Mail 2.0: Should be smarter about sending attachments to Outlook users

Posted by Pierre Igot in: Mail, Microsoft
October 3rd, 2005 • 9:48 am

There is a well-known problem for Mail users who send e-mail messages containing attachments to recipients who use Microsoft Outlook on Windows. If the attachment is located anywhere in the body of the message other than at the very bottom of it (below the signature and everything), then Mail encodes the message in several pieces, one that contains all the text that appears before the attachments, one that contains the attachment itself, and one (a separate text file) that contains the rest of the text in the message body (i.e. the text that appears after the attachment).

The problem is that Microsoft Outlook doesn’t handle such messages properly. Instead of rebuilding the original message properly from the three pieces, it actually presents the Outlook-using recipient with a message with two attachments. The body of the received message itself only contains the text that came before the attachment in the original message, and then the message is presented as having two attachments, one which is the actual attached file, and the other one which is the text file containing the rest of the body of the original message.

This problem causes a lot of confusion, of course, because Outlook users only experience it with messages coming from Mac OS X users using Mail, and then only experience it when these messages include attachments that are inserted somewhere within the body of the message. And because Windows users are what they are (i.e. users who tend to brush aside unexplained behaviours as part of the usual weirdness and unpredictability of the Windows computing experience), they don’t necessarily inform their Mac OS X using correspondents of the problem, and so the original Mac OS X user who sent the message might not even be aware of it and of the fact that the recipient will not see the entirety of his message body unless he actually opens that second file attached to the message.

This can lead to all kinds of very damaging misunderstandings, and is actually a very significant problem from a social point of view. When you send a message, you usually assume that the recipient will read the body in its entirety, even if he doesn’t reply to all of it. With this particular Outlook bug, there is actually a good chance that your recipient will not read the section of your message body that appears after the attachment, and you might assume that he’s seen it when he actually hasn’t.

As far as I understand it, this problem is not strictly speaking a bug in Mail. It’s a bug in Outlook. Mail encodes the message using appropriate MIME conventions, but apparently in this case the conventions it uses happen to not be supported properly by Outlook. I don’t know what happens when you use other e-mail clients to compose your message and include your attachment in the middle of the body of the message. Do they use different conventions that do not cause a problem in Outlook? I guess we’d have to ask an e-mail encoding specialist.

The larger problem here is that this has been an issue for years, and neither Apple nor Microsoft appears willing to do anything about it. If Apple is actually complying with established standards, in a way it’s not its problem. On the other hand, since it’s only a problem that affects Mac OS X users sending e-mails to Windows users running Microsoft Outlook, we just know that Microsoft is never going to bother to fix the problem. And it certainly wouldn’t be the first time that Apple would have to work around problems created by Microsoft.

There are several things that come to mind as possible workarounds. When you are composing a new message in Mail, there is obviously no way that Mail can tell whether the recipient uses Outlook or not. But when you are composing a reply to an existing message, Mail does know. The information about the e-mail application used by the author of the original message is included in the “User-Agent:” line in the message header, or in the “X-Mailer:” line. For example, I am looking at the full headers of a message sent to me the other day, and it quite clearly says:

X-Mailer: Microsoft Outlook IMO, Build 9.0.6604 (9.0.2911.0)

In other words, I know, and Mail should know, that this message was sent by a Windows user running Microsoft Outlook 9.0. And Mail should know that, if I am composing a reply to this message, then this reply is going to be received by a Windows user running Microsoft Outlook. Mail should therefore be smart enough to anticipate that there will problems if I include attachments within the body of my reply, and should do something to avoid the problems.

I don’t really care what it does to avoid the problem. But it seems to me that Mail should be smarter about this, and try to eliminate the problem as much as possible. This is what computers are for. In this particular case, Mail certainly has enough information to know for sure that there will be a problem if I include an attachment within the body of my message.

This is all the more obvious since Mail already has such mechanisms in place to accommodate the variety of e-mail applications used by our correspondents. For example, if you receive a message from a Windows user running Microsoft Outlook, the character set used for the message will probably be “Windows-1252” instead of the standard “ISO-Latin.” Mail is able to detect this automatically when you reply to such a message, and it will encode your own reply using the same “Windows-1252” character set, even though it should normally use the “ISO-Latin” standard (or even Unicode).

The only reason that it has to use “Windows-1252” here is because Microsoft couldn’t be bothered to embrace character encoding standards. Obviously Apple is willing to adjust its software to work better with the Microsoft software used by the majority. So why doesn’t it do so here with this problem with attachments in the body of the message?

At least when your message has the wrong character set, the recipient can still read most of it, and is immediately aware that it’s a technical problem. But when the recipient receives a message with two attachments instead of the expected one, and the body of the message is truncated (but not necessarily in an obvious fashion, depending on where the text is cut), there is a far greater potential for misunderstanding and communication failure, especially since Windows users are told to be very wary of unidentified and unexpected attachment files, because of the prevalence of viruses, worms, etc.

The bottom-line here is that, even if this is purely an Outlook bug, Apple really ought to do something about in order to eliminate the very real risks involved for Mac OS X users trying to communicate via e-mail with Windows correspondents.

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