Does it keep watching the folder in the background?

Yes. AutoMailSender monitors the folder and sends new files as they appear, with automatic retry on temporary errors and a macOS notification when each send completes.

Yes. Files go straight from your Mac to your email provider over TLS. There is no cloud, no tracking, and credentials are stored in the macOS Keychain.

AutoMailSender Use case · Folder routing

Auto-email files from a folder on your Mac

Q: Can macOS automatically email files from a folder?

Not on its own, but AutoMailSender adds folder routing: you link a folder to a recipient, and every new file dropped in that folder is emailed automatically over SMTP — no compose window and no manual step.

Link a folder to a person. Every new file that lands in it is emailed automatically — no opening Mail, no compose window, no manual send.

Get AutoMailSender — free for 200 emails

Why macOS can't do this alone

Apple Mail lets you drag a file onto its Dock icon to start a message — but you still address it and hit send every time. There's no built-in way to say "anything that appears in this folder should just go to that person." For anyone with a routine — receipts to an accountant, exports to a client, scans to an archive — that's the same chore, repeated daily.

How folder routing works

Connect your email once — Gmail, Outlook, iCloud, Yahoo, or any custom SMTP server.
Add a watched folder and link it to a recipient (give them a name, color, even their own drop zone).
Drop or save a file into that folder — from any app, or automatically from a scanner, export, or download. AutoMailSender detects it and emails it to the linked person.

It runs quietly in the background, retries automatically on a temporary failure, and shows a macOS notification when each file is sent. Multiple folders can route to different people at the same time.

Real examples

A scanner saves PDFs to ~/Scans → they auto-email to your accountant.
Lightroom exports to ~/Client Deliveries → each export goes straight to the client.
A reporting tool drops a daily CSV → it's emailed to the team without you lifting a finger.

Private by design

Your files go directly from your Mac to your email provider over an encrypted TLS connection. There is no cloud middleman, no analytics, and no tracking. Your email credentials live in the macOS Keychain — never in a file or on a server.

Pricing

Free for your first 200 emails — no subscription and no account. Unlimited sending is a one-time €9.99 in-app purchase.

Download on the Mac App Store

FAQ

Can macOS automatically email files from a folder?

Not on its own. AutoMailSender adds folder routing so every new file in a watched folder is emailed automatically to a linked recipient over SMTP.

Does it keep watching in the background?

Yes — it monitors the folder and sends new files as they appear, with automatic retry and a notification on completion.

Which email providers work?

Gmail, Outlook, iCloud, Yahoo, and any custom SMTP server.