sims-hq/apps/hq/src/gmail.ts

import { uuidv7 } from '@sims/domain'
import { decrypt } from './crypto'
import type { DB } from './db'
import { getDocument, markStatus } from './repos-documents'
import { getAccount, logEmail, markAccountDead } from './repos-email'

/**
 * Gmail send via REST (no SDK): refresh-token → access-token exchange, raw
 * MIME build, users.me/messages.send. fetch is injected (Fetcher) so tests
 * stub the network. The one non-retryable failure — `invalid_grant`, Google
 * revoked or expired the refresh token — surfaces as TokenDeadError and
 * flips the account to 'dead' so the dashboard banner shows immediately.
 */

export type Fetcher = typeof fetch

const TOKEN_URL = 'https://oauth2.googleapis.com/token'
const SEND_URL = 'https://gmail.googleapis.com/gmail/v1/users/me/messages/send'

/** Refresh token revoked/expired — re-run gmail-connect to fix. */
export class TokenDeadError extends Error {
  constructor() { super('Gmail refresh token is dead (invalid_grant)') }
}

export async function getAccessToken(
  refreshToken: string, clientId: string, clientSecret: string, f: Fetcher,
): Promise<string> {
  const res = await f(TOKEN_URL, {
    method: 'POST',
    headers: { 'content-type': 'application/x-www-form-urlencoded' },
    body: new URLSearchParams({
      grant_type: 'refresh_token', refresh_token: refreshToken,
      client_id: clientId, client_secret: clientSecret,
    }).toString(),
  })
  const json = await res.json() as { access_token?: string; error?: string }
  if (json.error === 'invalid_grant') throw new TokenDeadError()
  if (!res.ok || typeof json.access_token !== 'string') {
    throw new Error(`Gmail token exchange failed: ${json.error ?? `HTTP ${res.status}`}`)
  }
  return json.access_token
}

export interface MimeInput {
  from: string; to: string; subject: string; bodyText: string
  attachment?: { filename: string; contentType: string; data: Buffer }
}

/** RFC 2822 message (multipart when attaching), base64url-encoded for Gmail's `raw`. */
export function buildMime(m: MimeInput): string {
  const boundary = 'sims-hq-boundary-7f3a9c'
  const headers = [
    `From: ${m.from}`,
    `To: ${m.to}`,
    `Subject: ${m.subject}`,
    'MIME-Version: 1.0',
  ]
  const body = m.attachment === undefined
    ? [
        ...headers,
        'Content-Type: text/plain; charset="UTF-8"',
        '',
        m.bodyText,
      ]
    : [
        ...headers,
        `Content-Type: multipart/mixed; boundary="${boundary}"`,
        '',
        `--${boundary}`,
        'Content-Type: text/plain; charset="UTF-8"',
        '',
        m.bodyText,
        '',
        `--${boundary}`,
        `Content-Type: ${m.attachment.contentType}; name="${m.attachment.filename}"`,
        'Content-Transfer-Encoding: base64',
        `Content-Disposition: attachment; filename="${m.attachment.filename}"`,
        '',
        m.attachment.data.toString('base64'),
        `--${boundary}--`,
      ]
  return Buffer.from(body.join('\r\n'), 'utf8').toString('base64url')
}

export interface GmailDeps { f: Fetcher; clientId: string; clientSecret: string; keyHex: string }

export interface SendDocumentInput {
  documentId: string; to: string; subject: string; bodyText: string
  pdf: Buffer; userId: string
}

export type SendResult = { ok: true } | { ok: false; error: string }

export async function sendDocumentEmail(
  db: DB, deps: GmailDeps, args: SendDocumentInput,
): Promise<SendResult> {
  const doc = await getDocument(db, args.documentId)
  if (doc === null) throw new Error('Document not found')
  // Only issued documents leave the building — a draft has no legal number.
  if (doc.docNo === null) throw new Error('Only issued documents can be emailed')
  const account = await getAccount(db)
  if (account === null) throw new Error('Gmail is not connected — run gmail-connect on the server')

  const fail = async (error: string): Promise<SendResult> => {
    await logEmail(db, { documentId: args.documentId, to: args.to, subject: args.subject, status: 'failed', error })
    return { ok: false, error }
  }
  if (account.status === 'dead') return fail('gmail-token-dead')

  let accessToken: string
  try {
    const refreshToken = decrypt(account.refreshTokenEnc, deps.keyHex)
    accessToken = await getAccessToken(refreshToken, deps.clientId, deps.clientSecret, deps.f)
  } catch (err) {
    if (err instanceof TokenDeadError) {
      await markAccountDead(db)
      return fail('gmail-token-dead')
    }
    return fail(err instanceof Error ? err.message : String(err))
  }

  const raw = buildMime({
    from: account.address, to: args.to, subject: args.subject, bodyText: args.bodyText,
    attachment: {
      filename: `${doc.docNo.replaceAll('/', '-')}.pdf`, // '/' is not legal in a filename
      contentType: 'application/pdf', data: args.pdf,
    },
  })
  let gmailMessageId: string | undefined
  try {
    const res = await deps.f(SEND_URL, {
      method: 'POST',
      headers: { authorization: `Bearer ${accessToken}`, 'content-type': 'application/json' },
      body: JSON.stringify({ raw }),
    })
    const json = await res.json().catch(() => ({})) as { id?: string }
    if (!res.ok) return fail(`Gmail send failed: HTTP ${res.status}`)
    gmailMessageId = json.id
  } catch (err) {
    return fail(err instanceof Error ? err.message : String(err))
  }

  await logEmail(db, {
    documentId: args.documentId, to: args.to, subject: args.subject, status: 'sent',
    ...(gmailMessageId !== undefined ? { gmailMessageId } : {}),
  })
  if (doc.status === 'draft') {
    // markStatus appends the 'sent' document_event and the audit row.
    await markStatus(db, args.userId, args.documentId, 'sent')
  } else {
    // Re-send of an already-sent/accepted doc: trace the event, status unchanged.
    await db.run(
      `INSERT INTO document_event (id, document_id, at_wall, kind, meta) VALUES (?, ?, ?, ?, ?)`,
      uuidv7(), args.documentId, new Date().toISOString(), 'sent',
      JSON.stringify({ to: args.to, resend: true }))
  }
  return { ok: true }
}

export interface ReminderMailInput {
  to: string; subject: string; bodyText: string
  attachment?: { filename: string; data: Buffer }
  documentId?: string
}

/**
 * Send a templated reminder — attachment optional, no document-status side effects.
 * Mirrors sendDocumentEmail's account/token-death handling and logs every attempt,
 * so the dashboard banner and email_log stay consistent across both send paths.
 */
export async function sendReminderEmail(
  db: DB, deps: GmailDeps, args: ReminderMailInput,
): Promise<SendResult> {
  const logFail = async (error: string): Promise<SendResult> => {
    await logEmail(db, {
      ...(args.documentId !== undefined ? { documentId: args.documentId } : {}),
      to: args.to, subject: args.subject, status: 'failed', error,
    })
    return { ok: false, error }
  }
  const account = await getAccount(db)
  if (account === null) return logFail('gmail-not-connected')
  if (account.status === 'dead') return logFail('gmail-token-dead')

  let accessToken: string
  try {
    const refreshToken = decrypt(account.refreshTokenEnc, deps.keyHex)
    accessToken = await getAccessToken(refreshToken, deps.clientId, deps.clientSecret, deps.f)
  } catch (err) {
    if (err instanceof TokenDeadError) { await markAccountDead(db); return logFail('gmail-token-dead') }
    return logFail(err instanceof Error ? err.message : String(err))
  }

  const raw = buildMime({
    from: account.address, to: args.to, subject: args.subject, bodyText: args.bodyText,
    ...(args.attachment !== undefined
      ? { attachment: { filename: args.attachment.filename, contentType: 'application/pdf', data: args.attachment.data } }
      : {}),
  })
  let gmailMessageId: string | undefined
  try {
    const res = await deps.f(SEND_URL, {
      method: 'POST',
      headers: { authorization: `Bearer ${accessToken}`, 'content-type': 'application/json' },
      body: JSON.stringify({ raw }),
    })
    const json = await res.json().catch(() => ({})) as { id?: string }
    if (!res.ok) return logFail(`Gmail send failed: HTTP ${res.status}`)
    gmailMessageId = json.id
  } catch (err) {
    return logFail(err instanceof Error ? err.message : String(err))
  }

  await logEmail(db, {
    ...(args.documentId !== undefined ? { documentId: args.documentId } : {}),
    to: args.to, subject: args.subject, status: 'sent',
    ...(gmailMessageId !== undefined ? { gmailMessageId } : {}),
  })
  return { ok: true }
}