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.
If you start from a task email, the Connect your email button in its drawer or dialog takes you to Settings > Integrations. After you connect Gmail or Outlook, DocJacket returns you to the deal and tab you started from. The Gmail and Outlook connect buttons on a deal's Email tab do the same. If you refuse consent or the connection fails, you stay on Settings > Integrations so the error shows.
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 mailbox 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; approve a draft in the Review queue; or use Review & send | The mailbox chosen in the From field (see Email you send by hand) |
| Task emails, reminders, scheduled emails, portal link emails, and automation-rule emails | The deal's assignee's default mailbox. If the deal is unassigned, or the assignee has no connected mailbox, see Requiring a connected mailbox |
| Transaction Summaries and other scheduled reports | The person who created the schedule |
If that person hasn't connected a mailbox, what happens depends on one organization setting:
- Setting off (the default): automated email goes out through DocJacket's email service from a
@docjacket.comaddress instead. - Setting on (Only send transaction email from a connected mailbox): it goes from the account owner's connected mailbox. If nobody has a connected mailbox, the email waits and the owner is nudged to connect one.
Your default mailbox
Each login has one default mailbox for sending, shared across Gmail and Outlook. It is marked Default for sending under Settings > Integrations (open Manage accounts on the Gmail card, or look under the Outlook Mail card), and you change it by selecting the radio button on a different mailbox.
- Connecting another mailbox never changes your default. Only choosing one does.
- If your default needs reconnecting, it stays your default. Your earliest-connected other mailbox sends in the meantime, and sending returns to your default as soon as you reconnect it.
- If you remove your default mailbox, the earliest-connected remaining mailbox becomes the default.
Automated email leaves from the deal assignee's default mailbox, so each team member's own default decides how their deals' automated email looks to clients.
Email you send by hand
On Review & send, the deal's Email tab (compose and reply), approving a draft in the Review queue (including one-click approve), and the draft composer, DocJacket picks the From mailbox in this order:
- The mailbox you picked in the From field on this email
- The deal's pin, if the pinned mailbox is yours (see below)
- One of your own connected mailboxes whose address matches the deal assignee's mailbox
- Your default mailbox
DocJacket only ever uses mailboxes connected to the login you are signed in with, never a teammate's. If you change the From by hand, DocJacket keeps your choice.
Pinning a mailbox to a deal
When you have more than one mailbox connected, the composer shows a Use this mailbox for all email on this file checkbox next to From. A deal has one pin. Checking the box sets the deal's pin to the mailbox you selected, replacing any earlier pin on that deal, including one a teammate set.
The pin only applies to the person who owns the pinned mailbox: automated email for a deal assigned to them, and email they send by hand. For anyone else the pin is ignored and the usual order applies. If you later move the dropdown to another mailbox, the checkbox clears but the pin stays until you check it again on the mailbox you want.
When the From doesn't match the assignee
If the From isn't the deal assignee's mailbox, a note under it says who the deal is assigned to and which address the email will go from, for example "This deal is assigned to Sam (sam@example.com). This email will go from pat@example.com." If the assignee's address is one of your own connected mailboxes, the note also offers Switch to that address. One click and the From changes. It never offers another member's mailbox.
One person working deals under two logins
Some people work under two logins, for example a transaction coordinator login and a personal agent login, each with its own mailbox. To make email go from the right address on every deal:
- On each login, go to Settings > Integrations and connect both mailboxes.
- On each login, choose that login's Default for sending. Each login keeps its own default, and that default is what automated email from that login's deals uses.
- Assign each deal to the login whose address should send its automated email.
- When you send by hand on a deal, DocJacket starts on your connected copy of the assignee's mailbox, so the email goes out from the assignee's address. If you want a different address on one deal, change the From, or pin a mailbox to that deal.
If a deal is assigned to a login whose mailbox you haven't connected on the login you're using, you'll see the note described above and your own default is used.
When the sender has left your organization
Automated deal email never sends from someone who is no longer an active member of your organization, whether they were removed, deactivated, or moved to another organization. DocJacket treats them as having no connected mailbox, and their mailbox is left alone. Reassign their deals to an active member so automated email goes out from that person's mailbox.
What happens to an email for such a deal depends on the Only send transaction email from a connected mailbox setting (see Requiring a connected mailbox):
- Setting on: the email goes from the account owner's connected mailbox. If the owner has none, the email is held and the owner is nudged to connect one.
- Setting off (the default): the email goes through DocJacket's email service, with the account owner as the Reply-To address, so replies reach the owner.
A one-off email that a departed member scheduled is not sent. It is marked failed with this message: "The person who scheduled this email is no longer an active member of this organization. Open the scheduled message and send it from your own mailbox."
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.)
Because DocJacket never reads your inbox, a reply that only went to Gmail or Outlook does not appear on the deal by itself. To file replies and their attachments on the deal, CC the deal's DocDrop address or auto-forward deal mail to your intake address — see Getting Email Into DocJacket.
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. If the sender hasn't connected one, automated email goes from the account owner's instead.
- 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. So no, connecting Gmail does not make every message trackable; it does the opposite.
| 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.