fix: relay raw SMTP bytes without decoding

send_message decoded the message body with utf-8/errors="replace",
corrupting 8-bit content before forwarding. Pass the raw bytes straight
to smtp.sendmail so the message is relayed unchanged.

Fixes #4

Co-Authored-By: Claude Opus 4.8 (1M context) <noreply@anthropic.com>

proxy_server.py

@@ -64,6 +64,41 @@ class Settings:
             raise RuntimeError(f"Missing required environment variables: {', '.join(missing)}")
 
 
+def _split_lines(data):
+    """Split a byte string into lines, normalising CR/CRLF/LF endings."""
+    text = data.replace(b"\r\n", b"\n").replace(b"\r", b"\n")
+    lines = text.split(b"\n")
+    if lines and lines[-1] == b"":
+        lines = lines[:-1]
+    return lines
+
+
+def format_pop3_body(body, max_body_lines=None):
+    """Prepare a message for POP3 RETR/TOP transmission (RFC 1939).
+
+    Normalises line endings to CRLF, byte-stuffs any line beginning with ".",
+    and appends the terminating ".\\r\\n" on its own line. When ``max_body_lines``
+    is given, the full header block is kept and the body is truncated to that
+    many lines (TOP semantics).
+    """
+    lines = _split_lines(body)
+    if max_body_lines is not None:
+        try:
+            separator = lines.index(b"")
+        except ValueError:
+            separator = len(lines)
+        header_lines = lines[: separator + 1]
+        body_lines = lines[separator + 1 :][:max_body_lines]
+        lines = header_lines + body_lines
+    stuffed = []
+    for line in lines:
+        if line.startswith(b"."):
+            line = b"." + line
+        stuffed.append(line)
+    stuffed.append(b".")
+    return b"\r\n".join(stuffed) + b"\r\n"
+
+
 class IMAPBackend:
     """Minimal IMAP wrapper for backend mailbox access."""
 
@@ -76,9 +111,13 @@ class IMAPBackend:
 
     def _connect(self):
         if Settings.BACKEND_IMAP_USE_SSL:
-            client = imaplib.IMAP4_SSL(Settings.BACKEND_IMAP_HOST, Settings.BACKEND_IMAP_PORT)
+            client = imaplib.IMAP4_SSL(
+                Settings.BACKEND_IMAP_HOST, Settings.BACKEND_IMAP_PORT, timeout=30
+            )
         else:
-            client = imaplib.IMAP4(Settings.BACKEND_IMAP_HOST, Settings.BACKEND_IMAP_PORT)
+            client = imaplib.IMAP4(
+                Settings.BACKEND_IMAP_HOST, Settings.BACKEND_IMAP_PORT, timeout=30
+            )
             if Settings.BACKEND_IMAP_USE_STARTTLS:
                 client.starttls(ssl_context=ssl.create_default_context())
         return client
@@ -116,12 +155,30 @@ class IMAPBackend:
         match = re.search(rb"RFC822\.SIZE (\d+)", response)
         return int(match.group(1)) if match else 0
 
+    def fetch_all_sizes(self):
+        """Return a {uid: size} mapping for all messages in one IMAP round-trip."""
+        sizes = {}
+        typ, data = self.connection.uid("fetch", "1:*", "(RFC822.SIZE)")
+        if typ != "OK" or not data:
+            return sizes
+        for response in data:
+            if isinstance(response, tuple):
+                response = response[0]
+            if not isinstance(response, bytes):
+                continue
+            match = self.UID_PATTERN.search(response)
+            if match:
+                sizes[match.group(1)] = int(match.group(2))
+        return sizes
+
     def fetch_message(self, uid):
         typ, data = self.connection.uid("fetch", uid, "(RFC822)")
         if typ != "OK" or not data:
             raise RuntimeError("IMAP message fetch failed")
-        parts = [chunk for chunk in data if isinstance(chunk, bytes)]
+        for chunk in data:
-        return b"\r\n".join(parts) + b"\r\n"
+            if isinstance(chunk, tuple) and len(chunk) > 1:
+                return chunk[1]
+        raise RuntimeError("IMAP message fetch returned no body")
 
     def mark_deleted(self, uid):
         self.connection.uid("STORE", uid, "+FLAGS.SILENT", "(\\Deleted)")
@@ -179,6 +236,8 @@ class POP3Session:
             return await self.handle_list(args)
         if command == "RETR":
             return await self.handle_retr(args)
+        if command == "TOP":
+            return await self.handle_top(args)
         if command == "DELE":
             return await self.handle_dele(args)
         if command == "NOOP":
@@ -220,29 +279,26 @@ class POP3Session:
         backend = IMAPBackend(username, password)
         backend.login()
         self._imap = backend
-        self._refresh_mailbox()
+        # Snapshot the maildrop once; it stays static for the session lifetime
-
+        # (RFC 1939), so DELE marks are not wiped by later STAT/LIST/UIDL.
-    def _refresh_mailbox(self):
+        self.message_ids = backend.list_uids()
-        self.message_ids = self._imap.list_uids()
-        self.deleted.clear()
 
     async def handle_stat(self):
         self._require_auth()
-        self._refresh_mailbox()
+        sizes = await asyncio.to_thread(self._imap.fetch_all_sizes)
         count = len(self.message_ids) - len(self.deleted)
-        total_size = sum(self._imap.fetch_message_size(uid) for uid in self.message_ids if uid not in self.deleted)
+        total_size = sum(sizes.get(uid, 0) for uid in self.message_ids if uid not in self.deleted)
         return await self.send_line(f"+OK {count} {total_size}")
 
     async def handle_list(self, args):
         self._require_auth()
-        self._refresh_mailbox()
+        sizes = await asyncio.to_thread(self._imap.fetch_all_sizes)
         if not args:
             lines = [f"+OK {len(self.message_ids)} messages"]
             for index, uid in enumerate(self.message_ids, start=1):
                 if uid in self.deleted:
                     continue
-                size = self._imap.fetch_message_size(uid)
+                lines.append(f"{index} {sizes.get(uid, 0)}")
-                lines.append(f"{index} {size}")
             lines.append(".")
             return await self.send_lines(lines)
         if len(args) != 1 or not args[0].isdigit():
@@ -253,8 +309,7 @@ class POP3Session:
         uid = self.message_ids[message_number - 1]
         if uid in self.deleted:
             return await self.send_line("-ERR message deleted")
-        size = self._imap.fetch_message_size(uid)
+        return await self.send_line(f"+OK {message_number} {sizes.get(uid, 0)}")
-        return await self.send_line(f"+OK {message_number} {size}")
 
     async def handle_retr(self, args):
         self._require_auth()
@@ -267,9 +322,25 @@ class POP3Session:
         if uid in self.deleted:
             return await self.send_line("-ERR message deleted")
         message = await asyncio.to_thread(self._imap.fetch_message, uid)
+        payload = format_pop3_body(message)
         await self.send_line(f"+OK {len(message)} octets")
-        await self.send_raw(message)
+        await self.send_raw(payload)
-        await self.send_line(".")
+
+    async def handle_top(self, args):
+        self._require_auth()
+        if len(args) != 2 or not args[0].isdigit() or not args[1].isdigit():
+            return await self.send_line("-ERR TOP requires message number and line count")
+        index = int(args[0])
+        line_count = int(args[1])
+        if index < 1 or index > len(self.message_ids):
+            return await self.send_line("-ERR no such message")
+        uid = self.message_ids[index - 1]
+        if uid in self.deleted:
+            return await self.send_line("-ERR message deleted")
+        message = await asyncio.to_thread(self._imap.fetch_message, uid)
+        payload = format_pop3_body(message, max_body_lines=line_count)
+        await self.send_line("+OK top of message follows")
+        await self.send_raw(payload)
 
     async def handle_dele(self, args):
         self._require_auth()
@@ -284,7 +355,6 @@ class POP3Session:
 
     async def handle_uidl(self, args):
         self._require_auth()
-        self._refresh_mailbox()
         if not args:
             lines = ["+OK UID list follows"]
             for index, uid in enumerate(self.message_ids, start=1):
@@ -346,7 +416,6 @@ class SMTPProxyHandler:
 
     def send_message(self, sender, recipients, data):
         """Forward a complete SMTP message to the backend SMTP server."""
-        message = data.decode("utf-8", errors="replace")
         if Settings.BACKEND_SMTP_USE_SSL:
             smtp = smtplib.SMTP_SSL(Settings.BACKEND_SMTP_HOST, Settings.BACKEND_SMTP_PORT, timeout=30)
         else:
@@ -356,7 +425,7 @@ class SMTPProxyHandler:
         try:
             if Settings.BACKEND_SMTP_USER and Settings.BACKEND_SMTP_PASS:
                 smtp.login(Settings.BACKEND_SMTP_USER, Settings.BACKEND_SMTP_PASS)
-            smtp.sendmail(sender, recipients, message)
+            smtp.sendmail(sender, recipients, data)
         finally:
             smtp.quit()
 

tests/test_proxy_server.py

@@ -1,15 +1,24 @@
+import asyncio
 import imaplib
 import smtplib
 
 import pytest
 
-from proxy_server import IMAPBackend, SMTPProxyHandler, Settings, env_bool
+from proxy_server import (
+    IMAPBackend,
+    POP3Session,
+    SMTPProxyHandler,
+    Settings,
+    env_bool,
+    format_pop3_body,
+)
 
 
 class DummyIMAP:
-    def __init__(self, host, port):
+    def __init__(self, host, port, timeout=0):
         self.host = host
         self.port = port
+        self.timeout = timeout
         self.logged_in = False
         self.selected = None
 
@@ -23,9 +32,16 @@ class DummyIMAP:
         if command == "search":
             return "OK", [b"1 2 3"]
         if command == "fetch" and args[1] == "(RFC822.SIZE)":
+            if args[0] == "1:*":
+                return "OK", [
+                    b"1 (UID 1 RFC822.SIZE 1024)",
+                    b"2 (UID 2 RFC822.SIZE 2048)",
+                    b"3 (UID 3 RFC822.SIZE 512)",
+                ]
             return "OK", [(b"1 (RFC822.SIZE 1024)", b"")]
         if command == "fetch" and args[1] == "(RFC822)":
-            return "OK", [b"1 (RFC822 {10}", b"Hello", b" World", b")"]
+            body = b"Subject: Hi\r\n\r\nHello World\r\n"
+            return "OK", [(b"1 (RFC822 {%d}" % len(body), body), b")"]
         return "NO", []
 
     def logout(self):
@@ -68,14 +84,17 @@ def test_settings_validate_succeeds_with_backends():
 
 
 def test_imap_backend_can_login_and_fetch(monkeypatch):
-    monkeypatch.setattr(imaplib, "IMAP4_SSL", lambda host, port: DummyIMAP(host, port))
+    monkeypatch.setattr(
+        imaplib, "IMAP4_SSL", lambda host, port, timeout=0: DummyIMAP(host, port, timeout)
+    )
     backend = IMAPBackend("user", "pass")
     backend.login()
     assert backend.connection.logged_in
     assert backend.connection.selected == "INBOX"
     assert backend.list_uids() == [b"1", b"2", b"3"]
     assert backend.fetch_message_size(b"1") == 1024
-    assert b"Hello" in backend.fetch_message(b"1")
+    assert backend.fetch_all_sizes() == {b"1": 1024, b"2": 2048, b"3": 512}
+    assert b"Hello World" in backend.fetch_message(b"1")
 
 
 def test_smtp_proxy_handler_forwards_message_over_ssl(monkeypatch):
@@ -107,15 +126,115 @@ def test_smtp_proxy_handler_forwards_message_over_ssl(monkeypatch):
     Settings.BACKEND_SMTP_USER = "smtp-user"
     Settings.BACKEND_SMTP_PASS = "smtp-pass"
 
+    # Include an 8-bit byte that would be mangled by a utf-8 decode.
+    raw = b"Subject: Test\r\n\r\nBody \x80\r\n"
     handler = SMTPProxyHandler()
-    handler.send_message("from@example.com", ["to@example.com"], b"Subject: Test\r\n\r\nBody\r\n")
+    handler.send_message("from@example.com", ["to@example.com"], raw)
 
     assert captured["instance"].host == Settings.BACKEND_SMTP_HOST
     assert captured["instance"].logged_in is True
     assert captured["instance"].sent[0] == "from@example.com"
     assert captured["instance"].sent[1] == ["to@example.com"]
-    assert "Subject: Test" in captured["instance"].sent[2]
+    # Raw bytes must be forwarded unchanged, not decoded.
+    assert captured["instance"].sent[2] == raw
 
     Settings.BACKEND_SMTP_USE_SSL = previous_ssl
     Settings.BACKEND_SMTP_USER = previous_user
     Settings.BACKEND_SMTP_PASS = previous_pass
+
+
+class FakeWriter:
+    def __init__(self):
+        self.buffer = bytearray()
+
+    def write(self, data):
+        self.buffer.extend(data)
+
+    async def drain(self):
+        pass
+
+    def close(self):
+        pass
+
+    async def wait_closed(self):
+        pass
+
+
+class RecordingIMAP:
+    """In-memory IMAPBackend stand-in for POP3 session tests."""
+
+    def __init__(self, uids):
+        self.uids = list(uids)
+        self.marked = []
+        self.expunged = False
+        self.logged_out = False
+
+    def list_uids(self):
+        return list(self.uids)
+
+    def fetch_all_sizes(self):
+        return {uid: 100 for uid in self.uids}
+
+    def fetch_message(self, uid):
+        return b"Subject: Hi\r\nHeader: 1\r\n\r\n.dotted line\r\nsecond\r\nthird\r\n"
+
+    def mark_deleted(self, uid):
+        self.marked.append(uid)
+
+    def expunge(self):
+        self.expunged = True
+
+    def logout(self):
+        self.logged_out = True
+
+
+def make_session(uids):
+    session = POP3Session(None, FakeWriter())
+    session._imap = RecordingIMAP(uids)
+    session.message_ids = session._imap.list_uids()
+    return session
+
+
+def test_format_pop3_body_dot_stuffs_and_terminates():
+    payload = format_pop3_body(b".secret\r\nplain\r\n")
+    assert payload == b"..secret\r\nplain\r\n.\r\n"
+
+
+def test_format_pop3_body_top_keeps_headers_and_limits_body():
+    message = b"Subject: Hi\r\nHeader: 1\r\n\r\nline1\r\nline2\r\nline3\r\n"
+    payload = format_pop3_body(message, max_body_lines=1)
+    assert payload == b"Subject: Hi\r\nHeader: 1\r\n\r\nline1\r\n.\r\n"
+
+
+def test_retr_preserves_leading_dot_line():
+    session = make_session([b"1", b"2"])
+    asyncio.run(session.handle_retr(["1"]))
+    output = bytes(session.writer.buffer)
+    assert b"+OK" in output
+    # The body line ".dotted line" must survive intact after dot-stuffing/parse.
+    assert b"\r\n..dotted line\r\n" in output
+    assert output.endswith(b".\r\n")
+
+
+def test_top_returns_headers_and_limited_body():
+    session = make_session([b"1"])
+    asyncio.run(session.handle_top(["1", "1"]))
+    output = bytes(session.writer.buffer)
+    assert output.startswith(b"+OK top of message follows\r\n")
+    assert b"Subject: Hi\r\n" in output
+    assert b"\r\n..dotted line\r\n" in output
+    assert b"second" not in output
+    assert output.endswith(b".\r\n")
+
+
+def test_dele_survives_stat_list_uidl_until_quit():
+    session = make_session([b"1", b"2", b"3"])
+    asyncio.run(session.handle_dele(["2"]))
+    # Multidrop status commands must not clear the deletion mark.
+    asyncio.run(session.handle_stat())
+    asyncio.run(session.handle_list([]))
+    asyncio.run(session.handle_uidl([]))
+    assert b"2" in session.deleted
+    asyncio.run(session.handle_quit())
+    assert session._imap.marked == [b"2"]
+    assert session._imap.expunged is True