How to Check Attachments Before Sending in Gmail (Missing and Wrong Files)

Two different attachment mistakes

There are two ways an attachment goes wrong:

1. The missing attachment. You wrote "please find attached" and forgot to attach anything. Embarrassing, and it costs a second email.

2. The wrong attachment. You attached last month's invoice, the draft instead of the final, or the file meant for a different client. This one can be a data breach.

Gmail helps a little with the first and not at all with the second. Outlook add-ins like VIPRE SafeSend handle the second by listing every attachment for you to confirm before the email goes. Here is what you can do in Gmail.

Gmail's forgotten attachment reminder

Gmail reads your email when you click Send. If it finds a phrase like "I've attached" or "see the attached file" and there is no file, it asks whether you meant to attach something. You can attach it or send anyway.

It is on for everyone and there is no setting for it.

Where it falls short:

• It only knows certain phrases. Common English ones work well. Less common wording, like "the deck is enclosed", "PFA" or "sharing the file here", may not trigger it.
• It does not know about links. "Here is the link to the folder" with no link is just as broken, and Gmail does not notice.
• It never looks at the file you did attach. If there is any attachment at all, Gmail is satisfied.

Catching the wrong file

No setting fixes this one. What works is a habit and a few naming rules:

• Read the file name in the compose window before you send, the way SafeSend makes people do. It sounds too simple, but most wrong-file emails come from never looking.
• Put the client or recipient name in the file name. "Invoice-Acme-Oct.pdf" is hard to send to the wrong client by accident. "Invoice (3).pdf" is easy.
• Remove old versions from your Downloads folder after you send, so the file picker has one candidate, not five.
• Share a link instead of a file for anything sensitive. A Google Drive link limited to named people can be revoked if it goes to the wrong person. An attachment cannot.

A check at Send for both

Presend is a Chrome extension that checks each email when you click Send in Gmail.

• Its Missing attachment check catches "attached", "attachment" or "enclosed" in an email with nothing attached. It ignores the legal footer at the bottom of your email, which mentions attachments in every message.
• Its Missing link check catches "see the link below" with no link in the email.
• With External recipients set to Block, any email going outside your company stops at "Hold on" with the outside addresses listed. That pause is also the moment to glance at the file name, which is how SafeSend's attachment review works in practice.
• You can write a rule for your own risk, such as "Warn me if the email mentions one client and goes to an address at a different company".

What Presend does not do is open your attachments and read them. It checks the email you wrote, not what is inside the PDF.

For the basics of attaching files in Gmail and Outlook, see our guide on how to send an email with an attachment. If the wrong file has already gone, here is how to send a correction email.