The document checklist

The document checklist is the set of document requests inside an organizer. Each request asks for one specific document — for example, “W-2 from primary employer”. The client uploads, Assure Pro classifies, and the request gets marked Uploaded.

There’s no separate “AI checklist” feature. The organizer’s document items are the checklist. The personalization comes from:

• The template you picked (return-type-specific).
• Conditional logic (items hidden until a triggering question is answered).
• Scenarios bundled into the template.

Adding a checklist item

When you build a template, every document item you add becomes a checklist row in the resulting organizer.

In the template editor:

1. Click into a section.
2. Click + Add document.
3. The config drawer opens. Fill in:

The drawer saves automatically. The item appears in the section’s item list with a Document type chip.

What the client sees

Inside the organizer wizard, document items render as a drop zone with the label:

W-2 from primary employer *

  ┌────────────────────────────────────────────┐
  │                                            │
  │   Drag and drop a file here, or click to   │
  │   pick one                                 │
  │                                            │
  │   Take photo (mobile)                      │
  │                                            │
  └────────────────────────────────────────────┘

When the client uploads:

1. Assure Pro stores the file securely in the client’s documents.
2. AI classifies the document by type.
3. If the classification is confident enough, the file auto-matches the checklist request.
4. The drop zone is replaced with a thumbnail, filename, and status badge.

[Screenshot: Document checklist in the client wizard]

Statuses per item

The reason for N/A is visible to you in review.

Conditional documents

A document request can be conditional on an earlier question. Common pattern:

1. Question: “Did you sell any stocks or crypto in 2025?” (Yes / No)
2. Document: “1099-B from each broker” — Show only if conditions are met → equals Yes.

Until the client answers Yes, the document doesn’t appear in the checklist. The instant they switch the answer, the document appears as a new row.

In the editor, the question shows a sub-row: “Triggers: 1099-B from each broker”. This is your visual marker that the question controls a document request.

What “matching” means

When a client uploads a document, Assure Pro tries to match it to a checklist request based on:

1. AI classification — the document type the classifier assigned (for example, W-2).
2. Matching checklist rows — rows whose document type equals the classified type.

If exactly one open request matches, the upload is auto-attached.

If multiple requests could match (you asked for two W-2s and the client uploaded one):

• The first unfulfilled matching row gets the upload.
• Other matching rows stay pending — they’re waiting for the next upload.

If no requests match (the classifier picked a type you didn’t request):

• The document still lands in the client’s documents folder.
• The checklist row stays pending.
• You see it in the Unmatched documents group when reviewing.

Matching documents that arrive outside the organizer

Documents emailed to you, dropped via your firm-side upload, or saved into client folders directly can still match checklist items — as long as the classified type matches an open request and the engagement linkage is set.

The match is automatic. Assure Pro runs the match on every new upload.

Tracking the checklist in review

Open the organizer in review. Document items show:

• Uploaded — green badge with a View document link to open the file.
• Pending — amber badge.
• N/A — grey badge with the client’s reason.

The section header shows item counts (for example, “Income · 3/5 items”). The overall header shows the same as a progress bar.

Re-requesting a document

If the client uploaded the wrong file:

1. In review, open the document by clicking it.
2. Either delete it from the Documents module, or
3. Click Request changes on the organizer with a message: “Please upload the W-2 again — the one you sent is for the wrong year.”

The organizer changes to Changes requested and the client can re-upload.

Document-missing blockers

If a required document hasn’t been uploaded by the expected date, Assure Pro can auto-create a Document missing blocker on the engagement (see Blockers). The blocker:

• Names the specific missing document.
• Resolves itself when the document is uploaded, classified, and matched.
• Shows up in the AI morning brief under “Stuck”.

Tips

”I want the same checklist for every 1040 client”

Put your standard document items in a template and mark it as the default for 1040 in the current tax year. Every new 1040 engagement uses this template.

”Some clients have an HSA, some don’t — how do I avoid asking everyone?”

Add an early-section Yes / No: “Did you contribute to or take distributions from an HSA in 2025?” Conditional-show the Form 5498-SA and Form 1099-SA document items on equals Yes. Clients who say no never see those rows.

”Client uploaded a 1099 I didn’t ask for”

It still gets classified and saved in their client folder. If you DO need it for the return, check the engagement’s documents — it’s there. Otherwise leave it; you’ll archive at year-end.

Permissions

Next

• Document classification — what drives auto-matching.
• Extraction & review — pulling field values out of uploaded forms.
• Question types & conditional logic — building conditional document rules.