I've always been confused with the way that attachments are handled in mail.app (the Mac's default email application).
Traditionally, if you'd wanted to attach a file to an email you'd just drag it into the composition window and (usually in a separate location in that window somewhere) there'd be a list of attachments that the email had.
Once sent, on the receiving end, you'd receive the text of the email, and a list of attachments (which you could then and download or preview individually).
On the other hand when dragging an attachment into the compose window of mail.app, it doesn't drop the attachment into a separate section of the email, but inserts the attachment inline.
This causes a few problems with some mail applications as:
- There usually isn't an easy way to download images which are inline
- You can't select all inline images and download them all in one hit
- And more an annoyance than a bug, but when downloading the email, all the images will be downloaded there and then, instead of just downloading the text
The worse thing was that it was inconstant. Sometimes it would send the attachments inline and other times it wouldn't. But this was only on machines which weren't using mail.app. When using mail.app though, all images would always be displayed inline and there would also be an option to download all inline images in one hit. (Yes things are beautiful within Apple's wall garden).
I needed to find a way to send emails from mail.app so that people receiving my emails had a way to download the images I sent.
So I did a bit of googling and found an option (which many people claimed on message boards) called "Always send Windows-Friendly Attachments" which would fix the problem

A bit of experimenting with this and no. With respect to this problem this option doesn't do anything at all.
After spending a bit more time searching on the Internets I decided to check out the problem myself and maybe it was the way that mail.app was sending the emails and differences in the MIME encoding.
Viewing the source I realised that on emails where attachments were inline, the email contained MIME types of both plain text and HTML, and emails where attachments weren't inline the email only contained plain text. I did a quick test email to myself (note how I've got the word HTML underlined - more on this later):

And receiving it on the gmail end:

This confirmed one half of my suspicion. (Note how in the gmail screen shot there is no option to download the image which is attached)
I then decided to send this email again but forcing plain text this time (keyboard shortcut apple-shift-t):

Loading up in gmail shows up as expected, with no inline images, and an option to download the image.

So the reason for the inconstancy? Even though I've sent emails which have had the attachments downloadable (like in the second screen shot) and I've never forced plain text before (until this day), is that mail.app (even though I've set it to always send rich text emails) only sends emails in HTML if your email contains HTML formatting (the reason why I underlined the word HTML in my first email).
So looking back in my history, it seems that most cases that mail.app has inlined images is when I've sent an email with a link (HTML formatting) and an image from that link.

So in future, if I am sending a set of photos, I'll be forcing plain text emails. Otherwise it's the lolcat image with the relevant hyperlinks.
(Or I could just disable HTML emails altogher)
Note: In the raw email sent, mail.app doesn't just compose the email with the plain text at the top and the attachment at the end. It actually sends a plain text MIME component, then the attachment (the inline image) then another plain text MIME component at the end.
Most email readers (gmail included) seem to have trouble displaying this image inline when surrounded by plain text components, and instead puts all plain text elements together and provides an option to download the image.