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:
- Start a new email.
- On the ribbon, open MailTail. The panel opens on the right and loads your signature.
- 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.