How to get the most out of Mail Drop

Sending large files can be a major hassle. Using a third party app or website, requiring passwords, registration and advanced sharing options aren’t great solutions.

If you have an iCloud account you get to bypass all these tedious solutions and use Mail Drop instead. Mail Drop is a fantastic and easy to use method to send those large files, but if you’re running into issues with Mail Drop, we want to help you figure it out.

You’d think it would be simple enough, but there are any number of ways that the interpretation of information can be lost in translation between different email clients and operating platforms.

The problems that typically occur, in a nutshell, can be due to sending files that are over the size limits, or the miscommunications between different email systems and different operating systems. Other issues could stem from the recipient having an old email app that doesn’t support certain encoding, or certain email apps refusing to handle messages above a certain size.

Here’s how to avoid these issues and get your Mail Drop doing what you need it to do:

Make sure your Apple devices meet compatibility requirements

Mail Drop only works with a Mac operating with OS X Yosemite or later. For iPhone, iPad, or iPod touch you must have iOS 9.2 or later. And you Mac or PC must have an updated browser.

Allow Mail Drop for non-iCloud accounts

Mail Drop is turned on for iCloud by default. To enable this feature for non-iCloud email accounts, go to Mail > Preferences, click “Accounts.” Then choose your non-iCloud email account. Under “Account Information,” check the box for Send large attachments with Mail Drop.

Watch your size limits

Mail Drop allows attachments up to 5GB. If your attachment is over 5GB you can send the content in multiple emails or compress your attachments.

Additionally, Mail Drop gives you a total maximum of 1TB for your storage limit. Each attachment you send expires after 30 days, so if you reached your storage limit you will have to wait until some of that space clears up.

Make your attachments Windows-friendly

Some email clients and operating systems can’t read certain graphics files sent from macOS. To avoid this in Mail Drop choose Edit > Attachments > Always Send Windows-Friendly Attachments.

Windows also relies on file extensions so make sure to always include your file extensions in emails. Before you drag or attach it, make sure it has a file extension. To be able to see this easier open Finder > Preferences, click Advanced and select the Show All Filename Extensions box.

Make sure attachments appear at the end of the message

The drag and drop feature in Mail Drop will place your attachment in the spot where you dropped it. In some operating systems and email clients this can cause an issue with inline graphics or inline display. To make sure all attachments automatically appear at the bottom of your message you can select Edit > Attachments > Always Insert Attachments at End of Message.

We understand how frustrating it can be when your Mail Drop is functioning how you need it to. If you follow these steps you should be avoid to avoid most common Mail Drop issues.

Have you tried these steps out and you’re still having issues? Drop us a line.

Luke Kumanchik

Entrepreneur, programmer, backyard farmer & Dungeon Master Extraordinaire.