"""Plugin: SMTP email verification via MX resolution and raw SMTP conversation."""

from __future__ import annotations

import asyncio
import json
import logging
import re
import urllib.request

from derp.http import create_connection
from derp.http import urlopen as _urlopen
from derp.plugin import command

log = logging.getLogger(__name__)

_MAX_BATCH = 5
_SMTP_TIMEOUT = 15
_DOH_PROVIDERS = [
    "https://dns.google/resolve",
    "https://cloudflare-dns.com/dns-query",
    "https://dns.quad9.net:5053/dns-query",
]
_DOH_ATTEMPTS = 5
_EMAIL_RE = re.compile(r"^[a-zA-Z0-9._%+\-]+@[a-zA-Z0-9.\-]+\.[a-zA-Z]{2,}$")


def _doh_query(name: str, qtype: str) -> list[dict]:
    """Query DNS-over-HTTPS via SOCKS5 proxy with provider rotation.

    Retries across multiple DoH providers to work around unreliable
    Tor exit nodes that drop or MITM HTTPS connections.
    """
    last_err = None
    for attempt in range(_DOH_ATTEMPTS):
        provider = _DOH_PROVIDERS[attempt % len(_DOH_PROVIDERS)]
        url = f"{provider}?name={name}&type={qtype}"
        req = urllib.request.Request(url, headers={
            "Accept": "application/dns-json",
            "User-Agent": "derp-bot",
        })
        try:
            with _urlopen(req, timeout=10) as resp:
                data = json.loads(resp.read())
            return data.get("Answer", [])
        except Exception as exc:
            last_err = exc
            log.debug("emailcheck: DoH attempt %d/%d failed (%s): %s",
                      attempt + 1, _DOH_ATTEMPTS, provider, exc)
    raise last_err  # type: ignore[misc]


def _resolve_mx(domain: str) -> list[str]:
    """Resolve MX records via DNS-over-HTTPS. Returns list of MX hosts."""
    answers = _doh_query(domain, "MX")
    if not answers:
        return []

    # DoH MX data is "priority host." format
    mx_entries = []
    for ans in answers:
        val = ans.get("data", "")
        parts = val.split(None, 1)
        if len(parts) == 2:
            mx_entries.append((int(parts[0]), parts[1].rstrip(".")))
        else:
            mx_entries.append((0, val.rstrip(".")))
    mx_entries.sort(key=lambda x: x[0])
    return [host for _, host in mx_entries]


def _resolve_a(domain: str) -> str | None:
    """Resolve A record via DNS-over-HTTPS as fallback."""
    answers = _doh_query(domain, "A")
    if answers:
        return answers[0].get("data", "")
    return None


def _smtp_check(email: str, mx_host: str) -> tuple[int, str]:
    """Raw SMTP conversation via SOCKS proxy. Returns (response_code, response_text)."""
    sock = create_connection((mx_host, 25), timeout=_SMTP_TIMEOUT)
    try:
        fp = sock.makefile("rb")

        def _read_reply() -> tuple[int, str]:
            lines = []
            while True:
                line = fp.readline()
                if not line:
                    break
                text = line.decode("utf-8", errors="replace").rstrip()
                lines.append(text)
                # Multi-line: "250-..." continues, "250 ..." ends
                if len(text) >= 4 and text[3] == " ":
                    break
            if not lines:
                return 0, "no response"
            try:
                code = int(lines[-1][:3])
            except (ValueError, IndexError):
                code = 0
            return code, lines[-1][4:] if len(lines[-1]) > 4 else lines[-1]

        # Read banner
        code, text = _read_reply()
        if code != 220:
            return code, f"banner: {text}"

        # EHLO
        sock.sendall(b"EHLO derp.bot\r\n")
        code, text = _read_reply()
        if code != 250:
            return code, f"EHLO: {text}"

        # MAIL FROM
        sock.sendall(b"MAIL FROM:<>\r\n")
        code, text = _read_reply()
        if code != 250:
            return code, f"MAIL FROM: {text}"

        # RCPT TO
        sock.sendall(f"RCPT TO:<{email}>\r\n".encode())
        code, text = _read_reply()

        # QUIT
        try:
            sock.sendall(b"QUIT\r\n")
        except OSError:
            pass

        return code, text
    finally:
        sock.close()


@command("emailcheck", help="SMTP verify: !emailcheck <email> [email2 ...]", admin=True)
async def cmd_emailcheck(bot, message):
    """Check email deliverability via SMTP RCPT TO verification.

    Usage:
        !emailcheck user@example.com                    Single check
        !emailcheck user@example.com user2@test.org     Batch (max 5)
    """
    parts = message.text.split()
    if len(parts) < 2:
        await bot.reply(message, "Usage: !emailcheck <email> [email2 ...]")
        return

    emails = parts[1:1 + _MAX_BATCH]

    # Validate format
    for email in emails:
        if not _EMAIL_RE.match(email):
            await bot.reply(message, f"Invalid email format: {email}")
            return

    loop = asyncio.get_running_loop()

    async def _check_one(email: str) -> str:
        domain = email.split("@", 1)[1]

        # Resolve MX
        try:
            mx_hosts = await loop.run_in_executor(None, _resolve_mx, domain)
        except Exception as exc:
            log.debug("emailcheck: MX lookup failed for %s: %s", domain, exc)
            mx_hosts = []

        # Fallback to A record
        if not mx_hosts:
            try:
                a_record = await loop.run_in_executor(None, _resolve_a, domain)
            except Exception:
                a_record = None
            if a_record:
                mx_hosts = [domain]
            else:
                return f"{email} -- no MX or A record for {domain}"

        # Try each MX host
        for mx in mx_hosts:
            try:
                code, text = await loop.run_in_executor(None, _smtp_check, email, mx)
                return f"{email} -- SMTP {code} {text} (mx: {mx})"
            except Exception as exc:
                log.debug("emailcheck: SMTP failed for %s via %s: %s", email, mx, exc)
                continue

        return f"{email} -- all MX hosts unreachable"

    if len(emails) > 1:
        await bot.reply(message, f"Checking {len(emails)} addresses...")

    results = await asyncio.gather(*[_check_one(e) for e in emails])
    for line in results:
        await bot.reply(message, line)