My Damn Email Won’t Send

From the ITPTSD mailbag:

“I’m trying to email somebody a bunch of photos and videos, and it won’t send. What am I doing wrong?”

Probably nothing.

Except trying to email a bunch of photos and videos.

Email was invented for sending messages. Over the years, humans collectively decided it should also transport photographs, PDFs, spreadsheets, videos, PowerPoint presentations and apparently anything else you can drag into a window.

This works surprisingly well.

Until it doesn't.

The problem is that email has limits on how large a message can be. The exact limit depends on your email provider and sometimes the recipient's provider.

And today's files are enormous.

A photo from your phone can be several megabytes.

A video can be hundreds of megabytes.

Attach enough of them and eventually your email application will look at what you're attempting and essentially say:

Absolutely not.

So what should you do?

Don't send the files. Send a link.

That's the trick.

Instead of stuffing 47 photographs and three videos into an email, put the files somewhere designed to hold files and email the recipient a link.

The recipient clicks the link.

The files download.

Your email doesn't have to drag a Buick behind it.

The easiest answer may be WeTransfer.

WeTransfer exists largely to solve this exact problem.

Go to WeTransfer.

Upload your photos and videos.

It gives you a link.

Paste the link into your email.

Send.

That's it.

The recipient doesn't need to understand your cloud storage, navigate your folders or know where you keep your vacation photographs.

You've essentially given them a claim ticket for the files.

There are limits on how much you can send for free, and free transfers don't remain available forever. But for the everyday problem of “I have a bunch of stuff that's too big to email,” it's remarkably painless.

Hightail does much the same thing and is particularly oriented toward people working with large creative files. There are free and paid options, with different limits depending on what you're sending.

The basic idea is the same:

Upload big thing. Get little link. Email little link.

Technology occasionally gets something right.

You may already have another way.

If you use an iPhone or Mac, you can share photos and videos through iCloud.

Select the items, choose Share, and look for the option to create or copy an iCloud link.

Paste that into your email.

Google Drive works the same basic way.

So does Microsoft OneDrive.

And Dropbox.

Put the files there, create a sharing link and send the link instead of the files.

Think of it this way.

You wouldn't try to shove a refrigerator through the mail slot in your front door.

You'd have somebody deliver it.

Email is the mail slot.

WeTransfer, iCloud, Google Drive, OneDrive, Dropbox and Hightail are the truck.

Apple Mail may offer to rescue you.

If you're using Apple's Mail app, you may encounter Mail Drop.

When an attachment is too large to send normally, Mail Drop can put the attachment in iCloud instead. The recipient gets your message and downloads the large file separately.

You don't have to understand what's happening behind the scenes.

This is generally a feature.

For one or two oversized attachments, Mail Drop can be wonderfully convenient.

For a whole collection of photographs and videos, I prefer deliberately sharing them with a link. It's clearer for everyone involved.

Don't forget the permissions.

Before sending a cloud-storage link, make sure the person you're sending it to can actually open it.

Sharing systems have permissions.

Sometimes the link works for anybody who has it.

Sometimes it works only for particular people.

Sometimes it requires the recipient to sign in.

Sometimes you send the link to Aunt Martha and receive an email four minutes later saying:

IT SAYS I NEED PERMISSION.

You have now become tech support.

Welcome to my world.

For ordinary photographs, choosing an option along the lines of “Anyone with the link can view” is often the simplest approach.

For sensitive documents, don't automatically do that.

If you're sending tax records, financial information, medical documents or the launch codes, pay attention to who can access the link.

And please don't send the photos one at a time.

You know who you are.

Twenty-seven emails arrive.

IMG_4837.

IMG_4838.

IMG_4839.

Everybody's phone starts vibrating like there's an incoming missile.

There is a better way.

Put them together.

Share the link.

Send one email.

Human civilization advances another tiny step.

The short version

If an email containing photos or videos won't send, stop trying to make the email send them.

For the simplest one-off solution, try WeTransfer.

If you already use iCloud, Google Drive, OneDrive or Dropbox, those work beautifully too.

Hightail is another option, particularly for people regularly exchanging large creative files.

And if Apple Mail offers you Mail Drop, that's perfectly fine for an occasional oversized attachment.

The important part isn't which service you choose.

It's understanding the trick:

The big files don't go in the email.

The link does.

Your recipient gets the files.

Your email gets sent.

And somewhere, an overworked mail server quietly whispers:

Thank you.