padding for max blocksize
+_PADDING = memoryview(bytearray(range(1, 1 + 16)))
+
+
+@dataclass
+class _SSHCipher:
+    alg: type[algorithms.AES]
+    key_len: int
+    mode: type[modes.CTR] | type[modes.CBC] | type[modes.GCM]
+    block_len: int
+    iv_len: int
+    tag_len: int | None
+    is_aead: bool
+
+
+# ciphers that are actually used in key wrapping
+_SSH_CIPHERS: dict[bytes, _SSHCipher] = {
+    b"aes256-ctr": _SSHCipher(
+        alg=algorithms.AES,
+        key_len=32,
+        mode=modes.CTR,
+        block_len=16,
+        iv_len=16,
+        tag_len=None,
+        is_aead=False,
+    ),
+    b"aes256-cbc": _SSHCipher(
+        alg=algorithms.AES,
+        key_len=32,
+        mode=modes.CBC,
+        block_len=16,
+        iv_len=16,
+        tag_len=None,
+        is_aead=False,
+    ),
+    b"aes256-gcm@openssh.com": _SSHCipher(
+        alg=algorithms.AES,
+        key_len=32,
+        mode=modes.GCM,
+        block_len=16,
+        iv_len=12,
+        tag_len=16,
+        is_aead=True,
+    ),
+}
+
+# map local curve name to key type
+_ECDSA_KEY_TYPE = {
+    "secp256r1": _ECDSA_NISTP256,
+    "secp384r1": _ECDSA_NISTP384,
+    "secp521r1": _ECDSA_NISTP521,
+}
+
+
+def _get_ssh_key_type(key: SSHPrivateKeyTypes | SSHPublicKeyTypes) -> bytes:
+    if isinstance(key, ec.EllipticCurvePrivateKey):
+        key_type = _ecdsa_key_type(key.public_key())
+    elif isinstance(key, ec.EllipticCurvePublicKey):
+        key_type = _ecdsa_key_type(key)
+    elif isinstance(key, (rsa.RSAPrivateKey, rsa.RSAPublicKey)):
+        key_type = _SSH_RSA
+    elif isinstance(key, (dsa.DSAPrivateKey, dsa.DSAPublicKey)):
+        key_type = _SSH_DSA
+    elif isinstance(
+        key, (ed25519.Ed25519PrivateKey, ed25519.Ed25519PublicKey)
+    ):
+        key_type = _SSH_ED25519
+    else:
+        raise ValueError("Unsupported key type")
+
+    return key_type
+
+
+def _ecdsa_key_type(public_key: ec.EllipticCurvePublicKey) -> bytes:
+    """Return SSH key_type and curve_name for private key."""
+    curve = public_key.curve
+    if curve.name not in _ECDSA_KEY_TYPE:
+        raise ValueError(
+            f"Unsupported curve for ssh private key: {curve.name!r}"
+        )
+    return _ECDSA_KEY_TYPE[curve.name]
+
+
+def _ssh_pem_encode(
+    data: utils.Buffer,
+    prefix: bytes = _SK_START + b"\n",
+    suffix: bytes = _SK_END + b"\n",
+) -> bytes:
+    return b"".join([prefix, _base64_encode(data), suffix])
+
+
+def _check_block_size(data: utils.Buffer, block_len: int) -> None:
+    """Require data to be full blocks"""
+    if not data or len(data) % block_len != 0:
+        raise ValueError("Corrupt data: missing padding")
+
+
+def _check_empty(data: utils.Buffer) -> None:
+    """All data should have been parsed."""
+    if data:
+        raise ValueError("Corrupt data: unparsed data")
+
+
+def _init_cipher(
+    ciphername: bytes,
+    password: bytes | None,
+    salt: bytes,
+    rounds: int,
+) -> Cipher[modes.CBC | modes.CTR | modes.GCM]:
+    """Generate key + iv and return cipher."""
+    if not password:
+        raise TypeError(
+            "Key is password-protected, but password was not provided."
+        )
+
+    ciph = _SSH_CIPHERS[ciphername]
+    seed = _bcrypt_kdf(
+        password, salt, ciph.key_len + ciph.iv_len, rounds, True
+    )
+    return Cipher(
+        ciph.alg(seed[: ciph.key_len]),
+        ciph.mode(seed[ciph.key_len :]),
+    )
+
+
+def _get_u32(data: memoryview) -> tuple[int, memoryview]:
+    """Uint32"""
+    if len(data) < 4:
+        raise ValueError("Invalid data")
+    return int.from_bytes(data[:4], byteorder="big"), data[4:]
+
+
+def _get_u64(data: memoryview) -> tuple[int, memoryview]:
+    """Uint64"""
+    if len(data) < 8:
+        raise ValueError("Invalid data")
+    return int.from_bytes(data[:8], byteorder="big"), data[8:]
+
+
+def _get_sshstr(data: memoryview) -> tuple[memoryview, memoryview]:
+    """Bytes with u32 length prefix"""
+    n, data = _get_u32(data)
+    if n > len(data):
+        raise ValueError("Invalid data")
+    return data[:n], data[n:]
+
+
+def _get_mpint(data: memoryview) -> tuple[int, memoryview]:
+    """Big integer."""
+    val, data = _get_sshstr(data)
+    if val and val[0] > 0x7F:
+        raise ValueError("Invalid data")
+    return int.from_bytes(val, "big"), data
+
+
+def _to_mpint(val: int) -> bytes:
+    """Storage format for signed bigint."""
+    if val < 0:
+        raise ValueError("negative mpint not allowed")
+    if not val:
+        return b""
+    nbytes = (val.bit_length() + 8) // 8
+    return utils.int_to_bytes(val, nbytes)
+
+
+class _FragList:
+    """Build recursive structure without data copy."""
+
+    flist: list[utils.Buffer]
+
+    def __init__(self, init: list[utils.Buffer] | None = None) -> None:
+        self.flist = []
+        if init:
+            self.flist.extend(init)
+
+    def put_raw(self, val: utils.Buffer) -> None:
+        """Add plain bytes"""
+        self.flist.append(val)
+
+    def put_u32(self, val: int) -> None:
+        """Big-endian uint32"""
+        self.flist.append(val.to_bytes(length=4, byteorder="big"))
+
+    def put_u64(self, val: int) -> None:
+        """Big-endian uint64"""
+        self.flist.append(val.to_bytes(length=8, byteorder="big"))
+
+    def put_sshstr(self, val: bytes | _FragList) -> None:
+        """Bytes prefixed with u32 length"""
+        if isinstance(val, (bytes, memoryview, bytearray)):
+            self.put_u32(len(val))
+            self.flist.append(val)
+        else:
+            self.put_u32(val.size())
+            self.flist.extend(val.flist)
+
+    def put_mpint(self, val: int) -> None:
+        """Big-endian bigint prefixed with u32 length"""
+        self.put_sshstr(_to_mpint(val))
+
+    def size(self) -> int:
+        """Current number of bytes"""
+        return sum(map(len, self.flist))
+
+    def render(self, dstbuf: memoryview, pos: int = 0) -> int:
+        """Write into bytearray"""
+        for frag in self.flist:
+            flen = len(frag)
+            start, pos = pos, pos + flen
+            dstbuf[start:pos] = frag
+        return pos
+
+    def tobytes(self) -> bytes:
+        """Return as bytes"""
+        buf = memoryview(bytearray(self.size()))
+        self.render(buf)
+        return buf.tobytes()
+
+
+class _SSHFormatRSA:
+    """Format for RSA keys.
+
+    Public:
+        mpint e, n
+    Private:
+        mpint n, e, d, iqmp, p, q
+    """
+
+    def get_public(
+        self, data: memoryview
+    ) -> tuple[tuple[int, int], memoryview]:
+        """RSA public fields"""
+        e, data = _get_mpint(data)
+        n, data = _get_mpint(data)
+        return (e, n), data
+
+    def load_public(
+        self, data: memoryview
+    ) -> tuple[rsa.RSAPublicKey, memoryview]:
+        """Make RSA public key from data."""
+        (e, n), data = self.get_public(data)
+        public_numbers = rsa.RSAPublicNumbers(e, n)
+        public_key = public_numbers.public_key()
+        return public_key, data
+
+    def load_private(
+        self, data: memoryview, pubfields, unsafe_skip_rsa_key_validation: bool
+    ) -> tuple[rsa.RSAPrivateKey, memoryview]:
+        """Make RSA private key from data."""
+        n, data = _get_mpint(data)
+        e, data = _get_mpint(data)
+        d, data = _get_mpint(data)
+        iqmp, data = _get_mpint(data)
+        p, data = _get_mpint(data)
+        q, data = _get_mpint(data)
+
+        if (e, n) != pubfields:
+            raise ValueError("Corrupt data: rsa field mismatch")
+        dmp1 = rsa.rsa_crt_dmp1(d, p)
+        dmq1 = rsa.rsa_crt_dmq1(d, q)
+        public_numbers = rsa.RSAPublicNumbers(e, n)
+        private_numbers = rsa.RSAPrivateNumbers(
+            p, q, d, dmp1, dmq1, iqmp, public_numbers
+        )
+        private_key = private_numbers.private_key(
+            unsafe_skip_rsa_key_validation=unsafe_skip_rsa_key_validation
+        )
+        return private_key, data
+
+    def encode_public(
+        self, public_key: rsa.RSAPublicKey, f_pub: _FragList
+    ) -> None:
+        """Write RSA public key"""
+        pubn = public_key.public_numbers()
+        f_pub.put_mpint(pubn.e)
+        f_pub.put_mpint(pubn.n)
+
+    def encode_private(
+        self, private_key: rsa.RSAPrivateKey, f_priv: _FragList
+    ) -> None:
+        """Write RSA private key"""
+        private_numbers = private_key.private_numbers()
+        public_numbers = private_numbers.public_numbers
+
+        f_priv.put_mpint(public_numbers.n)
+        f_priv.put_mpint(public_numbers.e)
+
+        f_priv.put_mpint(private_numbers.d)
+        f_priv.put_mpint(private_numbers.iqmp)
+        f_priv.put_mpint(private_numbers.p)
+        f_priv.put_mpint(private_numbers.q)
+
+
+class _SSHFormatDSA:
+    """Format for DSA keys.
+
+    Public:
+        mpint p, q, g, y
+    Private:
+        mpint p, q, g, y, x
+    """
+
+    def get_public(self, data: memoryview) -> tuple[tuple, memoryview]:
+        """DSA public fields"""
+        p, data = _get_mpint(data)
+        q, data = _get_mpint(data)
+        g, data = _get_mpint(data)
+        y, data = _get_mpint(data)
+        return (p, q, g, y), data
+
+    def load_public(
+        self, data: memoryview
+    ) -> tuple[dsa.DSAPublicKey, memoryview]:
+        """Make DSA public key from data."""
+        (p, q, g, y), data = self.get_public(data)
+        parameter_numbers = dsa.DSAParameterNumbers(p, q, g)
+        public_numbers = dsa.DSAPublicNumbers(y, parameter_numbers)
+        self._validate(public_numbers)
+        public_key = public_numbers.public_key()
+        return public_key, data
+
+    def load_private(
+        self, data: memoryview, pubfields, unsafe_skip_rsa_key_validation: bool
+    ) -> tuple[dsa.DSAPrivateKey, memoryview]:
+        """Make DSA private key from data."""
+        (p, q, g, y), data = self.get_public(data)
+        x, data = _get_mpint(data)
+
+        if (p, q, g, y) != pubfields:
+            raise ValueError("Corrupt data: dsa field mismatch")
+        parameter_numbers = dsa.DSAParameterNumbers(p, q, g)
+        public_numbers = dsa.DSAPublicNumbers(y, parameter_numbers)
+        self._validate(public_numbers)
+        private_numbers = dsa.DSAPrivateNumbers(x, public_numbers)
+        private_key = private_numbers.private_key()
+        return private_key, data
+
+    def encode_public(
+        self, public_key: dsa.DSAPublicKey, f_pub: _FragList
+    ) -> None:
+        """Write DSA public key"""
+        public_numbers = public_key.public_numbers()
+        parameter_numbers = public_numbers.parameter_numbers
+        self._validate(public_numbers)
+
+        f_pub.put_mpint(parameter_numbers.p)
+        f_pub.put_mpint(parameter_numbers.q)
+        f_pub.put_mpint(parameter_numbers.g)
+        f_pub.put_mpint(public_numbers.y)
+
+    def encode_private(
+        self, private_key: dsa.DSAPrivateKey, f_priv: _FragList
+    ) -> None:
+        """Write DSA private key"""
+        self.encode_public(private_key.public_key(), f_priv)
+        f_priv.put_mpint(private_key.private_numbers().x)
+
+    def _validate(self, public_numbers: dsa.DSAPublicNumbers) -> None:
+        parameter_numbers = public_numbers.parameter_numbers
+        if parameter_numbers.p.bit_length() != 1024:
+            raise ValueError("SSH supports only 1024 bit DSA keys")
+
+
+class _SSHFormatECDSA:
+    """Format for ECDSA keys.
+
+    Public:
+        str curve
+        bytes point
+    Private:
+        str curve
+        bytes point
+        mpint secret
+    """
+
+    def __init__(self, ssh_curve_name: bytes, curve: ec.EllipticCurve):
+        self.ssh_curve_name = ssh_curve_name
+        self.curve = curve
+
+    def get_public(
+        self, data: memoryview
+    ) -> tuple[tuple[memoryview, memoryview], memoryview]:
+        """ECDSA public fields"""
+        curve, data = _get_sshstr(data)
+        point, data = _get_sshstr(data)
+        if curve != self.ssh_curve_name:
+            raise ValueError("Curve name mismatch")
+        if point[0] != 4:
+            raise NotImplementedError("Need uncompressed point")
+        return (curve, point), data
+
+    def load_public(
+        self, data: memoryview
+    ) -> tuple[ec.EllipticCurvePublicKey, memoryview]:
+        """Make ECDSA public key from data."""
+        (_, point), data = self.get_public(data)
+        public_key = ec.EllipticCurvePublicKey.from_encoded_point(
+            self.curve, point.tobytes()
+        )
+        return public_key, data
+
+    def load_private(
+        self, data: memoryview, pubfields, unsafe_skip_rsa_key_validation: bool
+    ) -> tuple[ec.EllipticCurvePrivateKey, memoryview]:
+        """Make ECDSA private key from data."""
+        (curve_name, point), data = self.get_public(data)
+        secret, data = _get_mpint(data)
+
+        if (curve_name, point) != pubfields:
+            raise ValueError("Corrupt data: ecdsa field mismatch")
+        private_key = ec.derive_private_key(secret, self.curve)
+        return private_key, data
+
+    def encode_public(
+        self, public_key: ec.EllipticCurvePublicKey, f_pub: _FragList
+    ) -> None:
+        """Write ECDSA public key"""
+        point = public_key.public_bytes(
+            Encoding.X962, PublicFormat.UncompressedPoint
+        )
+        f_pub.put_sshstr(self.ssh_curve_name)
+        f_pub.put_sshstr(point)
+
+    def encode_private(
+        self, private_key: ec.EllipticCurvePrivateKey, f_priv: _FragList
+    ) -> None:
+        """Write ECDSA private key"""
+        public_key = private_key.public_key()
+        private_numbers = private_key.private_numbers()
+
+        self.encode_public(public_key, f_priv)
+        f_priv.put_mpint(private_numbers.private_value)
+
+
+class _SSHFormatEd25519:
+    """Format for Ed25519 keys.
+
+    Public:
+        bytes point
+    Private:
+        bytes point
+        bytes secret_and_point
+    """
+
+    def get_public(
+        self, data: memoryview
+    ) -> tuple[tuple[memoryview], memoryview]:
+        """Ed25519 public fields"""
+        point, data = _get_sshstr(data)
+        return (point,), data
+
+    def load_public(
+        self, data: memoryview
+    ) -> tuple[ed25519.Ed25519PublicKey, memoryview]:
+        """Make Ed25519 public key from data."""
+        (point,), data = self.get_public(data)
+        public_key = ed25519.Ed25519PublicKey.from_public_bytes(
+            point.tobytes()
+        )
+        return public_key, data
+
+    def load_private(
+        self, data: memoryview, pubfields, unsafe_skip_rsa_key_validation: bool
+    ) -> tuple[ed25519.Ed25519PrivateKey, memoryview]:
+        """Make Ed25519 private key from data."""
+        (point,), data = self.get_public(data)
+        keypair, data = _get_sshstr(data)
+
+        secret = keypair[:32]
+        point2 = keypair[32:]
+        if point != point2 or (point,) != pubfields:
+            raise ValueError("Corrupt data: ed25519 field mismatch")
+        private_key = ed25519.Ed25519PrivateKey.from_private_bytes(secret)
+        return private_key, data
+
+    def encode_public(
+        self, public_key: ed25519.Ed25519PublicKey, f_pub: _FragList
+    ) -> None:
+        """Write Ed25519 public key"""
+        raw_public_key = public_key.public_bytes(
+            Encoding.Raw, PublicFormat.Raw
+        )
+        f_pub.put_sshstr(raw_public_key)
+
+    def encode_private(
+        self, private_key: ed25519.Ed25519PrivateKey, f_priv: _FragList
+    ) -> None:
+        """Write Ed25519 private key"""
+        public_key = private_key.public_key()
+        raw_private_key = private_key.private_bytes(
+            Encoding.Raw, PrivateFormat.Raw, NoEncryption()
+        )
+        raw_public_key = public_key.public_bytes(
+            Encoding.Raw, PublicFormat.Raw
+        )
+        f_keypair = _FragList([raw_private_key, raw_public_key])
+
+        self.encode_public(public_key, f_priv)
+        f_priv.put_sshstr(f_keypair)
+
+
+def load_application(data) -> tuple[memoryview, memoryview]:
+    """
+    U2F application strings
+    """
+    application, data = _get_sshstr(data)
+    if not application.tobytes().startswith(b"ssh:"):
+        raise ValueError(
+            "U2F application string does not start with b'ssh:' "
+            f"({application})"
+        )
+    return application, data
+
+
+class _SSHFormatSKEd25519:
+    """
+    The format of a sk-ssh-ed25519@openssh.com public key is:
+
+        string		"sk-ssh-ed25519@openssh.com"
+        string		public key
+        string		application (user-specified, but typically "ssh:")
+    """
+
+    def load_public(
+        self, data: memoryview
+    ) -> tuple[ed25519.Ed25519PublicKey, memoryview]:
+        """Make Ed25519 public key from data."""
+        public_key, data = _lookup_kformat(_SSH_ED25519).load_public(data)
+        _, data = load_application(data)
+        return public_key, data
+
+    def get_public(self, data: memoryview) -> typing.NoReturn:
+        # Confusingly `get_public` is an entry point used by private key
+        # loading.
+        raise UnsupportedAlgorithm(
+            "sk-ssh-ed25519 private keys cannot be loaded"
+        )
+
+
+class _SSHFormatSKECDSA:
+    """
+    The format of a sk-ecdsa-sha2-nistp256@openssh.com public key is:
+
+        string		"sk-ecdsa-sha2-nistp256@openssh.com"
+        string		curve name
+        ec_point	Q
+        string		application (user-specified, but typically "ssh:")
+    """
+
+    def load_public(
+        self, data: memoryview
+    ) -> tuple[ec.EllipticCurvePublicKey, memoryview]:
+        """Make ECDSA public key from data."""
+        public_key, data = _lookup_kformat(_ECDSA_NISTP256).load_public(data)
+        _, data = load_application(data)
+        return public_key, data
+
+    def get_public(self, data: memoryview) -> typing.NoReturn:
+        # Confusingly `get_public` is an entry point used by private key
+        # loading.
+        raise UnsupportedAlgorithm(
+            "sk-ecdsa-sha2-nistp256 private keys cannot be loaded"
+        )
+
+
+_KEY_FORMATS = {
+    _SSH_RSA: _SSHFormatRSA(),
+    _SSH_DSA: _SSHFormatDSA(),
+    _SSH_ED25519: _SSHFormatEd25519(),
+    _ECDSA_NISTP256: _SSHFormatECDSA(b"nistp256", ec.SECP256R1()),
+    _ECDSA_NISTP384: _SSHFormatECDSA(b"nistp384", ec.SECP384R1()),
+    _ECDSA_NISTP521: _SSHFormatECDSA(b"nistp521", ec.SECP521R1()),
+    _SK_SSH_ED25519: _SSHFormatSKEd25519(),
+    _SK_SSH_ECDSA_NISTP256: _SSHFormatSKECDSA(),
+}
+
+
+def _lookup_kformat(key_type: utils.Buffer):
+    """Return valid format or throw error"""
+    if not isinstance(key_type, bytes):
+        key_type = memoryview(key_type).tobytes()
+    if key_type in _KEY_FORMATS:
+        return _KEY_FORMATS[key_type]
+    raise UnsupportedAlgorithm(f"Unsupported key type: {key_type!r}")
+
+
+SSHPrivateKeyTypes = typing.Union[
+    ec.EllipticCurvePrivateKey,
+    rsa.RSAPrivateKey,
+    dsa.DSAPrivateKey,
+    ed25519.Ed25519PrivateKey,
+]
+
+
+def load_ssh_private_key(
+    data: utils.Buffer,
+    password: bytes | None,
+    backend: typing.Any = None,
+    *,
+    unsafe_skip_rsa_key_validation: bool = False,
+) -> SSHPrivateKeyTypes:
+    """Load private key from OpenSSH custom encoding."""
+    utils._check_byteslike("data", data)
+    if password is not None:
+        utils._check_bytes("password", password)
+
+    m = _PEM_RC.search(data)
+    if not m:
+        raise ValueError("Not OpenSSH private key format")
+    p1 = m.start(1)
+    p2 = m.end(1)
+    data = binascii.a2b_base64(memoryview(data)[p1:p2])
+    if not data.startswith(_SK_MAGIC):
+        raise ValueError("Not OpenSSH private key format")
+    data = memoryview(data)[len(_SK_MAGIC) :]
+
+    # parse header
+    ciphername, data = _get_sshstr(data)
+    kdfname, data = _get_sshstr(data)
+    kdfoptions, data = _get_sshstr(data)
+    nkeys, data = _get_u32(data)
+    if nkeys != 1:
+        raise ValueError("Only one key supported")
+
+    # load public key data
+    pubdata, data = _get_sshstr(data)
+    pub_key_type, pubdata = _get_sshstr(pubdata)
+    kformat = _lookup_kformat(pub_key_type)
+    pubfields, pubdata = kformat.get_public(pubdata)
+    _check_empty(pubdata)
+
+    if ciphername != _NONE or kdfname != _NONE:
+        ciphername_bytes = ciphername.tobytes()
+        if ciphername_bytes not in _SSH_CIPHERS:
+            raise UnsupportedAlgorithm(
+                f"Unsupported cipher: {ciphername_bytes!r}"
+            )
+        if kdfname != _BCRYPT:
+            raise UnsupportedAlgorithm(f"Unsupported KDF: {kdfname!r}")
+        blklen = _SSH_CIPHERS[ciphername_bytes].block_len
+        tag_len = _SSH_CIPHERS[ciphername_bytes].tag_len
+        # load secret data
+        edata, data = _get_sshstr(data)
+        # see https://bugzilla.mindrot.org/show_bug.cgi?id=3553 for
+        # information about how OpenSSH handles AEAD tags
+        if _SSH_CIPHERS[ciphername_bytes].is_aead:
+            tag = bytes(data)
+            if len(tag) != tag_len:
+                raise ValueError("Corrupt data: invalid tag length for cipher")
+        else:
+            _check_empty(data)
+        _check_block_size(edata, blklen)
+        salt, kbuf = _get_sshstr(kdfoptions)
+        rounds, kbuf = _get_u32(kbuf)
+        _check_empty(kbuf)
+        ciph = _init_cipher(ciphername_bytes, password, salt.tobytes(), rounds)
+        dec = ciph.decryptor()
+        edata = memoryview(dec.update(edata))
+        if _SSH_CIPHERS[ciphername_bytes].is_aead:
+            assert isinstance(dec, AEADDecryptionContext)
+            _check_empty(dec.finalize_with_tag(tag))
+        else:
+            # _check_block_size requires data to be a full block so there
+            # should be no output from finalize
+            _check_empty(dec.finalize())
+    else:
+        if password:
+            raise TypeError(
+                "Password was given but private key is not encrypted."
+            )
+        # load secret data
+        edata, data = _get_sshstr(data)
+        _check_empty(data)
+        blklen = 8
+        _check_block_size(edata, blklen)
+    ck1, edata = _get_u32(edata)
+    ck2, edata = _get_u32(edata)
+    if ck1 != ck2:
+        raise ValueError("Corrupt data: broken checksum")
+
+    # load per-key struct
+    key_type, edata = _get_sshstr(edata)
+    if key_type != pub_key_type:
+        raise ValueError("Corrupt data: key type mismatch")
+    private_key, edata = kformat.load_private(
+        edata,
+        pubfields,
+        unsafe_skip_rsa_key_validation=unsafe_skip_rsa_key_validation,
+    )
+    # We don't use the comment
+    _, edata = _get_sshstr(edata)
+
+    # yes, SSH does padding check *after* all other parsing is done.
+    # need to follow as it writes zero-byte padding too.
+    if edata != _PADDING[: len(edata)]:
+        raise ValueError("Corrupt data: invalid padding")
+
+    if isinstance(private_key, dsa.DSAPrivateKey):
+        warnings.warn(
+            "SSH DSA keys are deprecated and will be removed in a future "
+            "release.",
+            utils.DeprecatedIn40,
+            stacklevel=2,
+        )
+
+    return private_key
+
+
+def _serialize_ssh_private_key(
+    private_key: SSHPrivateKeyTypes,
+    password: bytes,
+    encryption_algorithm: KeySerializationEncryption,
+) -> bytes:
+    """Serialize private key with OpenSSH custom encoding."""
+    utils._check_bytes("password", password)
+    if isinstance(private_key, dsa.DSAPrivateKey):
+        warnings.warn(
+            "SSH DSA key support is deprecated and will be "
+            "removed in a future release",
+            utils.DeprecatedIn40,
+            stacklevel=4,
+        )
+
+    key_type = _get_ssh_key_type(private_key)
+    kformat = _lookup_kformat(key_type)
+
+    # setup parameters
+    f_kdfoptions = _FragList()
+    if password:
+        ciphername = _DEFAULT_CIPHER
+        blklen = _SSH_CIPHERS[ciphername].block_len
+        kdfname = _BCRYPT
+        rounds = _DEFAULT_ROUNDS
+        if (
+            isinstance(encryption_algorithm, _KeySerializationEncryption)
+            and encryption_algorithm._kdf_rounds is not None
+        ):
+            rounds = encryption_algorithm._kdf_rounds
+        salt = os.urandom(16)
+        f_kdfoptions.put_sshstr(salt)
+        f_kdfoptions.put_u32(rounds)
+        ciph = _init_cipher(ciphername, password, salt, rounds)
+    else:
+        ciphername = kdfname = _NONE
+        blklen = 8
+        ciph = None
+    nkeys = 1
+    checkval = os.urandom(4)
+    comment = b""
+
+    # encode public and private parts together
+    f_public_key = _FragList()
+    f_public_key.put_sshstr(key_type)
+    kformat.encode_public(private_key.public_key(), f_public_key)
+
+    f_secrets = _FragList([checkval, checkval])
+    f_secrets.put_sshstr(key_type)
+    kformat.encode_private(private_key, f_secrets)
+    f_secrets.put_sshstr(comment)
+    f_secrets.put_raw(_PADDING[: blklen - (f_secrets.size() % blklen)])
+
+    # top-level structure
+    f_main = _FragList()
+    f_main.put_raw(_SK_MAGIC)
+    f_main.put_sshstr(ciphername)
+    f_main.put_sshstr(kdfname)
+    f_main.put_sshstr(f_kdfoptions)
+    f_main.put_u32(nkeys)
+    f_main.put_sshstr(f_public_key)
+    f_main.put_sshstr(f_secrets)
+
+    # copy result info bytearray
+    slen = f_secrets.size()
+    mlen = f_main.size()
+    buf = memoryview(bytearray(mlen + blklen))
+    f_main.render(buf)
+    ofs = mlen - slen
+
+    # encrypt in-place
+    if ciph is not None:
+        ciph.encryptor().update_into(buf[ofs:mlen], buf[ofs:])
+
+    return _ssh_pem_encode(buf[:mlen])
+
+
+SSHPublicKeyTypes = typing.Union[
+    ec.EllipticCurvePublicKey,
+    rsa.RSAPublicKey,
+    dsa.DSAPublicKey,
+    ed25519.Ed25519PublicKey,
+]
+
+SSHCertPublicKeyTypes = typing.Union[
+    ec.EllipticCurvePublicKey,
+    rsa.RSAPublicKey,
+    ed25519.Ed25519PublicKey,
+]
+
+
+class SSHCertificateType(enum.Enum):
+    USER = 1
+    HOST = 2
+
+
+class SSHCertificate:
+    def __init__(
+        self,
+        _nonce: memoryview,
+        _public_key: SSHPublicKeyTypes,
+        _serial: int,
+        _cctype: int,
+        _key_id: memoryview,
+        _valid_principals: list[bytes],
+        _valid_after: int,
+        _valid_before: int,
+        _critical_options: dict[bytes, bytes],
+        _extensions: dict[bytes, bytes],
+        _sig_type: memoryview,
+        _sig_key: memoryview,
+        _inner_sig_type: memoryview,
+        _signature: memoryview,
+        _tbs_cert_body: memoryview,
+        _cert_key_type: bytes,
+        _cert_body: memoryview,
+    ):
+        self._nonce = _nonce
+        self._public_key = _public_key
+        self._serial = _serial
+        try:
+            self._type = SSHCertificateType(_cctype)
+        except ValueError:
+            raise ValueError("Invalid certificate type")
+        self._key_id = _key_id
+        self._valid_principals = _valid_principals
+        self._valid_after = _valid_after
+        self._valid_before = _valid_before
+        self._critical_options = _critical_options
+        self._extensions = _extensions
+        self._sig_type = _sig_type
+        self._sig_key = _sig_key
+        self._inner_sig_type = _inner_sig_type
+        self._signature = _signature
+        self._cert_key_type = _cert_key_type
+        self._cert_body = _cert_body
+        self._tbs_cert_body = _tbs_cert_body
+
+    @property
+    def nonce(self) -> bytes:
+        return bytes(self._nonce)
+
+    def public_key(self) -> SSHCertPublicKeyTypes:
+        # make mypy happy until we remove DSA support entirely and
+        # the underlying union won't have a disallowed type
+        return typing.cast(SSHCertPublicKeyTypes, self._public_key)
+
+    @property
+    def serial(self) -> int:
+        return self._serial
+
+    @property
+    def type(self) -> SSHCertificateType:
+        return self._type
+
+    @property
+    def key_id(self) -> bytes:
+        return bytes(self._key_id)
+
+    @property
+    def valid_principals(self) -> list[bytes]:
+        return self._valid_principals
+
+    @property
+    def valid_before(self) -> int:
+        return self._valid_before
+
+    @property
+    def valid_after(self) -> int:
+        return self._valid_after
+
+    @property
+    def critical_options(self) -> dict[bytes, bytes]:
+        return self._critical_options
+
+    @property
+    def extensions(self) -> dict[bytes, bytes]:
+        return self._extensions
+
+    def signature_key(self) -> SSHCertPublicKeyTypes:
+        sigformat = _lookup_kformat(self._sig_type)
+        signature_key, sigkey_rest = sigformat.load_public(self._sig_key)
+        _check_empty(sigkey_rest)
+        return signature_key
+
+    def public_bytes(self) -> bytes:
+        return (
+            bytes(self._cert_key_type)
+            + b" "
+            + binascii.b2a_base64(bytes(self._cert_body), newline=False)
+        )
+
+    def verify_cert_signature(self) -> None:
+        signature_key = self.signature_key()
+        if isinstance(signature_key, ed25519.Ed25519PublicKey):
+            signature_key.verify(
+                bytes(self._signature), bytes(self._tbs_cert_body)
+            )
+        elif isinstance(signature_key, ec.EllipticCurvePublicKey):
+            # The signature is encoded as a pair of big-endian integers
+            r, data = _get_mpint(self._signature)
+            s, data = _get_mpint(data)
+            _check_empty(data)
+            computed_sig = asym_utils.encode_dss_signature(r, s)
+            hash_alg = _get_ec_hash_alg(signature_key.curve)
+            signature_key.verify(
+                computed_sig, bytes(self._tbs_cert_body), ec.ECDSA(hash_alg)
+            )
+        else:
+            assert isinstance(signature_key, rsa.RSAPublicKey)
+            if self._inner_sig_type == _SSH_RSA:
+                hash_alg = hashes.SHA1()
+            elif self._inner_sig_type == _SSH_RSA_SHA256:
+                hash_alg = hashes.SHA256()
+            else:
+                assert self._inner_sig_type == _SSH_RSA_SHA512
+                hash_alg = hashes.SHA512()
+            signature_key.verify(
+                bytes(self._signature),
+                bytes(self._tbs_cert_body),
+                padding.PKCS1v15(),
+                hash_alg,
+            )
+
+
+def _get_ec_hash_alg(curve: ec.EllipticCurve) -> hashes.HashAlgorithm:
+    if isinstance(curve, ec.SECP256R1):
+        return hashes.SHA256()
+    elif isinstance(curve, ec.SECP384R1):
+        return hashes.SHA384()
+    else:
+        assert isinstance(curve, ec.SECP521R1)
+        return hashes.SHA512()
+
+
+def _load_ssh_public_identity(
+    data: utils.Buffer,
+    _legacy_dsa_allowed=False,
+) -> SSHCertificate | SSHPublicKeyTypes:
+    utils._check_byteslike("data", data)
+
+    m = _SSH_PUBKEY_RC.match(data)
+    if not m:
+        raise ValueError("Invalid line format")
+    key_type = orig_key_type = m.group(1)
+    key_body = m.group(2)
+    with_cert = False
+    if key_type.endswith(_CERT_SUFFIX):
+        with_cert = True
+        key_type = key_type[: -len(_CERT_SUFFIX)]
+    if key_type == _SSH_DSA and not _legacy_dsa_allowed:
+        raise UnsupportedAlgorithm(
+            "DSA keys aren't supported in SSH certificates"
+        )
+    kformat = _lookup_kformat(key_type)
+
+    try:
+        rest = memoryview(binascii.a2b_base64(key_body))
+    except (TypeError, binascii.Error):
+        raise ValueError("Invalid format")
+
+    if with_cert:
+        cert_body = rest
+    inner_key_type, rest = _get_sshstr(rest)
+    if inner_key_type != orig_key_type:
+        raise ValueError("Invalid key format")
+    if with_cert:
+        nonce, rest = _get_sshstr(rest)
+    public_key, rest = kformat.load_public(rest)
+    if with_cert:
+        serial, rest = _get_u64(rest)
+        cctype, rest = _get_u32(rest)
+        key_id, rest = _get_sshstr(rest)
+        principals, rest = _get_sshstr(rest)
+        valid_principals = []
+        while principals:
+            principal, principals = _get_sshstr(principals)
+            valid_principals.append(bytes(principal))
+        valid_after, rest = _get_u64(rest)
+        valid_before, rest = _get_u64(rest)
+        crit_options, rest = _get_sshstr(rest)
+        critical_options = _parse_exts_opts(crit_options)
+        exts, rest = _get_sshstr(rest)
+        extensions = _parse_exts_opts(exts)
+        # Get the reserved field, which is unused.
+        _, rest = _get_sshstr(rest)
+        sig_key_raw, rest = _get_sshstr(rest)
+        sig_type, sig_key = _get_sshstr(sig_key_raw)
+        if sig_type == _SSH_DSA and not _legacy_dsa_allowed:
+            raise UnsupportedAlgorithm(
+                "DSA signatures aren't supported in SSH certificates"
+            )
+        # Get the entire cert body and subtract the signature
+        tbs_cert_body = cert_body[: -len(rest)]
+        signature_raw, rest = _get_sshstr(rest)
+        _check_empty(rest)
+        inner_sig_type, sig_rest = _get_sshstr(signature_raw)
+        # RSA certs can have multiple algorithm types
+        if (
+            sig_type == _SSH_RSA
+            and inner_sig_type
+            not in [_SSH_RSA_SHA256, _SSH_RSA_SHA512, _SSH_RSA]
+        ) or (sig_type != _SSH_RSA and inner_sig_type != sig_type):
+            raise ValueError("Signature key type does not match")
+        signature, sig_rest = _get_sshstr(sig_rest)
+        _check_empty(sig_rest)
+        return SSHCertificate(
+            nonce,
+            public_key,
+            serial,
+            cctype,
+            key_id,
+            valid_principals,
+            valid_after,
+            valid_before,
+            critical_options,
+            extensions,
+            sig_type,
+            sig_key,
+            inner_sig_type,
+            signature,
+            tbs_cert_body,
+            orig_key_type,
+            cert_body,
+        )
+    else:
+        _check_empty(rest)
+        return public_key
+
+
+def load_ssh_public_identity(
+    data: bytes,
+) -> SSHCertificate | SSHPublicKeyTypes:
+    return _load_ssh_public_identity(data)
+
+
+def _parse_exts_opts(exts_opts: memoryview) -> dict[bytes, bytes]:
+    result: dict[bytes, bytes] = {}
+    last_name = None
+    while exts_opts:
+        name, exts_opts = _get_sshstr(exts_opts)
+        bname: bytes = bytes(name)
+        if bname in result:
+            raise ValueError("Duplicate name")
+        if last_name is not None and bname < last_name:
+            raise ValueError("Fields not lexically sorted")
+        value, exts_opts = _get_sshstr(exts_opts)
+        if len(value) > 0:
+            value, extra = _get_sshstr(value)
+            if len(extra) > 0:
+                raise ValueError("Unexpected extra data after value")
+        result[bname] = bytes(value)
+        last_name = bname
+    return result
+
+
+def ssh_key_fingerprint(
+    key: SSHPublicKeyTypes,
+    hash_algorithm: hashes.MD5 | hashes.SHA256,
+) -> bytes:
+    if not isinstance(hash_algorithm, (hashes.MD5, hashes.SHA256)):
+        raise TypeError("hash_algorithm must be either MD5 or SHA256")
+
+    key_type = _get_ssh_key_type(key)
+    kformat = _lookup_kformat(key_type)
+
+    f_pub = _FragList()
+    f_pub.put_sshstr(key_type)
+    kformat.encode_public(key, f_pub)
+
+    ssh_binary_data = f_pub.tobytes()
+
+    # Hash the binary data
+    hash_obj = hashes.Hash(hash_algorithm)
+    hash_obj.update(ssh_binary_data)
+    return hash_obj.finalize()
+
+
+def load_ssh_public_key(
+    data: utils.Buffer, backend: typing.Any = None
+) -> SSHPublicKeyTypes:
+    cert_or_key = _load_ssh_public_identity(data, _legacy_dsa_allowed=True)
+    public_key: SSHPublicKeyTypes
+    if isinstance(cert_or_key, SSHCertificate):
+        public_key = cert_or_key.public_key()
+    else:
+        public_key = cert_or_key
+
+    if isinstance(public_key, dsa.DSAPublicKey):
+        warnings.warn(
+            "SSH DSA keys are deprecated and will be removed in a future "
+            "release.",
+            utils.DeprecatedIn40,
+            stacklevel=2,
+        )
+    return public_key
+
+
+def serialize_ssh_public_key(public_key: SSHPublicKeyTypes) -> bytes:
+    """One-line public key format for OpenSSH"""
+    if isinstance(public_key, dsa.DSAPublicKey):
+        warnings.warn(
+            "SSH DSA key support is deprecated and will be "
+            "removed in a future release",
+            utils.DeprecatedIn40,
+            stacklevel=4,
+        )
+    key_type = _get_ssh_key_type(public_key)
+    kformat = _lookup_kformat(key_type)
+
+    f_pub = _FragList()
+    f_pub.put_sshstr(key_type)
+    kformat.encode_public(public_key, f_pub)
+
+    pub = binascii.b2a_base64(f_pub.tobytes()).strip()
+    return b"".join([key_type, b" ", pub])
+
+
+SSHCertPrivateKeyTypes = typing.Union[
+    ec.EllipticCurvePrivateKey,
+    rsa.RSAPrivateKey,
+    ed25519.Ed25519PrivateKey,
+]
+
+
+# This is an undocumented limit enforced in the openssh codebase for sshd and
+# ssh-keygen, but it is undefined in the ssh certificates spec.
+_SSHKEY_CERT_MAX_PRINCIPALS = 256
+
+
+class SSHCertificateBuilder:
+    def __init__(
+        self,
+        _public_key: SSHCertPublicKeyTypes | None = None,
+        _serial: int | None = None,
+        _type: SSHCertificateType | None = None,
+        _key_id: bytes | None = None,
+        _valid_principals: list[bytes] = [],
+        _valid_for_all_principals: bool = False,
+        _valid_before: int | None = None,
+        _valid_after: int | None = None,
+        _critical_options: list[tuple[bytes, bytes]] = [],
+        _extensions: list[tuple[bytes, bytes]] = [],
+    ):
+        self._public_key = _public_key
+        self._serial = _serial
+        self._type = _type
+        self._key_id = _key_id
+        self._valid_principals = _valid_principals
+        self._valid_for_all_principals = _valid_for_all_principals
+        self._valid_before = _valid_before
+        self._valid_after = _valid_after
+        self._critical_options = _critical_options
+        self._extensions = _extensions
+
+    def public_key(
+        self, public_key: SSHCertPublicKeyTypes
+    ) -> SSHCertificateBuilder:
+        if not isinstance(
+            public_key,
+            (
+                ec.EllipticCurvePublicKey,
+                rsa.RSAPublicKey,
+                ed25519.Ed25519PublicKey,
+            ),
+        ):
+            raise TypeError("Unsupported key type")
+        if self._public_key is not None:
+            raise ValueError("public_key already set")
+
+        return SSHCertificateBuilder(
+            _public_key=public_key,
+            _serial=self._serial,
+            _type=self._type,
+            _key_id=self._key_id,
+            _valid_principals=self._valid_principals,
+            _valid_for_all_principals=self._valid_for_all_principals,
+            _valid_before=self._valid_before,
+            _valid_after=self._valid_after,
+            _critical_options=self._critical_options,
+            _extensions=self._extensions,
+        )
+
+    def serial(self, serial: int) -> SSHCertificateBuilder:
+        if not isinstance(serial, int):
+            raise TypeError("serial must be an integer")
+        if not 0 <= serial < 2**64:
+            raise ValueError("serial must be between 0 and 2**64")
+        if self._serial is not None:
+            raise ValueError("serial already set")
+
+        return SSHCertificateBuilder(
+            _public_key=self._public_key,
+            _serial=serial,
+            _type=self._type,
+            _key_id=self._key_id,
+            _valid_principals=self._valid_principals,
+            _valid_for_all_principals=self._valid_for_all_principals,
+            _valid_before=self._valid_before,
+            _valid_after=self._valid_after,
+            _critical_options=self._critical_options,
+            _extensions=self._extensions,
+        )
+
+    def type(self, type: SSHCertificateType) -> SSHCertificateBuilder:
+        if not isinstance(type, SSHCertificateType):
+            raise TypeError("type must be an SSHCertificateType")
+        if self._type is not None:
+            raise ValueError("type already set")
+
+        return SSHCertificateBuilder(
+            _public_key=self._public_key,
+            _serial=self._serial,
+            _type=type,
+            _key_id=self._key_id,
+            _valid_principals=self._valid_principals,
+            _valid_for_all_principals=self._valid_for_all_principals,
+            _valid_before=self._valid_before,
+            _valid_after=self._valid_after,
+            _critical_options=self._critical_options,
+            _extensions=self._extensions,
+        )
+
+    def key_id(self, key_id: bytes) -> SSHCertificateBuilder:
+        if not isinstance(key_id, bytes):
+            raise TypeError("key_id must be bytes")
+        if self._key_id is not None:
+            raise ValueError("key_id already set")
+
+        return SSHCertificateBuilder(
+            _public_key=self._public_key,
+            _serial=self._serial,
+            _type=self._type,
+            _key_id=key_id,
+            _valid_principals=self._valid_principals,
+            _valid_for_all_principals=self._valid_for_all_principals,
+            _valid_before=self._valid_before,
+            _valid_after=self._valid_after,
+            _critical_options=self._critical_options,
+            _extensions=self._extensions,
+        )
+
+    def valid_principals(
+        self, valid_principals: list[bytes]
+    ) -> SSHCertificateBuilder:
+        if self._valid_for_all_principals:
+            raise ValueError(
+                "Principals can't be set because the cert is valid "
+                "for all principals"
+            )
+        if (
+            not all(isinstance(x, bytes) for x in valid_principals)
+            or not valid_principals
+        ):
+            raise TypeError(
+                "principals must be a list of bytes and can't be empty"
+            )
+        if self._valid_principals:
+            raise ValueError("valid_principals already set")
+
+        if len(valid_principals) > _SSHKEY_CERT_MAX_PRINCIPALS:
+            raise ValueError(
+                "Reached or exceeded the maximum number of valid_principals"
+            )
+
+        return SSHCertificateBuilder(
+            _public_key=self._public_key,
+            _serial=self._serial,
+            _type=self._type,
+            _key_id=self._key_id,
+            _valid_principals=valid_principals,
+            _valid_for_all_principals=self._valid_for_all_principals,
+            _valid_before=self._valid_before,
+            _valid_after=self._valid_after,
+            _critical_options=self._critical_options,
+            _extensions=self._extensions,
+        )
+
+    def valid_for_all_principals(self):
+        if self._valid_principals:
+            raise ValueError(
+                "valid_principals already set, can't set "
+                "valid_for_all_principals"
+            )
+        if self._valid_for_all_principals:
+            raise ValueError("valid_for_all_principals already set")
+
+        return SSHCertificateBuilder(
+            _public_key=self._public_key,
+            _serial=self._serial,
+            _type=self._type,
+            _key_id=self._key_id,
+            _valid_principals=self._valid_principals,
+            _valid_for_all_principals=True,
+            _valid_before=self._valid_before,
+            _valid_after=self._valid_after,
+            _critical_options=self._critical_options,
+            _extensions=self._extensions,
+        )
+
+    def valid_before(self, valid_before: int | float) -> SSHCertificateBuilder:
+        if not isinstance(valid_before, (int, float)):
+            raise TypeError("valid_before must be an int or float")
+        valid_before = int(valid_before)
+        if valid_before < 0 or valid_before >= 2**64:
+            raise ValueError("valid_before must [0, 2**64)")
+        if self._valid_before is not None:
+            raise ValueError("valid_before already set")
+
+        return SSHCertificateBuilder(
+            _public_key=self._public_key,
+            _serial=self._serial,
+            _type=self._type,
+            _key_id=self._key_id,
+            _valid_principals=self._valid_principals,
+            _valid_for_all_principals=self._valid_for_all_principals,
+            _valid_before=valid_before,
+            _valid_after=self._valid_after,
+            _critical_options=self._critical_options,
+            _extensions=self._extensions,
+        )
+
+    def valid_after(self, valid_after: int | float) -> SSHCertificateBuilder:
+        if not isinstance(valid_after, (int, float)):
+            raise TypeError("valid_after must be an int or float")
+        valid_after = int(valid_after)
+        if valid_after < 0 or valid_after >= 2**64:
+            raise ValueError("valid_after must [0, 2**64)")
+        if self._valid_after is not None:
+            raise ValueError("valid_after already set")
+
+        return SSHCertificateBuilder(
+            _public_key=self._public_key,
+            _serial=self._serial,
+            _type=self._type,
+            _key_id=self._key_id,
+            _valid_principals=self._valid_principals,
+            _valid_for_all_principals=self._valid_for_all_principals,
+            _valid_before=self._valid_before,
+            _valid_after=valid_after,
+            _critical_options=self._critical_options,
+            _extensions=self._extensions,
+        )
+
+    def add_critical_option(
+        self, name: bytes, value: bytes
+    ) -> SSHCertificateBuilder:
+        if not isinstance(name, bytes) or not isinstance(value, bytes):
+            raise TypeError("name and value must be bytes")
+        # This is O(n**2)
+        if name in [name for name, _ in self._critical_options]:
+            raise ValueError("Duplicate critical option name")
+
+        return SSHCertificateBuilder(
+            _public_key=self._public_key,
+            _serial=self._serial,
+            _type=self._type,
+            _key_id=self._key_id,
+            _valid_principals=self._valid_principals,
+            _valid_for_all_principals=self._valid_for_all_principals,
+            _valid_before=self._valid_before,
+            _valid_after=self._valid_after,
+            _critical_options=[*self._critical_options, (name, value)],
+            _extensions=self._extensions,
+        )
+
+    def add_extension(
+        self, name: bytes, value: bytes
+    ) -> SSHCertificateBuilder:
+        if not isinstance(name, bytes) or not isinstance(value, bytes):
+            raise TypeError("name and value must be bytes")
+        # This is O(n**2)
+        if name in [name for name, _ in self._extensions]:
+            raise ValueError("Duplicate extension name")
+
+        return SSHCertificateBuilder(
+            _public_key=self._public_key,
+            _serial=self._serial,
+            _type=self._type,
+            _key_id=self._key_id,
+            _valid_principals=self._valid_principals,
+            _valid_for_all_principals=self._valid_for_all_principals,
+            _valid_before=self._valid_before,
+            _valid_after=self._valid_after,
+            _critical_options=self._critical_options,
+            _extensions=[*self._extensions, (name, value)],
+        )
+
+    def sign(self, private_key: SSHCertPrivateKeyTypes) -> SSHCertificate:
+        if not isinstance(
+            private_key,
+            (
+                ec.EllipticCurvePrivateKey,
+                rsa.RSAPrivateKey,
+                ed25519.Ed25519PrivateKey,
+            ),
+        ):
+            raise TypeError("Unsupported private key type")
+
+        if self._public_key is None:
+            raise ValueError("public_key must be set")
+
+        # Not required
+        serial = 0 if self._serial is None else self._serial
+
+        if self._type is None:
+            raise ValueError("type must be set")
+
+        # Not required
+        key_id = b"" if self._key_id is None else self._key_id
+
+        # A zero length list is valid, but means the certificate
+        # is valid for any principal of the specified type. We require
+        # the user to explicitly set valid_for_all_principals to get
+        # that behavior.
+        if not self._valid_principals and not self._valid_for_all_principals:
+            raise ValueError(
+                "valid_principals must be set if valid_for_all_principals "
+                "is False"
+            )
+
+        if self._valid_before is None:
+            raise ValueError("valid_before must be set")
+
+        if self._valid_after is None:
+            raise ValueError("valid_after must be set")
+
+        if self._valid_after > self._valid_before:
+            raise ValueError("valid_after must be earlier than valid_before")
+
+        # lexically sort our byte strings
+        self._critical_options.sort(key=lambda x: x[0])
+        self._extensions.sort(key=lambda x: x[0])
+
+        key_type = _get_ssh_key_type(self._public_key)
+        cert_prefix = key_type + _CERT_SUFFIX
+
+        # Marshal the bytes to be signed
+        nonce = os.urandom(32)
+        kformat = _lookup_kformat(key_type)
+        f = _FragList()
+        f.put_sshstr(cert_prefix)
+        f.put_sshstr(nonce)
+        kformat.encode_public(self._public_key, f)
+        f.put_u64(serial)
+        f.put_u32(self._type.value)
+        f.put_sshstr(key_id)
+        fprincipals = _FragList()
+        for p in self._valid_principals:
+            fprincipals.put_sshstr(p)
+        f.put_sshstr(fprincipals.tobytes())
+        f.put_u64(self._valid_after)
+        f.put_u64(self._valid_before)
+        fcrit = _FragList()
+        for name, value in self._critical_options:
+            fcrit.put_sshstr(name)
+            if len(value) > 0:
+                foptval = _FragList()
+                foptval.put_sshstr(value)
+                fcrit.put_sshstr(foptval.tobytes())
+            else:
+                fcrit.put_sshstr(value)
+        f.put_sshstr(fcrit.tobytes())
+        fext = _FragList()
+        for name, value in self._extensions:
+            fext.put_sshstr(name)
+            if len(value) > 0:
+                fextval = _FragList()
+                fextval.put_sshstr(value)
+                fext.put_sshstr(fextval.tobytes())
+            else:
+                fext.put_sshstr(value)
+        f.put_sshstr(fext.tobytes())
+        f.put_sshstr(b"")  # RESERVED FIELD
+        # encode CA public key
+        ca_type = _get_ssh_key_type(private_key)
+        caformat = _lookup_kformat(ca_type)
+        caf = _FragList()
+        caf.put_sshstr(ca_type)
+        caformat.encode_public(private_key.public_key(), caf)
+        f.put_sshstr(caf.tobytes())
+        # Sigs according to the rules defined for the CA's public key
+        # (RFC4253 section 6.6 for ssh-rsa, RFC5656 for ECDSA,
+        # and RFC8032 for Ed25519).
+        if isinstance(private_key, ed25519.Ed25519PrivateKey):
+            signature = private_key.sign(f.tobytes())
+            fsig = _FragList()
+            fsig.put_sshstr(ca_type)
+            fsig.put_sshstr(signature)
+            f.put_sshstr(fsig.tobytes())
+        elif isinstance(private_key, ec.EllipticCurvePrivateKey):
+            hash_alg = _get_ec_hash_alg(private_key.curve)
+            signature = private_key.sign(f.tobytes(), ec.ECDSA(hash_alg))
+            r, s = asym_utils.decode_dss_signature(signature)
+            fsig = _FragList()
+            fsig.put_sshstr(ca_type)
+            fsigblob = _FragList()
+            fsigblob.put_mpint(r)
+            fsigblob.put_mpint(s)
+            fsig.put_sshstr(fsigblob.tobytes())
+            f.put_sshstr(fsig.tobytes())
+
+        else:
+            assert isinstance(private_key, rsa.RSAPrivateKey)
+            # Just like Golang, we're going to use SHA512 for RSA
+            # https://cs.opensource.google/go/x/crypto/+/refs/tags/
+            # v0.4.0:ssh/certs.go;l=445
+            # RFC 8332 defines SHA256 and 512 as options
+            fsig = _FragList()
+            fsig.put_sshstr(_SSH_RSA_SHA512)
+            signature = private_key.sign(
+                f.tobytes(), padding.PKCS1v15(), hashes.SHA512()
+            )
+            fsig.put_sshstr(signature)
+            f.put_sshstr(fsig.tobytes())
+
+        cert_data = binascii.b2a_base64(f.tobytes()).strip()
+        # load_ssh_public_identity returns a union, but this is
+        # guaranteed to be an SSHCertificate, so we cast to make
+        # mypy happy.
+        return typing.cast(
+            SSHCertificate,
+            load_ssh_public_identity(b"".join([cert_prefix, b" ", cert_data])),
+        )