Connect another Gmail or Outlook mailbox

TL;DR

You can run several mailboxes under one Chiefy login. Open Settings → Integrations → Connected Mailboxes, choose Gmail or Outlook, and approve access. The new mailbox starts working right away — searchable and ready for Ask Chiefy.

Rolling out. Connecting additional mailboxes is currently available to a limited set of accounts while we roll it out. If you don’t see these options yet, they’re on the way.

Most people have more than one inbox — a work Gmail, a personal Outlook, a shared booking address. Connected Mailboxes brings them together so Chiefy can read across all of them from a single login. You can connect up to eight mailboxes, in any mix of Gmail and Outlook.

Before you start

You’ll need to be signed in to Chiefy with the mailbox you already use. That first mailbox — the one you log in with — is your sign-in mailbox, and it’s always connected. Everything below is about adding another one alongside it.

New to Chiefy and connecting your first inbox? Start with Connect Gmail or Outlook instead.

Connect another mailbox

  1. Open Connected Mailboxes A

    Go to Settings → Integrations → Connected Mailboxes. You’ll see every mailbox already synced to your account, with a Connect mailbox button at the top.

    Chiefy · Settings → Integrations → Connected Mailboxes
    Connect mailbox A Add another Gmail or Outlook account to this Chiefy account
    Settings → Integrations → Connected Mailboxes → Connect mailbox.
  2. Choose a provider B

    Select Connect mailbox, then pick Gmail (a Google account) or Outlook (a Microsoft account) from the chooser.

    Chiefy · Choose a provider
    Gmail B Google account
    Outlook Microsoft account
    Pick the provider that matches the account you want to add.
  3. Sign in and approve access

    A sign-in window opens for the provider you chose. Sign in to the account you want to add and approve the permissions — Chiefy asks for mail access so it can read your mail there. Keep the mail permission checked, or the connection can’t complete.

  4. See it confirmed C

    When the window closes, a Mailbox connected banner appears and the new mailbox joins the list.

    Chiefy · Settings → Integrations → Connected Mailboxes
    Mailbox connected C bookings@example.com connected
    The new mailbox is connected and starts syncing immediately.

What happens after you connect

A newly connected mailbox is on by default. As soon as it finishes syncing, its email is searchable and available to Ask Chiefy, so you can ask questions across all your inboxes at once.

A connected mailbox is automatically included in search and Ask Chiefy — there’s no separate switch to turn that on or off. If you want to stop Chiefy reading a mailbox, disconnect it. Your sign-in mailbox is always included and can’t be disconnected, because you use it to log in.

Reading across mailboxes and writing on them are separate things. For exactly what runs automatically on a secondary mailbox, see What automates on secondary mailboxes.

Set up Smart Drafts per mailbox

Smart Drafts can be tuned for each mailbox on its own. For every connected mailbox you can:

  • Turn Smart Drafts on or off for that mailbox
  • Set how often it offers a draft (its sensitivity)
  • Choose the signature it uses

So your work mailbox and your personal mailbox can behave completely differently. To turn on the automatic mode, see Turn on Autodraft.

Limits and common errors

A few things to know going in:

  • Eight mailboxes, total. You can connect up to eight non-disconnected mailboxes across Gmail and Outlook combined, including your sign-in mailbox. If you reach the limit, disconnect one you no longer need before adding another.
  • The sign-in mailbox can’t be disconnected. It’s the identity you log in with, so it always stays connected.
  • A mailbox can only belong to one Chiefy account. If the address is already connected to a different Chiefy account, you’ll see an error. Disconnect it from that account first, or contact support to move it over.
  • Permission needed. If the connection fails with a permission error, run it again and accept the Gmail or Outlook mail access when prompted.

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