AutoMailSenderBest Mac apps to email files automatically
If you email the same kind of file to the same people over and over, AutoMailSender is the most direct option — a drag becomes a sent email, or a watched folder auto-mails on its own. It's free for your first 25 emails, then a one-time €9.99 (no subscription). For broader "do anything when a file appears" automation, Hazel or Zapier reach further.
Try AutoMailSender — free for 25 emailsThe short list
"Automatically" can mean two different things: one drag = one sent email, or a file lands in a folder and gets mailed with no action at all. The apps below cover both, and none of them need you to keep a compose window open. Here's how they compare.
| App | No scripting | Local / private | One-time price | Folder → email | Best for |
|---|---|---|---|---|---|
| AutoMailSender | Yes | Yes | Yes | Yes — built in | Emailing files to preset people, on repeat |
| Hazel | Some — rules, plus scripts for email | Yes | Paid, one-time | Yes, via a rule/script | Broad folder rules and file organising |
| Automator / Shortcuts | Fiddly to wire up mail | Yes | Free (built in) | Yes, with Folder Actions | Free native automation, if you tinker |
| Dropzone | Mostly — drag targets | Yes | Paid, one-time | Drag target, not a watched folder | Drag-and-drop actions across many tasks |
| Zapier | Visual builder | Cloud service | Subscription | Yes, via cloud storage triggers | Connecting many web apps together |
How each one stacks up
AutoMailSender — Purpose-built for exactly this task: send a file to people you email repeatedly. You set up recipients once, then a drag-and-drop sends with no compose window, and watched folders can auto-email on their own. Native macOS (macOS 14+, ~1.7 MB), works with Gmail, Outlook / Office 365, iCloud, Yahoo or any custom SMTP over TLS, credentials in the Keychain. Free for 25 emails, then a one-time €9.99; €49.99 Enterprise adds scheduled/recurring sends. It doesn't try to be a general automation tool — that focus is the whole point.
Hazel — A paid, well-loved folder-watching utility. It shines at watching folders and acting on files: rename, move, sort, tag. It can email a file, but usually by running a script or handing off to Mail, so the email side takes setup. If you want one tool for a lot of file housekeeping and don't mind wiring up the mail step, Hazel is broad and powerful.
Automator / Shortcuts — Free and native. With Folder Actions you can trigger a workflow when a file is dropped, and route it into Mail. It's genuinely capable, but the email step is fiddly to get reliable, and there's no preset-recipient concept — you build it yourself. Great if you enjoy assembling automations and want to spend nothing.
Dropzone — A paid drag-target utility that puts actions behind a grid you drop files onto. Excellent as a general "drop a file, do a thing" hub across many tasks, and it can hand a file to email. It's drag-driven rather than a true watched folder, so it's less about unattended automation and more about fast manual routing.
Zapier — A subscription cloud service that connects hundreds of web apps. If your files already live in cloud storage, a Zap can watch for a new file and email it. It's the most flexible for multi-app workflows, but it runs in the cloud (not local/private) and it's overkill if you just want files off your Mac to a few fixed people.
Which should you pick?
Pick AutoMailSender if the job is "the same file to the same people, again and again" and you want it done with a drag and no subscription. Pick Hazel or Zapier if you need broad automation — sorting, renaming, multi-app pipelines — and emailing is just one branch of it. Pick Automator/Shortcuts if free and native matters most and you're happy to tinker.
Download on the Mac App StoreFAQ
What's the easiest way to email files automatically on a Mac?
AutoMailSender is the most direct: preset your recipients once, then a drag sends the file — or drop it in a watched folder and it mails itself. No scripting and no compose window.
Can Hazel or Automator email files without extra setup?
They can email files, but usually by running a script or handing off to Mail, so the email step takes configuration. They're stronger as general automation tools than as a one-tap file sender.
Do any of these keep my files private?
AutoMailSender, Hazel, Automator and Dropzone all run locally on your Mac. Zapier is a cloud service, so files pass through its servers — fine for many people, but not local-only.