Documentation

Sending Watermarked Content

Send from the web app, Outlook add-in, or standalone file uploads.

Review page showing individualized versions per recipient

Overview

LeakLocked supports three sending workflows:

  1. Web app — compose, review signatures, and send from the browser
  2. Outlook add-in — send from Outlook while composing
  3. Standalone files — watermark and distribute Word documents outside email

Web app: send an email

Step 1 — Create a draft

  1. Go to Drafts → New Message (or open an existing draft).
  2. Add recipients — one email per recipient. Each gets a unique version.
  3. Write your subject and body. Rich text is supported.
  4. Optionally attach PDF files (watermarked on send per your marking policy).

Drafts auto-save as you edit.

Step 2 — Review signatures

LeakLocked analyzes your content and finds signatures — places where wording can vary:

  • Comma-separated lists: "innovation, customer loyalty, and strategic alliances"
  • Interchangeable phrases: "belief and perseverance"
  • Bullet or numbered lists

For each signature you can:

  • Select or deselect — only selected signatures are used for watermarking
  • See permutation count — how many unique orderings are possible

Important: You need enough permutations for your recipient count. If you have 10 recipients but only 6 possible permutations, some recipients may share the same version. Add more signatures or expand list items before sending.

Step 3 — Review and send

  1. Click Review.
  2. Use the version switcher to preview each recipient's unique copy side by side.
  3. Confirm recipients and content look correct.
  4. Click Send.

Each recipient receives their individualized version via your connected email account (OAuth) or verified domain.

If the Send button is disabled, check the Review page for a version error — usually insufficient permutations for the recipient count.

Outlook add-in

For teams that compose email in Outlook, use the LeakLocked Outlook add-in.

Install the add-in

Your LeakLocked account team will provide:

  • The add-in manifest (or central deployment via Microsoft 365 admin center)
  • Installation instructions for your tenant

The add-in works in Outlook on desktop and web when composing messages.

Connect your account

  1. Open the LeakLocked taskpane while composing an email.
  2. Paste your API token from Account in the web app.
  3. The add-in confirms the token is loaded.

Send a watermarked email

  1. Compose your email in Outlook as usual — recipients, subject, body, attachments.
  2. Open the LeakLocked taskpane.
  3. Click Send with LeakLocked.

The add-in sends your draft through LeakLocked's watermarking pipeline. Each recipient gets a unique version, same as the web app.

Reset the add-in token

In the taskpane, click the link to reset your token, then paste a fresh token from the web app Account page.

Standalone documents

For sensitive files not sent as email attachments:

  1. Go to Files.
  2. Upload a Word document (.docx).
  3. Add recipients.
  4. Review detected signatures in the document text.
  5. Go to Review → send individualized copies.

Use this for board packs, policy documents, or any file shared outside email.

Sent files appear under Files alongside attachments from sent messages.

After sending

  • Sent messages appear under Sent.
  • Each message stores all generated versions for future investigation.
  • From a sent message, use Upload Leak to start an investigation if content leaks.

Next steps