Pointers: Send photo attachments PC users can open

They can't handle Macs' inline images so help them out

We've had special requests for different Pointers tutorials before. We've also had things come up in the news as Apple changes or improves or removes something. This time what what happened is that someone asked us for an image, we emailed it over and they sent back a plaintive message saying "could you please send it as an attachment?" We say plaintive, the truth is that there was an undercurrent of frustration. Not to mention sarcasm.

This comes up a lot. When you email a photo, Apple shows it to you and to them right in the message: it isn't just a file attachment, the actual image is visible. If your recipient is on a Mac, they see the photo and can detach it as normal. If they're on a PC, they might be able to do that but often they can't. Often all they get is the image in the message without any way to detach it, drag it or do anything really apart from complain to us.

This does not work

Perhaps you've tried this already. When you're composing an email to someone and you drag in an image, it displays at full size. You can right click on it and say you want it to be displayed as an icon instead. Apple Mail then does this and, nicely, does it for all the images you've dragged in so far.

Only, it's no use to your recipient. It only affects what you're seeing and so all it really does is make it easier for you to read the text in your email. Once you hit send and the message is on its way, that Show as Icon setting is forgotten.

It's because Apple tries to help and maybe so does Windows but they should really take a minute to call each other in the morning. There is an option called Send Windows-Friendly Attachments: switch it on in the Edit menu's Attachments section but shrug while you're doing it. For it makes no difference that's ever helped us.

The old solution

The friendly attachment idea must work sometimes but it isn't reliable, it isn't predictable and we got into a habit of working around it. We hit this so often that we had developed a habit of sending the photo as usual but then also popping a copy onto Dropbox and including a link to that in the message of the email.

Only, if the greater part of this recurring problem is that our computers get in the way, a little part of it is that so do we and our recipients. If you're sending something a client, they don't care why it's gone wrong, they just know it has. We can't count the number of times we've heard "But we don't have this problem with anyone else". Grrr.

When your recipient isn't into technology -- and to be fair, it's not their job to be and it'd be a dull world if we were all interested in the same things -- then they are only a little more likely to have heard of Dropbox than of inline attachment images. So sometimes we just know this isn't going to work with them, it isn't going to fly.

That's why we have an alternative. Unfortunately, it's also just technical enough that we cross our fingers when we do it. We'll select the image in the Finder, then right click on it and in the menu that appears, we'll choose Compress. This creates a .zip file with the image in. Nothing else. As it's an image zipping it doesn't actually compress it: the JPEG is already compressed. Yet it's enough to mean your Mac doesn't treat it as an image any more.

It's the same logic that means we will zip up a dozen documents and images to send to someone. We don't especially care whether they get compressed or not, it's just easier to send one file instead of many.

Recipient won't unzip a file

Oh, give us a break. Okay: there are companies whose IT policy won't allow unzipping of attachments. When that's the case or your client is just awkward, you've no alternative but to dig into Terminal.

We've covered the use of Terminal in Pointers before but never with the greatest of enthusiasm. Terminal is the way that you can type direct and pretty arcane commands to control your Mac. It's fine, you can do this in your sleep, but if you nod off at the wrong point you can accidentally do a lot of damage. That's not why we're reluctant, though: we also just find it tedious that you have to do this instead ticking a box somewhere.

Needs must, though. So open Terminal (it's in Applications/Terminal) and wait for it to start up. When it's stopped filling your screen with text that reminds you of DOS in the 1980s, paste in this:

defaults write com.apple.mail DisableInlineAttachmentViewing -bool YES

Make sure you select all of that before you copy and then paste it. Then hit Return and off it goes. Depending on your Mac, you'll be waiting a second or a minute but when it's done, you'll get the Terminal cursor back. Type the word exit and press return. Then quit Terminal.

From now on, images are included in your outgoing messages as regular attachments. The only problem, and this is another reason we dislike using Terminal, is that this is an all or nothing change: if you want to see images you drag in, you have to go back to Terminal and enter:

defaults write com.apple.mail DisableInlineAttachmentViewing -bool NO

We should also say that even having done this, we're hearing that there are still PC users who occasionally have problems. We have a solution for them, though: we're going to phone them up and describe the image to them instead.

-William Gallagher (@WGallagher)
  1. Avatar
    jrietz Fresh-Faced Recruit Joined: Jul 09, 2013

    This has always worked for me. Make sure the attachment is not the last thing in the message, i.e. there is some text after the file.

  2. Avatar
    Mike Wuerthele Managing Editor Joined: Jul 19, 2012

    That is a good, simple, solution. Not quite as universal as William's options, but worth a shot for sure.

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