You can include or exclude large attachments in replies. You can also use Mail Drop to send large attachments.
How to send large email attachments using Mail Drop
You can use Mail Drop to send files that exceed the maximum size allowed by your email account provider. Mail Drop uploads large attachments to iCloud, where they’re encrypted and stored for up to 30 days.
- If you have an iCloud account. If you are signed in to iCloud when you click Send, Mail automatically sends the attachments using Mail Drop. Mail Drop attachments don’t count against your iCloud storage.
- If you don’t have an iCloud account or are not signed in to iCloud. Mail asks you whether to use Mail Drop (to always use Mail Drop select “Don’t ask again for this account”).
If a recipient uses Mail in OS X 10.10 or later, the attachments are included in your message. For other recipients, your message includes links for downloading the attachments, and their expiration date.
Note: see the Apple Support article Mail Drop limits.
How to turn Mail Drop on or off
- Go to the Mail app on your Mac.
- Choose Mail > Settings.
- Click Accounts, select the account, then click Account Information.
- Select or deselect “Send large attachments with Mail Drop.”
How to Include or exclude email attachments in replies
- Go to the Mail app on your Mac.
- Do one of the following:
- Include or exclude original attachments in a reply: In the toolbar of the message window, click the paper clip icon to include or exclude attachments.
- Choose attachments settings for all replies: In the menu bar, choose Edit > Include Attachments With Replies, then select an option.
You can change how attachments are displayed in the Compose window (this doesn’t determine how attachments are shown for your recipients). To display an attachment (such as a one-page PDF document or an image) as an icon, Control-click the attachment in your message, then choose View as Icon. To show the attachment again, Control-click it, then choose View in Place.
This how-to is based on information from the Apple Support pages and my own personal testing.