---
sidebar_label: How Email Sending Works
sidebar_position: 2
description: How DocJacket sends transaction email from your connected Gmail or Outlook, who each email sends as, and where replies go.
---

<!-- Canonical: https://help.docjacket.com/docs/messages/how-email-sending-works -->
<!-- Source: docs/messages/how-email-sending-works.mdx -->

# How Email Sending Works

When DocJacket sends email from a transaction, it sends **through your connected
Gmail or Outlook account** — not from a generic DocJacket address. The message
goes out from your email address, a copy lands in your **Sent** folder, and any
reply comes back to **your inbox**, exactly as if you'd sent it yourself.

DocJacket only ever **sends** on your behalf. It does **not** read your inbox.

## Connect your mailbox first

Sending from your own address requires a connected mailbox. Connect Gmail or
Outlook from **Settings > Integrations**. See
[Google Workspace](../integrations/google-workspace.mdx) or
[Microsoft Outlook](../integrations/microsoft-outlook.mdx).

Until a mailbox is connected, manual sends from a deal prompt you to connect one,
and automated email falls back to DocJacket's own email service (a
`@docjacket.com` address) unless your organization requires a connected mailbox
(see below).

## Which account an email sends from

Every transaction email sends from a specific person's connected mailbox,
depending on how it was sent:

| Email | Sends from |
|---|---|
| You compose, reply, or forward from a deal | **You** (the signed-in user) |
| Task emails, reminders, and automation-rule emails | The deal's **assigned coordinator** — or the **account owner** if the deal is unassigned |
| Situation reports and other scheduled reports | The person who **created the schedule** |

If that person hasn't connected a mailbox, see the fallback behavior below.

## Where replies go

Because the email is sent from your real mailbox, replies go straight back to
**your inbox** in Gmail or Outlook — the normal way. You reply from your own inbox
like any other email. (Sent and received messages from a deal are also listed on
the transaction's **Email** tab for reference.)

## Requiring a connected mailbox

Organizations that want every deal email to come from a real mailbox — never a
`@docjacket.com` address — can turn on **Only send transaction email from a
connected mailbox** in **Settings > Organization**.

When this is on:

- Email sends from the sender's connected mailbox, or the account owner's if the
  sender hasn't connected one.
- If no mailbox is connected, a send you trigger yourself is **blocked** with a
  prompt to connect one, and an automated send is **held** until a mailbox is
  connected (the account owner is notified).

When it's off (the default), email still prefers a connected mailbox but falls
back to DocJacket's email service when none is available.

:::tip
Connect a mailbox for every team member who sends deal email, so their messages
always come from their own address and replies reach them directly.
:::