import nodemailer from 'nodemailer';

// Defaults written for Gmail. An environment on a different provider — QA is on
// Brevo — has to set host, port and SMTP_SECURE explicitly rather than
// inheriting these, and getting that wrong fails at send time rather than at
// boot. See #64 on validating this at startup instead.
// #260 put the first awaited send on a user-facing request path (the admin
// creating an upload link). nodemailer's defaults are two minutes to connect
// and ten minutes on the socket, which is fine for a fire-and-forget send but
// is not a bound anyone waiting on a response can live with: the link row and
// its token are already committed by the time sendMail is called, the token
// is shown exactly once, and a request that hangs long enough for the browser
// or reverse proxy to give up first loses it for good. Five seconds each is
// long enough for a reachable host and short enough that a dead one fails
// fast, leaving the admin with the "not emailed" warning and a link they can
// still copy, instead of a stuck spinner and a token nobody ever saw.
const transporter = nodemailer.createTransport({
  host: process.env.SMTP_HOST || 'smtp.gmail.com',
  port: parseInt(process.env.SMTP_PORT || '465', 10),
  secure: process.env.SMTP_SECURE !== 'false',
  auth: {
    user: process.env.SMTP_USER,
    pass: process.env.SMTP_PASSWORD
  },
  connectionTimeout: 5000,
  greetingTimeout: 5000,
  socketTimeout: 5000
});

interface ParsedAddress {
  local: string;
  domain: string;
}

// Lowercased, and with any `+suffix` removed from the local part. Returns null
// for anything that is not a usable address, so a caller can refuse rather than
// compare nonsense.
function parseAddress(address: string): ParsedAddress | null {
  const trimmed = address.trim().toLowerCase();
  const at = trimmed.lastIndexOf('@');
  // Needs something on both sides of a single trailing @.
  if (at <= 0 || at === trimmed.length - 1) {
    return null;
  }
  const localWithSuffix = trimmed.slice(0, at);
  return {
    // split always yields at least one element, so this cannot actually be
    // undefined — but String.split's type cannot express that.
    local: localWithSuffix.split('+')[0] ?? localWithSuffix,
    domain: trimmed.slice(at + 1)
  };
}

/**
 * Whether this environment is permitted to email this recipient.
 *
 * `allowlist` is the raw MAIL_ALLOWLIST value: a comma-separated list where an
 * entry is either a full address, which also covers its `+suffix` variants, or
 * `@domain`, which covers every mailbox there.
 *
 * Undefined means unrestricted, which is production — it must be able to mail
 * real customers. Present but empty means refuse everyone: someone writing
 * `MAIL_ALLOWLIST=` is expressing an intent to restrict, and reading that as
 * "no restriction" would turn a typo into an outbound mail incident.
 *
 * Comparison is by exact equality on both halves, never a suffix test, so a
 * lookalike domain ending in an allowed one does not get through.
 *
 * Exported for its unit test. This function is the entire safety property of
 * mail in a non-production environment, and it is pure, so it is worth testing
 * directly rather than through a send.
 */
export function isAllowedRecipient(to: string, allowlist: string | undefined): boolean {
  if (allowlist === undefined) {
    return true;
  }

  const entries = allowlist
    .split(',')
    .map((entry) => entry.trim().toLowerCase())
    .filter((entry) => entry !== '');

  if (entries.length === 0) {
    return false;
  }

  const recipient = parseAddress(to);
  if (!recipient) {
    return false;
  }

  return entries.some((entry) => {
    if (entry.startsWith('@')) {
      return recipient.domain === entry.slice(1);
    }
    const allowed = parseAddress(entry);
    return allowed !== null && allowed.local === recipient.local && allowed.domain === recipient.domain;
  });
}

/**
 * What a send attempt actually did.
 *
 * `sendMail` returns early in two cases that used to be indistinguishable from
 * success — no SMTP credentials, and a recipient outside MAIL_ALLOWLIST — which
 * meant a caller could report "emailed" for a message nobody would ever
 * receive. QA restricts delivery by design, so that was not a hypothetical: it
 * is the normal case there. See #260.
 */
export type MailOutcome = 'sent' | 'skipped-unconfigured' | 'skipped-blocked';

export async function sendMail(to: string, subject: string, html: string): Promise<MailOutcome> {
  if (!process.env.SMTP_USER || !process.env.SMTP_PASSWORD) {
    console.warn(`SMTP not configured — skipping email to ${to}: "${subject}"`);
    return 'skipped-unconfigured';
  }

  // Guarded here rather than at the four call sites, so every sender is covered
  // by construction and a fifth added later cannot bypass it by forgetting.
  //
  // Skipping rather than throwing, and reporting the skip through MailOutcome
  // rather than pretending nothing happened: three of the callers already
  // swallow send failures into a log, so throwing would mostly be caught and
  // logged anyway while risking a 500 on the signup path. The flow under test
  // finishes, and both the log and the returned outcome say why no mail
  // arrived — which is the part that was missing when QA was simply muted.
  if (!isAllowedRecipient(to, process.env.MAIL_ALLOWLIST)) {
    console.warn(`[mail-blocked] ${to} is not on MAIL_ALLOWLIST — skipping "${subject}"`);
    return 'skipped-blocked';
  }

  await transporter.sendMail({
    from: process.env.SMTP_FROM || process.env.SMTP_USER,
    to,
    subject,
    html
  });
  return 'sent';
}