Lion/Mountain Lion’s Mail: Workaround for removing attachments from sent messages

Posted by Pierre Igot in: Mail
November 13th, 2012 • 9:28 am

In Lion (OS X 10.7) and Mountain Lion (OS X 10.8), 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” command is greyed out, even though the messages do contain attachments, which can be confirmed by looking at the message contents of the individual messages.

There is a discussion thread about this particular problem on the Apple forums, which clearly shows that a number of users are affected. Over time, with Apple seemingly unable or unwilling to fix this bug, people have come up with various workarounds. The one I have come up with works reliably for me, although it is a bit tedious.

But now, on another discussion thread about the same issue, a user named oakmontoz has come up with a better workaround:

OK, I have no idea why, but the following worked.

I created a rule in the Preferences pane:
sender is me
attachment contains “.” (every file does)
set color to (anything)

The rule worked.
Furthermore, the paperclips appeared!!!

On the main discussion thread, a user named iBiM has come up with a more detailed description:

1 – Create a rule in the Mail Preferences pane
2 – Call it “Get My Paperclip Icons Back!”
3 – Set conditions as below :
A – If ALL of the following conditions are met :
B – From Ends With [Your email address here] (you can do this for multiple too]
C – Any Attachment Name Contain “.” [with the quotations around the dot]
Perform the following actions :
D – Mark as Read [which really makes no impact on how its viewed]

And the amazing thing is that it works! You still have to manually select the sent messages and use the “Apply Rules” command to force Mail to apply the rules (including the fix) to the selected messages, but after that, the paperclip icon indeed appears and the “Remove Attachments” command is no longer greyed out and works to remove the attachments from the message.

It is still rather shameful that Apple has not done anything about this bug in over a year (some people say that Apple has responded to their bug report by saying that it’s a “known issue”, which is more encouraging than Apple completely ignoring the problem, but they still haven’t done anything about this “known issue”), but at least we now have a workaround that is fairly easy to implement and use and will enable us to fix the problem manually until Apple finally fixes the bug itself.

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