Getting Started

Automatic signatures in classic Outlook for Windows

Last updated 6 August 2026

MailTail applies your signature to new emails automatically in the classic Outlook desktop app on Windows, the same as Outlook on the web and on Mac. The add-in signs in on its own and pulls your current signature each time. There's nothing to switch on and no button to press per email.

If a signature doesn't appear the first time

Occasionally, on a machine that's just had the add-in deployed, the first new email can come through without a signature. Open the MailTail panel once to sort it:

  1. Start a new email.
  2. On the ribbon, open MailTail. The panel opens on the right and loads your signature.
  3. Start a fresh email. The signature now applies on its own.

Opening the panel gives the add-in a signed-in starting point and saves a copy of your signature to your mailbox as a backup, so new emails stay covered even if a sign-in is ever slow.

Still not appearing?

  • Fully restart Outlook. Close it completely and reopen it, so it picks up the latest version of the add-in.
  • Check auto-apply is on. In the MailTail panel, the "Auto-apply on desktop/web" switch should be on.
  • Then start a new email.

If it's still blank, email us at support@mailtail.io and tell us it's the classic Outlook desktop app on Windows.

Outlook on the web and Mac

Nothing to do. Signatures apply automatically on new emails.

Still stuck? Email support@mailtail.io with your Outlook version and we'll take a look.

More in Getting Started