The Ask dock puts a Transaction assistant on top of everything the transaction knows — the transaction record, the documents, and the POS requirements. It opens on the right of any tab from the Ask this file button in the header or with ⌘/ (Ctrl+/ on Windows), and it narrows the tab you're on rather than covering it — so the answer, the page it cites, and what you were reading are all on screen at once. It stays open until you close it, including next time you open a transaction.
What to ask
Anything you'd otherwise dig through the file for:
- What's required to close this transaction?
- What's missing or still outstanding?
- Summarize the key terms.
- Or specifics: What's the loan contingency deadline? Who pays for the sewer lateral inspection?
- Which contingencies are still open? — the assistant answers from the same contingency record the deadline rail uses, which also knows what has been removed (and by which signed form, on what date), waived or struck. It says what the app read off the signed removal, not a legal conclusion, and if a scanned form's text looks different from that reading it tells you so and points you to the original.
Scope: the transaction, a folder, a document — or any mix
Every conversation is pinned to a scope, so answers come from exactly the documents you mean — and most of the time you don't have to set it. The chip in the dock's header always says what the assistant is reading right now, and it follows what you're looking at: open a document in the preview drawer and it reads that document; open a subfolder on Files and it reads that folder; otherwise it reads the whole transaction.
To pin it yourself, click the chip: the Focus list shows the transaction's folder tree and documents with checkboxes — check All documents, a whole folder (its nested subfolders count too), a single document, or any hand-picked combination. A scope you pick by hand stays put until you clear it.
Three shortcuts land in the same place:
- On the Files tab, the chat icon on any folder or document row opens the dock with that scope already selected (so does Ask folder while you're inside a folder).
- On the Overview tab, a value that can't be pinpointed on a page carries a small chat icon; clicking it opens that document's own page — the document on the left, the assistant on the right — with the question written for you. Nothing is sent until you press Enter, and when the answer comes back its citations scroll the document beside it to the passage they quote. This works from the Transaction Record card, the Parties roster, the Milestones dates, and the People tab alike. See The transaction record.
- Open any document and use the chat pane beside the viewer. The assistant sees only that document, and clicking a citation jumps the viewer to the cited page.
A conversation keeps its scope for life — picking a different scope starts a new conversation, and the transcript marks where the switch happened. History lists every conversation on the transaction, each badged with its scope; selecting an old one switches the scope back to match it.
It shows its work
While it works, a status line shows what the assistant is doing — Reading the transaction record, Checking POS requirements, Searching a document — and the answer itself comes with citations linking to the source document (and page, where available). Click a citation to verify the answer against the paper.
AI answers can be wrong, and they aren't legal or tax advice — a note under the question box says so. The requirement list the assistant reads is what LetterScript maps to the address, not a complete legal answer: it can't see facts only the seller knows, exemptions that turn on the kind of sale, or when each disclosure was actually delivered. For questions like whether someone can cancel, whether a seller is exempt, or what tax is owed, the assistant gives the facts it found and points you to your broker, escrow, or an attorney or tax professional.
Past conversations live under History, most recently active first — asking a follow-up in an older conversation moves it back to the top. Pin the ones you keep returning to (they stay in a Pinned section on top), rename them, or delete them from the same menu. They're searchable from the ⌘K palette too.
Usage
Each question uses a smart answer. On purchased transactions smart answers are unmetered — no question allowance and no per-question charge. Your free first transaction includes 10 smart answers; any purchase lifts that cap. See Plans and usage.
Answers also draw on the transaction's AI-processing allowance, which reading its documents uses too. The allowance covers far more than a typical transaction needs; if a transaction ever reaches it, the assistant tells you why instead of leaving a blank reply. A question that never reached the assistant goes back into the box so you can send it again.