Change mtail service to read /dev/stdin instead of "-"

The shell alias "-" should work for stdin, but on one of my servers it
was not working and stracing the process showed it kept trying to open a
file named /-. I do not know how or why this was the case, but altering
it to read /dev/stdin instead solved the issue.

.github/workflows/ci.yaml

@@ -14,8 +14,7 @@ jobs:
         # Otherwise `test_deployed_state` will be unhappy.
         with:
           ref: ${{ github.event.pull_request.head.sha }}
-      - name: download filtermail
+
-        run: curl -L https://github.com/chatmail/filtermail/releases/download/v0.1.2/filtermail-x86_64 -o /usr/local/bin/filtermail && chmod +x /usr/local/bin/filtermail
       - name: run chatmaild tests 
         working-directory: chatmaild
         run: pipx run tox

README.md

@@ -1,25 +1,20 @@
 
-# No-DNS Chatmail relay
+# Chatmail relays for end-to-end encrypted email
 
-With this branch, you don't need DNS at all,
+Chatmail relay servers are interoperable Mail Transport Agents (MTAs) designed for: 
-just a VPS with an IPv4 address,
-let's take `77.42.80.106` as an example.
-First, choose a random domain name (it doesn't need working DNS)
-and create a chatmail.ini config file:
 
-```
+-  **Zero State:** no private data or metadata collected, messages are auto-deleted, low disk usage
-cmdeploy init [77.42.80.106]
-```
 
-Then, in `cmdeploy/src/cmdeploy/postfix/transport`,
+-  **Instant/Realtime:** sub-second message delivery, realtime P2P
-remove the line corresponding to your relay,
+   streaming, privacy-preserving Push Notifications for Apple, Google, and Huawei;
-and add other for relays you know.
-Now you can deploy the relay to your IP address:
 
-```
+-  **Security Enforcement**: only strict TLS, DKIM and OpenPGP with minimized metadata accepted
-cmdeploy run --skip-dns-check --ssh-host 77.42.80.106
-```
 
-Finally, you can login with a `dclogin://` code like this, with the correct "domain name" and IP address:
+-  **Reliable Federation and Decentralization:** No spam or IP reputation checks, federating
+   depends on established IETF standards and protocols.
+
+This repository contains everything needed to setup a ready-to-use chatmail relay on an ssh-reachable host. 
+For getting started and more information please refer to the web version of this repositories' documentation at
+
+[https://chatmail.at/doc/relay](https://chatmail.at/doc/relay)
 
-`dclogin:s0mer4nd0@[77.42.80.106]?p=w7i8da7h8uads92ycc2rufyl&v=1&ih=77.42.80.106&sh=77.42.80.106&sp=443&ip=443&ic=3&sc=3`

chatmaild/pyproject.toml

@@ -24,6 +24,7 @@ where = ['src']
 [project.scripts]
 doveauth = "chatmaild.doveauth:main"
 chatmail-metadata = "chatmaild.metadata:main"
+filtermail = "chatmaild.filtermail:main"
 chatmail-metrics = "chatmaild.metrics:main"
 chatmail-expire = "chatmaild.expire:main"
 chatmail-fsreport = "chatmaild.fsreport:main"

chatmaild/src/chatmaild/config.py

@@ -32,13 +32,13 @@ class Config:
         self.passthrough_senders = params["passthrough_senders"].split()
         self.passthrough_recipients = params["passthrough_recipients"].split()
         self.www_folder = params.get("www_folder", "")
-        self.filtermail_smtp_port = int(params.get("filtermail_smtp_port", "10080"))
+        self.filtermail_smtp_port = int(params["filtermail_smtp_port"])
         self.filtermail_smtp_port_incoming = int(
-            params.get("filtermail_smtp_port_incoming", "10081")
+            params["filtermail_smtp_port_incoming"]
         )
-        self.postfix_reinject_port = int(params.get("postfix_reinject_port", "10025"))
+        self.postfix_reinject_port = int(params["postfix_reinject_port"])
         self.postfix_reinject_port_incoming = int(
-            params.get("postfix_reinject_port_incoming", "10026")
+            params["postfix_reinject_port_incoming"]
         )
         self.mtail_address = params.get("mtail_address")
         self.disable_ipv6 = params.get("disable_ipv6", "false").lower() == "true"

chatmaild/src/chatmaild/filtermail.py

@@ -0,0 +1,378 @@
+#!/usr/bin/env python3
+import asyncio
+import base64
+import binascii
+import sys
+import time
+from email import policy
+from email.parser import BytesParser
+from email.utils import parseaddr
+from smtplib import SMTP as SMTPClient
+
+from aiosmtpd.controller import Controller
+from aiosmtpd.smtp import SMTP
+
+from .config import read_config
+
+ENCRYPTION_NEEDED_523 = "523 Encryption Needed: Invalid Unencrypted Mail"
+
+
+def check_openpgp_payload(payload: bytes):
+    """Checks the OpenPGP payload.
+
+    OpenPGP payload must consist only of PKESK and SKESK packets
+    terminated by a single SEIPD packet.
+
+    Returns True if OpenPGP payload is correct,
+    False otherwise.
+
+    May raise IndexError while trying to read OpenPGP packet header
+    if it is truncated.
+    """
+    i = 0
+    while i < len(payload):
+        # Only OpenPGP format is allowed.
+        if payload[i] & 0xC0 != 0xC0:
+            return False
+
+        packet_type_id = payload[i] & 0x3F
+        i += 1
+
+        while payload[i] >= 224 and payload[i] < 255:
+            # Partial body length.
+            partial_length = 1 << (payload[i] & 0x1F)
+            i += 1 + partial_length
+
+        if payload[i] < 192:
+            # One-octet length.
+            body_len = payload[i]
+            i += 1
+        elif payload[i] < 224:
+            # Two-octet length.
+            body_len = ((payload[i] - 192) << 8) + payload[i + 1] + 192
+            i += 2
+        elif payload[i] == 255:
+            # Five-octet length.
+            body_len = (
+                (payload[i + 1] << 24)
+                | (payload[i + 2] << 16)
+                | (payload[i + 3] << 8)
+                | payload[i + 4]
+            )
+            i += 5
+        else:
+            # Impossible, partial body length was processed above.
+            return False
+
+        i += body_len
+
+        if i == len(payload):
+            # Last packet should be
+            # Symmetrically Encrypted and Integrity Protected Data Packet (SEIPD)
+            #
+            # This is the only place where this function may return `True`.
+            return packet_type_id == 18
+        elif packet_type_id not in [1, 3]:
+            # All packets except the last one must be either
+            # Public-Key Encrypted Session Key Packet (PKESK)
+            # or
+            # Symmetric-Key Encrypted Session Key Packet (SKESK)
+            return False
+
+    return False
+
+
+def check_armored_payload(payload: str, outgoing: bool):
+    """Check the armored PGP message for invalid content.
+
+    :param payload: the armored PGP message
+    :param outgoing: whether the message is outgoing or incoming
+    :return: whether the message is a valid PGP message
+    """
+    prefix = "-----BEGIN PGP MESSAGE-----\r\n"
+    if not payload.startswith(prefix):
+        return False
+    payload = payload.removeprefix(prefix)
+
+    while payload.endswith("\r\n"):
+        payload = payload.removesuffix("\r\n")
+    suffix = "-----END PGP MESSAGE-----"
+    if not payload.endswith(suffix):
+        return False
+    payload = payload.removesuffix(suffix)
+
+    version_comment = "Version: "
+    if payload.startswith(version_comment):
+        if outgoing:  # Disallow comments in outgoing messages
+            return False
+        # Remove comments from incoming messages
+        payload = payload.partition("\r\n")[2]
+
+    while payload.startswith("\r\n"):
+        payload = payload.removeprefix("\r\n")
+
+    # Remove CRC24.
+    payload = payload.rpartition("=")[0]
+
+    try:
+        payload = base64.b64decode(payload)
+    except binascii.Error:
+        return False
+
+    try:
+        return check_openpgp_payload(payload)
+    except IndexError:
+        return False
+
+
+def is_securejoin(message):
+    if message.get("secure-join") not in ["vc-request", "vg-request"]:
+        return False
+    if not message.is_multipart():
+        return False
+    parts_count = 0
+    for part in message.iter_parts():
+        parts_count += 1
+        if parts_count > 1:
+            return False
+        if part.is_multipart():
+            return False
+        if part.get_content_type() != "text/plain":
+            return False
+
+        payload = part.get_payload().strip().lower()
+        if payload not in ("secure-join: vc-request", "secure-join: vg-request"):
+            return False
+    return True
+
+
+def check_encrypted(message, outgoing=True):
+    """Check that the message is an OpenPGP-encrypted message.
+
+    MIME structure of the message must correspond to <https://www.rfc-editor.org/rfc/rfc3156>.
+    """
+    if not message.is_multipart():
+        return False
+    if message.get_content_type() != "multipart/encrypted":
+        return False
+    parts_count = 0
+    for part in message.iter_parts():
+        # We explicitly check Content-Type of each part later,
+        # but this is to be absolutely sure `get_payload()` returns string and not list.
+        if part.is_multipart():
+            return False
+
+        if parts_count == 0:
+            if part.get_content_type() != "application/pgp-encrypted":
+                return False
+
+            payload = part.get_payload()
+            if payload.strip() != "Version: 1":
+                return False
+        elif parts_count == 1:
+            if part.get_content_type() != "application/octet-stream":
+                return False
+
+            if not check_armored_payload(part.get_payload(), outgoing=outgoing):
+                return False
+        else:
+            return False
+        parts_count += 1
+    return True
+
+
+async def asyncmain_beforequeue(config, mode):
+    if mode == "outgoing":
+        port = config.filtermail_smtp_port
+        handler = OutgoingBeforeQueueHandler(config)
+    else:
+        port = config.filtermail_smtp_port_incoming
+        handler = IncomingBeforeQueueHandler(config)
+    HackedController(
+        handler,
+        hostname="127.0.0.1",
+        port=port,
+        data_size_limit=config.max_message_size,
+    ).start()
+
+
+def recipient_matches_passthrough(recipient, passthrough_recipients):
+    for addr in passthrough_recipients:
+        if recipient == addr:
+            return True
+        if addr[0] == "@" and recipient.endswith(addr):
+            return True
+    return False
+
+
+class HackedController(Controller):
+    def factory(self):
+        return SMTPDiscardRCPTO_options(self.handler, **self.SMTP_kwargs)
+
+
+class SMTPDiscardRCPTO_options(SMTP):
+    def _getparams(self, params):
+        # Ignore RCPT TO parameters.
+        #
+        # Otherwise parameters such as `ORCPT=...`
+        # or `NOTIFY=DELAY,FAILURE` (generated by Stalwart)
+        # make aiosmtpd reject the message here:
+        # <https://github.com/aio-libs/aiosmtpd/blob/98f578389ae86e5345cc343fa4e5a17b21d9c96d/aiosmtpd/smtp.py#L1379-L1384>
+        return {}
+
+
+class OutgoingBeforeQueueHandler:
+    def __init__(self, config):
+        self.config = config
+        self.send_rate_limiter = SendRateLimiter()
+
+    async def handle_MAIL(self, server, session, envelope, address, mail_options):
+        log_info(f"handle_MAIL from {address}")
+        envelope.mail_from = address
+        max_sent = self.config.max_user_send_per_minute
+        if not self.send_rate_limiter.is_sending_allowed(address, max_sent):
+            return f"450 4.7.1: Too much mail from {address}"
+
+        parts = envelope.mail_from.split("@")
+        if len(parts) != 2:
+            return f"500 Invalid from address <{envelope.mail_from!r}>"
+
+        return "250 OK"
+
+    async def handle_DATA(self, server, session, envelope):
+        loop = asyncio.get_running_loop()
+        return await loop.run_in_executor(None, self.sync_handle_DATA, envelope)
+
+    def sync_handle_DATA(self, envelope):
+        log_info("handle_DATA before-queue")
+        error = self.check_DATA(envelope)
+        if error:
+            return error
+        log_info("re-injecting the mail that passed checks")
+        client = SMTPClient("localhost", self.config.postfix_reinject_port)
+        client.sendmail(
+            envelope.mail_from, envelope.rcpt_tos, envelope.original_content
+        )
+        return "250 OK"
+
+    def check_DATA(self, envelope):
+        """the central filtering function for e-mails."""
+        log_info(f"Processing DATA message from {envelope.mail_from}")
+
+        message = BytesParser(policy=policy.default).parsebytes(envelope.content)
+        mail_encrypted = check_encrypted(message, outgoing=True)
+
+        _, from_addr = parseaddr(message.get("from").strip())
+
+        if envelope.mail_from.lower() != from_addr.lower():
+            return f"500 Invalid FROM <{from_addr!r}> for <{envelope.mail_from!r}>"
+
+        if mail_encrypted or is_securejoin(message):
+            print("Outgoing: Filtering encrypted mail.", file=sys.stderr)
+            return
+
+        print("Outgoing: Filtering unencrypted mail.", file=sys.stderr)
+
+        if envelope.mail_from in self.config.passthrough_senders:
+            return
+
+        # allow self-sent Autocrypt Setup Message
+        if envelope.rcpt_tos == [from_addr]:
+            if message.get("subject") == "Autocrypt Setup Message":
+                if message.get_content_type() == "multipart/mixed":
+                    return
+
+        passthrough_recipients = self.config.passthrough_recipients
+
+        for recipient in envelope.rcpt_tos:
+            if recipient_matches_passthrough(recipient, passthrough_recipients):
+                continue
+
+            print("Rejected unencrypted mail.", file=sys.stderr)
+            return ENCRYPTION_NEEDED_523
+
+
+class IncomingBeforeQueueHandler:
+    def __init__(self, config):
+        self.config = config
+
+    async def handle_DATA(self, server, session, envelope):
+        loop = asyncio.get_running_loop()
+        return await loop.run_in_executor(None, self.sync_handle_DATA, envelope)
+
+    def sync_handle_DATA(self, envelope):
+        log_info("handle_DATA before-queue")
+        error = self.check_DATA(envelope)
+        if error:
+            return error
+        log_info("re-injecting the mail that passed checks")
+
+        client = SMTPClient(
+            "localhost",
+            self.config.postfix_reinject_port_incoming,
+        )
+        client.sendmail(
+            envelope.mail_from, envelope.rcpt_tos, envelope.original_content
+        )
+        return "250 OK"
+
+    def check_DATA(self, envelope):
+        """the central filtering function for e-mails."""
+        log_info(f"Processing DATA message from {envelope.mail_from}")
+
+        message = BytesParser(policy=policy.default).parsebytes(envelope.content)
+        mail_encrypted = check_encrypted(message, outgoing=False)
+
+        if mail_encrypted or is_securejoin(message):
+            print("Incoming: Filtering encrypted mail.", file=sys.stderr)
+            return
+
+        print("Incoming: Filtering unencrypted mail.", file=sys.stderr)
+
+        # we want cleartext mailer-daemon messages to pass through
+        # chatmail core will typically not display them as normal messages
+        if message.get("auto-submitted"):
+            _, from_addr = parseaddr(message.get("from").strip())
+            if from_addr.lower().startswith("mailer-daemon@"):
+                if message.get_content_type() == "multipart/report":
+                    return
+
+        for recipient in envelope.rcpt_tos:
+            user = self.config.get_user(recipient)
+            if user is None or user.is_incoming_cleartext_ok():
+                continue
+
+            print("Rejected unencrypted mail.", file=sys.stderr)
+            return ENCRYPTION_NEEDED_523
+
+
+class SendRateLimiter:
+    def __init__(self):
+        self.addr2timestamps = {}
+
+    def is_sending_allowed(self, mail_from, max_send_per_minute):
+        last = self.addr2timestamps.setdefault(mail_from, [])
+        now = time.time()
+        last[:] = [ts for ts in last if ts >= (now - 60)]
+        if len(last) <= max_send_per_minute:
+            last.append(now)
+            return True
+        return False
+
+
+def log_info(msg):
+    print(msg, file=sys.stderr)
+
+
+def main():
+    args = sys.argv[1:]
+    assert len(args) == 2
+    config = read_config(args[0])
+    mode = args[1]
+    loop = asyncio.new_event_loop()
+    asyncio.set_event_loop(loop)
+    assert mode in ["incoming", "outgoing"]
+    task = asyncmain_beforequeue(config, mode)
+    loop.create_task(task)
+    log_info("entering serving loop")
+    loop.run_forever()

chatmaild/src/chatmaild/tests/test_filtermail.py

@@ -0,0 +1,361 @@
+import pytest
+
+from chatmaild.filtermail import (
+    IncomingBeforeQueueHandler,
+    OutgoingBeforeQueueHandler,
+    SendRateLimiter,
+    check_armored_payload,
+    check_encrypted,
+    is_securejoin,
+)
+
+
+@pytest.fixture
+def maildomain():
+    # let's not depend on a real chatmail instance for the offline tests below
+    return "chatmail.example.org"
+
+
+@pytest.fixture
+def handler(make_config, maildomain):
+    config = make_config(maildomain)
+    return OutgoingBeforeQueueHandler(config)
+
+
+@pytest.fixture
+def inhandler(make_config, maildomain):
+    config = make_config(maildomain)
+    return IncomingBeforeQueueHandler(config)
+
+
+def test_reject_forged_from(maildata, gencreds, handler):
+    class env:
+        mail_from = gencreds()[0]
+        rcpt_tos = [gencreds()[0]]
+
+    # test that the filter lets good mail through
+    to_addr = gencreds()[0]
+    env.content = maildata(
+        "encrypted.eml", from_addr=env.mail_from, to_addr=to_addr
+    ).as_bytes()
+
+    assert not handler.check_DATA(envelope=env)
+
+    # test that the filter rejects forged mail
+    env.content = maildata(
+        "encrypted.eml", from_addr="forged@c3.testrun.org", to_addr=to_addr
+    ).as_bytes()
+    error = handler.check_DATA(envelope=env)
+    assert "500" in error
+
+
+def test_filtermail_no_encryption_detection(maildata):
+    msg = maildata(
+        "plain.eml", from_addr="some@example.org", to_addr="other@example.org"
+    )
+    assert not check_encrypted(msg)
+
+    # https://xkcd.com/1181/
+    msg = maildata(
+        "fake-encrypted.eml", from_addr="some@example.org", to_addr="other@example.org"
+    )
+    assert not check_encrypted(msg)
+
+
+def test_filtermail_securejoin_detection(maildata):
+    msg = maildata(
+        "securejoin-vc.eml", from_addr="some@example.org", to_addr="other@example.org"
+    )
+    assert is_securejoin(msg)
+
+    msg = maildata(
+        "securejoin-vc-fake.eml",
+        from_addr="some@example.org",
+        to_addr="other@example.org",
+    )
+    assert not is_securejoin(msg)
+
+
+def test_filtermail_encryption_detection(maildata):
+    msg = maildata(
+        "encrypted.eml",
+        from_addr="1@example.org",
+        to_addr="2@example.org",
+        subject="Subject does not matter, will be replaced anyway",
+    )
+    assert check_encrypted(msg)
+
+
+def test_filtermail_no_literal_packets(maildata):
+    """Test that literal OpenPGP packet is not considered an encrypted mail."""
+    msg = maildata("literal.eml", from_addr="1@example.org", to_addr="2@example.org")
+    assert not check_encrypted(msg)
+
+
+def test_filtermail_unencrypted_mdn(maildata, gencreds):
+    """Unencrypted MDNs should not pass."""
+    from_addr = gencreds()[0]
+    to_addr = gencreds()[0] + ".other"
+    msg = maildata("mdn.eml", from_addr=from_addr, to_addr=to_addr)
+
+    assert not check_encrypted(msg)
+
+
+def test_send_rate_limiter():
+    limiter = SendRateLimiter()
+    for i in range(100):
+        if limiter.is_sending_allowed("some@example.org", 10):
+            if i <= 10:
+                continue
+            pytest.fail("limiter didn't work")
+        else:
+            assert i == 11
+            break
+
+
+def test_cleartext_excempt_privacy(maildata, gencreds, handler):
+    from_addr = gencreds()[0]
+    to_addr = "privacy@testrun.org"
+    handler.config.passthrough_recipients = [to_addr]
+    false_to = "privacy@something.org"
+
+    msg = maildata("plain.eml", from_addr=from_addr, to_addr=to_addr)
+
+    class env:
+        mail_from = from_addr
+        rcpt_tos = [to_addr]
+        content = msg.as_bytes()
+
+    # assert that None/no error is returned
+    assert not handler.check_DATA(envelope=env)
+
+    class env2:
+        mail_from = from_addr
+        rcpt_tos = [to_addr, false_to]
+        content = msg.as_bytes()
+
+    assert "523" in handler.check_DATA(envelope=env2)
+
+
+def test_cleartext_self_send_autocrypt_setup_message(maildata, gencreds, handler):
+    from_addr = gencreds()[0]
+    to_addr = from_addr
+
+    msg = maildata("asm.eml", from_addr=from_addr, to_addr=to_addr)
+
+    class env:
+        mail_from = from_addr
+        rcpt_tos = [to_addr]
+        content = msg.as_bytes()
+
+    assert not handler.check_DATA(envelope=env)
+
+
+def test_cleartext_send_fails(maildata, gencreds, handler):
+    from_addr = gencreds()[0]
+    to_addr = gencreds()[0]
+
+    msg = maildata("plain.eml", from_addr=from_addr, to_addr=to_addr)
+
+    class env:
+        mail_from = from_addr
+        rcpt_tos = [to_addr]
+        content = msg.as_bytes()
+
+    res = handler.check_DATA(envelope=env)
+    assert "523 Encryption Needed" in res
+
+
+def test_cleartext_incoming_fails(maildata, gencreds, inhandler):
+    from_addr = gencreds()[0]
+    to_addr, password = gencreds()
+
+    msg = maildata("plain.eml", from_addr=from_addr, to_addr=to_addr)
+
+    class env:
+        mail_from = from_addr
+        rcpt_tos = [to_addr]
+        content = msg.as_bytes()
+
+    user = inhandler.config.get_user(to_addr)
+    user.set_password(password)
+    res = inhandler.check_DATA(envelope=env)
+    assert "523 Encryption Needed" in res
+
+    user.allow_incoming_cleartext()
+    assert not inhandler.check_DATA(envelope=env)
+
+
+def test_cleartext_incoming_mailer_daemon(maildata, gencreds, inhandler):
+    from_addr = "mailer-daemon@example.org"
+    to_addr = gencreds()[0]
+
+    msg = maildata("mailer-daemon.eml", from_addr=from_addr, to_addr=to_addr)
+
+    class env:
+        mail_from = from_addr
+        rcpt_tos = [to_addr]
+        content = msg.as_bytes()
+
+    assert not inhandler.check_DATA(envelope=env)
+
+
+def test_cleartext_passthrough_domains(maildata, gencreds, handler):
+    from_addr = gencreds()[0]
+    to_addr = "privacy@x.y.z"
+    handler.config.passthrough_recipients = ["@x.y.z"]
+    false_to = "something@x.y"
+
+    msg = maildata("plain.eml", from_addr=from_addr, to_addr=to_addr)
+
+    class env:
+        mail_from = from_addr
+        rcpt_tos = [to_addr]
+        content = msg.as_bytes()
+
+    # assert that None/no error is returned
+    assert not handler.check_DATA(envelope=env)
+
+    class env2:
+        mail_from = from_addr
+        rcpt_tos = [to_addr, false_to]
+        content = msg.as_bytes()
+
+    assert "523" in handler.check_DATA(envelope=env2)
+
+
+def test_cleartext_passthrough_senders(gencreds, handler, maildata):
+    acc1 = gencreds()[0]
+    to_addr = "recipient@something.org"
+    handler.config.passthrough_senders = [acc1]
+
+    msg = maildata("plain.eml", from_addr=acc1, to_addr=to_addr)
+
+    class env:
+        mail_from = acc1
+        rcpt_tos = to_addr
+        content = msg.as_bytes()
+
+    # assert that None/no error is returned
+    assert not handler.check_DATA(envelope=env)
+
+
+def test_check_armored_payload():
+    prefix = "-----BEGIN PGP MESSAGE-----\r\n"
+    comment = "Version: ProtonMail\r\n"
+    payload = """\r
+wU4DSqFx0d1yqAoSAQdAYkX/ZN/Az4B0k7X47zKyWrXxlDEdS3WOy0Yf2+GJTFgg\r
+Zk5ql0mLG8Ze+ZifCS0XMO4otlemSyJ0K1ZPdFMGzUDBTgNqzkFabxXoXRIBB0AM\r
+755wlX41X6Ay3KhnwBq7yEqSykVH6F3x11iHPKraLCAGZoaS8bKKNy/zg5slda1X\r
+pt14b4aC1VwtSnYhcRRELNLD/wE2TFif+g7poMmFY50VyMPLYjVP96Z5QCT4+z4H\r
+Ikh/pRRN8S3JNMrRJHc6prooSJmLcx47Y5un7VFy390MsJ+LiUJuQMDdYWRAinfs\r
+Ebm89Ezjm7F03qbFPXE0X4ZNzVXS/eKO0uhJQdiov/vmbn41rNtHmNpqjaO0vi5+\r
+sS9tR7yDUrIXiCUCN78eBLVioxtktsPZm5cDORbQWzv+7nmCEz9/JowCUcBVdCGn\r
+1ofOaH82JCAX/cRx08pLaDNj6iolVBsi56Dd+2bGxJOZOG2AMcEyz0pXY0dOAJCD\r
+iUThcQeGIdRnU3j8UBcnIEsjLu2+C+rrwMZQESMWKnJ0rnqTk0pK5kXScr6F/L0L\r
+UE49ccIexNm3xZvYr5drszr6wz3Tv5fdue87P4etBt90gF/Vzknck+g1LLlkzZkp\r
+d8dI0k2tOSPjUbDPnSy1x+X73WGpPZmj0kWT+RGvq0nH6UkJj3AQTG2qf1T8jK+3\r
+rTp3LR9vDkMwDjX4R8SA9c0wdnUzzr79OYQC9lTnzcx+fM6BBmgQ2GrS33jaFLp7\r
+L6/DFpCl5zhnPjM/2dKvMkw/Kd6XS/vjwsO405FQdjSDiQEEAZA+ZvAfcjdccbbU\r
+yCO+x0QNdeBsufDVnh3xvzuWy4CICdTQT4s1AWRPCzjOj+SGmx5WqCLWfsd8Ma0+\r
+w/C7SfTYu1FDQILLM+llpq1M/9GPley4QZ8JQjo262AyPXsPF/OW48uuZz0Db1xT\r
+Yh4iHBztj4VSdy7l2+IyaIf7cnL4EEBFxv/MwmVDXvDlxyvfAfIsd3D9SvJESzKZ\r
+VWDYwaocgeCN+ojKu1p885lu1EfRbX3fr3YO02K5/c2JYDkc0Py0W3wUP/J1XUax\r
+pbKpzwlkxEgtmzsGqsOfMJqBV3TNDrOA2uBsa+uBqP5MGYLZ49S/4v/bW9I01Cr1\r
+D2ZkV510Y1Vgo66WlP8mRqOTyt/5WRhPD+MxXdk67BNN/PmO6tMlVoJDuk+XwWPR\r
+t2TvNaND/yabT9eYI55Og4fzKD6RIjouUX8DvKLkm+7aXxVs2uuLQ3Jco3O82z55\r
+dbShU1jYsrw9oouXUz06MHPbkdhNbF/2hfhZ2qA31sNeovJw65iUv7sDKX3LVWgJ\r
+10jlywcDwqlU8CO7WC9lGixYTbnOkYZpXCGEl8e6Jbs79l42YFo4ogYpFK1NXFhV\r
+kOXRmDf/wmfj+c/ld3L2PkvwlgofhCudOQknZbo3ub1gjiTn7L+lMGHIj/3suMIl\r
+ID4EUxAXScIM1ZEz2fjtW5jATlqYcLjLTbf/olw6HFyPNH+9IssqXeZNKnGwPUB9\r
+3lTXsg0tpzl+x7F/2WjEw1DSNhjC0KnHt1vEYNMkUGDGFdN9y3ERLqX/FIgiASUb\r
+bTvAVupnAK3raBezGmhrs6LsQtLS9P0VvQiLU3uDhMqw8Z4SISLpcD+NnVBHzQqm\r
+6W5Qn/8xsCL6av18yUVTi2G3igt3QCNoYx9evt2ZcIkNoyyagUVjfZe5GHXh8Dnz\r
+GaBXW/hg3HlXLRGaQu4RYCzBMJILcO25OhZOg6jbkCLiEexQlm2e9krB5cXR49Al\r
+UN4fiB0KR9JyG2ayUdNJVkXZSZLnHyRgiaadlpUo16LVvw==\r
+=b5Kp\r
+-----END PGP MESSAGE-----\r
+\r
+\r
+"""
+
+    commented_payload = prefix + comment + payload
+    assert check_armored_payload(commented_payload, outgoing=False) == True
+    assert check_armored_payload(commented_payload, outgoing=True) == False
+
+    payload = prefix + payload
+    assert check_armored_payload(payload, outgoing=False) == True
+    assert check_armored_payload(payload, outgoing=True) == True
+
+    payload = payload.removesuffix("\r\n")
+    assert check_armored_payload(payload, outgoing=False) == True
+    assert check_armored_payload(payload, outgoing=True) == True
+
+    payload = payload.removesuffix("\r\n")
+    assert check_armored_payload(payload, outgoing=False) == True
+    assert check_armored_payload(payload, outgoing=True) == True
+
+    payload = payload.removesuffix("\r\n")
+    assert check_armored_payload(payload, outgoing=False) == True
+    assert check_armored_payload(payload, outgoing=True) == True
+
+    payload = """-----BEGIN PGP MESSAGE-----\r
+\r
+HELLOWORLD
+-----END PGP MESSAGE-----\r
+\r
+"""
+    assert check_armored_payload(payload, outgoing=False) == False
+    assert check_armored_payload(payload, outgoing=True) == False
+
+    payload = """-----BEGIN PGP MESSAGE-----\r
+\r
+=njUN
+-----END PGP MESSAGE-----\r
+\r
+"""
+    assert check_armored_payload(payload, outgoing=False) == False
+    assert check_armored_payload(payload, outgoing=True) == False
+
+    # Test payload using partial body length
+    # as generated by GopenPGP.
+    payload = """-----BEGIN PGP MESSAGE-----\r
+\r
+wV4DdCVjRfOT3TQSAQdAY5+pjT6mlCxPGdR3be4w7oJJRUGIPI/Vnh+mJxGSm34w\r
+LNlVc89S1g22uQYFif2sUJsQWbpoHpNkuWpkSgOaHmNvrZiY/YU5iv+cZ3LbmtUG\r
+0uoBisSHh9O1c+5sYZSbrvYZ1NOwlD7Fv/U5/Mw4E5+CjxfdgNGp5o3DDddzPK78\r
+jseDhdSXxnaiIJC93hxNX6R1RPt3G2gukyzx69wciPQShcF8zf3W3o75Ed7B8etV\r
+QEeB16xzdFhKa9JxdjTu3osgCs21IO7wpcFkjc7nZzlW6jPnELJJaNmv4yOOCjMp\r
+6YAkaN/BkL+jHTznHDuDsT5ilnTXpwHDU1Cm9PIx/KFcNCQnIB+2DcdIHPHUH1ci\r
+jvqoeXAVWjKXEjS7PqPFuP/xGbrWG2ugs+toXJOKbgRkExvKs1dwPFKrgghvCVbW\r
+AcKejQKAPArLwpkA7aD875TZQShvGt74fNs45XBlGOYOnNOAJ1KAmzrXLIDViyyB\r
+kDsmTBk785xofuCkjBpXSe6vsMprPzCteDfaUibh8FHeJjucxPerwuOPEmnogNaf\r
+YyL4+iy8H8I9/p7pmUqILprxTG0jTOtlk0bTVzeiF56W1xbtSEMuOo4oFbQTyOM2\r
+bKXaYo774Jm+rRtKAnnI2dtf9RpK19cog6YNzfYjesLKbXDsPZbN5rmwyFiCvvxC\r
+kQ6JLob+B2fPdY2gzy7LypxktS8Zi1HJcWDHJGVmQodaDLqKUObb4M26bXDe6oxI\r
+NS8PJz5exVbM3KhZnUOEn6PJRBBf5a/ZqxlhZPcQo/oBuhKpBRpO5kSDwPIUByu3\r
+UlXLSkpMqe9pUarAOEuQjfl2RVY7U+RrQYp4YP5keMO+i8NCefAFbowTTufO1JIq\r
+2nVgCi/QVnxZyEc9OYt/8AE3g4cdojE+vsSDifZLSWYIetpfrohHv3dT3StD1QRG\r
+0QE6qq6oKpg/IL0cjvuX4c7a7bslv2fXp8t75y37RU6253qdIebhxc/cRhPbc/yu\r
+p0YLyD4SrvKTLP2ZV95jT4IPEpqm4AN3QmiOzdtqR2gLyb62L8QfqI/FdwsIiRiM\r
+hqydwoqt/lfSqG1WKPh+6EkMkH+TDiCC1BQdbN1MNcyUtcjb35PR2c8Ld2TF3guA\r
+jLIqMt/Vb7hBoMb2FcsOYY25ka9oV62OwgKWLXnFzk+modMR5fzb4kxVVAYEqP+D\r
+T5KO1Vs76v1fyPGOq6BbBCvLwTqe/e6IZInJles4v5jrhnLcGKmNGivCUDe6X6NY\r
+UKNt5RsZllwDQpaAb5dMNhyrk8SgIE7TBI7rvqIdUCE52Vy+0JDxFg5olRpFUfO6\r
+/MyTW3Yo/ekk/npHr7iYYqJTCc21bDGLWQcIo/XO7WPxrKNWGBNPFnkRdw0MaKr4\r
++cEM3V8NFnSEpC12xA+RX/CezuJtwXZK5MpG76eYqMO6qyC+c25YcFecEufDZDxx\r
+ZLqRszVRyxyWPtk/oIeQK2v9wOqY6N9/ff01gHz69vqYqN5bUw/QKZsmx1zW+gPw\r
+6x2tDK2BHeYl182gCbhlKISRFwCtbjqZSkiKWao/VtygHkw0fK34avJuyQ/X9YaN\r
+BRy+7Lf3VA53pnB5WJ1xwRXN8VDvmZeXzv2krHveCMemj0OjnRoCLu117xN0A5m9\r
+Fm/RoDix5PolDHtWTtr2m1n2hp2LHnj8at9lFEd0SKhAYHVL9KjzycwWODZRXt+x\r
+zGDDuooEeTvdY5NLyKcl4gETz1ZP4Ez5jGGjhPSwSpq1mU7UaJ9ZXXdr4KHyifW6\r
+ggNzNsGhXTap7IWZpTtqXABydfiBshmH2NjqtNDwBweJVSgP10+r0WhMWlaZs6xl\r
+V3o5yskJt6GlkwpJxZrTvN6Tiww/eW7HFV6NGf7IRSWY5tJc/iA7/92tOmkdvJ1q\r
+myLbG7cJB787QjplEyVe2P/JBO6xYvbkJLf9Q+HaviTO25rugRSrYsoKMDfO8VlQ\r
+1CcnTPVtApPZJEQzAWJEgVAM8uIlkqWJJMgyWT34sTkdBeCUFGloXQFs9Yxd0AGf\r
+/zHEkYZSTKpVSvAIGu4=\r
+=6iHb\r
+-----END PGP MESSAGE-----\r
+"""
+    assert check_armored_payload(payload, outgoing=False) == True
+    assert check_armored_payload(payload, outgoing=True) == True

cmdeploy/src/cmdeploy/basedeploy.py

@@ -17,8 +17,9 @@ def configure_remote_units(mail_domain, units) -> None:
 
     # install systemd units
     for fn in units:
+        execpath = fn if fn != "filtermail-incoming" else "filtermail"
         params = dict(
-            execpath=f"{remote_venv_dir}/bin/{fn}",
+            execpath=f"{remote_venv_dir}/bin/{execpath}",
             config_path=remote_chatmail_inipath,
             remote_venv_dir=remote_venv_dir,
             mail_domain=mail_domain,

cmdeploy/src/cmdeploy/cmdeploy.py

@@ -89,7 +89,6 @@ def run_cmd(args, out):
     """Deploy chatmail services on the remote server."""
 
     ssh_host = args.ssh_host if args.ssh_host else args.config.mail_domain
-    ssh_host = ssh_host.strip("[").strip("]")
     sshexec = get_sshexec(ssh_host)
     require_iroh = args.config.enable_iroh_relay
     if not args.dns_check_disabled:

cmdeploy/src/cmdeploy/deployers.py

@@ -17,6 +17,7 @@ from pyinfra.operations import apt, files, pip, server, systemd
 
 from cmdeploy.cmdeploy import Out
 
+from .acmetool import AcmetoolDeployer
 from .basedeploy import (
     Deployer,
     Deployment,
@@ -25,7 +26,6 @@ from .basedeploy import (
     get_resource,
 )
 from .dovecot.deployer import DovecotDeployer
-from .filtermail.deployer import FiltermailDeployer
 from .mtail.deployer import MtailDeployer
 from .nginx.deployer import NginxDeployer
 from .opendkim.deployer import OpendkimDeployer
@@ -416,6 +416,8 @@ class ChatmailVenvDeployer(Deployer):
     def __init__(self, config):
         self.config = config
         self.units = (
+            "filtermail",
+            "filtermail-incoming",
             "chatmail-metadata",
             "lastlogin",
             "chatmail-expire",
@@ -532,6 +534,7 @@ def deploy_chatmail(config_path: Path, disable_mail: bool, website_only: bool) -
     port_services = [
         (["master", "smtpd"], 25),
         ("unbound", 53),
+        ("acmetool", 80),
         (["imap-login", "dovecot"], 143),
         ("nginx", 443),
         (["master", "smtpd"], 465),
@@ -561,11 +564,11 @@ def deploy_chatmail(config_path: Path, disable_mail: bool, website_only: bool) -
     all_deployers = [
         ChatmailDeployer(mail_domain),
         LegacyRemoveDeployer(),
-        FiltermailDeployer(),
         JournaldDeployer(),
         UnboundDeployer(),
         TurnDeployer(mail_domain),
         IrohDeployer(config.enable_iroh_relay),
+        AcmetoolDeployer(config.acme_email, tls_domains),
         WebsiteDeployer(config),
         ChatmailVenvDeployer(config),
         MtastsDeployer(),

cmdeploy/src/cmdeploy/dovecot/dovecot.conf.j2

@@ -7,7 +7,6 @@ listen = *
 protocols = imap lmtp
 
 auth_mechanisms = plain
-auth_username_chars = abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ01234567890.-_@[]
 
 {% if debug == true %}
 auth_verbose = yes
@@ -229,8 +228,8 @@ service anvil {
 }
 
 ssl = required
-ssl_cert = </etc/ssl/certs/ssl-cert-snakeoil.pem
+ssl_cert = </var/lib/acme/live/{{ config.mail_domain }}/fullchain
-ssl_key = </etc/ssl/private/ssl-cert-snakeoil.key
+ssl_key = </var/lib/acme/live/{{ config.mail_domain }}/privkey
 ssl_dh = </usr/share/dovecot/dh.pem
 ssl_min_protocol = TLSv1.3
 ssl_prefer_server_ciphers = yes

cmdeploy/src/cmdeploy/filtermail/deployer.py

@@ -1,52 +0,0 @@
-from pyinfra import facts, host
-from pyinfra.operations import files, systemd
-
-from cmdeploy.basedeploy import Deployer, get_resource
-
-
-class FiltermailDeployer(Deployer):
-    services = ["filtermail", "filtermail-incoming"]
-    bin_path = "/usr/local/bin/filtermail"
-    config_path = "/usr/local/lib/chatmaild/chatmail.ini"
-
-    def __init__(self):
-        self.need_restart = False
-
-    def install(self):
-        arch = host.get_fact(facts.server.Arch)
-        url = f"https://github.com/chatmail/filtermail/releases/download/v0.1.2/filtermail-{arch}"
-        sha256sum = {
-            "x86_64": "de7de6e011ffc06881d3a05fc9788e327ba2389219e77280ace38b429e11a5ce",
-            "aarch64": "a78fcdfb81eb3d9c8a8b6f84f6c0a75519b8be01aa25bd4617d72aae543992b4",
-        }[arch]
-        self.need_restart |= files.download(
-            name="Download filtermail",
-            src=url,
-            sha256sum=sha256sum,
-            dest=self.bin_path,
-            mode="755",
-        ).changed
-
-    def configure(self):
-        for service in self.services:
-            self.need_restart |= files.template(
-                src=get_resource(f"filtermail/{service}.service.j2"),
-                dest=f"/etc/systemd/system/{service}.service",
-                user="root",
-                group="root",
-                mode="644",
-                bin_path=self.bin_path,
-                config_path=self.config_path,
-            ).changed
-
-    def activate(self):
-        for service in self.services:
-            systemd.service(
-                name=f"Start and enable {service}",
-                service=f"{service}.service",
-                running=True,
-                enabled=True,
-                restarted=self.need_restart,
-                daemon_reload=True,
-            )
-        self.need_restart = False

cmdeploy/src/cmdeploy/mtail/delivered_mail.mtail

@@ -44,37 +44,21 @@ counter warning_count
 }
 
 
-counter filtered_outgoing_mail_count
+counter filtered_mail_count
 
-counter outgoing_encrypted_mail_count
+counter encrypted_mail_count
-/Outgoing: Filtering encrypted mail\./ {
+/Filtering encrypted mail\./ {
-  outgoing_encrypted_mail_count++
+  encrypted_mail_count++
-  filtered_outgoing_mail_count++
+  filtered_mail_count++
 }
 
-counter outgoing_unencrypted_mail_count
+counter unencrypted_mail_count
-/Outgoing: Filtering unencrypted mail\./ {
+/Filtering unencrypted mail\./ {
-  outgoing_unencrypted_mail_count++
+  unencrypted_mail_count++
-  filtered_outgoing_mail_count++
+  filtered_mail_count++
 }
 
-
-counter filtered_incoming_mail_count
-
-counter incoming_encrypted_mail_count
-/Incoming: Filtering encrypted mail\./ {
-  incoming_encrypted_mail_count++
-  filtered_incoming_mail_count++
-}
-
-counter incoming_unencrypted_mail_count
-/Incoming: Filtering unencrypted mail\./ {
-  incoming_unencrypted_mail_count++
-  filtered_incoming_mail_count++
-}
-
-
 counter rejected_unencrypted_mail_count
-/Rejected unencrypted mail/ {
+/Rejected unencrypted mail\./ {
   rejected_unencrypted_mail_count++
 }

cmdeploy/src/cmdeploy/mtail/mtail.service.j2

@@ -3,7 +3,7 @@ Description=mtail
 
 [Service]
 Type=simple
-ExecStart=/bin/sh -c "journalctl -f -o short-iso -n 0 | /usr/local/bin/mtail --address={{ address }} --port={{ port }} --progs /etc/mtail --logtostderr --logs -"
+ExecStart=/bin/sh -c "journalctl -f -o short-iso -n 0 | /usr/local/bin/mtail --address={{ address }} --port={{ port }} --progs /etc/mtail --logtostderr --logs /dev/stdin"
 Restart=on-failure
 
 [Install]

cmdeploy/src/cmdeploy/nginx/nginx.conf.j2

@@ -53,8 +53,8 @@ http {
 
 	ssl_protocols TLSv1 TLSv1.1 TLSv1.2 TLSv1.3;
 	ssl_prefer_server_ciphers on;
-	ssl_certificate /etc/ssl/certs/ssl-cert-snakeoil.pem;
+	ssl_certificate /var/lib/acme/live/{{ config.domain_name }}/fullchain;
-	ssl_certificate_key /etc/ssl/private/ssl-cert-snakeoil.key;
+	ssl_certificate_key /var/lib/acme/live/{{ config.domain_name }}/privkey;
 
 	gzip on;
 

cmdeploy/src/cmdeploy/postfix/deployer.py

@@ -60,19 +60,7 @@ class PostfixDeployer(Deployer):
             mode="644",
         )
         need_restart |= lmtp_header_cleanup.changed
-        # Transport map that discards messages to nine.testrun.org
+
-        transport_map = files.put(
-            src=get_resource("postfix/transport"),
-            dest="/etc/postfix/transport",
-            user="root",
-            group="root",
-            mode="644",
-        )
-        need_restart |= transport_map.changed
-        if transport_map.changed:
-            server.shell(
-                commands=["postmap /etc/postfix/transport"],
-            )
         # Login map that 1:1 maps email address to login.
         login_map = files.put(
             src=get_resource("postfix/login_map"),

cmdeploy/src/cmdeploy/postfix/main.cf.j2

@@ -15,12 +15,12 @@ readme_directory = no
 compatibility_level = 3.6
 
 # TLS parameters
-smtpd_tls_cert_file=/etc/ssl/certs/ssl-cert-snakeoil.pem
+smtpd_tls_cert_file=/var/lib/acme/live/{{ config.mail_domain }}/fullchain
-smtpd_tls_key_file=/etc/ssl/private/ssl-cert-snakeoil.key
+smtpd_tls_key_file=/var/lib/acme/live/{{ config.mail_domain }}/privkey
 smtpd_tls_security_level=may
 
 smtp_tls_CApath=/etc/ssl/certs
-smtp_tls_security_level=encrypt
+smtp_tls_security_level=verify
 # Send SNI extension when connecting to other servers.
 # <https://www.postfix.org/postconf.5.html#smtp_tls_servername>
 smtp_tls_servername = hostname
@@ -54,15 +54,14 @@ smtpd_tls_exclude_ciphers = aNULL, RC4, MD5, DES
 tls_preempt_cipherlist = yes
 
 smtpd_relay_restrictions = permit_mynetworks permit_sasl_authenticated defer_unauth_destination
+myhostname = {{ config.mail_domain }}
 alias_maps = hash:/etc/aliases
 alias_database = hash:/etc/aliases
 
 # Postfix does not deliver mail for any domain by itself.
 # Primary domain is listed in `virtual_mailbox_domains` instead
 # and handed over to Dovecot.
-mydestination = {{ config.mail_domain }}
+mydestination =
-local_transport = lmtp:unix:private/dovecot-lmtp
-local_recipient_maps =
 
 relayhost = 
 mynetworks = 127.0.0.0/8 [::ffff:127.0.0.0]/104 [::1]/128
@@ -76,15 +75,14 @@ inet_protocols = ipv4
 inet_protocols = all
 {% endif %}
 
+virtual_transport = lmtp:unix:private/dovecot-lmtp
+virtual_mailbox_domains = {{ config.mail_domain }}
 lmtp_header_checks = regexp:/etc/postfix/lmtp_header_cleanup
 
 mua_client_restrictions = permit_sasl_authenticated, reject
 mua_sender_restrictions = reject_sender_login_mismatch, permit_sasl_authenticated, reject
 mua_helo_restrictions = permit_mynetworks, reject_invalid_helo_hostname, reject_non_fqdn_helo_hostname, permit
 
-# Discard messages to nine.testrun.org
-transport_maps = hash:/etc/postfix/transport
-
 # 1:1 map MAIL FROM to SASL login name.
 smtpd_sender_login_maps = regexp:/etc/postfix/login_map
 

cmdeploy/src/cmdeploy/postfix/master.cf.j2

@@ -86,7 +86,7 @@ filter    unix -        n       n       -       -       lmtp
 # Local SMTP server for reinjecting incoming filtered mail 
 127.0.0.1:{{ config.postfix_reinject_port_incoming }} inet  n       -       n       -       100      smtpd
   -o syslog_name=postfix/reinject_incoming
-#  -o smtpd_milters=unix:opendkim/opendkim.sock
+  -o smtpd_milters=unix:opendkim/opendkim.sock
 
 # Cleanup `Received` headers for authenticated mail
 # to avoid leaking client IP.

cmdeploy/src/cmdeploy/postfix/transport

@@ -1,2 +0,0 @@
-nine.testrun.org discard:
-* :

cmdeploy/src/cmdeploy/service/filtermail-incoming.service.f

@@ -2,10 +2,11 @@
 Description=Incoming Chatmail Postfix before queue filter 
 
 [Service]
-ExecStart={{ bin_path }} {{ config_path }} incoming
+ExecStart={execpath} {config_path} incoming
 Restart=always
 RestartSec=30
 User=vmail
 
 [Install]
 WantedBy=multi-user.target
+

cmdeploy/src/cmdeploy/service/filtermail.service.f

@@ -2,7 +2,7 @@
 Description=Outgoing Chatmail Postfix before queue filter
 
 [Service]
-ExecStart={{ bin_path }} {{ config_path }} outgoing
+ExecStart={execpath} {config_path} outgoing
 Restart=always
 RestartSec=30
 User=vmail

cmdeploy/src/cmdeploy/tests/online/test_1_basic.py

@@ -189,23 +189,17 @@ def test_exceed_rate_limit(cmsetup, gencreds, maildata, chatmail_config):
     mail = maildata(
         "encrypted.eml", from_addr=user1.addr, to_addr=user2.addr
     ).as_string()
-
+    for i in range(chatmail_config.max_user_send_per_minute + 5):
-    timestamps = []
-    i = 0
-    while len(timestamps) <= chatmail_config.max_user_send_per_minute * 1.7:
         print("Sending mail", str(i))
-        i += 1
         try:
             user1.smtp.sendmail(user1.addr, [user2.addr], mail)
-            timestamps.append(time.time())
         except smtplib.SMTPException as e:
-            if len(timestamps) < chatmail_config.max_user_send_per_minute:
+            if i < chatmail_config.max_user_send_per_minute:
                 pytest.fail(f"rate limit was exceeded too early with msg {i}")
             outcome = e.recipients[user2.addr]
             assert outcome[0] == 450
             assert b"4.7.1: Too much mail from" in outcome[1]
             return
-        timestamps[:] = [ts for ts in timestamps if ts >= (time.time() - 60)]
     pytest.fail("Rate limit was not exceeded")