Images sent from a mac as email attachments appearing as embedded on a PC.

by David Hughes
Posted on: February 15th, 2012

This post originally appeared on the David and Associates blog. It was one of the more popular and with the closing of that blog I thought it worth bringing over here.

If I had a penny for every time I’ve sent email attachments from my Mac to PC users, only to be told that the image arrived embedded rather than attached, I’d be able to give up the day job.

It doesn’t matter whether I check the ‘Send windows friendly attachments’ checkbox or not. And it doesn’t appear to be consistently a problem for all PC recipients.

I’ve often resorted to sending the files via an email download service such as

Today I thought I’d found the workaround: once you have attached the image to your email missive, right-click on the image and choose ‘view as icon’. The colourful image that Mail displays inline is replaced by a little downloadable image icon. And this, theoretically, is treated properly as an attachment by the PC user’s mail client. Not that intuitive and not very Apple-ish. Oh, and it doesn’t work. Or at least it didn’t work with a recent test sent to a friend using a PC.

I see there’s also a small plug-in application for Apple Mail that automates this and a number of other work-arounds available for the princely sum of $14.99 USD from Lokiware.

If anyone knows of a built in solution to the problem without resorting to third party applications do leave a comment below.

Postscript: since the initial posting the first comment and the solution I now regularly adopt (even though it is a pain) came from Chris (See below). Zip it (Compress it in OSX). It’s foolproof, or at least this fool (me) thinks so.

Also reproduced here are a number of other suggested solutions that came through on the original post’s comments.

Chris: Zip (‘Compress’ in OS X) the image file first, then attach it.

Melissa: Zipping your attachments does work (as Chris stated above). Of course, you always run into people who don’t know what that is. Also, make sure your e-mail is in plain text.

There is easy no solution to this. It’s my understanding that it has to do with how Microsoft handles rich text. (And the paranoid part of me believes it’s a deliberate attempt to sabotage Macs.) I’m sure there are also some settings on the PC side that mess with Mac attachments. I am one of only 2 Macs where I work, and everyone else is on PC. Some people get my attachments just fine (assuming I make them icons and use plain text formatting), some don’t. Sometimes they are just embedded; sometimes they are reduced to tiny thumbnails and embedded. But in the end, I find that zipping attachments ALWAYS works regardless of anything else I might or might not do.

Rizwan Shabbir: I face this problem only when I press Reply or Reply All and attach .jpg file, all the recipients find it embedded. But if I send them the file again attaching it in the New Message it appears as attachment to them. But mostly I have to Reply to others and not only send the file, because I have to also reply on the others comments and even I cannot first copy all the conversation from the mail and paste it in the New Message and then send it, only it works if I just press New Message, put recipients, put Subject and attach file and send.

Frank: It also occurs with new composed mails in my case with gmail with jpg files. The images are high res previews for work and I don’t want them resized or embedded. I just wonder if images are seen as recreational photos and not as important attachments.

Also sending images from Apple Mail is extremely slow compared to Gmail with Firefox.

Jay Budzilowski: My workaround was converting the message to plain text, then attaching the image…

Jim Stewart: This is not a Mac to PC problem; it’s that the default Apple Mail application ( behaves differently than most other email clients. There are two ways you can fix this, though: if you drag-and-drop a file–even an image–into Mail’s compose window, it will become a real attachment; or if you want to fix the default behavior, do this in a terminal:

defaults write DisableInlineAttachmentViewing -bool yes