How can I prevent mail attachments embedding when sending mail

The issue with Plain Text has been present in all recent versions of OSX and Mail. In Lion, it is only the inability to assure Plain Text that is problematic. In earlier versions of OSX and Mail, if only one font and color of font was used, Mail automatically changed to use Plain Text. That is gone.

I would need to examine the Raw Source of mesages sent from these different SMTP to understand what would be different, and that could be an important difference if the case.

In the case of the Sent mailbox issue, I have determined that if a message with attachment is composed and Sent in Snow Leopard with Mail 4.5, say, and the account is IMAP, then in Lion and Mail 5.x the message can be seen in the same account's Sent mailbox in a proper manner. Likewise, the message sent from Mail 5.x will be seen to be in proper form when viewed in the same Sent mailbox via Mail 4.5 in Snow Leopard.

There is much to learn about this latter, odd, issue.

Ernie

Sorry, I cannot provide the complete source of the mails due to restricted access (only via Outlook). And the only difference in the usual "long headers" are those concerning the SMTP server. I cannot see the headers for the attachements forinstance, sorry!

Jürgen

Oh, I didn't expect you to. But if you wished to send me test messages from you two SMTPs, you can find my address by clickig on my name.

Ernie

Done! Cheers, Jürgen

Jürgen from OHZ wrote:

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

Many ISPs will filter incoming and/or outgoing e-mail to disable phishing attempts and remove viruses. To do this, they sometimes disassemble e-mail messages and then reassemble them. In this case, it sounds like Google is doing something to the message. Strato seems to be working as expected. Outlook 2002 will only save as BMP. You can send a JPG from 2002 to yourself on Outlook 2002 and you will still only be able to save as BMP. That's just life in Windows ten years ago.

So how come we've still heard no official word from Apple on this? When will there be a fix?

BTW, this DOES NOT affect the iPhone or iPad... Just apple mail.

Apple, we need a fix!

Very interesting. At first glance did not find the difference between the two SMTP, but only a hurried look. Most interesting is the one sent with the addition extra text attachment. It achieved Plain Text -- that is it eliminated the presence of any HTML.

This will take some careful analysis with the first two.

Please tell me exactly the process with the third message that has the empty text attachment. I would like to try to replicate.

Ernie

etresoft wrote:

Outlook 2002 will only save as BMP. You can send a JPG from 2002 to yourself on Outlook 2002 and you will still only be able to save as BMP. That's just life in Windows ten years ago.

No, until a few weeks ago (=sent using Snow Leopard) mails with JPG were 1) flagged as "with attachment" and 2) the JPG could be saved via "Save attachments" by Outlook.

Just wrote the mail, attached the JPG (via the attachment-button) and then attached the TXT (again via attachement-button).

Jürgen

Did you attach the JPEG in the same manner on the other two messages?

I can simply borrow your empty attachment for my test, then.

Ernie

Jürgen from OHZ wrote:

No, until a few weeks ago (=sent using Snow Leopard) mails with JPG were 1) flagged as "with attachment" and 2) the JPG could be saved via "Save attachments" by Outlook.

You were probably sending plain text messages. In Lion, messages sent with attachments are always sent as rich text. This is to avoid a different bug in Outlook. Apple has to decide which Outlook bug you will encounter. In Lion, your e-mail message has a higher probability of appearing correctly in Outlook. In Outlook 2002, you you can only save the image as BMP. In Outlook 2007, you can't save it at all. You can only copy it to the clipboard. I think it works correctly in Outlook 2010.

Jeremy Kinsey wrote:

So how come we've still heard no official word from Apple on this? When will there be a fix?

BTW, this DOES NOT affect the iPhone or iPad... Just apple mail.

Apple, we need a fix!

Apple can't fix bugs in Microsoft products. Microsoft has already fixed this bug.

I'm sorry I couldn't take any longer replying. The results of my unscientific poll include people using AOL and Gmail clients finding my .jpg attachment embedded in the message they received. This problem appears to be not confined to Outlook users.

Yes, and two of "my" editors unable to save attached JPG were using Outlook 2007. They were able to save before I switched to OS X Lion. Just like myself with Outlook 2002 in my office: no problem with my private mails as long as I was sending them with Snow Leopard. And why does Mail change its "send-behaviour" when an additional TXT-file is attached?

@Ernie: Yes, I attached the JPG in exactely the same manner in all three mails sent to you.

Good morning! Jürgen

This is a documented bug in Outlook 2007

http://support.microsoft.com/kb/917120

These issues have nothing to do with Apple. You will experience identical problems when sending JPG images from Outlook itself. What are you going to do if one of your clients is using a system without any graphical display? They won't be able to see the image at all. Would that be Apple Mail's fault too? Apple designs for the future, not the past.