How can I prevent mail attachments embedding when sending mail

Commanding Mail to use Plain Text is for the moment broken in Mail 5.0. The ways to send in Plain Text are at present limited, and cannot be achieved if you for example compose a message in iPhoto or Aperture of images, nor with the photo browser.

What has worked is to simply set your Mail Preferences/Composing to only use Plain Text, and then only use direct attachment. One way that I have found is to drag a JPEG onto the Mail Icon and begin the compositon that way.

It is very annoying, but should get fixed.

Ernie

Is this why people claim to not be receiving certain files I send? I'm baffled as to what's going on here. I'm a very long time Apple fan (early 90s!) but I'm surprised by how many basic things in Lion are a mess.

Using other than Plain Text is responsible for most of these reports, and is almost always related to their use of Outlook or Outlook Express. Not Apple's problem per se, but caused by MS proprietary approach to Rich Text, and those apps not appreeing with RTF from Mail (and other sources). What is broken in Lion and Mail 5.0 is actually achieving Plain Text after commanding it.

Ernie

Any word on whether any of this is fixed by the 10.7.1 update?

Was not fixed in this update.

Ernie

Where is the "content disposition" setting in a message header? How is "inline" denoted?

Content disposition is in the header of each attachment, and you only see it with the use View Raw Source. The issue of Plain vs Rich text is not precisely the same issue as Inline disposition, but they are related in most instances.

Ernie

Thank you. Found it.

I conducted an unscientific survey of 53 members of a service club to which I belong. On my iMac (Lion) I ATTACHED a photo (.jpg) to a message and sent it with the Mail app.. EVERY non-Mac user reported receiving the image embedded. This is a Mac OS Mail problem. Apple oughta fix it.

Thanks -- I appreciate the results of this survey. Apple ought to provide a better workaround, but the problem in reality is generally with MS email clients. I suspect all those non-Mac users were running Outlook or Outlook Express? I generally found in tests long ago that Thunderbird on Windows would handle it fine.

It does not take much searching to find similar problems involving messages sent between versions of Outlook, and/or Outlook Express, and not related to Macs at all.

Ernie

Hi folks!

I'd like to hook up in this thread, as I'm experiencing the same problem. There has always been a mail-attachment problem between mac and win, at least when the latter used outlook. To my knowledge and personal experience there has always been a work-around (several of them posted here).

But: since upgrading to lion I'm totally frustrated, because none of those work-arounds works anymore. As a photographer, I just have to be able to send jpg's to many recipients with a variety of non-mac IT-configurations. And I can't blame them, because this new problem with lion's mail.app is definitely not a microsoft-problem. Not even mail.app itself recognizes it's own attached jpg-files as attachments, as you can easily check in your send-folder after enabling the "attachment-flag" for the displayed mail-list.

Two recipients (both on winXP and outlook 2002) were able to save my jpg's when I sent them using the finder by dropping the file into mail.app without adding any text (not even above the attachment). The file still wasn't marked as an attachement in their inbox, but they could save it as jpg. Two other editors couldn't handle them this way either.

Maybe this helps you too: today I found out that sending the mail via googlemail solves the problem for all recipients tested so far. Funny enough, the mail is still flagged "without attachment" in my send-box, but when sending it cc: to myself it shows up "with attachment" in my in-box. So now I re-configured all my mail-accounts to use the googlemail server for outgoing traffic and added the "Answer to"-field (? called "Antwort an:" in my german version of mail.app) to every mail I send.

Not very amusing, and I can only share your disappointment.

Cheers, Jürgen

Hi, me again,

today I found that two editors still were not able to save my JPG even when sent via googlemail-smtp. With those, another trick from a kind user in another forum (sorry, forgot his/her name) worked:

-->If you want to attach a JPG, always attach a TXT or RTF file as well (may be empty). I do not have any explanation, but with those 2 files attached, the JPG suddenly displays "attached" and not "inline" in Outlook and everybody (up to now) was able to save it.

Still not amused, Jürgen

This situation is not impacted by what SMTP you may be using, Gmail or otherwise.

This issue about some Windows users not seeing the attachments is related to Mail 5.x not actually sending in Plain Text, even if you request it. I have been informed that has been done on purpose by Apple engineering, but I am of the opinion that change is a grave mistake, and will continue to be problematic. I continue to collect reports about that in the hopes I can ulitimately convince someone it is a bad change.

Ernie

I can confirm that SMTP server does make a difference. Send same mail (text + jpg) to my office (Win XP / Outlook 2002) yesterday and checked them today:

- via Strato (german hoster) SMTP: Mail not flagged as "with attachment", photo seen "inline", unable to save as JPG (save as BMP is possible)

- via googlemail SMTP: Mail flagged as "with attachment", photo seen "inline", no problem when saving as JPG

And, funny enough: same mail with just an additional empty TXT-file (text + JPG + TXT-file):

- via Strato SMTP: Mail flagged as "with attachment", JPG not shown inline, only as symbol. No problem saving it as JPG.

I cannot believe that this misbehaviour of Mail is solely based on the "Plain Text" thing, taking into account that Mail itself is unable to flag mails with attachment properly in it's Send-Box. But anyway, I do not know anything better ...

Jürgen