How to Email Big Files on Mac with Mail Drop

Even when you have all the power and versatility of a full Mac at your disposal, trying to email a big file to somebody else can still be super frustrating. Fortunately, Apple’s Mail Drop can make it easy. Here’s how it works.

Apple introduced Mail Drop a couple of years ago as a way of simplifying sending big files. Ah, you ask. Why would I want to bother with Mail Drop on a Mac? I can just upload a file to Dropbox or Google Drive or a million other services, instead.

Read: How to Email Big Files from your Phone with Mail Drop

That’s a good option, though you can’t set it to upload and walk away (someone still needs to send an email, after all). But not everyone is going to be sufficiently computer savvy to navigate those waters. Additionally, downloading from one of these cloud services can often be confusing or intimidating if you aren’t too comfortable with those kinds of services. Emailing files is so attractive because it’s generally pretty simple – attach, send, click.Mailboxes in a rowWhere email falls down is when you need to send something sizeable. Even if you could attach and send it off, all too many people – especially those relying on corporate-provided email accounts – wouldn’t be able to see it since their allotted mailbox space is too small to store inside.

Mail Drop gets around this by uploading your attachments to a secure Apple server. Instead of attaching your original attachment to the email message, it inserts a link to the uploaded file instead. That means your recipient doesn’t have to worry about filling up their mailbox or trying to log into this website or that website; all they’ll need to do is click a link, and the file will download.

Screenshot 2016-02-03 00.05.28There are a couple of things to keep in mind before you start using Mail Drop. Firstly, it only accepts files of up to or including 5GB in size. If you need to send a single file of more than that size, you’ll have to use a different service. Additionally, Apple only lets you send a terabyte of files within a given 30-day period, so if you find yourself sending more than 33GB a day (which is unlikely for most people) you’ll likewise need a different service.

How to use Mail Drop to Email Big Files on Mac


For whatever reason, on new versions of OS X, Mail Drop is disabled by default. So the first order of business is to re-enable it. Open up your Mail app (Mail Drop only works with Mail), and go into your Mail Preferences. You can do this by hitting hte Command and comma keys at the same time, or by click on Mail in the title bar at the top of your screen, then clicking on Preferences, in the drop-down menu.

Screenshot 2016-02-03 00.04.44You’ll see a screen pop up with one or more accounts. Click on your email account, then move your mouse over and click on “Advanced.” There will be a list of checkboxes, and the last one will read, “Send large attachments with Mail Drop.” Make sure it’s selected, and you’ll be good to go!

To use Mail Drop, simply compose an email message like you normally would. Once you’ve finished writing, drag the attachments over and onto your message, then click send (it’s the little paper airplane icon, if you’re unfamiliar with the Mac’s Mail app. If they’re large enough (tests seem to indicate that Mail Drop is triggered by attachments larger than twenty megabytes), you’ll see a dialog box pop up and ask, “Would you like to send this attachment using Mail Drop?”

Screenshot 2016-02-03 00.11.40Click the button that says “Use Mail Drop” and your Mac will start uploading your files to one of Apple’s private servers somewhere. From your point of view, it’ll look like the email has been sent. In reality, Mail will wait for the files to get upload and then send your message away automatically, so don’t click send and put your Mac to sleep if you’re using Mail Drop.

On the other end of the email’s journey, your recipient will simply see a link to the file within their email. From the moment you send an email, however, Apple puts a time limit on those Mail Drop files – your sendee will have precisely 30 days to click that link and download the files, or you might need to resend them.

Something to keep in mind: you don’t need to use Mail Drop for every attachment you send. If you know for sure what the attachment limit for your mail server is, you can override the Mail Drop dialog and send your files normally.