"""mailu — recipe-specific functional test #3 (Phase 2 P3, the characteristic end-to-end mail flow).

Provision a mailbox, SEND a uniquely-marked message to it over SMTP, then RETRIEVE it over IMAP and
assert the marker arrived. This is mailu's defining behaviour (it is a mail server): a full
deliver→store→fetch round-trip across postfix + rspamd + dovecot — not an API/health stand-in.

To avoid rspamd greylisting (which defers an unknown inbound sender's first attempt for minutes), we
send via AUTHENTICATED submission as the user itself (authenticated mail is not greylisted). notls
deploy → submission accepts AUTH on 587; we try 587 (STARTTLS-if-offered) then fall back to 25.
Retrieval polls INBOX (and Junk, in case rspamd files it) for the marker.
"""

from __future__ import annotations

import email.message
import imaplib
import os
import smtplib
import sys
import time
import uuid

sys.path.insert(0, os.path.dirname(__file__))
import _mailu  # noqa: E402


def _send(addr_from: str, addr_to: str, password: str, marker: str) -> None:
    msg = email.message.EmailMessage()
    msg["From"] = addr_from
    msg["To"] = addr_to
    msg["Subject"] = marker
    msg.set_content(f"cc-ci mail-flow test body {marker}")

    last = None
    # Authenticated submission on 587 (no greylist); fall back to plain 25 local delivery.
    for port in (587, 25):
        try:
            smtp = smtplib.SMTP("127.0.0.1", port, timeout=30)
            try:
                smtp.ehlo()
                if smtp.has_extn("starttls"):
                    smtp.starttls()
                    smtp.ehlo()
                if smtp.has_extn("auth"):
                    try:
                        smtp.login(addr_from, password)
                    except smtplib.SMTPException as e:  # noqa: PERF203
                        last = e  # 25 may not offer/allow AUTH; local delivery still works
                smtp.send_message(msg)
                return
            finally:
                try:
                    smtp.quit()
                except Exception:  # noqa: BLE001
                    pass
        except (smtplib.SMTPException, OSError) as e:
            last = e
    raise AssertionError(f"could not send mail via SMTP 587/25: {last}")


def _retrieve(email_addr: str, password: str, marker: str, timeout: int = 150) -> bool:
    deadline = time.time() + timeout
    while time.time() < deadline:
        try:
            imap = imaplib.IMAP4("127.0.0.1", 143)
            try:
                imap.login(email_addr, password)
                for box in ("INBOX", "Junk"):
                    typ, _ = imap.select(box)
                    if typ != "OK":
                        continue
                    typ, data = imap.search(None, "SUBJECT", f'"{marker}"')
                    if typ == "OK" and data and data[0].split():
                        return True
                imap.logout()
            finally:
                try:
                    imap.shutdown()
                except Exception:  # noqa: BLE001
                    pass
        except (imaplib.IMAP4.error, OSError):  # noqa: PERF203
            pass
        time.sleep(5)
    return False


def test_send_and_receive_mail(live_app):
    mail_domain = live_app
    local = "ccci-flow-" + uuid.uuid4().hex[:8]
    password = "CcCi-" + uuid.uuid4().hex[:16] + "-Aa1!"
    _mailu.ensure_domain(live_app, mail_domain)
    email_addr = _mailu.create_user(live_app, local, mail_domain, password)

    marker = "ccci-mailflow-" + uuid.uuid4().hex
    _send(email_addr, email_addr, password, marker)

    assert _retrieve(email_addr, password, marker), (
        f"mail with marker {marker!r} was sent to {email_addr} but never arrived in INBOX/Junk "
        f"over IMAP within the delivery window (postfix→rspamd→dovecot)"
    )