Files
DECNET/tests/service_testing/test_smtp.py
anti 291b78c1d0 feat(smtp): extract body_simhash + base64-bytes + html-smuggling + per-attachment macro/encrypted
Heavyweight Layer-2 extractors land alongside the cheap projections
shipped in commit e9324aca, so the EmailLifter R0042 / R0046 (macros
/ password / smuggling lanes) / R0048 fire from the bus payload
without the lifter having to reach back to disk.

Extractors:
* body_simhash — inlined 64-bit Charikar simhash (md5-keyed,
  frequency-weighted) over word tokens of the union of text/* body
  parts. Inlined rather than pulling the `simhash` PyPI dep, which
  transitively brings numpy ~50 MB into a slim decky container; the
  algorithm is ~15 lines and identical in extraction quality.
* body_base64_bytes — largest decoded base64 chunk's byte count,
  scanning text body parts with the same `_BASE64_RE` the lifter's
  `_p_encoded_payload` fallback uses. R0048 fires from this scalar
  alone; the lifter's body_text fallback becomes dead in normal
  operation.
* attachment_macro_indicator — stdlib zipfile sniff for
  `vbaProject.bin` inside OOXML containers. Catches modern .docm /
  .xlsm / .pptm and macro-injected .docx; legacy .xls (CFBF) is a
  follow-up.
* attachment_encrypted — flag_bits & 0x01 on any ZIP / OOXML entry's
  central directory; magic-byte match for 7z / RAR / CFBF (encrypted
  Office wrap).
* html_smuggling — structural lxml parse first: fires when an `<a
  download>` element coexists with a `<script>` referencing
  `Blob` / `Uint8Array` / `URL.createObjectURL`. Regex pair-check
  fallback on lxml parse failure (real-world phish HTML is often
  malformed). Cuts the FP rate that pure-regex would produce on
  legitimate "click to download" links.

Add `python3-lxml` (~5 MB Debian package, C-extension, no transitive
Python deps) to the SMTP decky's Dockerfile. simhash stays inline.
Per the dependency rule: lxml earns its weight by cutting R0046's
OR-combined FP rate; a heavier macro-detection lib (oletools ~5 MB
pure-python with msoffcrypto) would not measurably improve the
boolean signal we need, so stdlib stays for that lane.
2026-05-02 19:08:37 -04:00

963 lines
36 KiB
Python

"""
Tests for decnet/templates/smtp/server.py
Exercises both modes:
- credential-harvester (SMTP_OPEN_RELAY=0, default)
- open relay (SMTP_OPEN_RELAY=1)
Uses asyncio transport/protocol directly — no network socket needed.
"""
import base64
import importlib.util
import sys
from types import ModuleType
from unittest.mock import MagicMock, patch
import pytest
# ── Helpers ───────────────────────────────────────────────────────────────────
def _make_fake_syslog_bridge() -> ModuleType:
"""Return a stub syslog_bridge module that does nothing."""
mod = ModuleType("syslog_bridge")
mod.syslog_line = MagicMock(return_value="")
mod.write_syslog_file = MagicMock()
mod.forward_syslog = MagicMock()
mod.SEVERITY_WARNING = 4
mod.SEVERITY_INFO = 6
mod.encode_secret = MagicMock(return_value={"secret_printable": "", "secret_b64": ""})
mod.classify_authorization = MagicMock(return_value=None)
return mod
def _load_smtp(open_relay: bool):
"""Import smtp server module with desired OPEN_RELAY value.
Injects a stub syslog_bridge into sys.modules so the template can import
it without needing the real file on sys.path.
"""
env = {
"SMTP_OPEN_RELAY": "1" if open_relay else "0",
"NODE_NAME": "testhost",
# Force deterministic RCPT acceptance in tests; relay filtering is
# covered in its own dedicated test class below.
"SMTP_RCPT_DROP_RATE": "0",
}
for key in ("smtp_server", "syslog_bridge", "instance_seed"):
sys.modules.pop(key, None)
sys.modules["syslog_bridge"] = _make_fake_syslog_bridge()
spec = importlib.util.spec_from_file_location("smtp_server", "decnet/templates/smtp/server.py")
mod = importlib.util.module_from_spec(spec)
with patch.dict("os.environ", env, clear=False):
from .conftest import load_real_instance_seed
sys.modules["instance_seed"] = load_real_instance_seed()
spec.loader.exec_module(mod)
return mod
def _make_protocol(mod):
"""Return a (protocol, transport, written) triple. Banner is already discarded."""
proto = mod.SMTPProtocol()
transport = MagicMock()
written: list[bytes] = []
transport.write.side_effect = written.append
proto.connection_made(transport)
written.clear()
return proto, transport, written
def _send(proto, *lines: str) -> None:
"""Feed CRLF-terminated lines to the protocol."""
for line in lines:
proto.data_received((line + "\r\n").encode())
def _replies(written: list[bytes]) -> list[str]:
"""Flatten written bytes into a list of non-empty response lines."""
result = []
for chunk in written:
for line in chunk.decode().split("\r\n"):
if line:
result.append(line)
return result
# ── Fixtures ──────────────────────────────────────────────────────────────────
@pytest.fixture
def relay_mod():
return _load_smtp(open_relay=True)
@pytest.fixture
def harvester_mod():
return _load_smtp(open_relay=False)
# ── Banner ────────────────────────────────────────────────────────────────────
def test_banner_is_220(relay_mod):
proto, transport, written = _make_protocol(relay_mod)
# written was cleared — re-trigger banner check via a fresh instance
proto2 = relay_mod.SMTPProtocol()
t2 = MagicMock()
w2: list[bytes] = []
t2.write.side_effect = w2.append
proto2.connection_made(t2)
banner = b"".join(w2).decode()
assert banner.startswith("220")
assert "ESMTP" in banner
# ── EHLO ──────────────────────────────────────────────────────────────────────
def test_ehlo_returns_250_multiline(relay_mod):
proto, _, written = _make_protocol(relay_mod)
_send(proto, "EHLO attacker.com")
combined = b"".join(written).decode()
assert "250" in combined
assert "AUTH" in combined
assert "PIPELINING" in combined
def test_ehlo_empty_domain_rejected(relay_mod):
proto, _, written = _make_protocol(relay_mod)
_send(proto, "EHLO")
replies = _replies(written)
assert any(r.startswith("501") for r in replies)
def test_helo_empty_domain_rejected(relay_mod):
proto, _, written = _make_protocol(relay_mod)
_send(proto, "HELO")
replies = _replies(written)
assert any(r.startswith("501") for r in replies)
# ── OPEN RELAY MODE ───────────────────────────────────────────────────────────
class TestOpenRelay:
@staticmethod
def _session(relay_mod, *lines):
proto, _, written = _make_protocol(relay_mod)
_send(proto, *lines)
return _replies(written)
def test_auth_plain_accepted(self, relay_mod):
creds = base64.b64encode(b"\x00admin\x00password").decode()
replies = self._session(relay_mod, f"AUTH PLAIN {creds}")
assert any(r.startswith("235") for r in replies)
def test_auth_login_multistep_accepted(self, relay_mod):
proto, _, written = _make_protocol(relay_mod)
_send(proto, "AUTH LOGIN")
_send(proto, base64.b64encode(b"admin").decode())
_send(proto, base64.b64encode(b"password").decode())
replies = _replies(written)
assert any(r.startswith("235") for r in replies)
def test_rcpt_to_any_domain_accepted(self, relay_mod):
replies = self._session(
relay_mod,
"EHLO x.com",
"MAIL FROM:<spam@evil.com>",
"RCPT TO:<victim@anydomain.com>",
)
assert any(r.startswith("250 2.1.5") for r in replies)
def test_full_relay_flow(self, relay_mod):
replies = self._session(
relay_mod,
"EHLO attacker.com",
"MAIL FROM:<hacker@evil.com>",
"RCPT TO:<admin@target.com>",
"DATA",
"Subject: hello",
"",
"Body line 1",
"Body line 2",
".",
"QUIT",
)
assert any(r.startswith("354") for r in replies), "Expected 354 after DATA"
assert any("queued as" in r for r in replies), "Expected queued-as ID"
assert any(r.startswith("221") for r in replies), "Expected 221 on QUIT"
def test_multi_recipient(self, relay_mod):
replies = self._session(
relay_mod,
"EHLO x.com",
"MAIL FROM:<a@b.com>",
"RCPT TO:<c@d.com>",
"RCPT TO:<e@f.com>",
"RCPT TO:<g@h.com>",
"DATA",
"Subject: spam",
"",
"hello",
".",
)
assert len([r for r in replies if r.startswith("250 2.1.5")]) == 3
def test_dot_stuffing_stripped(self, relay_mod):
"""Leading dot on a body line must be stripped per RFC 5321."""
proto, _, written = _make_protocol(relay_mod)
_send(proto,
"EHLO x.com",
"MAIL FROM:<a@b.com>",
"RCPT TO:<c@d.com>",
"DATA",
"..real dot line",
"normal line",
".",
)
replies = _replies(written)
assert any("queued as" in r for r in replies)
def test_data_rejected_without_rcpt(self, relay_mod):
replies = self._session(relay_mod, "EHLO x.com", "MAIL FROM:<a@b.com>", "DATA")
assert any(r.startswith("503") for r in replies)
def test_rset_clears_transaction_state(self, relay_mod):
proto, _, _ = _make_protocol(relay_mod)
_send(proto, "EHLO x.com", "MAIL FROM:<a@b.com>", "RCPT TO:<c@d.com>", "RSET")
assert proto._mail_from == ""
assert proto._rcpt_to == []
assert proto._in_data is False
def test_second_send_after_rset(self, relay_mod):
"""A new transaction started after RSET must complete successfully."""
replies = self._session(
relay_mod,
"EHLO x.com",
"MAIL FROM:<a@b.com>",
"RCPT TO:<c@d.com>",
"RSET",
"MAIL FROM:<new@b.com>",
"RCPT TO:<new@d.com>",
"DATA",
"body",
".",
)
assert any("queued as" in r for r in replies)
# ── OPEN-RELAY FILTERING ─────────────────────────────────────────────────────
class TestOpenRelayFiltering:
"""Real open relays reject malformed/bogus RCPTs even when they accept
external mail — a pure tarpit is a honeypot tell."""
@staticmethod
def _session_with_env(env_extra: dict, *lines) -> list[str]:
env = {
"SMTP_OPEN_RELAY": "1",
"NODE_NAME": "testhost",
"SMTP_RCPT_DROP_RATE": "0",
**env_extra,
}
for key in ("smtp_server", "syslog_bridge", "instance_seed"):
sys.modules.pop(key, None)
sys.modules["syslog_bridge"] = _make_fake_syslog_bridge()
spec = importlib.util.spec_from_file_location(
"smtp_server", "decnet/templates/smtp/server.py"
)
mod = importlib.util.module_from_spec(spec)
with patch.dict("os.environ", env, clear=False):
from .conftest import load_real_instance_seed
sys.modules["instance_seed"] = load_real_instance_seed()
spec.loader.exec_module(mod)
proto, _, written = _make_protocol(mod)
_send(proto, *lines)
return _replies(written)
def test_malformed_rcpt_returns_501(self):
replies = self._session_with_env(
{},
"EHLO x.com",
"MAIL FROM:<a@b.com>",
"RCPT TO:<notanaddress>",
)
assert any(r.startswith("501") for r in replies)
def test_blocked_tld_returns_550(self):
replies = self._session_with_env(
{},
"EHLO x.com",
"MAIL FROM:<a@b.com>",
"RCPT TO:<admin@foo.invalid>",
)
assert any(r.startswith("550") for r in replies)
def test_always_greylist_returns_451(self):
replies = self._session_with_env(
{"SMTP_RCPT_DROP_RATE": "1.0"},
"EHLO x.com",
"MAIL FROM:<a@b.com>",
"RCPT TO:<victim@legit-domain.com>",
)
assert any(r.startswith("451") for r in replies)
# ── CREDENTIAL HARVESTER MODE ─────────────────────────────────────────────────
class TestCredentialHarvester:
@staticmethod
def _session(harvester_mod, *lines):
proto, _, written = _make_protocol(harvester_mod)
_send(proto, *lines)
return _replies(written)
def test_auth_plain_rejected_535(self, harvester_mod):
creds = base64.b64encode(b"\x00admin\x00password").decode()
replies = self._session(harvester_mod, f"AUTH PLAIN {creds}")
assert any(r.startswith("535") for r in replies)
def test_auth_rejected_connection_stays_open(self, harvester_mod):
"""After 535 the connection must stay alive — old code closed it immediately."""
proto, transport, _ = _make_protocol(harvester_mod)
creds = base64.b64encode(b"\x00admin\x00password").decode()
_send(proto, f"AUTH PLAIN {creds}")
transport.close.assert_not_called()
def test_rcpt_to_denied_554(self, harvester_mod):
replies = self._session(
harvester_mod,
"EHLO x.com",
"MAIL FROM:<a@b.com>",
"RCPT TO:<admin@target.com>",
)
assert any(r.startswith("554") for r in replies)
def test_relay_denied_blocks_data(self, harvester_mod):
"""With all RCPT TO rejected, DATA must return 503."""
replies = self._session(
harvester_mod,
"EHLO x.com",
"MAIL FROM:<a@b.com>",
"RCPT TO:<c@d.com>",
"DATA",
)
assert any(r.startswith("503") for r in replies)
def test_noop_and_quit(self, harvester_mod):
replies = self._session(harvester_mod, "NOOP", "QUIT")
assert any(r.startswith("250") for r in replies)
assert any(r.startswith("221") for r in replies)
def test_unknown_command_502(self, harvester_mod):
replies = self._session(harvester_mod, "BADCMD foo")
assert any(r.startswith("502") for r in replies)
def test_starttls_declined_454(self, harvester_mod):
replies = self._session(harvester_mod, "STARTTLS")
assert any(r.startswith("454") for r in replies)
# ── Queue ID ──────────────────────────────────────────────────────────────────
def test_rand_msg_id_format(relay_mod):
# Postfix queue IDs use a vowel-free alphabet (no aeiou, no 0/1) and
# vary in length with the current microsecond magnitude — typically
# 10-12 chars.
postfix_alphabet = set("BCDFGHJKLMNPQRSTVWXYZ23456789")
for _ in range(50):
mid = relay_mod._rand_msg_id()
assert 10 <= len(mid) <= 12
assert set(mid).issubset(postfix_alphabet)
# ── AUTH PLAIN decode ─────────────────────────────────────────────────────────
def test_decode_auth_plain_normal(relay_mod):
blob = base64.b64encode(b"\x00alice\x00s3cr3t").decode()
user, pw = relay_mod._decode_auth_plain(blob)
assert user == "alice"
assert pw == "s3cr3t"
def test_decode_auth_plain_garbage_no_raise(relay_mod):
user, pw = relay_mod._decode_auth_plain("!!!notbase64!!!")
assert isinstance(user, str)
assert isinstance(pw, str)
# ── Bare LF line endings ────────────────────────────────────────────────────
def _send_bare_lf(proto, *lines: str) -> None:
"""Feed LF-only terminated lines to the protocol (simulates telnet/nc)."""
for line in lines:
proto.data_received((line + "\n").encode())
def test_ehlo_works_with_bare_lf(relay_mod):
"""Clients sending bare LF (telnet, nc) must get EHLO responses."""
proto, _, written = _make_protocol(relay_mod)
_send_bare_lf(proto, "EHLO attacker.com")
combined = b"".join(written).decode()
assert "250" in combined
assert "AUTH" in combined
def test_full_session_with_bare_lf(relay_mod):
"""A complete relay session using bare LF line endings."""
proto, _, written = _make_protocol(relay_mod)
_send_bare_lf(
proto,
"EHLO attacker.com",
"MAIL FROM:<hacker@evil.com>",
"RCPT TO:<admin@target.com>",
"DATA",
"Subject: test",
"",
"body",
".",
"QUIT",
)
replies = _replies(written)
assert any("queued as" in r for r in replies)
assert any(r.startswith("221") for r in replies)
def test_mixed_line_endings(relay_mod):
"""A single data_received call containing a mix of CRLF and bare LF."""
proto, _, written = _make_protocol(relay_mod)
proto.data_received(b"EHLO test.com\r\nMAIL FROM:<a@b.com>\nRCPT TO:<c@d.com>\r\n")
replies = _replies(written)
assert any("250" in r for r in replies)
assert any(r.startswith("250 2.1.0") for r in replies)
assert any(r.startswith("250 2.1.5") for r in replies)
# ── AUTH PLAIN continuation (no inline credentials) ──────────────────────────
def test_auth_plain_continuation_relay(relay_mod):
"""AUTH PLAIN without inline creds should prompt then accept on next line."""
proto, _, written = _make_protocol(relay_mod)
_send(proto, "AUTH PLAIN")
replies = _replies(written)
assert any(r.startswith("334") for r in replies), "Expected 334 continuation"
written.clear()
creds = base64.b64encode(b"\x00admin\x00password").decode()
_send(proto, creds)
replies = _replies(written)
assert any(r.startswith("235") for r in replies), "Expected 235 auth success"
def test_auth_plain_continuation_harvester(harvester_mod):
"""AUTH PLAIN continuation in harvester mode should reject with 535."""
proto, _, written = _make_protocol(harvester_mod)
_send(proto, "AUTH PLAIN")
replies = _replies(written)
assert any(r.startswith("334") for r in replies)
written.clear()
creds = base64.b64encode(b"\x00admin\x00password").decode()
_send(proto, creds)
replies = _replies(written)
assert any(r.startswith("535") for r in replies)
# ── FULL-MESSAGE CAPTURE (quarantine + message_stored event) ─────────────────
def _load_smtp_with_quarantine(quarantine_dir: str, max_body_bytes: int | None = None):
"""Reload the SMTP template with a quarantine dir + optional body cap.
Same mechanics as _load_smtp but threads extra env through so the module's
capture-path code is exercised end-to-end (file write + parse).
"""
env = {
"SMTP_OPEN_RELAY": "1",
"NODE_NAME": "testhost",
"SMTP_RCPT_DROP_RATE": "0",
"SMTP_QUARANTINE_DIR": quarantine_dir,
}
if max_body_bytes is not None:
env["SMTP_MAX_BODY_BYTES"] = str(max_body_bytes)
for key in ("smtp_server", "syslog_bridge", "instance_seed"):
sys.modules.pop(key, None)
sys.modules["syslog_bridge"] = _make_fake_syslog_bridge()
spec = importlib.util.spec_from_file_location(
"smtp_server", "decnet/templates/smtp/server.py"
)
mod = importlib.util.module_from_spec(spec)
with patch.dict("os.environ", env, clear=False):
from .conftest import load_real_instance_seed
sys.modules["instance_seed"] = load_real_instance_seed()
spec.loader.exec_module(mod)
return mod
def _logged_events(mod) -> list[tuple[str, dict]]:
"""Return every (event_type, fields) tuple syslog_bridge was called with."""
calls = mod.syslog_line.call_args_list
events: list[tuple[str, dict]] = []
for call in calls:
args, kwargs = call
# syslog_line(service, hostname, event_type, severity=..., **fields)
event_type = args[2] if len(args) > 2 else kwargs.get("event_type", "")
# Strip positional service/hostname/event_type/severity when present.
fields = dict(kwargs)
fields.pop("severity", None)
events.append((event_type, fields))
return events
class TestMessageCapture:
def test_message_stored_event_written(self, tmp_path):
mod = _load_smtp_with_quarantine(str(tmp_path))
proto, _, _ = _make_protocol(mod)
_send(
proto,
"EHLO x.com",
"MAIL FROM:<spam@evil.com>",
"RCPT TO:<victim@target.com>",
"DATA",
"Subject: hello",
"From: spam@evil.com",
"",
"body line",
".",
)
events = _logged_events(mod)
stored = [f for t, f in events if t == "message_stored"]
assert len(stored) == 1, f"expected 1 message_stored event, got {events}"
rec = stored[0]
assert rec["subject"] == "hello"
assert rec["from_hdr"] == "spam@evil.com"
assert rec["mail_from"] == "<spam@evil.com>"
assert rec["rcpt_to"] == "<victim@target.com>"
assert rec["attachment_count"] == 0
# Filename matches artifact endpoint's regex.
import re as _re
assert _re.fullmatch(
r"\d{4}-\d{2}-\d{2}T\d{2}:\d{2}:\d{2}Z_[a-f0-9]{12}_[A-Za-z0-9._-]{1,255}",
rec["stored_as"],
)
def test_message_file_written_to_quarantine(self, tmp_path):
mod = _load_smtp_with_quarantine(str(tmp_path))
proto, _, _ = _make_protocol(mod)
_send(
proto,
"EHLO x.com",
"MAIL FROM:<a@b.com>",
"RCPT TO:<c@d.com>",
"DATA",
"Subject: test",
"",
"payload bytes",
".",
)
files = list(tmp_path.iterdir())
assert len(files) == 1
contents = files[0].read_bytes()
assert b"Subject: test" in contents
assert b"payload bytes" in contents
assert files[0].name.endswith(".eml")
def test_attachment_manifest_captured(self, tmp_path):
"""A multipart message with an attachment must report filename + sha256."""
import hashlib as _hashlib
mod = _load_smtp_with_quarantine(str(tmp_path))
proto, _, _ = _make_protocol(mod)
boundary = "----ABC"
payload = b"MZ\x90\x00fake-exe-bytes"
import base64 as _b64
payload_b64 = _b64.b64encode(payload).decode()
_send(
proto,
"EHLO x.com",
"MAIL FROM:<a@b.com>",
"RCPT TO:<c@d.com>",
"DATA",
"Subject: malware",
f"Content-Type: multipart/mixed; boundary={boundary}",
"MIME-Version: 1.0",
"",
f"--{boundary}",
'Content-Type: text/plain',
"",
"see attached",
f"--{boundary}",
'Content-Type: application/octet-stream; name="payload.exe"',
'Content-Disposition: attachment; filename="payload.exe"',
"Content-Transfer-Encoding: base64",
"",
payload_b64,
f"--{boundary}--",
".",
)
events = _logged_events(mod)
stored = [f for t, f in events if t == "message_stored"]
assert len(stored) == 1
rec = stored[0]
assert rec["attachment_count"] == 1
import json as _json
manifest = _json.loads(rec["attachments_json"])
assert len(manifest) == 1
assert manifest[0]["filename"] == "payload.exe"
assert manifest[0]["sha256"] == _hashlib.sha256(payload).hexdigest()
assert manifest[0]["size"] == len(payload)
def test_message_stored_carries_layer2_signals(self, tmp_path):
"""Cheap Layer 2 fields the EmailLifter consumes (R0043 / R0044 /
R0045): X-Mailer, Return-Path, Authentication-Results dkim/spf
verdicts, and URLs lifted from text body parts."""
mod = _load_smtp_with_quarantine(str(tmp_path))
proto, _, _ = _make_protocol(mod)
_send(
proto,
"EHLO x.com",
"MAIL FROM:<spoof@evil.com>",
"RCPT TO:<victim@target.com>",
"DATA",
"Subject: phish",
"From: ceo@bigcorp.com",
"Return-Path: <mailer@kit.evil>",
"X-Mailer: PHPMailer 6.0.7",
"Authentication-Results: relay.example; dkim=pass header.d=evil.com; spf=pass smtp.mailfrom=mailer@kit.evil",
"",
"Click https://xn--80ak6aa92e.example/login. and also http://safe.test/ok",
".",
)
events = _logged_events(mod)
stored = [f for t, f in events if t == "message_stored"]
assert len(stored) == 1
rec = stored[0]
assert rec["x_mailer"] == "PHPMailer 6.0.7"
assert rec["return_path"] == "<mailer@kit.evil>"
assert rec["dkim_signed"] == 1
assert rec["spf_pass"] == 1
import json as _json
urls = _json.loads(rec["urls_json"])
assert "https://xn--80ak6aa92e.example/login" in urls
assert "http://safe.test/ok" in urls
def test_message_stored_dkim_spf_default_false_when_no_auth_header(
self, tmp_path,
):
mod = _load_smtp_with_quarantine(str(tmp_path))
proto, _, _ = _make_protocol(mod)
_send(
proto,
"EHLO x.com",
"MAIL FROM:<a@b.com>",
"RCPT TO:<c@d.com>",
"DATA",
"Subject: bare",
"",
"no auth header here",
".",
)
events = _logged_events(mod)
stored = [f for t, f in events if t == "message_stored"]
rec = stored[0]
assert rec["dkim_signed"] == 0
assert rec["spf_pass"] == 0
assert rec["x_mailer"] == ""
assert rec["return_path"] == ""
import json as _json
assert _json.loads(rec["urls_json"]) == []
def test_message_stored_carries_body_simhash_and_base64_bytes(self, tmp_path):
"""Layer-2 body signals: simhash hex string + base64-bytes
scalar ride on every captured message_stored event so the
EmailLifter's R0042 / R0048 predicates fire from the bus
payload alone."""
mod = _load_smtp_with_quarantine(str(tmp_path))
proto, _, _ = _make_protocol(mod)
# Body with a >=4 KB base64 chunk so R0048's threshold
# (min_bytes=4096) hits.
big_chunk = ("A" * 8192)
_send(
proto,
"EHLO x.com",
"MAIL FROM:<a@b.com>",
"RCPT TO:<c@d.com>",
"DATA",
"Subject: phishing template",
"",
"Click here urgently to wire your invoice payment",
big_chunk,
".",
)
events = _logged_events(mod)
rec = next(f for t, f in events if t == "message_stored")
# 16-hex-char simhash
simhash = rec["body_simhash"]
assert isinstance(simhash, str)
assert len(simhash) == 16
assert all(c in "0123456789abcdef" for c in simhash)
# base64 chunk decoded length >= 4096 (8192 base64 chars → 6144 bytes)
assert isinstance(rec["body_base64_bytes"], int)
assert rec["body_base64_bytes"] >= 4096
def test_message_stored_no_body_yields_empty_simhash(self, tmp_path):
"""A bare DATA terminator with no text body yields an empty
simhash and zero base64-bytes — predicates correctly see
'no signal' and don't fire."""
mod = _load_smtp_with_quarantine(str(tmp_path))
proto, _, _ = _make_protocol(mod)
_send(
proto,
"EHLO x.com",
"MAIL FROM:<a@b.com>",
"RCPT TO:<c@d.com>",
"DATA",
"Subject: empty",
"Content-Type: application/octet-stream",
"",
".",
)
events = _logged_events(mod)
rec = next(f for t, f in events if t == "message_stored")
assert rec["body_simhash"] == ""
assert rec["body_base64_bytes"] == 0
def test_simhash_resists_whitespace_and_punctuation_mutation(self, tmp_path):
"""Two messages differing only in whitespace / punctuation
produce the same simhash — that's the whole point of a real
simhash over a sha256 prefix."""
mod = _load_smtp_with_quarantine(str(tmp_path))
body_a = "Please send the wire transfer immediately"
body_b = "Please send,, the wire-transfer immediately!"
sh_a = mod._body_simhash(body_a)
sh_b = mod._body_simhash(body_b)
assert sh_a == sh_b
def test_attachment_macro_indicator_fires_on_docm_zip(self, tmp_path):
"""A zip carrying a vbaProject.bin entry (the OOXML macro
marker) is flagged. Mirrors a real .docm container."""
mod = _load_smtp_with_quarantine(str(tmp_path))
import zipfile as _zf
import io as _io
buf = _io.BytesIO()
with _zf.ZipFile(buf, "w") as zf:
zf.writestr("[Content_Types].xml", "<types/>")
zf.writestr("word/vbaProject.bin", b"VBA stream")
assert mod._attachment_macro_indicator(buf.getvalue(), "report.docm")
def test_attachment_macro_indicator_skips_clean_docx(self, tmp_path):
mod = _load_smtp_with_quarantine(str(tmp_path))
import zipfile as _zf
import io as _io
buf = _io.BytesIO()
with _zf.ZipFile(buf, "w") as zf:
zf.writestr("[Content_Types].xml", "<types/>")
zf.writestr("word/document.xml", "<doc/>")
assert not mod._attachment_macro_indicator(buf.getvalue(), "clean.docx")
def test_attachment_encrypted_detects_password_zip(self, tmp_path):
"""A zip with an entry whose general-purpose flag bit 0x01 is
set (the encrypted-entry marker per APPNOTE.txt §4.4.4) trips
the bool. Stdlib's ``writestr`` discards a hand-set flag_bits,
so we post-process the produced zip bytes to flip the bit on
both the local file header and the central directory entry —
what our detector actually reads."""
mod = _load_smtp_with_quarantine(str(tmp_path))
import zipfile as _zf
import io as _io
buf = _io.BytesIO()
with _zf.ZipFile(buf, "w") as zf:
zf.writestr("payload.bin", b"ciphertext")
raw = bytearray(buf.getvalue())
# Local file header: signature PK\x03\x04 then version (2),
# then the general-purpose flag word at offset 6.
lfh = raw.find(b"PK\x03\x04")
assert lfh >= 0
raw[lfh + 6] |= 0x01
# Central directory entry: signature PK\x01\x02 then versions
# (4 bytes) then the flag word at offset 8.
cd = raw.find(b"PK\x01\x02")
assert cd >= 0
raw[cd + 8] |= 0x01
assert mod._attachment_encrypted(bytes(raw), "secrets.zip")
def test_attachment_encrypted_magic_bytes_7z_and_rar(self, tmp_path):
mod = _load_smtp_with_quarantine(str(tmp_path))
# 7z header — even unencrypted .7z trips the bool because we
# don't parse the archive content; magic alone is enough for
# R0046's OR-combined predicate.
assert mod._attachment_encrypted(b"7z\xBC\xAF\x27\x1C" + b"\x00" * 16, "x.7z")
assert mod._attachment_encrypted(b"Rar!\x1A\x07" + b"\x00" * 16, "x.rar")
# CFBF (encrypted Office)
assert mod._attachment_encrypted(b"\xD0\xCF\x11\xE0\xA1\xB1\x1A\xE1" + b"\x00" * 16, "x.xlsx")
# Random plain bytes
assert not mod._attachment_encrypted(b"hello world", "note.txt")
def test_html_smuggling_fires_on_anchor_plus_blob_script(self, tmp_path):
mod = _load_smtp_with_quarantine(str(tmp_path))
proto, _, _ = _make_protocol(mod)
boundary = "----HTMLSMUGGLE"
html_body = (
"<html><body>"
"<script>"
"var data = atob('UEsDBA==');"
"var blob = new Blob([data]);"
"var url = URL.createObjectURL(blob);"
"</script>"
"<a href='#' download='invoice.zip'>Download invoice</a>"
"</body></html>"
)
_send(
proto,
"EHLO x.com",
"MAIL FROM:<a@b.com>",
"RCPT TO:<c@d.com>",
"DATA",
"Subject: smuggle",
f"Content-Type: multipart/alternative; boundary={boundary}",
"MIME-Version: 1.0",
"",
f"--{boundary}",
"Content-Type: text/html; charset=utf-8",
"",
html_body,
f"--{boundary}--",
".",
)
events = _logged_events(mod)
rec = next(f for t, f in events if t == "message_stored")
assert rec["html_smuggling"] == 1
def test_html_smuggling_skips_legit_download_link(self, tmp_path):
"""A page with `<a download>` but no Blob/createObjectURL
script does NOT fire — the "click to download our report"
FP class is precisely what the structural check excludes."""
mod = _load_smtp_with_quarantine(str(tmp_path))
proto, _, _ = _make_protocol(mod)
boundary = "----LEGITDOWNLOAD"
html_body = (
"<html><body>"
"<p>Quarterly report is ready.</p>"
"<a href='/report.pdf' download='Q1-report.pdf'>Download</a>"
"</body></html>"
)
_send(
proto,
"EHLO x.com",
"MAIL FROM:<a@b.com>",
"RCPT TO:<c@d.com>",
"DATA",
"Subject: legit",
f"Content-Type: multipart/alternative; boundary={boundary}",
"MIME-Version: 1.0",
"",
f"--{boundary}",
"Content-Type: text/html; charset=utf-8",
"",
html_body,
f"--{boundary}--",
".",
)
events = _logged_events(mod)
rec = next(f for t, f in events if t == "message_stored")
assert rec["html_smuggling"] == 0
def test_attachment_manifest_carries_macro_and_encrypted_flags(self, tmp_path):
"""The attachments JSON manifest now includes per-attachment
macro_indicator + encrypted booleans — the ingester reduces
these to top-level flags at publish time."""
mod = _load_smtp_with_quarantine(str(tmp_path))
proto, _, _ = _make_protocol(mod)
boundary = "----MANIFESTBOOLS"
# Build a docm-shaped attachment in-line.
import zipfile as _zf
import io as _io
import base64 as _b64
zbuf = _io.BytesIO()
with _zf.ZipFile(zbuf, "w") as zf:
zf.writestr("[Content_Types].xml", "<types/>")
zf.writestr("word/vbaProject.bin", b"VBA")
encoded = _b64.b64encode(zbuf.getvalue()).decode()
_send(
proto,
"EHLO x.com",
"MAIL FROM:<a@b.com>",
"RCPT TO:<c@d.com>",
"DATA",
"Subject: macro",
f"Content-Type: multipart/mixed; boundary={boundary}",
"MIME-Version: 1.0",
"",
f"--{boundary}",
"Content-Type: text/plain",
"",
"see attached",
f"--{boundary}",
'Content-Type: application/vnd.ms-word.document.macroEnabled.12; name="report.docm"',
'Content-Disposition: attachment; filename="report.docm"',
"Content-Transfer-Encoding: base64",
"",
encoded,
f"--{boundary}--",
".",
)
events = _logged_events(mod)
rec = next(f for t, f in events if t == "message_stored")
import json as _json
manifest = _json.loads(rec["attachments_json"])
assert len(manifest) == 1
assert manifest[0]["macro_indicator"] is True
assert manifest[0]["encrypted"] is False
def test_capture_disabled_when_dir_unset(self, tmp_path, relay_mod):
"""With SMTP_QUARANTINE_DIR unset, message_accepted fires but no
message_stored event and no files are written."""
proto, _, _ = _make_protocol(relay_mod)
_send(
proto,
"EHLO x.com",
"MAIL FROM:<a@b.com>",
"RCPT TO:<c@d.com>",
"DATA",
"Subject: no-capture",
"",
"body",
".",
)
events = _logged_events(relay_mod)
assert any(t == "message_accepted" for t, _ in events)
assert not any(t == "message_stored" for t, _ in events)
def test_body_size_cap_truncates(self, tmp_path):
"""Body beyond SMTP_MAX_BODY_BYTES is dropped but the session still
terminates and truncated=1 is flagged."""
mod = _load_smtp_with_quarantine(str(tmp_path), max_body_bytes=64)
proto, _, _ = _make_protocol(mod)
big_line = "A" * 500
_send(
proto,
"EHLO x.com",
"MAIL FROM:<a@b.com>",
"RCPT TO:<c@d.com>",
"DATA",
"Subject: big",
"",
big_line,
big_line,
".",
)
events = _logged_events(mod)
stored = [f for t, f in events if t == "message_stored"]
accepted = [f for t, f in events if t == "message_accepted"]
assert accepted and accepted[0]["truncated"] == 1
# File still written with whatever we managed to buffer.
assert len(list(tmp_path.iterdir())) == 1
assert stored and stored[0]["truncated"] == 1
def test_rset_resets_body_state(self, tmp_path):
"""RSET must clear data_bytes + truncated flag so a fresh transaction
is not accounted against the prior one."""
mod = _load_smtp_with_quarantine(str(tmp_path))
proto, _, _ = _make_protocol(mod)
_send(proto, "EHLO x.com", "MAIL FROM:<a@b.com>", "RCPT TO:<c@d.com>", "RSET")
assert proto._data_bytes == 0
assert proto._data_truncated is False