Enable Mail Drop for an Email Account in OS X Mail

Mail Drop attachments operate no differently than attachments sent directly with a message. For recipients using macOS Mail, Mail Drop attachments present as regularly attached files. Here’s how to turn on Mail Drop so large attachments sent from an Apple Mail account are automatically processed using Mail Drop:

Send Large File Attachments (Up to 5 GB) in Apple Mail

Here’s how to send files up to 5 GB in size via email from macOS Mail: For attachments exceeding a certain size (it depends on your email provider), Mail automatically uploads the file in the background to an iCloud web server, where recipients can download the file by following a link in the message. The files are available for 30 days.

Position the text cursor where you want the attachment to appear. Select the Paperclip icon (📎) in the message’s toolbar. Highlight the desired document or folder, then select Choose File.Make sure the cursor is where you want to insert the file or files. Select File > Attach Files… from the menu or press Command+Shift+A. Select the desired files and folders, then select Choose File.Drag and drop the desired document or folder onto the message body where you want the attachment to appear.

Is Bigger Better for Attachments?

As anyone who has ever tried to attach a large file to an email has discovered, bigger is not always better. Big files cause delays, waiting, errors, repetition, and undelivered messages, not to mention frustration. You can go hunting for services, plug-ins, and apps to work around the problem, including file transfer services like Dropbox and WeTransfer, or you can use Apple’s built-in solution.