import { createTransport, type Transporter } from "nodemailer";
import type SMTPTransport from "nodemailer/lib/smtp-transport/index.js";
import type { MailProviderConfig } from "./config.js";
import { MailError } from "./message.js";
import type { MailProvider, MailSendResult } from "./provider.js";

/**
 * Ekklesia's first real `MailProvider`, speaking SMTP.
 *
 * **It is not named after a service, and it must not become one.** No provider's hostname appears
 * anywhere in this file, and a test asserts that. Everything specific to a deployment arrives as
 * validated configuration, so the same code addresses a Google Workspace relay, Microsoft 365, a
 * transactional provider's SMTP endpoint, a local Postfix, or anything else that speaks the
 * protocol (ADR 0037).
 *
 * Server-only, and structurally so: this module imports Nodemailer and reaches the network, and no
 * browser package can import it — a surface cannot import Core at all, which the boundary checker
 * enforces.
 */

/**
 * How long a single SMTP exchange may take before it is abandoned.
 *
 * These exist because the object-storage pass learned the lesson the hard way: a network client left
 * on its library's defaults will wait indefinitely, and a provider that accepts a connection and
 * then goes silent holds the calling request open forever. Nodemailer's own defaults are two
 * minutes for a connection and ten for a socket, which is not a deadline anyone would choose for a
 * password-reset email a person is waiting on.
 *
 * `socketTimeout` is the most generous of the three because it also covers transmitting the message
 * body, and it is inactivity-based rather than total elapsed time, so a large message is never cut
 * off for being large — only for going quiet. A wholly unresponsive server therefore surfaces as a
 * structured `MAIL_PROVIDER_UNAVAILABLE` in well under a minute rather than never.
 */
export interface SmtpTransportBounds {
  /** Milliseconds allowed to establish the TCP connection. */
  readonly connectionTimeoutMs: number;
  /** Milliseconds allowed for the server's opening greeting. */
  readonly greetingTimeoutMs: number;
  /** Milliseconds the socket may sit idle mid-exchange; resets whenever bytes move. */
  readonly socketTimeoutMs: number;
}

const DEFAULT_TRANSPORT_BOUNDS: SmtpTransportBounds = Object.freeze({
  connectionTimeoutMs: 10_000,
  greetingTimeoutMs: 10_000,
  socketTimeoutMs: 30_000,
});

export const SMTP_CONNECTION_TIMEOUT_MS = DEFAULT_TRANSPORT_BOUNDS.connectionTimeoutMs;
export const SMTP_GREETING_TIMEOUT_MS = DEFAULT_TRANSPORT_BOUNDS.greetingTimeoutMs;
export const SMTP_SOCKET_TIMEOUT_MS = DEFAULT_TRANSPORT_BOUNDS.socketTimeoutMs;

interface SmtpLikeError {
  readonly code?: unknown;
  readonly responseCode?: unknown;
  readonly rejected?: unknown;
}

function errorCode(error: unknown): string {
  const candidate = error as SmtpLikeError | null;
  return typeof candidate?.code === "string" ? candidate.code : "";
}

function responseCode(error: unknown): number | undefined {
  const candidate = error as SmtpLikeError | null;
  return typeof candidate?.responseCode === "number" ? candidate.responseCode : undefined;
}

/**
 * Reduces any Nodemailer or socket failure to one of the contract's closed codes.
 *
 * **Nothing from the caught error survives this function** — not its message, not the server's
 * response text, not the greeting, not the auth challenge, and not the envelope. SMTP servers
 * routinely echo back what was sent to them, and an authentication failure's response can name the
 * account; forwarding any of that verbatim is how a credential or a recipient reaches a log.
 */
export function translateMailError(error: unknown): MailError {
  const code = errorCode(error);
  const status = responseCode(error);

  // A named recipient the server refused: the one failure a human can usually act on, so it keeps
  // its own code rather than collapsing into a generic send failure.
  if (code === "EENVELOPE") {
    const rejected = (error as SmtpLikeError).rejected;
    if (Array.isArray(rejected) && rejected.length > 0) {
      return new MailError("MAIL_RECIPIENT_INVALID");
    }
  }

  // Connection-level failures, including both timeouts configured above.
  if (
    code === "ECONNECTION" ||
    code === "ESOCKET" ||
    code === "ETIMEDOUT" ||
    code === "EDNS" ||
    code === "ECONNRESET" ||
    code === "ECONNREFUSED" ||
    code === "EHOSTUNREACH" ||
    code === "ENOTFOUND"
  ) {
    return new MailError("MAIL_PROVIDER_UNAVAILABLE");
  }

  if (status !== undefined) {
    // 4xx is SMTP's "try later" and 5xx its "no". Splitting on that is what lets a caller tell a
    // transient outage from a message that will never be accepted.
    return status >= 500
      ? new MailError("MAIL_REJECTED")
      : new MailError("MAIL_PROVIDER_UNAVAILABLE");
  }

  return new MailError("MAIL_SEND_FAILED");
}

function transportOptions(
  config: MailProviderConfig,
  bounds: SmtpTransportBounds,
): SMTPTransport.Options {
  return {
    // Bounded on every axis. See the constants above.
    connectionTimeout: bounds.connectionTimeoutMs,
    // Defence in depth: this platform never sends attachments, so Nodemailer must never be able to
    // read a local file or fetch a URL on the strength of something that reached a message body.
    disableFileAccess: true,
    disableUrlAccess: true,
    greetingTimeout: bounds.greetingTimeoutMs,
    host: config.host,
    // The identity this client announces in `EHLO`. Left to Nodemailer when the deployment
    // configures none — it derives one from the machine hostname, falling back to the address
    // literal `[127.0.0.1]` when that hostname is not fully qualified, which some relays refuse
    // with a `421` before a message is ever offered (ADR 0037).
    ...(config.heloName === undefined ? {} : { name: config.heloName }),
    // Deliberately not a pooled transport: `pool` is absent, which is Nodemailer's default and is
    // what this type permits. A pool keeps sockets open and reuses them across sends, which for a
    // platform sending a handful of transactional messages buys nothing and makes the failure modes
    // harder to reason about.
    port: config.port,
    // `secure` means implicit TLS from the first byte. For STARTTLS it must be false and the upgrade
    // demanded separately, below.
    secure: config.security === "implicit-tls",
    socketTimeout: bounds.socketTimeoutMs,
    // The downgrade guard. With `requireTLS`, a STARTTLS transport refuses to continue in the clear
    // if the server does not offer the upgrade — so a server that stops advertising it, or an
    // attacker who strips it from the EHLO response, produces a failed send rather than a plaintext
    // session carrying a password. `ignoreTLS` is the opposite instruction and is set only for the
    // mode that has explicitly asked for no TLS at all, which production configuration refuses.
    ...(config.security === "starttls" ? { requireTLS: true } : {}),
    ...(config.security === "plaintext" ? { ignoreTLS: true } : {}),
    // Certificate verification is left at Nodemailer's default, which verifies. There is
    // deliberately no configuration path that could switch it off, and a test asserts this file
    // never names the option: a setting that disables verification is one someone eventually
    // disables in production.
    ...(config.username === undefined || config.password === undefined
      ? {}
      : { auth: { pass: config.password, user: config.username } }),
  };
}

export function createSmtpMailProvider(
  config: MailProviderConfig,
  /** Tightened only by the live provider suite, so it can prove a deadline actually fires without
   * spending the production budget waiting for it. Hosts always take the defaults. */
  bounds: Partial<SmtpTransportBounds> = {},
): MailProvider {
  const transporter: Transporter<SMTPTransport.SentMessageInfo> = createTransport(
    transportOptions(config, { ...DEFAULT_TRANSPORT_BOUNDS, ...bounds }),
  );

  // Built once, from host configuration, and applied to every message. A caller cannot reach it and
  // there is no per-message override, so no feature can send as anyone else.
  const from =
    config.fromName === undefined
      ? { address: config.fromAddress, name: "" }
      : { address: config.fromAddress, name: config.fromName };

  const provider: MailProvider = {
    async close(): Promise<void> {
      transporter.close();
    },

    async send(message): Promise<MailSendResult> {
      try {
        const accepted = await transporter.sendMail({
          from,
          subject: message.subject,
          to: [...message.to],
          ...(message.text === undefined ? {} : { text: message.text }),
          ...(message.html === undefined ? {} : { html: message.html }),
          ...(message.replyTo === undefined ? {} : { replyTo: message.replyTo }),
        });
        // Exactly one attempt. Nodemailer does not retry a `sendMail` on its own, and nothing here
        // adds one: a failure after the message data has gone out is ambiguous, and retrying an
        // ambiguous send is how one password-reset request becomes three emails (ADR 0037).
        const messageId = (accepted as { messageId?: unknown }).messageId;
        return Object.freeze(typeof messageId === "string" ? { messageId } : {});
      } catch (error) {
        throw translateMailError(error);
      }
    },

    async verify(): Promise<void> {
      try {
        await transporter.verify();
      } catch (error) {
        throw translateMailError(error);
      }
    },
  };
  return Object.freeze(provider);
}