Mail converting entire content to attachments after attaching a file

Question

Mail converting entire content to attachments after attaching a file

I have encountered an issue that is really perplexing me.

It seems that just over the last week Mail has started doing something quite strange.

Specs:
Outgoing Mail - OSX 10.6.7, Mail 4.5

Receiving Mail - XP using Outlook 2007 and Windows 7 using Outlook 2010.

Mail server - OSX Server 10.5.8 (All this is internal so it only goes through the one email server)

I can reply and forward several times and attach jpegs along the way with out any trouble.

However as soon as I attach a zip or a pdf or anything that does not display inline it converts the entire message to attachments.

By this I mean that all the footers and reply quotes and message content all converts to separate .htm files and appears as attachments in the receivers Outlook.

So there is nothing in the body of the email and multiple attachments of .htm and .jpg and .whatever.

I have only been able to test this on two Macs both running OSX 10.6.7 sending to two PC's, one running Outlook 2007 on XP and the other running Outlook 2010 on Windows 7. All on the same server as stated above. It is happening externally as well but I have conducted extended testing on the above configuration.

Any clues would be appreciated.

Posted on Jun 8, 2011 6:36 PM

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Answer 1

etresoft

Level 9

56,326 points

Jun 8, 2011 7:01 PM in response to Andrew Waters1

Any mail message with something more complicated than plain text is going to consist of nothing but attachments. It is the responsibility of the recipient's e-mail program to parse and display it properly.

I'm interested that you say you say a PDF does not display inline. It should. That is one of the primary complaints about Apple Mail. Any image file or PDF can only be attached inline. You have to download some 3rd party tool to force it to be displayed as an icon attachment. Have you done that?

I would be happy to take a look at one of your e-mail messages. Send it to info at etresoft dot com.

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Answer 2

Jun 8, 2011 8:18 PM in response to etresoft

It's just that this has only just started happening. We don't have any third party tools installed.

Perhaps I used the wrong terminology when I said "inline" what I mean is that anything that normally shows up as an attachment at the other end causes the problem. i.e. zip files and pdf files.
Where as Jpegs and gifs do not normally appear as attachments they appear as though they are embedded in the body of the email and they do not cause the problem.

I would send you the emails to have a look but of course I have no way of knowing what they will display like for you.

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Answer 3

etresoft

Level 9

56,326 points

Jun 9, 2011 4:07 AM in response to Andrew Waters1

Since I use Apple Mail, the same program used to send them, they will probably display fine. But I wouldn't look at them that way. I would use Message > View > Raw message feature to look at the internals of the message to see what is really going on with this message. I could just blame it on the PC, that that doesn't help you much.

What you describe is a known limitation of old versions of Outlook, but you are using newer versions. Plus, that limitation usually only applies to text messages, not rich text messages. Since you said htm attachments show up, that implies you are sending rich text, which shouldn't exhibit this problem. Apple Msil has been specifically coded so that such messages display properly in Outlook, so it is a bit mysterious why they don't.

The standard way to fix these issues is to use the Apple Mail setting to always put attachments at the end of the message, but since you want to put some attachments inline, that doesn't seem appropriate. Plus, I thought that hack was only needed for text messages with attachments.

So, I would like to see one of these raw messages. Also, it would be nice if you could save one of these test messages as raw source, compress it, and send that to me as an attachment. That way, I could see what your private email server is doing. Having a private email server is a bit unusual. Depending on how it is setup, it could be causing the issue.

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Answer 4

Jun 9, 2011 4:06 PM in response to etresoft

Thank you for your help in this I will send them through now.

Cheers.

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Answer 5

Jun 10, 2011 6:08 PM in response to Andrew Waters1

I have been communicating with etresoft about this issue via email so he can see exactly what is being sent out but we are still no closer to solving the issue.

If anyone else has any suggestions I would appreciate them.

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Answer 6

pfb1968

Level 1

5 points

Mar 19, 2013 2:30 AM in response to Andrew Waters1

I am having the same problem. I've just been told by a work friend that she has received several emails from me this way. That is, attachments attached, but text content also wrapped into an attachment ("Untitled attachment 00027.htm). She is on a windows / outlook platform. Don't know the version. I've been notified of same by at least one other recipient also.

I just raised another discussion / question before seeing this one. This one seems to describe my problem exactly.

Grateful to know if any solutions have arised since you guys originally discussed this in 07.

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Answer 7

Mar 20, 2013 12:15 AM in response to pfb1968

The suggestion to put those type of attachments at the bottom of my e-mail (after all other content) is what I am still doing today.

I now have OS X 10.8.3 and a brand new 2013 iMac and mail is still doing exactly the same thing as all those years ago.

Sometimes I even have to remove the jpeg in my signature so there are no other attachments in the body of the e-mail to stop the html thing happening.

I don't have any confidence that it will ever be solved to tell you the truth.

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