How to Check Attachments Before Sending an Email (Missing and Wrong Files)
Gmail, Outlook and Apple Mail can all remind you when you write "attached" and forget the file. None of them checks that you attached the right file, which is the mistake that turns into a data breach. What each app catches, the habits that catch the rest, and how to add a check at Send.
Two mistakes, not one
Attachments go wrong in two ways:
1. Missing. You wrote "please find attached" and nothing is attached. Annoying, and it costs a second email.
2. Wrong. You attached the draft instead of the final, last month's invoice, or another client's file. This is the one that matters. If the file has someone else's data in it, it may be a reportable breach.
Email apps help with the first and not at all with the second. That is why Outlook add-ins like VIPRE SafeSend list every attachment for you to confirm before an outside email goes.
What your email app catches
Gmail
When you click Send, Gmail looks for phrases like "I've attached" or "see the attached file". If there is no file, it asks whether you meant to attach one. It is always on.
Outlook
Outlook has an attachment reminder that works the same way. In classic Outlook on Windows it is under File, Options, Mail, then Warn me when I send a message that may be missing an attachment. It is on by default. Outlook on the web and new Outlook have it too.
Apple Mail
Recent versions of Mail on the Mac and iPhone can also notice when a message mentions an attachment that is not there, and remind you before it sends.
What they all miss
- Unusual wording. "PFA", "the deck is enclosed" or "sharing the file here" may not trigger the reminder.
- Links. "Here is the link to the folder" with no link is the same mistake, and none of them notice.
- The wrong file. If any file is attached, the reminder is satisfied. None of them look at whether it is the right one.
Catching the wrong file
No setting fixes this. What works:
- Read the file name before you click Send. This is all SafeSend's attachment review really does: it makes you look. Most wrong-file emails come from never looking.
- Put the client's name in the file name. "Invoice-Acme-Oct.pdf" is hard to send to the wrong client. "Invoice (3).pdf" is easy.
- Clear old versions out of Downloads once a file has gone, so the file picker shows one candidate, not five.
- Send a link instead of a file for anything sensitive. A Google Drive, OneDrive or Dropbox link shared with named people can be taken back. An attachment cannot.
A check at Send
Presend is a Chrome extension that checks each email when you click Send, in Gmail, Outlook on the web and other places you write in the browser.
- Missing attachment catches "attached", "attachment", "enclosed" and similar words in an email with nothing attached. It ignores the legal footer at the bottom of an email, which mentions attachments in every message.
- Missing link catches "see the link below" with no link in the email.
- External recipients set to Block stops every outside email at "Hold on" with the outside addresses listed. That pause is the moment to glance at the file name, which is how SafeSend's attachment review works in practice.
- Your own rules cover your own risk, such as "Warn me if the email mentions one client and goes to an address at a different company".
Presend does not open your attachments and read what is inside them. It checks the email you wrote.
For the Gmail version of this guide, see checking attachments before sending in Gmail. If the wrong file has already gone, here is how to send a correction email.
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