Apple Mail is stupid bad

I don't normally dive into technical esoterica in this blog, but bits and pieces of this issue have bugged me for awhile. We deal with creative types a lot here and, of course, about 75% of them use Apple Macs of one type or another. We also have to communicate with them by email. Naturally that means we get messages via their default clients (generally Apple Mail which comes with OS/X). We're a Microsoft house and use Outlook since that's what 90% of our clients use.

Anyway, I could never figure out why .JPG files from Mac users mostly come in as inline graphics (displayed within the body of the email) rather than as discrete attachments which you can save. Actually, I never paid it much attention since you can always just right-click on the image and save it out as a .PNG (or .BMP) file. Plus, a lot of folks put their work into ZIP files to consolidate them which doesn't create this issue in the first place.

However, today a friend of mine mentioned (in an online forum) that he was having trouble getting his photography work to some of his clients (mostly TV stations). They'd get the images inline regardless of the settings he used (text or rich text, attach or copy/paste) and they couldn't figure out what to do with the result. Apparently right-clicking and saving as .PNG was too high-tech for them plus what the heck is a .PNG file anyway? ;-)

After helping Mike play with a bunch of test messages and researching the issue on the web, we mostly came to the conclusion that Apple Mail just plain sucks at image attachments. Both Outlook and Mozilla Thunderbird behave nicely with each other handling attachments in plain text messages and HTML messages correctly. They also handle inline images much the same way. However, nothing my friend did in Apple Mail would let either Thunderbird or Outlook see jpeg images as attachments.

Bottom line for Mike to get his work to the stations as they require it is to either get another mail client or use their dropbox systems (a pain in the butt). By the way, Apple Mail to Apple Mail apparently allows you to save these images like they are attachments so if you're a member of the Cult of Mac, you won't notice anything wrong. (Must just be those dumb Windows users, right?)

The mind numbing technical details

You can skip the rest of this article if you don't care about HTML or other tech junk. Otherwise, press on...

In looking at the source code for emails he sent with image attachments, we could see clearly that no matter how Mike sent the message, Apple Mail would convert it to a bastardized HTML format and tag the attached images as "content-disposition: inline".

Here's a look at the Apple Mail message source:

You can see clearly that what started as a "plain text" message is actually a two-part message with a plain text part AND an HTML part. Uh hmmm. That's just wrong on so many levels. Some mail programs refer to this as "compatible HTML" (which is apparently what Apple is doing). They generate HTML with a part that will be ignored by simple plain-text only mail clients. But it's NOT plain text.

To compound the stupidity here, Apple clearly tags the image that's been attached as "inline", which pretty much guarantees that it's going to be displayed inline and not as attachment. I dunno, maybe that's Apple trying to do the thinking for its users but again, it's wrong.

FROM THE HEADER:

Content-Type: multipart/mixed;

FROM THE BODY:

boundary="------------000208000208080700070400"

This is a multi-part message in MIME format.
--------------000208000208080700070400
Content-Type: text/plain; charset=ISO-8859-1; format=flowed
Content-Transfer-Encoding: 7bit

Test message.

--------------000208000208080700070400
Content-Type: image/jpeg;
name="test.jpg"
Content-Transfer-Encoding: base64
Content-Disposition: attachment;
filename="test.jpg"
XXXXXXXXXXXXXXXX (image data removed)
--------------000208000208080700070400--

So, are there any work arounds? Sadly no. As one Mac site says, the workaround is to zip everything. Then Apple Mail won't try to think it's smarter than both it's users and recipients.

02.23.2012. 18:35

Comments

5happy 04.14.2013. 13:59

true for html emails. easy solution is to send the messages as plain text.

you can still drag and drop the attachments into the body of the email to attach... just make sure you look under the 'format' menu, last option.

you only need to do this when sending attachments.