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From your Mac

Gmail attachment failed on your Mac? Try these fixes.

Either the file is one Gmail won't take, or something in the browser is stopping the upload. Check the file first, then the browser.

Check the file first

  • Is it over 25 MB? That’s the limit for personal accounts. Over it, Gmail swaps the file for a Google Drive link. See File too large for Gmail? and Gmail attachment size limit.
  • Is it a blocked type? Gmail won’t attach executable files, and its list includes .dmg, the Mac installer format. It also blocks them inside a .zip, and password-protected archives.
  • Is your Google storage full? Attachments count toward the storage you share across Gmail, Drive and Photos. When it’s full, you can’t send or receive attachments.

If the upload keeps failing

Google’s fixes:

  1. Use a supported browser, like Chrome, Firefox, Safari or Edge, in its latest or previous version, with cookies and JavaScript on.
  2. Turn off your browser extensions one at a time, and try again after each.
  3. Clear your browser’s cache and cookies.
  4. Try attaching in another browser.
  5. If you’ve set up a browser proxy, turn it off.

In Safari

Apple’s fixes for a site that doesn’t work as expected in Safari:

  • Extensions: choose Safari > Settings > Extensions and turn each one off.
  • Private window: choose File > New Private Window (Shift-Command-N) and try Gmail there. If it works, choose Safari > Settings > Privacy > Manage Website Data, select the affected site, click Remove, then Done. You’ll need to sign in again.
  • Private Relay: if you use iCloud Private Relay, choose View > Reload and Show IP Address.
  • VPN or security software can get in the way too. Turn it off and try again.

What the error messages mean

  • “Couldn’t send message”: a file didn’t upload to Drive, maybe from low storage or a slow connection. Remove the attachment and add it again.
  • “Gmail’s adding files”: an upload from another device hasn’t finished. Wait, or remove it to send now.
  • Attachments unavailable: your network may block the address Google uses for attachments. Ask your network admin or internet provider.

Or skip the browser

Add your Gmail account to Mail on your Mac and send from there. See How to email a file from your Mac. Or send it another way: Send large files from your Mac.

Send from the notch with Sendoff

Sendoff is a Mac app that lives in the notch. It sends through your Gmail account without a compose window or an Attach button: drop the file, pick the person, press Send off. It remembers who gets Gmail and who gets iMessage, and if a file is too big for Gmail, like a 48 MB video, it goes by iMessage to people you also reach that way. You get 3 seconds to undo.

Join the waitlist below, and tick the beta box if you want to test it first.