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|
"""
TLS and STARTTLS handling.
"""
import copy
import ssl
import pytest
from aiosmtplib import (
SMTP,
SMTPConnectError,
SMTPException,
SMTPResponseException,
SMTPServerDisconnected,
SMTPStatus,
)
from .smtpd import (
mock_response_ehlo_minimal,
mock_response_tls_not_available,
mock_response_tls_ready_disconnect,
mock_response_unrecognized_command,
)
@pytest.mark.smtpd_options(tls=True)
async def test_tls_connection(smtp_client: SMTP) -> None:
"""
Use an explicit connect/quit here, as other tests use the context manager.
"""
await smtp_client.connect(use_tls=True)
assert smtp_client.is_connected
await smtp_client.quit()
assert not smtp_client.is_connected
@pytest.mark.smtpd_options(tls=False)
async def test_starttls(smtp_client: SMTP) -> None:
async with smtp_client:
response = await smtp_client.starttls()
assert response.code == SMTPStatus.ready
# Make sure our state has been cleared
assert not smtp_client.esmtp_extensions
assert not smtp_client.supported_auth_methods
assert not smtp_client.supports_esmtp
# Make sure our connection was actually upgraded. ssl protocol transport is
# private in UVloop, so just check the class name.
assert "SSL" in type(smtp_client.transport).__name__
response = await smtp_client.ehlo()
assert response.code == SMTPStatus.completed
async def test_starttls_init_kwarg(
hostname: str, smtpd_server_port: int, client_tls_context: ssl.SSLContext
) -> None:
smtp_client = SMTP(
hostname=hostname,
port=smtpd_server_port,
start_tls=True,
tls_context=client_tls_context,
timeout=1.0,
)
async with smtp_client:
# Make sure our connection was actually upgraded. ssl protocol transport is
# private in UVloop, so just check the class name.
assert "SSL" in type(smtp_client.transport).__name__
@pytest.mark.smtpd_options(tls=False)
async def test_starttls_connect_kwarg(smtp_client: SMTP) -> None:
await smtp_client.connect(start_tls=True)
# Make sure our connection was actually upgraded. ssl protocol transport is
# private in UVloop, so just check the class name.
assert "SSL" in type(smtp_client.transport).__name__
await smtp_client.quit()
async def test_starttls_auto(
hostname: str, smtpd_server_port: int, client_tls_context: ssl.SSLContext
) -> None:
smtp_client = SMTP(
hostname=hostname,
port=smtpd_server_port,
start_tls=None,
tls_context=client_tls_context,
timeout=1.0,
)
async with smtp_client:
# Make sure our connection was actually upgraded. ssl protocol transport is
# private in UVloop, so just check the class name.
assert "SSL" in type(smtp_client.transport).__name__
async def test_starttls_auto_connect_kwarg(
hostname: str,
smtpd_server_port: int,
client_tls_context: ssl.SSLContext,
) -> None:
smtp_client = SMTP(
hostname=hostname,
port=smtpd_server_port,
start_tls=False,
tls_context=client_tls_context,
timeout=1.0,
)
await smtp_client.connect(start_tls=None)
# Make sure our connection was actually upgraded. ssl protocol transport is
# private in UVloop, so just check the class name.
assert "SSL" in type(smtp_client.transport).__name__
await smtp_client.quit()
@pytest.mark.smtp_client_options(start_tls=None)
@pytest.mark.smtpd_options(tls=False)
@pytest.mark.smtpd_mocks(smtp_EHLO=mock_response_ehlo_minimal)
async def test_starttls_auto_connect_not_supported(smtp_client: SMTP) -> None:
async with smtp_client:
await smtp_client.ehlo()
# Make sure our connection was nul upgraded. ssl protocol transport is
# private in UVloop, so just check the class name.
assert "SSL" not in type(smtp_client.transport).__name__
@pytest.mark.smtpd_options(tls=False)
async def test_starttls_with_explicit_server_hostname(
smtp_client: SMTP,
hostname: str,
) -> None:
async with smtp_client:
await smtp_client.ehlo()
await smtp_client.starttls(server_hostname=hostname)
@pytest.mark.smtpd_options(tls=False)
@pytest.mark.smtpd_mocks(smtp_EHLO=mock_response_ehlo_minimal)
async def test_starttls_not_supported(smtp_client: SMTP) -> None:
async with smtp_client:
await smtp_client.ehlo()
with pytest.raises(SMTPException, match="STARTTLS extension not supported"):
await smtp_client.starttls()
@pytest.mark.smtpd_options(tls=False)
@pytest.mark.smtpd_mocks(smtp_STARTTLS=mock_response_tls_not_available)
async def test_starttls_advertised_but_not_supported(smtp_client: SMTP) -> None:
async with smtp_client:
await smtp_client.ehlo()
with pytest.raises(SMTPException):
await smtp_client.starttls()
@pytest.mark.smtpd_options(tls=False)
@pytest.mark.smtpd_mocks(smtp_STARTTLS=mock_response_tls_ready_disconnect)
async def test_starttls_disconnect_before_upgrade(smtp_client: SMTP) -> None:
async with smtp_client:
with pytest.raises(SMTPServerDisconnected):
await smtp_client.starttls()
@pytest.mark.smtpd_options(tls=False)
@pytest.mark.smtpd_mocks(smtp_STARTTLS=mock_response_unrecognized_command)
async def test_starttls_invalid_responses(smtp_client: SMTP) -> None:
async with smtp_client:
await smtp_client.ehlo()
old_extensions = copy.copy(smtp_client.esmtp_extensions)
with pytest.raises(SMTPResponseException) as exception_info:
await smtp_client.starttls()
assert exception_info.value.code == SMTPStatus.unrecognized_command
# Make sure our state has been _not_ been cleared
assert smtp_client.esmtp_extensions == old_extensions
assert smtp_client.supports_esmtp is True
# Make sure our connection was not upgraded. ssl protocol transport is
# private in UVloop, so just check the class name.
assert "SSL" not in type(smtp_client.transport).__name__
@pytest.mark.smtpd_options(tls=False)
async def test_starttls_with_client_cert(
hostname: str,
smtpd_server_port: int,
ca_cert_path: str,
valid_cert_path: str,
valid_key_path: str,
) -> None:
smtp_client = SMTP(
hostname=hostname, port=smtpd_server_port, start_tls=False, timeout=1.0
)
async with smtp_client:
response = await smtp_client.starttls(
client_cert=valid_cert_path,
client_key=valid_key_path,
cert_bundle=ca_cert_path,
)
assert response.code == SMTPStatus.ready
assert smtp_client.client_cert == valid_cert_path
assert smtp_client.client_key == valid_key_path
assert smtp_client.cert_bundle == ca_cert_path
@pytest.mark.smtpd_options(tls=False)
async def test_starttls_with_invalid_client_cert(
hostname: str,
smtpd_server_port: int,
invalid_cert_path: str,
invalid_key_path: str,
) -> None:
smtp_client = SMTP(
hostname=hostname, port=smtpd_server_port, start_tls=False, timeout=1.0
)
async with smtp_client:
with pytest.raises(ssl.SSLError):
await smtp_client.starttls(
client_cert=invalid_cert_path,
client_key=invalid_key_path,
cert_bundle=invalid_cert_path,
)
@pytest.mark.smtpd_options(tls=False)
async def test_starttls_with_invalid_client_cert_no_validate(
hostname: str,
smtpd_server_port: int,
invalid_cert_path: str,
invalid_key_path: str,
) -> None:
smtp_client = SMTP(
hostname=hostname, port=smtpd_server_port, start_tls=False, timeout=1.0
)
async with smtp_client:
response = await smtp_client.starttls(
client_cert=invalid_cert_path,
client_key=invalid_key_path,
cert_bundle=invalid_cert_path,
validate_certs=False,
timeout=1.0,
)
assert response.code == SMTPStatus.ready
assert smtp_client.client_cert == invalid_cert_path
assert smtp_client.client_key == invalid_key_path
assert smtp_client.cert_bundle == invalid_cert_path
@pytest.mark.smtpd_options(tls=False)
async def test_starttls_cert_error(
hostname: str,
smtpd_server_port: int,
unknown_client_tls_context: ssl.SSLContext,
) -> None:
smtp_client = SMTP(
hostname=hostname,
port=smtpd_server_port,
start_tls=False,
tls_context=unknown_client_tls_context,
timeout=1.0,
)
async with smtp_client:
with pytest.raises(ssl.SSLError):
await smtp_client.starttls()
@pytest.mark.smtpd_options(tls=False)
async def test_starttls_already_upgraded_error(
hostname: str,
smtpd_server_port: int,
client_tls_context: ssl.SSLContext,
) -> None:
smtp_client = SMTP(
hostname=hostname,
port=smtpd_server_port,
tls_context=client_tls_context,
timeout=1.0,
)
async with smtp_client:
with pytest.raises(SMTPException, match="Connection already using TLS"):
await smtp_client.starttls()
@pytest.mark.smtpd_options(tls=False)
async def test_starttls_cert_no_validate(hostname: str, smtpd_server_port: int) -> None:
smtp_client = SMTP(
hostname=hostname,
port=smtpd_server_port,
start_tls=False,
validate_certs=False,
timeout=1.0,
)
async with smtp_client:
response = await smtp_client.starttls()
assert response.code == SMTPStatus.ready
@pytest.mark.smtpd_options(tls=True)
@pytest.mark.smtp_client_options(use_tls=True)
async def test_tls_get_transport_info(
smtp_client: SMTP, smtpd_server_port: int
) -> None:
async with smtp_client:
compression = smtp_client.get_transport_info("compression")
assert compression is None # Compression is not used here
peername = smtp_client.get_transport_info("peername")
assert peername[0] in ("127.0.0.1", "::1") # IP v4 and 6
assert peername[1] == smtpd_server_port
sock = smtp_client.get_transport_info("socket")
assert sock is not None
sockname = smtp_client.get_transport_info("sockname")
assert sockname is not None
cipher = smtp_client.get_transport_info("cipher")
assert cipher is not None
peercert = smtp_client.get_transport_info("peercert")
assert peercert is not None
sslcontext = smtp_client.get_transport_info("sslcontext")
assert sslcontext is not None
sslobj = smtp_client.get_transport_info("ssl_object")
assert sslobj is not None
@pytest.mark.smtpd_options(tls=False)
async def test_tls_smtp_connect_to_non_tls_server(
smtp_client: SMTP,
smtpd_server_port: int,
) -> None:
with pytest.raises(SMTPConnectError):
await smtp_client.connect(use_tls=True, port=smtpd_server_port)
assert not smtp_client.is_connected
@pytest.mark.smtpd_options(tls=True)
async def test_tls_connection_with_existing_sslcontext(
smtp_client: SMTP,
client_tls_context: ssl.SSLContext,
) -> None:
await smtp_client.connect(use_tls=True, tls_context=client_tls_context)
assert smtp_client.is_connected
assert smtp_client.tls_context is client_tls_context
await smtp_client.quit()
assert not smtp_client.is_connected
@pytest.mark.smtpd_options(tls=True)
async def test_tls_connection_with_client_cert(
hostname: str,
smtpd_server_port: int,
ca_cert_path: str,
valid_cert_path: str,
valid_key_path: str,
) -> None:
smtp_client = SMTP(
hostname=hostname, port=smtpd_server_port, use_tls=True, timeout=1.0
)
await smtp_client.connect(
hostname=hostname,
client_cert=valid_cert_path,
client_key=valid_key_path,
cert_bundle=ca_cert_path,
)
assert smtp_client.is_connected
await smtp_client.quit()
assert not smtp_client.is_connected
@pytest.mark.smtpd_options(tls=True)
async def test_tls_connection_with_cert_error(
hostname: str,
smtpd_server_port: int,
) -> None:
smtp_client = SMTP(
hostname=hostname, port=smtpd_server_port, use_tls=True, timeout=1.0
)
with pytest.raises(SMTPConnectError) as exception_info:
await smtp_client.connect()
assert "CERTIFICATE" in str(exception_info.value).upper()
async def test_starttls_when_disconnected() -> None:
client = SMTP(timeout=1.0)
with pytest.raises(SMTPServerDisconnected):
await client.starttls()
|
