Apple device operating systems are chock full of features that can increase user productivity and flexibility. Each new release adds yet more capabilities and rarely takes any away.

Unless you intently follow release announcements, though, your acquisition of new skills may depend on your own discovery — or spending time learning from your technology coach. Otherwise, you’ll likely miss out on multitudes of hidden features that might actually be useful to you.

For example, how do you share large files over the Internet? You might have heard of the cloud storage solution Dropbox or the website WeTransfer. Among many others in the file sharing landscape, these are two popular approaches to sending items that are too big for email.

However, there are some other choices that are already built into your Apple devices: Mail and iCloud Drive.

Mail Drop

Do you use Mail to manage email on your Mac, iPhone, and/or iPad? I’ve discussed Mail extensively in Mac Mondays, including how to work with mailboxes, received attachments, and more. However, I haven’t documented some of the core features of Mail, such as sending and receiving messages.

When Apple released macOS Yosemite nearly a decade ago, it included a new feature in Mail called Mail Drop. This enables users to compose regular email messages and attach large files that are normally too big to send through email servers. A common server limit is 10–20MB per message.

Upon sharing one or more items this way, Mail uploads the attachment(s) to iCloud Drive and sends the message with a special link. If the recipient also uses Mail, the attachments download automatically into the received email message and the person can simply open them. Otherwise, they can click a link to view/download each attachment.

On macOS, Mail Drop is not enabled by default and its availability is account-specific. So, in Mail > Settings > Accounts, you can select an account with which you want to use the feature and enable Send large attachments with Mail Drop.

On iOS, Mail Drop arrived in version 9.2, released in late 2015. Here, the functionality is less flexible and more interactive. That is, you cannot switch Mail Drop on or off. When you attempt to send an email with an attachment too large for the server, a menu appears with an option to use Mail Drop.

Mail Drop has a few limitations worth mentioning:

  • Attachments sent with Mail Drop expire after 30 days
  • An email message containing one or more attachments sent using Mail Drop is limited in size to 5GB
  • When Mail Drop attachments accumulate, you are limited to 1TB of total storage used for them and must wait for the oldest ones to expire before sending more
  • You cannot attach a folder to an email unless you first compress it into a zip file (Compress is an available command in the Finder and in the Files app)

Share via iCloud Drive

Outside of Mail, there’s another built-in way to share files and folders using a Mac, iPhone, or iPad: using iCloud Drive, without limits of size or duration. Compared to other cloud storage platforms, this may be a no-brainer if you already pay for iCloud storage.

(Messages is a less common file sharing channel that I’m excluding from this discussion, except to note that it’s more secure than Mail for sending and receiving content due to its end-to-end encryption. Sending a link to an iCloud share via iMessage might be preferable to email, depending on the privacy of the content.)

You can select any file (or folder when using macOS 10.15.4 or iOS 13.4 or later) in iCloud Drive and share a link to it with anyone using any channel you like.

When you indicate that you want to share a file or folder in iCloud Drive, you can decide whether you want specific invitees or anyone with the link to access the item, and permit them to make changes to it or only view, which includes downloading a copy. If restricting to invited people, you also choose whether they can invite others as well.

Share with Link

While the default experience is to privately invite others to collaborate, I more commonly just want to provide a link to an item so a recipient can download a copy onto their device.

You can always use Mail, Messages, or AirDrop to send an invitation to share a file, and you may have other choices depending on apps or sharing extensions you have installed. Or, choose Copy Link or Invite with Link so you can paste and send the invitation link via any other channel.

In macOS Monterey and earlier, the sharing experience clearly provides these options:

  1. Who can access: Choose People you invite or Anyone with the link
  2. Permission: Select Can make changes or View only

When you have the options you want, click Share.

In macOS Ventura and later, the same workflow is a little more elusive because it’s contained entirely in the popover that appears when you click Share. Choose Collaborate from the popup menu (instead of Send Copy). Then, click Only invited people can edit to reveal the same access and permission options as described above. When you have the options you want, choose your desired channel or click Invite with Link.

In either of these cases, you won’t get any visual feedback after copying a link. Just trust that it is on the clipboard. If you don’t believe me and want proof, choose Show Clipboard from the Finder’s Edit menu. Plus, you can use Universal Clipboard to paste, as I mentioned in XCV Shortcuts and iPhone Hot Tips #1.

Share Files Using iPhone or iPad

This experience is quite similar in the Files app on iPhone and iPad. However, I found one gotcha worth sharing: Invite with Link may not be shown in the Share Sheet by default and this is the only way to copy a link to the shared item.

To add this option, scroll to the right end of the apps shown in the Share Sheet and tap more horizontal ellipsis (More). Then, tap Edit, find Invite with Link in the list of suggestions, and tap green plus next to it. If you wish, rearrange the choices in Favorites at the top and enable or disable Suggestions below. Then, tap Done and tap Done.

What large files have you been meaning to share with someone and didn’t know how? Do you run into any obstacles with this process? Also, what challenges do you face around building your tech savvy with new features?