Mail 5.1: Removing attachments still an issue

Posted by Pierre Igot in: Mail
September 30th, 2011 • 8:59 am

What is it exactly that Apple’s engineers have against people wanting to remove attachments from their e-mails? Ever since Apple added the “Remove Attachments” command to Mail’s interface, back in 2003, it has been plagued with problems.

It has always been, and still is, impossible to undo the command. Given that it is quite a destructive one, this makes very little sense, especially since there is no warning about it not being undoable.

And because the command was (still is?) essentially a hack, which consists of deleting the existing message and creating a new one without the attachment, for years the use of the command had the unfortunate consequence of deselecting the message that you were applying it to. Then Apple “fixed” this problem by causing the use of the “Remove Attachments” command to… select the next message in the list.

Then finally in Lion Apple fixed this problem by making sure that the message that you remove attachments from remains selected, which should have always been the case. That, folks, means that we’ve waited a full eight years for Apple to fix this particular problem.

Unfortunately, that is not the end of the story when it comes to the “Remove Attachments” command in Lion’s Mail, quite the contrary. Apple has actually managed to introduce new quirks and bugs.

The big one is that there is a very serious problem with sent messages containing attachments. As far as I can tell, it is simply impossible, in Lion’s Mail, to remove attachments from sent messages. Even when a sent message contains an attachment, Mail fails to include the paperclip icon next to the recipient’s name in the message list, and when you select such a message, the “Remove Attachments” command in the “Message” menu is disabled, which means that you cannot use it.

I did some additional testing before submitting this as a bug report to Apple and can confirm that, at least on my machine, the bug affects both POP and IMAP accounts. Even if you move the sent message containing an attachment from the Sent mailbox to another mailbox, Mail still refuses to show the paperclip icon or let you remove the attachment. In fact, even if you export the message from your own Mail environment and open it in another user’s Mail environment, the problem persists. So it appears that there is something about the way attachments are encoded by Lion’s Mail in sent messages that is wrong. Indeed, when I upgraded to Lion, I still had quite a few older sent messages in my Sent mailbox that had been created using a previous version of Mail, and these sent messages didn’t pose any problem, even in Lion’s Mail. The paperclip icon was there, and I was able to remove the attachments. The problem only affects messages composed and sent by Lion’s Mail.

It also affects the ability to send such messages again. If you select a sent message containing an attachment in the Sent mailbox and choose “Send Again” in the “Message” menu, Mail fails to include the attachment in the new copy of the message that it creates for you to send it.

In this discussion thread on Apple Support Communities, some users report being able to restore the functionality by moving the affected messages to other mailboxes or by rebuilding mailboxes, but neither fix works for me and I am not the only one who simply cannot get anything to work.

(As several contributors report, you can manually remove the attachment by opening the corresponding .emlx file in TextEdit and removing the section containing the encoded file, but it’s a royal pain, and it removes all traces of the attachment, without leaving any indication of what the file name of the attached file was.)

Then there is the very confusing situation caused by using the “Organize by Conversation” option in Lion’s Mail. When you select a conversation containing several messages, some of which contain attachments, the selected conversation heading (which looks just like any other message in the message list, except that it has a message count of more than 1) has a paperclip icon, but the “Remove Attachments” command is, as far as I can tell, disabled unless the last received message in the conversation contains an attachment — and then, if you can use the “Remove Attachments” command, it removes the attachment… from the older message in the conversation that contains one. It makes no sense whatsoever.

(There is a general fuzziness about which message is “selected” when you select a conversation, which deserves an entirely separate article.)

Why, oh why is removing attachments such a pain in Mac OS X’s Mail? I, for one, want to try and keep the size of my mailbox archive manageable and have no need to accumulate hundreds of old attachments within it. If I want to keep an attachment, I extract it from the corresponding message by saving it in a separate location on my hard drive, and then I remove it from the message in Mail. And of course, I have absolutely no need to keep copies of the attachments that I send with Mail in Mail, since I already have copies of them on my hard drive (which is how I was able to attach them in the first place, duh).

Right now, because of the major new bug with sent messages in Lion’s Mail, I have a a Sent mailbox that is becoming bigger and bigger by the day. (It’s already nearly 200 MB as we speak.) I sure hope that Apple fixes this particular bug soon, so that I can remove all these attachments and archive the sent messages without worrying about the amount of hard drive space that they are wasting.

But most important, we need Apple’s engineers to start taking the “Remove Attachments” feature seriously and make it an integral part of the Mail user interface, and not treat it as some neglected, buggy command that only a limited number of “advanced” users care about. Sadly, given the general dumbing-down trend that is characteristic of today’s computing technology, I am not sure there is any hope of this happening. Apple seems to think that most people do not archive their messages at all — or, more cynically, that if people’s mailbox archives grow to unseemly sizes faster, they’ll be encouraged to purchase new hardware faster.

2 Responses to “Mail 5.1: Removing attachments still an issue”

  1. Betalogue » Lion’s Mail: Export/import round-trip to remove attachments in sent messages says:

    […] while ago, I wrote about a new bug that I am experiencing in Lion’s Mail, where any sent message containing attachments is displayed […]

  2. Betalogue » Lion/Mountain Lion’s Mail: Workaround for removing attachments from sent messages says:

    […] Mail has a bug that, for certain types of e-mail accounts at least, causes the application to fail to identify sent messages containing attachments as such. The paperclip icon never appears in the message list, and the “Remove Attachments” […]