Send the same attachment to multiple people on a Mac

In Apple Mail you add several addresses (or BCC) to one message and send it once. With AutoMailSender you add the recipients — or a saved group — one time, then dropping the file a single time sends it to everyone over SMTP, no compose window. Free for your first 25 emails, then a one-time €9.99.

First, the native macOS way

Apple Mail already handles this: compose one message, add each person to the To field, and attach the file once. If you'd rather recipients not see each other's addresses, put them in BCC instead. It's free and it works fine for a one-off.

The friction shows up when it's the same group, over and over — a weekly report to the team, a price list to a set of clients. Every time you retype or re-pick the addresses and rebuild the message. That repetition is what a dedicated tool removes.

Do it with AutoMailSender

1. Connect your email account once — Gmail, Outlook / Office 365, iCloud, Yahoo, or any custom SMTP server. Credentials stay in the macOS Keychain.
2. Add multiple recipients or a group — bundle the people who always get the same file into one named group.
3. Drop the file once — it's sent to everyone in the group in one action, over SMTP, with no compose window.
4. Use per-recipient drop zones for regulars — give the people you send to most their own drop zone, so next time it's a single drag.

Apple Mail can attach a file. AutoMailSender removes the email entirely — set up recipients once, then a drag-and-drop is a sent email. Everything runs on your Mac: no cloud, no servers, no tracking.