Can I send a whole batch of receipts at once?

Yes. Drop multiple files together and AutoMailSender sends them with progress and automatic retry. You can also combine multiple files into a single email.

Is my accountant's address and my email password safe?

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

AutoMailSender Use case · Bookkeeping

Email receipts to your accountant — automatically

Q: How do I email receipts to my accountant automatically on a Mac?

Install AutoMailSender, set your accountant as a recipient once, and either drop each receipt onto the app to send it instantly, or point a watched folder at them so every receipt saved there is emailed automatically.

Set your accountant up once. Then drop a receipt and it's on its way — or let a watched folder send every receipt for you. No compose window, ever.

Get AutoMailSender — free for 25 emails

The daily chore this removes

If you're a freelancer, contractor, or run a small business, you probably forward receipts, invoices, and timesheets to your bookkeeper constantly. Each one is the same dance: open Mail, type their address, attach the file, add a subject, send. Multiply that across a month and it's an hour of pure friction.

Two ways to make it instant

Drag & send: add your accountant as a recipient once. From then on, drop a receipt onto AutoMailSender (or its screen-edge Quick Drop tab) and it's emailed immediately — no message to write.
Fully automatic: point a watched folder (say, ~/Receipts) at your accountant. Save or scan a receipt into it and AutoMailSender emails it on its own.

Nice touches for bookkeeping

Include the filename in the subject automatically, so receipts are easy to file.
Combine several files into one email, or send them individually.
Automatic retry if your provider hiccups, plus a notification when each send lands.

Private and native

AutoMailSender is a small native macOS app — no Electron, around 1.7 MB. Your receipts go directly from your Mac to your email provider over an encrypted connection. No cloud, no tracking, credentials kept in the macOS Keychain. Works with Gmail, Outlook, iCloud, Yahoo, or any custom SMTP.

Pricing

Free for your first 25 emails — no subscription, no account. Unlimited sending is a one-time €9.99 in-app purchase. Need scheduled or recurring sends, or more than two sender accounts? Enterprise is a one-time €49.99.

Download on the Mac App Store

FAQ

How do I email receipts to my accountant automatically on a Mac?

Set your accountant as a recipient once, then drop each receipt to send instantly, or use a watched folder so receipts saved there are emailed automatically.

Can I send a batch at once?

Yes — drop multiple files together, with progress and automatic retry, and optionally combine them into one email.

Does it work with Gmail and Outlook?

Yes, plus iCloud, Yahoo, and any custom SMTP server.