AutoMailSender Use case · Bookkeeping

Email receipts and bills to Xero from a Mac

Xero gives your organisation its own email address for supplier bills. You can send files to it from your Mac. AutoMailSender does that for you: drop a file, or save it into a folder.

Get AutoMailSender · free for 25 emails

What Xero expects

This part comes from Xero, not from us. Read Xero Central's article on emailing bills to your organisation. It tells you how to find your forwarding address: in Xero, open Purchases > Bills, click New bill, then click Copy your forwarding email address.

According to Xero Central:

• Xero uses smart document capture to create a draft bill with the document attached. It fills in contact, date, total, due date, reference and description when it can read the document.
• The bill must be an email attachment, not text in the body of the email.
• You can email up to 10 bills in one email. Xero creates a draft bill for each attachment.
• Xero supports most document and image formats. Executable, audio and video files are not supported. The maximum is 25MB in total per email.
• Accepted attachments include PDF, JPEG, PNG, DOC, DOCX, XLS, XLSX, ODT, ODS, ODP, PPT, PPTX, RTF, TXT and HTML.
• If the supplier is not yet a contact, the draft bill gets "No contact" as the contact name. You change it before you approve the bill.
• The bill is created in your organisation's base currency. For a foreign currency bill you change the currency yourself, which needs a plan with multicurrency.
• Xero recommends that you don't share the address outside your organisation.
• Some mail servers reject addresses that include an exclamation mark. Xero explains how to reset your documents inbox address to remove it. Your auto-forward rules then need the new address.

Send receipts from a Mac with AutoMailSender

1. Connect your email once. Gmail, iCloud, or any custom SMTP server.
2. Add your Xero bills address as a recipient. Copy it in Xero as described above. Give it a name, like "Xero bills".
3. Drop a receipt onto the app. It is emailed straight away. No compose window.
4. Check Purchases > Bills > Draft in Xero. Xero says it can take a few minutes for the bill to show. Review it, then save or approve it.

Dropping several files at once? AutoMailSender can send them as separate emails or as one email. Xero reads one draft bill per attachment, up to 10 per email, so both work. One send counts as one email toward your 25 free ones, however many files it carries.

Or let a folder do it

Link a watched folder, say ~/Receipts, to that recipient. Save or scan a receipt into it and AutoMailSender emails it on its own. It retries if your provider hiccups and shows a notification when each send lands. When a watched folder already holds files, AutoMailSender asks what to do with them first, so old receipts don't all go out by surprise. The setup is the same one described in auto-email files from a folder.

Using QuickBooks Online or Dext instead? See email receipts to QuickBooks and email receipts to Dext. Sending to a person? See email receipts to your accountant.

Private and native

AutoMailSender is a native macOS app, around 1.7 MB. Files go from your Mac to your email provider over TLS. No cloud, no tracking. Credentials stay in the macOS Keychain. Requires macOS 14 or later.

Pricing

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

Download on the Mac App Store

Xero is a trademark of its owner; AutoMailSender is not affiliated with Xero. Xero facts on this page come from Xero Central, checked on 27 October 2026.