Inline attachments sent to MS Outlook messes up message layout

michaelw wrote:
Why is this happening?

Because Outlook is a horrible e-mail client. Unfortunately, there is nothing you can do about it other than sending ZIPs, Word documents, or PDF files.

Michael,

Try resending the message (Message/Send Again) but before sending click on Format and choose Make Plain Text.

The ATT file attached is often a clue that you are in an environment where an Exchange server is being used?

Ernie

Michael,

My suggestion was not directed at the Att file attachment, but only at the Inline attachment issue. Can you be more specific on the Inline issue. If you wish, you can send me a sample message where this would happen. My address can be found by clicking on my name to the left, and looking in the bio line of the resulting Profile display.

Ernie

Michael,

The email looked the same as received (in Plain Text actually) as it does in the screenshot you also sent by a separate email. The only difference is that on your Mac it apparently displayed as RTF, but looking at the RAW Source, the message is only Plain Text -- when only one font is used, and there is an attachment, Mail automatically sends RTF as Plain Text.

However, something else is going on -- the attachment is not Inline. Its preceding header as viewed in RAW Source does not have the Content Disposition tag of Inline. Instead the Content-Type header reports, as you will see below, that it is "application/octet-stream"!

--Apple-Mail-80--197679133
Content-Disposition: attachment;
filename=attachment.doc
Content-Type: application/octet-stream;
x-unix-mode=0644;
name="attachment.doc"
Content-Transfer-Encoding: base64

I will have to do a little research, but, if memory correctly serves that improper header is caused by the Exchange Server. Should have this header in this case -- see:

http://kb.iu.edu/data/agtj.html

More shortly,

Ernie

Message was edited by: Ernie Stamper

Michael,

Initial research indicates that it is related to an Exchange Server configuration. Do both you and your intended recipient use Exchange Servers, and version 2003. See this link.

See the following link which I think delves into what setups on an Exchange Server may cause this, but I have not really studied it in that regard.

http://support.microsoft.com/kb/836555

Ernie

Michael,

The issue with the Att attachment has nothing to do with Mail, and everything to do with sitting behind an Exchange Server. The ATT attachment does not appear either in normal view or RAW Source view on the messages you sent me.

I am not clear what the other issue with attachments messed up, but I do know the Content Disposition header I found on the first message could be problematic for some recipients. This Content Disposition tag also originates with an Exchange Server and is not due to actions by Mail, I believe. It does not appear when you sent the screenshots.

It occurs to me that if limited to files created with MS Office, those files could in fact contain a micro-viri which is an application, and might cause the application/octet stream disposition tag.

There are viri that can infect Office -- this is actually not your Mac that would be infected, but only the application or applications in Office. This infection can pass with a shared file, and is cross-platform. See:

http://outlandishjosh.com/wp/index.php?p=861

In many instances, it is the SMTP server that flags a message as containing a micro-virus.

Ernie

Edit: I scanned the word doc you sent with ClamXav and no problems were found, so probably not a micro-virus issue.

Message was edited by: Ernie Stamper

Michael,

Check the message as it sits in the Sent mailbox, using a RAW Source view, please.

Ernie

Michael,

I believe you will find that the Exchange Server plays part in communications with all servers, including the Gmail SMTP.

When I send Word Document, using my Gmail account, and view the RAW Source, the Content-Type is application/msword and not octet-stream. The latter is not desirable, and is not the standard action of Mail.

Ernie

michaelw wrote:
Hi etresoft - I think there could be 3 culprits:

Sorry, but no. There are, at most, 2 culprits - both made by Microsoft. I'm not familiar with Exchange server. It is certainly possible that the Exchange server is scrambling your message. However, I can state with certainty that I have done simple tests with Outlook using my own server and can certify that Outlook will scramble e-mail messages without any server help.

Since many if not most people are using MS mail server and/or clients I'm concerned about how my email which I edited in my Mail app will look at the destination. If I cannot control how my mail will look at the destination this has serious implications as important information my got lost.

Welcome to the wonderful world of e-mail. Unfortunately, you are going to have to deal with it. If you want your message to look a certain way, then your best bet is PDF files. With e-mail, the best you can possibly get are some "hints" about how your message should be displayed. A client is under no requirement to display your message the way it looked when you sent it.

Most e-mail clients do a pretty good job. Unfortunately, you are using Apple Mail to compose and send your message. Apple Mail is a very good e-mail client and is perfectly capable of letting you construct e-mail messages that other clients cannot understand. Apple Mail is not doing anything wrong. Its messages are 100% compliant to the MIME e-mail standards. You have to realize that most PC people cannot even conceive of doing something like inline images. It is just impossible on most PCs.

In fact, Apple has, over the past few years, reduced the abilities of Mail in an effort to alleviate this problem. Apple Mail used to be a much better e-mail client 2 or 3 years ago. Apple works hard to get their messages to display as nicely as possible on Outlook, but Outlook is the limiting factor here. The future doesn't look any better. As more and more people go to web-based e-mail, there will be less and less support for fancy e-mail messages such as the ones you are trying to create.