"""
Module for using pyOpenSSL as a TLS backend. This module was relevant before
the standard library ``ssl`` module supported SNI, but now that we've dropped
support for Python 2.7 all relevant Python versions support SNI so
**this module is no longer recommended**.

This needs the following packages installed:

* `pyOpenSSL`_ (tested with 19.0.0)
* `cryptography`_ (minimum 2.3, from pyopenssl)
* `idna`_ (minimum 2.1, from cryptography)

However, pyOpenSSL depends on cryptography, so while we use all three directly here we
end up having relatively few packages required.

You can install them with the following command:

.. code-block:: bash

    $ python -m pip install pyopenssl cryptography idna

To activate certificate checking, call
:func:`~urllib3.contrib.pyopenssl.inject_into_urllib3` from your Python code
before you begin making HTTP requests. This can be done in a ``sitecustomize``
module, or at any other time before your application begins using ``urllib3``,
like this:

.. code-block:: python

    try:
        import pip._vendor.urllib3.contrib.pyopenssl as pyopenssl
        pyopenssl.inject_into_urllib3()
    except ImportError:
        pass

.. _pyopenssl: https://www.pyopenssl.org
.. _cryptography: https://cryptography.io
.. _idna: https://github.com/kjd/idna
"""

from __future__ import annotations

import OpenSSL.SSL  # type: ignore[import-not-found]
from cryptography import x509

try:
    from cryptography.x509 import UnsupportedExtension  # type: ignore[attr-defined]
except ImportError:
    # UnsupportedExtension is gone in cryptography >= 2.1.0
    class UnsupportedExtension(Exception):  # type: ignore[no-redef]
        pass


import logging
import ssl
import typing
from io import BytesIO
from socket import socket as socket_cls

from .. import util

if typing.TYPE_CHECKING:
    from OpenSSL.crypto import X509  # type: ignore[import-not-found]


__all__ = ["inject_into_urllib3", "extract_from_urllib3"]

# Map from urllib3 to PyOpenSSL compatible parameter-values.
_openssl_versions: dict[int, int] = {
    util.ssl_.PROTOCOL_TLS: OpenSSL.SSL.SSLv23_METHOD,  # type: ignore[attr-defined]
    util.ssl_.PROTOCOL_TLS_CLIENT: OpenSSL.SSL.SSLv23_METHOD,  # type: ignore[attr-defined]
    ssl.PROTOCOL_TLSv1: OpenSSL.SSL.TLSv1_METHOD,
}

if hasattr(ssl, "PROTOCOL_TLSv1_1") and hasattr(OpenSSL.SSL, "TLSv1_1_METHOD"):
    _openssl_versions[ssl.PROTOCOL_TLSv1_1] = OpenSSL.SSL.TLSv1_1_METHOD

if hasattr(ssl, "PROTOCOL_TLSv1_2") and hasattr(OpenSSL.SSL, "TLSv1_2_METHOD"):
    _openssl_versions[ssl.PROTOCOL_TLSv1_2] = OpenSSL.SSL.TLSv1_2_METHOD


_stdlib_to_openssl_verify = {
    ssl.CERT_NONE: OpenSSL.SSL.VERIFY_NONE,
    ssl.CERT_OPTIONAL: OpenSSL.SSL.VERIFY_PEER,
    ssl.CERT_REQUIRED: OpenSSL.SSL.VERIFY_PEER
    + OpenSSL.SSL.VERIFY_FAIL_IF_NO_PEER_CERT,
}
_openssl_to_stdlib_verify = {v: k for k, v in _stdlib_to_openssl_verify.items()}

# The SSLvX values are the most likely to be missing in the future
# but we check them all just to be sure.
_OP_NO_SSLv2_OR_SSLv3: int = getattr(OpenSSL.SSL, "OP_NO_SSLv2", 0) | getattr(
    OpenSSL.SSL, "OP_NO_SSLv3", 0
)
_OP_NO_TLSv1: int = getattr(OpenSSL.SSL, "OP_NO_TLSv1", 0)
_OP_NO_TLSv1_1: int = getattr(OpenSSL.SSL, "OP_NO_TLSv1_1", 0)
_OP_NO_TLSv1_2: int = getattr(OpenSSL.SSL, "OP_NO_TLSv1_2", 0)
_OP_NO_TLSv1_3: int = getattr(OpenSSL.SSL, "OP_NO_TLSv1_3", 0)

_openssl_to_ssl_minimum_version: dict[int, int] = {
    ssl.TLSVersion.MINIMUM_SUPPORTED: _OP_NO_SSLv2_OR_SSLv3,
    ssl.TLSVersion.TLSv1: _OP_NO_SSLv2_OR_SSLv3,
    ssl.TLSVersion.TLSv1_1: _OP_NO_SSLv2_OR_SSLv3 | _OP_NO_TLSv1,
    ssl.TLSVersion.TLSv1_2: _OP_NO_SSLv2_OR_SSLv3 | _OP_NO_TLSv1 | _OP_NO_TLSv1_1,
    ssl.TLSVersion.TLSv1_3: (
        _OP_NO_SSLv2_OR_SSLv3 | _OP_NO_TLSv1 | _OP_NO_TLSv1_1 | _OP_NO_TLSv1_2
    ),
    ssl.TLSVersion.MAXIMUM_SUPPORTED: (
        _OP_NO_SSLv2_OR_SSLv3 | _OP_NO_TLSv1 | _OP_NO_TLSv1_1 | _OP_NO_TLSv1_2
    ),
}
_openssl_to_ssl_maximum_version: dict[int, int] = {
    ssl.TLSVersion.MINIMUM_SUPPORTED: (
        _OP_NO_SSLv2_OR_SSLv3
        | _OP_NO_TLSv1
        | _OP_NO_TLSv1_1
        | _OP_NO_TLSv1_2
        | _OP_NO_TLSv1_3
    ),
    ssl.TLSVersion.TLSv1: (
        _OP_NO_SSLv2_OR_SSLv3 | _OP_NO_TLSv1_1 | _OP_NO_TLSv1_2 | _OP_NO_TLSv1_3
    ),
    ssl.TLSVersion.TLSv1_1: _OP_NO_SSLv2_OR_SSLv3 | _OP_NO_TLSv1_2 | _OP_NO_TLSv1_3,
    ssl.TLSVersion.TLSv1_2: _OP_NO_SSLv2_OR_SSLv3 | _OP_NO_TLSv1_3,
    ssl.TLSVersion.TLSv1_3: _OP_NO_SSLv2_OR_SSLv3,
    ssl.TLSVersion.MAXIMUM_SUPPORTED: _OP_NO_SSLv2_OR_SSLv3,
}

# OpenSSL will only write 16K at a time
SSL_WRITE_BLOCKSIZE = 16384

orig_util_SSLContext = util.ssl_.SSLContext


log = logging.getLogger(__name__)


def inject_into_urllib3() -> None:
    "Monkey-patch urllib3 with PyOpenSSL-backed SSL-support."

    _validate_dependencies_met()

    util.SSLContext = PyOpenSSLContext  # type: ignore[assignment]
    util.ssl_.SSLContext = PyOpenSSLContext  # type: ignore[assignment]
    util.IS_PYOPENSSL = True
    util.ssl_.IS_PYOPENSSL = True


def extract_from_urllib3() -> None:
    "Undo monkey-patching by :func:`inject_into_urllib3`."

    util.SSLContext = orig_util_SSLContext
    util.ssl_.SSLContext = orig_util_SSLContext
    util.IS_PYOPENSSL = False
    util.ssl_.IS_PYOPENSSL = False


def _validate_dependencies_met() -> None:
    """
    Verifies that PyOpenSSL's package-level dependencies have been met.
    Throws `ImportError` if they are not met.
    """
    # Method added in `cryptography==1.1`; not available in older versions
    from cryptography.x509.extensions import Extensions

    if getattr(Extensions, "get_extension_for_class", None) is None:
        raise ImportError(
            "'cryptography' module missing required functionality.  "
            "Try upgrading to v1.3.4 or newer."
        )

    # pyOpenSSL 0.14 and above use cryptography for OpenSSL bindings. The _x509
    # attribute is only present on those versions.
    from OpenSSL.crypto import X509

    x509 = X509()
    if getattr(x509, "_x509", None) is None:
        raise ImportError(
            "'pyOpenSSL' module missing required functionality. "
            "Try upgrading to v0.14 or newer."
        )


def _dnsname_to_stdlib(name: str) -> str | None:
    """
    Converts a dNSName SubjectAlternativeName field to the form used by the
    standard library on the given Python version.

    Cryptography produces a dNSName as a unicode string that was idna-decoded
    from ASCII bytes. We need to idna-encode that string to get it back, and
    then on Python 3 we also need to convert to unicode via UTF-8 (the stdlib
    uses PyUnicode_FromStringAndSize on it, which decodes via UTF-8).

    If the name cannot be idna-encoded then we return None signalling that
    the name given should be skipped.
    """

    def idna_encode(name: str) -> bytes | None:
        """
        Borrowed wholesale from the Python Cryptography Project. It turns out
        that we can't just safely call `idna.encode`: it can explode for
        wildcard names. This avoids that problem.
        """
        from pip._vendor import idna

        try:
            for prefix in ["*.", "."]:
                if name.startswith(prefix):
                    name = name[len(prefix) :]
                    return prefix.encode("ascii") + idna.encode(name)
            return idna.encode(name)
        except idna.core.IDNAError:
            return None

    # Don't send IPv6 addresses through the IDNA encoder.
    if ":" in name:
        return name

    encoded_name = idna_encode(name)
    if encoded_name is None:
        return None
    return encoded_name.decode("utf-8")


def get_subj_alt_name(peer_cert: X509) -> list[tuple[str, str]]:
    """
    Given an PyOpenSSL certificate, provides all the subject alternative names.
    """
    cert = peer_cert.to_cryptography()

    # We want to find the SAN extension. Ask Cryptography to locate it (it's
    # faster than looping in Python)
    try:
        ext = cert.extensions.get_extension_for_class(x509.SubjectAlternativeName).value
    except x509.ExtensionNotFound:
        # No such extension, return the empty list.
        return []
    except (
        x509.DuplicateExtension,
        UnsupportedExtension,
        x509.UnsupportedGeneralNameType,
        UnicodeError,
    ) as e:
        # A problem has been found with the quality of the certificate. Assume
        # no SAN field is present.
        log.warning(
            "A problem was encountered with the certificate that prevented "
            "urllib3 from finding the SubjectAlternativeName field. This can "
            "affect certificate validation. The error was %s",
            e,
        )
        return []

    # We want to return dNSName and iPAddress fields. We need to cast the IPs
    # back to strings because the match_hostname function wants them as
    # strings.
    # Sadly the DNS names need to be idna encoded and then, on Python 3, UTF-8
    # decoded. This is pretty frustrating, but that's what the standard library
    # does with certificates, and so we need to attempt to do the same.
    # We also want to skip over names which cannot be idna encoded.
    names = [
        ("DNS", name)
        for name in map(_dnsname_to_stdlib, ext.get_values_for_type(x509.DNSName))
        if name is not None
    ]
    names.extend(
        ("IP Address", str(name)) for name in ext.get_values_for_type(x509.IPAddress)
    )

    return names


class WrappedSocket:
    """API-compatibility wrapper for Python OpenSSL's Connection-class."""

    def __init__(
        self,
        connection: OpenSSL.SSL.Connection,
        socket: socket_cls,
        suppress_ragged_eofs: bool = True,
    ) -> None:
        self.connection = connection
        self.socket = socket
        self.suppress_ragged_eofs = suppress_ragged_eofs
        self._io_refs = 0
        self._closed = False

    def fileno(self) -> int:
        return self.socket.fileno()

    # Copy-pasted from Python 3.5 source code
    def _decref_socketios(self) -> None:
        if self._io_refs > 0:
            self._io_refs -= 1
        if self._closed:
            self.close()

    def recv(self, *args: typing.Any, **kwargs: typing.Any) -> bytes:
        try:
            data = self.connection.recv(*args, **kwargs)
        except OpenSSL.SSL.SysCallError as e:
            if self.suppress_ragged_eofs and e.args == (-1, "Unexpected EOF"):
                return b""
            else:
                raise OSError(e.args[0], str(e)) from e
        except OpenSSL.SSL.ZeroReturnError:
            if self.connection.get_shutdown() == OpenSSL.SSL.RECEIVED_SHUTDOWN:
                return b""
            else:
                raise
        except OpenSSL.SSL.WantReadError as e:
            if not util.wait_for_read(self.socket, self.socket.gettimeout()):
                raise TimeoutError("The read operation timed out") from e
            else:
                return self.recv(*args, **kwargs)

        # TLS 1.3 post-handshake authentication
        except OpenSSL.SSL.Error as e:
            raise ssl.SSLError(f"read error: {e!r}") from e
        else:
            return data  # type: ignore[no-any-return]

    def recv_into(self, *args: typing.Any, **kwargs: typing.Any) -> int:
        try:
            return self.connection.recv_into(*args, **kwargs)  # type: ignore[no-any-return]
        except OpenSSL.SSL.SysCallError as e:
            if self.suppress_ragged_eofs and e.args == (-1, "Unexpected EOF"):
                return 0
            else:
                raise OSError(e.args[0], str(e)) from e
        except OpenSSL.SSL.ZeroReturnError:
            if self.connection.get_shutdown() == OpenSSL.SSL.RECEIVED_SHUTDOWN:
                return 0
            else:
                raise
        except OpenSSL.SSL.WantReadError as e:
            if not util.wait_for_read(self.socket, self.socket.gettimeout()):
                raise TimeoutError("The read operation timed out") from e
            else:
                return self.recv_into(*args, **kwargs)

        # TLS 1.3 post-handshake authentication
        except OpenSSL.SSL.Error as e:
            raise ssl.SSLError(f"read error: {e!r}") from e

    def settimeout(self, timeout: float) -> None:
        return self.socket.settimeout(timeout)

    def _send_until_done(self, data: bytes) -> int:
        while True:
            try:
                return self.connection.send(data)  # type: ignore[no-any-return]
            except OpenSSL.SSL.WantWriteError as e:
                if not util.wait_for_write(self.socket, self.socket.gettimeout()):
                    raise TimeoutError() from e
                continue
            except OpenSSL.SSL.SysCallError as e:
                raise OSError(e.args[0], str(e)) from e

    def sendall(self, data: bytes) -> None:
        total_sent = 0
        while total_sent < len(data):
            sent = self._send_until_done(
                data[total_sent : total_sent + SSL_WRITE_BLOCKSIZE]
            )
            total_sent += sent

    def shutdown(self, how: int) -> None:
        try:
            self.connection.shutdown()
        except OpenSSL.SSL.Error as e:
            raise ssl.SSLError(f"shutdown error: {e!r}") from e

    def close(self) -> None:
        self._closed = True
        if self._io_refs <= 0:
            self._real_close()

    def _real_close(self) -> None:
        try:
            return self.connection.close()  # type: ignore[no-any-return]
        except OpenSSL.SSL.Error:
            return

    def getpeercert(
        self, binary_form: bool = False
    ) -> dict[str, list[typing.Any]] | None:
        x509 = self.connection.get_peer_certificate()

        if not x509:
            return x509  # type: ignore[no-any-return]

        if binary_form:
            return OpenSSL.crypto.dump_certificate(OpenSSL.crypto.FILETYPE_ASN1, x509)  # type: ignore[no-any-return]

        return {
            "subject": ((("commonName", x509.get_subject().CN),),),  # type: ignore[dict-item]
            "subjectAltName": get_subj_alt_name(x509),
        }

    def version(self) -> str:
        return self.connection.get_protocol_version_name()  # type: ignore[no-any-return]

    def selected_alpn_protocol(self) -> str | None:
        alpn_proto = self.connection.get_alpn_proto_negotiated()
        return alpn_proto.decode() if alpn_proto else None


WrappedSocket.makefile = socket_cls.makefile  # type: ignore[attr-defined]


class PyOpenSSLContext:
    """
    I am a wrapper class for the PyOpenSSL ``Context`` object. I am responsible
    for translating the interface of the standard library ``SSLContext`` object
    to calls into PyOpenSSL.
    """

    def __init__(self, protocol: int) -> None:
        self.protocol = _openssl_versions[protocol]
        self._ctx = OpenSSL.SSL.Context(self.protocol)
        self._options = 0
        self.check_hostname = False
        self._minimum_version: int = ssl.TLSVersion.MINIMUM_SUPPORTED
        self._maximum_version: int = ssl.TLSVersion.MAXIMUM_SUPPORTED
        self._verify_flags: int = ssl.VERIFY_X509_TRUSTED_FIRST

    @property
    def options(self) -> int:
        return self._options

    @options.setter
    def options(self, value: int) -> None:
        self._options = value
        self._set_ctx_options()

    @property
    def verify_flags(self) -> int:
        return self._verify_flags

    @verify_flags.setter
    def verify_flags(self, value: int) -> None:
        self._verify_flags = value
        self._ctx.get_cert_store().set_flags(self._verify_flags)

    @property
    def verify_mode(self) -> int:
        return _openssl_to_stdlib_verify[self._ctx.get_verify_mode()]

    @verify_mode.setter
    def verify_mode(self, value: ssl.VerifyMode) -> None:
        self._ctx.set_verify(_stdlib_to_openssl_verify[value], _verify_callback)

    def set_default_verify_paths(self) -> None:
        self._ctx.set_default_verify_paths()

    def set_ciphers(self, ciphers: bytes | str) -> None:
        if isinstance(ciphers, str):
            ciphers = ciphers.encode("utf-8")
        self._ctx.set_cipher_list(ciphers)

    def load_verify_locations(
        self,
        cafile: str | None = None,
        capath: str | None = None,
        cadata: bytes | None = None,
    ) -> None:
        if cafile is not None:
            cafile = cafile.encode("utf-8")  # type: ignore[assignment]
        if capath is not None:
            capath = capath.encode("utf-8")  # type: ignore[assignment]
        try:
            self._ctx.load_verify_locations(cafile, capath)
            if cadata is not None:
                self._ctx.load_verify_locations(BytesIO(cadata))
        except OpenSSL.SSL.Error as e:
            raise ssl.SSLError(f"unable to load trusted certificates: {e!r}") from e

    def load_cert_chain(
        self,
        certfile: str,
        keyfile: str | None = None,
        password: str | None = None,
    ) -> None:
        try:
            self._ctx.use_certificate_chain_file(certfile)
            if password is not None:
                if not isinstance(password, bytes):
                    password = password.encode("utf-8")  # type: ignore[assignment]
                self._ctx.set_passwd_cb(lambda *_: password)
            self._ctx.use_privatekey_file(keyfile or certfile)
        except OpenSSL.SSL.Error as e:
            raise ssl.SSLError(f"Unable to load certificate chain: {e!r}") from e

    def set_alpn_protocols(self, protocols: list[bytes | str]) -> None:
        protocols = [util.util.to_bytes(p, "ascii") for p in protocols]
        return self._ctx.set_alpn_protos(protocols)  # type: ignore[no-any-return]

    def wrap_socket(
        self,
        sock: socket_cls,
        server_side: bool = False,
        do_handshake_on_connect: bool = True,
        suppress_ragged_eofs: bool = True,
        server_hostname: bytes | str | None = None,
    ) -> WrappedSocket:
        cnx = OpenSSL.SSL.Connection(self._ctx, sock)

        # If server_hostname is an IP, don't use it for SNI, per RFC6066 Section 3
        if server_hostname and not util.ssl_.is_ipaddress(server_hostname):
            if isinstance(server_hostname, str):
                server_hostname = server_hostname.encode("utf-8")
            cnx.set_tlsext_host_name(server_hostname)

        cnx.set_connect_state()

        while True:
            try:
                cnx.do_handshake()
            except OpenSSL.SSL.WantReadError as e:
                if not util.wait_for_read(sock, sock.gettimeout()):
                    raise TimeoutError("select timed out") from e
                continue
            except OpenSSL.SSL.Error as e:
                raise ssl.SSLError(f"bad handshake: {e!r}") from e
            break

        return WrappedSocket(cnx, sock)

    def _set_ctx_options(self) -> None:
        self._ctx.set_options(
            self._options
            | _openssl_to_ssl_minimum_version[self._minimum_version]
            | _openssl_to_ssl_maximum_version[self._maximum_version]
        )

    @property
    def minimum_version(self) -> int:
        return self._minimum_version

    @minimum_version.setter
    def minimum_version(self, minimum_version: int) -> None:
        self._minimum_version = minimum_version
        self._set_ctx_options()

    @property
    def maximum_version(self) -> int:
        return self._maximum_version

    @maximum_version.setter
    def maximum_version(self, maximum_version: int) -> None:
        self._maximum_version = maximum_version
        self._set_ctx_options()


def _verify_callback(
    cnx: OpenSSL.SSL.Connection,
    x509: X509,
    err_no: int,
    err_depth: int,
    return_code: int,
) -> bool:
    return err_no == 0
