Batch-send emails with attachments on a Mac

macOS Mail has no easy built-in mail merge or batch mode, so honest batch-sending means a third-party tool. AutoMailSender sends many files to many recipients in one go — dropping multiple files, with live progress and automatic retry on failures, over SMTP and with no compose window. Free for your first 25 emails, then a one-time €9.99.

First, the native macOS reality

Apple Mail is built for one message at a time. There's no simple built-in mail-merge or batch feature that pairs a stack of files with a list of recipients and sends them in one pass. You can script it with AppleScript or Automator if you're comfortable there — that's genuinely powerful and free, but it's real setup and maintenance, not a quick job. For most people, batch-sending with attachments means reaching for a dedicated tool.

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 your recipients or groups — set up the people the batch should reach, optionally with per-recipient drop zones.
3. Drop multiple files to build the batch — drag several files in at once and queue them for the recipients you chose.
4. Watch progress and let retry handle failures — AutoMailSender sends the batch over SMTP, shows live progress, and automatically retries temporary errors so nothing quietly gets stuck.

Blocked file types are wrapped in a password-protected AES-256 ZIP so they still arrive. Everything runs on your Mac — no cloud, no servers, no tracking. If you also want sends to fire on a schedule or repeat, that's part of the one-time €49.99 Enterprise tier.