Easily send large e-mail attachments with iCloud in Yosemite

MailIconYosemiteXSending attachments via e-mail to a colleague or friend is perhaps the most common approach for sharing files, and is a method that is nearly as old as e-mail itself; however, one limitation that many e-mail services have is a cap on the size of attachments that you can send, which depending on the service is generally between 10-25MB per attachment. Even though this allows the sending of most standard documents, more and more frequently there may be times when you need to send files that exceed this size.

Unfortunately if either you or your recipient has a cap on the size of attachment, when you attempt this you may receive an error and not be able to send your message. However, this can be overcome in several ways:

Personal hosting

Classically, overcoming this limitation required you sign up with a Web host to store your files, and then make your files available through a Web link that you could then send to your contacts. This approach is still quite viable, but to do so you will need to sign up with one of many hosting companies, set up your Web disk access (FTP, WebDAV, HTTP, etc.), upload your files, and then get your link (sometimes assembling it manually) to copy into your e-mails.

Online Storage

Personal Web hosting options have for the most part evolved to online storage services like Dropbox, MediaFire, Amazon Cloud Drive, and others. These are essentially the same thing as personal hosting, except that managing files are far easier through integrated desktop apps or intuitive Web interfaces. Once signed up and logged in, you can drag and drop your files to the service, set whether or not you want the file to be accessed publicly, or by specific people, and then quickly get a link to the file for sending to another person.

If you manage e-mail from non-iCloud accounts, and using third-party e-mail clients, or if you use multiple operating systems, then this approach is likely the most convenient option.

Mail Drop with iCloud Drive

If you are on a Mac or iOS device and have an iCloud account, then by far the easiest option for managing large attachments is to use Apple’s iCloud Drive with its new Mail Drop service. While iCloud Drive is in some ways similar to other online storage options, from its inception Apple made it a storage option that augments applications behind the scenes, as opposed to being something you directly interact with (only recently has Apple tacked on the ability to access iCloud Drive’s storage and organization directly in the Finder).

Mail Drop attachment in OS X Mail

When you attach a large file, Mail will display it as any regular attachment, but handle it in the background through iCloud Drive. Without this, you would see the message size in red text, indicating it is too big for the mail service to handle.

One of these augmentations is Mail Drop, where when using Mail with an iCloud account, you can attach files of any size to your messages. Upon sending your message, Mail will attempt to send them as standard attachments, but if they are above 10-25MB in size, Mail will resort to using iCloud Drive to store them. In doing so, Mail may alert you about this and give you an option of either continuing to send the file as a standard attachment, or use iCloud to store it and send it as a link. If the message recipient is using Apple’s Mail client, then the received file will appear as a standard attachment, but if not then the attachment will show as a link that will open the user’s browser to iCloud where the file will download.

This approach is somewhat of an enhanced online storage option, that may be more convenient than resorting to Dropbox or others for sending large attachments. The best part about it is if you already use iCloud, then you do not have to do anything to configure it. The only requirement is that you are using Mail, an iCloud account, and OS X Yosemite, so if you have not yet upgraded to Yosemite, then this might be an incentive to give it a try.

Mail Drop limitations

Even though Mail Drop greatly enhances Mail’s ability to manage attachments, it does have some limitations, which Apple outlines in this knowledgebase document, with the most applicable ones being the following:

  • Attachments will be limited to whatever space is available in the user’s iCloud account, which is 5GB maximum for standard free accounts, with an upper limit of 1TB.
  • You cannot send a bare folder as an attachment, instead, you can right-click it in the Finder and choose the Compress option to save it as a zip archive.
  • You cannot send more than 200 messages per day, send to more than 1000 recipients per day, or include more than 100 recipients per message.
  • Mail Drop links will expire after 30 days, requiring you re-send the attachment.

11 thoughts on “Easily send large e-mail attachments with iCloud in Yosemite

    1. Stephen

      But that’s not automatic. And you’re still revealing the recipients’ addresses and the contents of your message to your mail provider – otherwise how would the mail be delivered? So much for your idea of “No e-email revealed to third parties”

  1. Blyth HUGHES

    Has this been extended to POP accounts yet? Some discussion pages indicate it only works for IMAP accounts.

    1. Topher Kessler Post author

      This feature is for people sending e-mail from Apple’s iCloud accounts, when using Apple’s Mail e-mail client. The specifics of POP and IMAP, and other protocols and settings do not matter. It only works with one configuration.

  2. Blyth HUGHES

    Thank you, that answers my question. Apple’s iCloud accounts are IMAP and that’s why it seems that POP accounts can’t use this feature. Presumably IMAP accounts with other ISPs can’t use this feature either, then.

  3. Blyth HUGHES

    This link https://discussions.apple.com/thread/6611214?searchText=mail%20drop%20POP states that POP accounts can not use Mail Drop but IMAP accounts can. Apple’s support page for Mail Drop states the following: “If a message, including its attachments, is larger than your Internet Service Provider (ISP) limit, Mail will ask you to send the attachments using Mail Drop.” which implies to me that using an ISP other than iCloud is suitable for Mail Drop.

  4. Ken

    Mail Drop does work with IMAP accounts other than Cloud. I normally use a Verizon mail account which does not support IMAP. I cannot use Mail Drop with that account but I can use it with my AOL account using Apple Mail.

  5. Stephen

    My experience, supported by that of various friends, is that attachment size issues occur more often at the receiving end. Maybe we all use ISPs with more generous limits than the people we send to, but why isn’t there a settable threshold for sending files via Mail Drop rather than as attachments?

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