Attachments & client context

You’ll often want to send a file with a message — a signed letter, a draft return, a W-2 the client uploaded. Assure Pro handles attachments a bit differently from a normal email client: every attached file is also a Document in the client’s documents tab.

How to attach a file

In the compose form, two attach buttons show up when a client is selected:

Both produce attachment chips above the compose body. Each chip has the filename and a remove (×).

How to pick from existing documents

Click the file icon. A popover opens with a two-pane layout:

┌──────────────────┬──────────────────────────┐
│  Folder tree     │  Documents in folder     │
│                  │  ────────────────────    │
│  ▶ Workpapers    │  ☐ W-2 — 2024.pdf       │
│  ▼ Source docs   │  ☐ 1099-MISC.pdf        │
│    • W-2s        │  ☐ Bank statement.pdf   │
│  ▶ Tax returns   │                          │
│  ▶ Messaging     │                          │
└──────────────────┴──────────────────────────┘
              [Cancel]  [Attach 2 docs]

[Screenshot: Document picker with folder tree on the left and selectable docs on the right]

Picking documents

• Click a folder on the left and its documents load on the right.
• Click a document name to open a preview side-pane (filename, type, size, last modified).
• Check the box to attach. Multi-select is supported.

Click Attach to confirm. The chips appear above the compose body.

What’s filtered out

• Trashed documents — not shown.
• Internal-only documents — visible to firm-side compose, but Assure Pro removes them before delivery when the recipient is a client. You’ll see a toast: “Internal document removed from email.”

Internal docs can’t leak to clients through messaging — Assure Pro enforces this on its own, no toggle required.

What about the Unsorted bucket?

If a client has uploaded files but none are filed, the Unsorted bucket appears at the top of the folder tree. Pick from there the same as any other folder.

How to upload a new file

Click the paperclip icon. A native file picker opens.

Where the file lands

When you upload from the compose form:

1. The file is saved to the client’s Messaging folder (created if missing — one auto-folder per client for message attachments).
2. A document record is created.
3. The file is added to your message’s attachment list.

The Messaging folder isn’t special — it’s the default home for files you attached in chat. You can move them later from the documents browser.

Constraints

• Max file size: 25 MB per file (same limit as the documents area).
• Allowed types: PDF, JPEG, PNG, HEIC, TIFF, plus Office files (DOCX, XLSX, PPTX).
• Multiple files: pick multiple in the native dialog and each becomes its own chip.

Files over 25 MB are refused with a toast. Files of an unsupported type show “Unsupported file type.” See Documents — Browsing & uploading for the full list of accepted types.

Attachment chips

Each attachment shows above the compose body:

┌─────────────────────────────────────┐
│  📄 W-2 — 2024.pdf  ×               │
│  📄 1099-MISC.pdf   ×               │
└─────────────────────────────────────┘

Click the × to remove an attachment from the current message. Removing doesn’t delete the underlying document — it unattaches it.

You can mix and match — picker for existing docs and upload for new — in the same message.

How each channel handles attachments

For portal messages, the client doesn’t get the file as an attachment — they get a link that opens in their portal. This keeps the file under access control.

How attachments show up in activity

Every attachment generates an activity log entry:

“Sarah attached W-2 — 2024.pdf to a message”

The entry shows up on the client’s profile timeline, in the documents tab, and in the conversation’s audit when you click into a message bubble.

How to use the client context drawer

In the thread header (right side), a small i button toggles the context drawer — a right-side panel that summarizes the selected client.

What’s in the drawer

Each item links to the client’s main profile for the full detail (see Clients overview).

Why it’s useful

You’re mid-reply to a question about Form 5471 and want to check what entity type the client is. The drawer is one keystroke (i) instead of opening a new tab. Especially handy for unfamiliar clients you’ve recently been re-assigned.

Keyboard

How clients are notified when you attach files

Common patterns

”Send the draft 1040 to the client”

1. Generate the draft PDF (see Documents overview).
2. Open the client’s thread in Communications.
3. Pick channel Email.
4. Compose body — “Here’s your draft 1040 for review. Let me know if anything looks off.”
5. Click the document picker → Tax returns → check “1040 — Draft v1”.
6. Click Send.

”Ask the client for a missing W-2”

1. Open the thread.
2. If the latest incoming message mentions a doc, the suggested-action chip Request document appears.
3. Click it, pick W-2, and click Send.

Or, skip the chip:

1. Compose the message: “We’re missing a W-2 — can you upload it?”
2. Click Send.
3. The client sees a portal notification with a link to Documents.

”Attach a screenshot I just took”

1. Save the screenshot to your computer.
2. Open the thread.
3. Click the paperclip and pick the screenshot.
4. It uploads to the Messaging folder and attaches to the message.
5. Click Send.

Limits

Permissions

The picker respects per-client access rules — if you’re not assigned to the client, you can’t browse their documents.

Next

• Documents — Browsing & uploading — where attachments come from.
• Inbox & triage — where the compose lives.
• AI drafts & intent — drafts that reference the attached files.