Every transaction has a built-in mailbox on its Email tab. Messages you send from there, and every reply that comes back, stay with the transaction — so the whole conversation history lives next to the documents and deadlines it's about.
Transaction email is included on every LetterScript workspace (see Plans and usage). Your free first transaction includes 10 sent emails; transactions on purchased transactions send without a meter.
The transaction's own email address
Open a transaction and go to the Email tab. At the top you'll see the transaction's unique address (it looks like d-a1b2c3d4e5f6@deals.letterscript.com) — click it to copy.
That address is the magic piece:
- Replies route themselves. Anything you send from the Email tab carries this address as its reply-to, so when escrow or the other agent hits Reply, their answer lands back in this tab — in the right conversation thread.
- CC it from anywhere. Add the transaction address as a CC on any email you send from your own inbox, and a copy files into the transaction automatically.
- Attachments come along. Files on inbound email are stored with the message — download them straight from the thread.
The address is unguessable on purpose: mail to anything that isn't a live transaction address is dropped, so the tab stays free of spam.
Emailed documents file themselves
When someone on the transaction emails a contract, disclosure, or report to the transaction address, the attachment doesn't just sit on the message — it's added to the transaction's documents and processed like an upload: the text is read, the document is classified, and the transaction record, checklist, and timeline update from it. Forward the executed purchase agreement and the transaction builds itself.
A few things happen behind the scenes to keep this safe and tidy:
- Senders you trust file automatically. A sender is trusted because of something you (or a teammate) did: you added them to the transaction's Parties, typed their address onto a party, verified their address on the People page, chose to trust them, or emailed them from the transaction (a party you added, or someone who wrote in first) — or they're a member of your workspace. Emailing a brand-new address from the transaction doesn't make it trusted: the composer marks it Not on this transaction, and what that person sends waits for your OK. Nor does emailing someone LetterScript found in the documents, if they've never written in (see the next point). And emailing someone trusts only what they send afterwards: files they'd already sent stay held, with the reason "This arrived before you emailed them", until you add them. An attachment that filed shows an In documents badge; one that filed on its own is marked · auto, and the message says why, for example "Filed automatically — You added them to this transaction", with Stop trusting this sender beside it. When files that were waiting for your OK file themselves later — because you trusted the sender some other way — a notice says how many, from whom, and why, with Review.
- An address LetterScript found isn't trusted on its own. When the documents name someone, they're added to Parties with the email the paperwork shows — but a document can name anyone, including the person who sent it, so that address doesn't let their mail file itself. Their files wait for your OK, and the banner says who the record says they are and where the address came from, for example "Dana Reyes (Escrow) — found on Escrow_Contact_Sheet.pdf", with Trust this sender. When the only file printing the address is one that same sender emailed in, the banner says so — "found only on Escrow_Contact_Sheet.pdf, which this sender emailed" — because a sender's own paperwork vouches for nothing. The same goes for an address LetterScript filled into a party you added without one, and for people that come from Follow Up Boss, whether they arrived with Import from FUB or a later sync. Once you edit the address on the party yourself, or verify it on the People page (where a person from Follow Up Boss is marked From Follow Up Boss until you do), it counts as yours; a verification covers the address the card had when you verified it, so a phone number or company filled in later doesn't undo it, but an address filled in later isn't covered. Taking a found person off Parties and clicking Undo puts them back as they were found, still not trusted.
- Unknown senders wait for your OK. Their files are held, with an Add to documents button on each attachment and a banner offering Trust sender & add all — one click files everything in that message and auto-files whatever they send later. Messages that fail email authentication checks are held too, even from a familiar-looking address, so a forged "listing agent" can't quietly change your transaction record. The banner names the reason as it stands now, not as it stood when the mail arrived: trust the sender afterwards and it changes to "… is trusted now — their files are still waiting for your OK", so a failed authentication check is never dressed up as a roster problem or the reverse.
- A file you left out stays out. If you add some of an email's attachments and leave another where it is, nothing files that one for you later — not trusting the sender, not a change to Parties, not deleting the file you did add. It waits until you click Add to documents on it (or Trust sender & add all on that message).
- Trusted senders, and stopping trust. The mailbox's Settings menu → Trusted senders lists every trusted address with the reason it's trusted, the addresses LetterScript found that are waiting for you (each with Trust), and the ones you've stopped trusting. Stop trusting really stops it: their mail waits for your approval even if they're still on Parties, you've emailed them, or they're in your workspace, and the confirmation says which of those it overrides. Files already in documents stay. LetterScript also won't put a stopped address onto Parties from the documents or Follow Up Boss — a party already showing it keeps it until you change it. Unblock puts the address back to how it stood before.
- A deleted document can be put back. If an attachment filed and the document was deleted later, the attachment shows Removed rather than a green In documents badge over nothing — and Add to documents returns, because the file itself is still held safely. Nothing files it again on its own, even after you trust the sender; only that click does.
- Attachments that didn't file now say so. Something the mailbox couldn't take — a file type it doesn't read, an inline signature image, an attachment that errored on the way in — carries a Not filed or Couldn't file tag, and hovering it gives the reason. The message shows a line saying how many weren't added, and the conversation list marks the thread N not filed, so you can see it without opening every message. The file is still there to download; it just isn't in the transaction's documents.
- Duplicates are caught. The same executed contract often arrives three times — from the agent, from escrow, from the coordinator on the other side. Identical copies get a Duplicate badge and aren't processed again, so they don't clutter the transaction or spend your pages.
- LetterScript's own sheets and letters aren't filed as documents. An attachment that's a sheet or letter made with LetterScript, such as a dates sheet or kickoff letter you sent coming back on a reply, or one another LetterScript user made and sent to the transaction, is marked Our own deliverable instead of being added to the documents. A document you attached from the transaction is different: when it comes back, it's handled like any other attachment, so a copy of one still on the transaction is marked Duplicate, and one you've deleted since can be filed again.
- Link-only emails get a nudge. If a message says "here's the signed contract" but carries a DocuSign or Drive link instead of a file, the thread shows a reminder to download and upload it yourself — LetterScript never follows external links on its own.
For known senders, the email text itself joins the transaction's record too: facts that only live in correspondence — an escrow officer's direct line in a signature, a lender's status update — become searchable, citable in transaction chat, and feed the extracted record. An email saying a contract date moved may not be an enforceable extension, though: get the change in a signed extension or amendment and upload that. On your free first transaction, each indexed email counts as one page of its included allowance; purchased transactions have no page meter.
Writing an email
The first time you send, LetterScript asks you to confirm your sending address — a one-time step at the top of the tab; New email and Reply stay disabled until you do it. Once confirmed, click New email and address it by picking from the suggestions (the transaction's parties, the people it's shared with, and, as you type, your People directory), choosing a group, or just typing an address and pressing Enter. Cc and Bcc beside the To line open those lines; a Bcc recipient is hidden from everyone else on the email.
Mail then goes out from your confirmed name and address — the composer shows "Sending as …" — with replies still routed to the transaction so they file back here. Until you've confirmed an address, messages are sent from your name "via LetterScript" instead. Sending is plain text — what you type is what they get.
Attach adds files from the transaction: Documents from this transaction…, or a generated Dates sheet, Kickoff letter, Closing-week summary or Forms list that you review before it's attached. Nothing is uploaded from your computer. One email carries up to 10 attachments, 10 MB in all. Some documents can't be emailed at all, such as a form LetterScript filled in or a W-9 carrying a taxpayer ID; the picker shows each one greyed out with the reason. On a workspace that hasn't bought a transaction yet, neither can a document that reads like wiring or payment instructions: when you tick one, it's greyed out with This can't be emailed from this workspace — share it another way. Send and share from a transaction covers what can be attached, what each file is called when it goes out, Cc and Bcc, and what happens with replies from people who aren't on the transaction.
To reply inside an existing conversation, open the thread and click Reply — the recipient and subject are pre-filled and the message threads correctly in the recipient's email client too. When a conversation has more than two people on it, Reply all appears beside it with the number it will reach; it carries everyone still on the thread into Cc, minus you and the transaction's own address. Every recipient is a chip you can remove before sending, so reply-all is a starting point rather than a commitment.
An unfinished message keeps itself. If you leave the composer — switching tabs, pressing Back, or closing the browser — the draft is saved on this device and restored the next time you open that reply, with a note saying when it was saved and a Start fresh button to throw it away. Discard asks first, and offers Leave it saved if you only meant to step away. Drafts are cleared once the message sends, and expire after a week. Attachments and Bcc recipients are kept with the draft too. A message started from a letter or a generated sheet (below) keeps a draft of its own, and so does one started from a person's address on the People tab (one per person), so none of them and a plain New email ever overwrite each other.
Starting an email from elsewhere on the transaction
You don't have to be on the Email tab to start a message. Each of these opens the composer here, and nothing goes out until you click Send:
- Send → New email, in the transaction's header, opens an empty composer.
- Send → Kickoff letter, Wire-fraud warning, Closing-week summary or Congratulations opens a review screen where you check, and can correct, every fact the letter is built from. Email… there opens the composer with the letter already written and its To line filled in from the people in the letter's roles. A party marked Unconfirmed on the People tab isn't put on the To line; a note above it names them, and any role with no email address on the transaction, so you can add them yourself. Send and share from a transaction covers what each letter contains and how the review works.
- Send → Dates sheet or Forms list, then Attach to an email on the review screen, opens the composer with the reviewed file already attached.
- Send → Email the read-only link… opens a message carrying your newest working read-only link and what it shows.
- A person's email address on the People tab. Click it and the composer opens addressed to them, or with the unfinished message you'd already started to them, announced as restored. If the person is marked Unconfirmed or Linked to the wrong contact, LetterScript asks first; Email anyway goes ahead.
- Draft email, under the soonest deadline in the Overview tab's What's next card, opens the composer with that deadline and the property's address as the subject. A deadline you renamed goes into the subject under its standard name, so your own wording stays private.
If you haven't confirmed your sending address yet, each of these takes you to that step at the top of the tab instead of opening the composer. Confirm it, then start the email again.
On a transaction shared with you, there's no Email tab, so clicking an address on the People tab opens your own email app instead. The same happens on a transaction you own when your plan doesn't include email: the Email tab still shows the mail already stored there, but nothing new can be written from it, so there's no Email group in the Send menu or Draft email button either. Addresses in your People directory always open your own email app.
Drafting with AI
In the composer, click Draft with AI, describe what the email should say — "ask escrow to confirm the closing date and list what's still needed" — and click Draft. The assistant writes a subject and body using only what it knows about this transaction (its record, parties, deadlines, and the conversation so far), and you can edit everything before sending.
On your free first transaction, each AI draft uses one smart answer from its included allowance — the same allowance the transaction assistant uses. Transactions on purchased transactions draft without a meter.
If a draft discusses moving money or changing payment details, the composer says so before you send: messages like that go out with a wire-fraud verification notice added for the recipient. A draft that contains a suspicious link is flagged the same way, with the link shown. Neither blocks sending — genuine closing email discusses wires — and the notice clears as soon as you edit the message, because what gets checked is whatever you actually send.
Drafts
LetterScript doesn't write or send a transaction's email on its own: nothing is drafted when a transaction changes stage or a deadline gets close, and nothing is sent without you. (The one automatic email left is a meeting reminder, and only if you turn it on.) The Drafts strip above the conversations holds the drafts still waiting for you: a follow-up drafted from a task, and any kickoff, wire-fraud, closing-week, congratulations or reminder drafts written before automatic drafting was removed. Each is labelled with what it is. Open one to change its recipients, subject or text and send it, save it for later, or discard it. Nothing in the strip sends until you click Send. One of the older automatic drafts that nobody has changed yet can be refreshed with the transaction's latest details when its record changes — a corrected escrow company, say. If that happens while you have it open and you've changed it, saving or sending is refused rather than putting your older copy back over the refresh: nothing is saved or sent, your text stays in the draft, and the new version is shown above it. Use the new draft drops your changes; Keep mine keeps your text, and your next Save for later or Send replaces the refreshed draft with it. The phone app offers the same choice: Show the new draft or Keep my text.
Recipient groups
Open the mailbox's Settings menu (the gear button in the top-right) and choose Recipient groups to create named CC lists for this transaction — for example "Buyer side" (buyer + buyer's agent) or "Escrow + lender". In the composer, picking a group adds all of its members in one click. Groups belong to the transaction, so each transaction can have its own.
Reading and threads
Conversations are grouped into threads on the left; unread ones are marked with a green dot and open automatically marks them read. Outbound messages show a delivery state (Sent → Delivered), so you know it arrived. If it didn't reach someone, the message says who and why — for example an address that doesn't exist, a full mailbox, or a message too large for their system — with their mail server's own words underneath in case their IT needs them, and the thread shows not delivered in the list. When only some recipients bounced, the badge says how many (for example 1 of 3 bounced). A delay shows the same way while delivery is still being retried. One thing we can't see: if someone forwards your email and their own system blocks the forwarded copy, that notice goes to them, not to you — so add everyone who needs a copy with Cc or Bcc instead of asking them to forward it. On a message you sent, the recipient line also lists your Bcc: recipients (only you see it), and each attachment downloads the file exactly as it was sent. An attachment whose document has since been deleted from the transaction shows as not available.
All transactions at once: the Inbox page
Inbox in the top bar opens the cross-transaction view: every transaction listed with its unread count and latest message, most recent activity first. Expand a transaction to see its conversations, and click any conversation to jump straight into that transaction's mailbox with the thread open. All mail / Unread narrows the list to transactions with something still unread, and the filter box narrows it by transaction name, address, sender, or subject — handy once several transactions have active email.
Good to know
- Recipients see the message from your confirmed sending name and address (or, before you've confirmed one, from your name "via LetterScript"), with replies routed to the transaction address — not from your personal email account.
- One send can address up to 25 people across To, Cc and Bcc. Reply all never includes the Bcc recipients of an earlier message.
- The mailbox is per-transaction. Mail never crosses between transactions, even when the same people are on both.