Digital Sharing for Apple Users: A Take Control Crash Course
by Joe Kissell

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Send Files to Others

You have a file you want to send to someone—a Pages document, a PDF, a ZIP file, or whatever—or maybe a few files. In this situation, you probably don’t want to Sync Folders with Others or Broadcast Download Links because there’s no need to provide ongoing access to the file or to generate a public URL; you need only a one-time, one-way delivery to a limited number of specific recipients. How should you do that?

Most of us over a certain age immediately think of email for this purpose. That’s not ideal for large files or when the recipient is using a mobile device—but there are now some clever ways to avoid the traditional problems with attachments. Alternatively, you can use other Apple technologies, including Messages and AirDrop.

Use Email Attachments

One way to avoid the aggravations of emailing large attachments is to send links instead. In other words: copy a file to cloud storage, follow the steps in Broadcast Download Links to get a URL for it, and then email that URL. But that’s quite a hassle for one-off files.

A better way, available in Apple Mail on 10.10 Yosemite and later, is a feature called Mail Drop. It’s enabled by default for iCloud accounts; for other account types, go to Mail > Preferences > Accounts > Account Name > Advanced and select Send Large Attachments with Mail Drop .

**①** Enable Mail Drop for each of your accounts to eliminate the pain of emailing large attachments.
Enable Mail Drop for each of your accounts to eliminate the pain of emailing large attachments.

With Mail Drop, you compose a message and drag files in to attach them, just as you normally would. But when you click the Send button, Mail uploads attachments totaling over 20 MB or so (and up to 5 GB) to iCloud and inserts a link to the files in the message.

The recipient sees a link that can be used to download the attachments. iCloud stores sent attachments for 30 days and then deletes them.

Use Messages

You can use the Messages app to send files of up to 100 MB to individuals or groups. The only catch is that the transfer must use the iMessage protocol (the default in Messages), which in turn means the other person must be logged in to an iMessage account on a Mac or iOS device.

To send a file in Messages for OS X, start a conversation and then drag and drop the file into the message field .

**②** Drag a file right into the message field to send it in Messages on OS X.
Drag a file right into the message field to send it in Messages on OS X.

On an iOS device, you can send photos or videos from within Messages (see View Privately). You can also send files via Messages from within many iOS apps. Although the exact procedure varies from one app to the next, here’s how you do it with Apple’s iWork apps (Pages, Numbers, and Keynote):

  1. Tap the Share icon > Send a Copy.
  2. If applicable, tap to choose a file format.
  3. Tap Message.
  4. Fill in the recipient(s), enter any desired text, and tap Send.

In other apps, look for a Share button or icon of some kind. (But note that some apps offer sharing only by email.)

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