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Connect your sending mailbox to Eli.

Eli sends from your mailbox, not a shared sender pool, that's how deliverability stays clean and replies land in your own inbox the way your prospects expect. This page walks you through wiring Gmail, Workspace, Microsoft 365, or a custom SMTP host into Eli in about three minutes.

Before you start

Have these three things ready

Anything missing here is the most common reason the connect step fails halfway.

  • A Google Workspace, Microsoft 365, or any IMAP-capable mailbox you control. Personal Gmail works too, paid Workspace deliverability is better.
  • Two-factor auth turned on for that mailbox. Google and Microsoft both require 2FA before they'll let you generate an app password.
  • Permission to generate an app password on the account, or admin-level access if your Workspace blocks app passwords by policy.

Walkthrough

01

Pick your provider

Eli supports four kinds of mailboxes. Pick the one that matches the account you're going to send from, the rest of the steps branch off this choice.

Gmail

Personal @gmail.com address. Needs an app password, 2FA must be on.

Google Workspace

Custom domain on Google. Same app-password flow as Gmail. If your admin disabled app passwords, ask them to flip the policy or use a service account.

Microsoft 365 / Outlook

Office 365 or @outlook.com. Generate an app password under your Microsoft account security.

Custom SMTP / IMAP

Anything else, FastMail, ProtonMail Bridge, Zoho, your own mail server. You'll fill the host and port by hand.

02

Generate an app password

This is where most setups stall. Eli does not log in with your regular password, that path is blocked by Google and Microsoft for third-party SMTP. You need a 16-character app password generated from your account's security panel.

Google / Workspace

  1. Open myaccount.google.com while signed into the mailbox you want to connect.
  2. Go to Security, then turn on 2-Step Verification if it isn't already.
  3. Search the page for App passwords (sometimes hidden under "How you sign in to Google"). Open it.
  4. Name the password Ciela and click Generate. Copy the 16-character string, spaces don't matter, paste it into Eli in step 4.

Microsoft 365 / Outlook

  1. Open account.microsoft.com and sign in.
  2. Go to Security, then Advanced security options.
  3. Turn on two-step verification if it's off, then find App passwords and click Create a new app password.
  4. Copy the generated password and paste it into Eli in step 4. Microsoft only shows the password once, regenerate if you lose it.

Custom SMTP hosts skip this step, your mail provider's panel will either give you the regular password or its own equivalent.

03

Open the connect modal

Head to /dashboard/settings, click the Connections tab, scroll to the Email Accounts card, and hit + Add account. The modal that opens is where you'll paste the app password from step 2.

If you're still in onboarding, the same modal opens from the "Connect mailbox" card on Step 4 of the wizard. Same fields, same test pass.

04

Fill the fields

The modal asks for five things, in this order.

  • ProviderGmail, Workspace, Microsoft, or Custom SMTP. Picking this autofills the SMTP and IMAP host and port for you.
  • Sender nameWhat recipients see in the From line. Use your real name, not a brand, the deliverability lift on a human sender is meaningful.
  • Sender emailThe address Eli sends from. Must match the mailbox the app password belongs to, mismatch is the second-most-common cause of auth failure.
  • App passwordThe 16-character string from step 2. Paste it whole, spaces or no spaces both work.
  • SMTP / IMAP host and portAutofilled for Gmail, Workspace, and Microsoft. Custom SMTP, fill these by hand from your provider's docs. Leave the SSL toggle on unless your host explicitly says otherwise.
05

Test connection

Hit Test and save. The modal opens an SMTP and IMAP handshake against your host, a wrong password fails fast (under two seconds) so you don't sit there wondering. If it passes, the account saves and the modal closes itself.

If it fails, the error code is the thing to read first, scroll down to the Common errors section below for what each one means.

06

Verify in settings

Back on /dashboard/settings, the new account appears under Email Accounts with a champagne dot and the status pill reading active. The daily counter shows 0/50 on day one, Eli ramps that up automatically as the mailbox warms.

If the dot is red and the row says "Disconnected, reconnect to resume sending," the password was rejected after save, head back to step 2 and regenerate.

Common errors

When the test fails, read this first

Five failure modes cover ninety-percent of rejected connections.

  • App password rejected

    By far the most common one. Either the password was typed wrong, or Google rotated it because the mailbox's 2FA was reset, or your Workspace admin disabled app passwords by policy. Regenerate the password (step 2) and paste it again. If your admin blocked app passwords, ask them to allow them for your account or move to a service account.

  • auth_failed

    Same family as above, the host accepted the connection but rejected the credentials. Almost always a wrong password or a sender email that doesn't match the mailbox the password belongs to.

  • Connection timeout / host_unreachable

    The host or port is wrong. For custom SMTP, double-check both against your provider's docs, port 587 with STARTTLS or 465 with SSL are the usual answers. For Gmail and Microsoft, click your provider in the dropdown again to re-autofill.

  • TLS handshake failed

    Your host doesn't support the encryption mode Eli tried. Toggle the SSL checkbox to the opposite state and re-test, that flips between STARTTLS on 587 and implicit TLS on 465.

  • Mailbox not found / 550

    The sender email you entered doesn't exist on that host, or it's an alias the host won't authenticate. Use the literal primary address of the mailbox the app password was generated for.

What happens next

Once Eli has a connected mailbox, he'll start drafting emails the moment you create an Email campaign or an Omnichannel flow that includes an email step. Drafts queue up against the mailbox you connected, daily volume ramps automatically (50 on day one, climbing as the mailbox warms), and replies land in your own inbox so you can handle the human conversations the way you always have. Eli watches for bounces and auth errors and pauses sending if the mailbox flips to disconnected, you'll see the red dot in settings if that happens.

Need help?

Ciela can walk you through any step. Or write to support@ciela.ai and we'll jump on the connection with you.

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