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 or Microsoft Outlook.
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:
| 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.
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.
Can you tell if a client opened an email?
Sometimes — and it depends on which mailbox actually sent the message, which is the same distinction as the rest of this page.
| How it was sent | Open tracking |
|---|---|
| From your connected Gmail or Outlook | No. DocJacket hands the message to your mailbox and it goes out as your own email. |
| From DocJacket's email service (no connected mailbox — the fallback described above) | Yes. DocJacket records when it was delivered and when it was first opened. |
When an email is tracked, an Email opened entry appears on the transaction's activity timeline, and the message shows its delivery status.
This surprises people, so it's worth stating plainly: connecting your mailbox gives up open tracking. That's not a setting you can toggle — it's a consequence of the message being sent by Gmail or Outlook rather than by DocJacket. Once Gmail sends it, it's an ordinary email from your account, and DocJacket has no more visibility into it than into anything else you send from Gmail.
Most teams consider that the right trade. Sending from your own mailbox means better deliverability, replies land in your inbox, and the message looks like it came from you — which matters more on a deal than knowing whether someone opened it.
Regardless of how a message was sent, the transaction's Email tab lists what was sent and what came back. Replies file themselves onto the deal when you started the thread from DocJacket — see Getting Email Into DocJacket. Read receipts and "has my client seen this" are the only things that depend on the sending path.