OS X Mail inline attachments erasing all text sent to Outlook

Patrick Masters Apple Mail, Outlook, Software 0 Comments


If you’re like me you’ve ripped your hair out on this one. This is especially prevelant in workplaces that adopt a BYOD policy. You’re using Apple Mail and including attachments throughout (which looks nice and is handy!) – however the recipient, who is using Outlook in this case gets all your text up to the first attachment. Then a bunch of random text attachments afterwards.

This is a major invocnvenicne and a drawback, but luckily there is a work around!

The Problem

Let’s recreate the problem; you’re conducting and email in Apple Mail and are including attachments (inline) just like the default behavior allows like below:


A mockup email we created in Apple Mail with inline attachments

Now let’s see how these will show up to someone using Apple Mail vs Outlook:

  • osx-mail-outlook-attachment-issue-email2

    This is how Apple Mail users would receive the email

  • osx-mail-outlook-attachment-issue-email3

    This is how Outlook users would receive the email

A simple Google search of exchange inline attachments will reveal that this is in fact an issue with how Exchange processes inline attachments.  Basically exchange will display all the text normally until the first attachment.  It then will attach this, and any text to the email as attachments.  Well having the text as attachments is what really makes the email screwy, since the average person can’t view this text now.

The Solution

Luckily for us the solution is relatively simple. Open up your Apple Mail application and make sure you’re currently not in the process of drafting any emails.

First make sure you send Windows-friendly attachments. To do so for all messages, from the main Mail window choose Edit > Attachments, then make sure Always Send Windows-Friendly Attachments is selected.  Typically this is checked by default.  The real magic happens next.   From the main Mail window, choose Edit > Attachments > Always Insert Attachments at End of Message. This will ensure no text is placed after your attachments and Outlook users will receive the emails as expected.  You do lose out on inline attachments but it just isn’t supported yet all around so we’ll do what’s best for the masses.


Here’s how our email is composed now with the new setting

So who wrote this?

Patrick Masters

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A Computer Engineering graduate of the University of South Florida - he now applies his skills towards website design, custom web app development, as well as constantly learning new techniques and technologies to satisfy his creative mind!

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