Here's another workaround for this very annoying bug: export the sent messages to a .mbox file and then reimport them. You can then remove the attachments:
I cannot reproduce this fix on my machine. No matter how and where I select the messages, Remove Attachments is disabled.
The difference is clear when you examine the actual mailbox folders and e-mail files in the Finder: for the sent messages, there is no "Attachments" folder next to the "Messages" folder. The "Attachments" folder should be there for messages containing attachments and contain copies of the attachments in folders whose names match the file names of the corresponding e-mail message files (.emlx).
For example, if an e-mail file's name is 143354.emlx and is enclosed in a folder called "Messages" inside the numerical hierarchy that Mail uses internally to organize its files (in the ~/Library/Mail folder), then next to that "Messages" folder there should be an "Attachments" folder containing a folder named "143354" which in turn contains a copy of the extracted attachment (inside yet more numbered folders).
With the sent messages I have, no matter where I put them, the enclosing mailbox folder in the Finder only contains a "Messages" folder with the message file(s). There is no "Attachments" folder with folders with the corresponding names. So somehow Mail has failed to "extract" the attachments and recognize them as such.
The only fix that works for me so far is to export and then reimport the sent messages using the .mbox file format. After that, Mail clearly "sees" the attachments, has the paperclip icon in the message list and has "Attachments" folders inside the mailbox folders for the reimported messages.
I have tried all the options and none really work.
I created a Smart Mailbox with the sent emails, and tried to delete the attachments once they have been put in another folder, but they keep on appearing again.
What I do now is that when I send an email with an attachment, I BCC myself, then I delete the email sent, and when I recieve the email I had BCC myself, I delete the attachments and then move the email to the appropiate folder.
Not a solution at all, but fairly clean process and when in the folder the rest of the data is on the email.
I have folder called 2010, 2011 and, since a few weeks, 2012, where I move sent mail. Interestingly, the new folder 2012 does not allow me to remove attachments using Email -> Remove Attachments. If I move these new mails to the folder 2011, however, I can remove the attachments. After the removal, I can move the emails to the new folder 2012. Browsing the directories in Library -> Mail -> Mailboxes does not reveal any differences in the names of the subdirectories and permissions.
It must be because the 2012 mailbox folder itself was created with Mail 5, whereas the 2010 and 2011 mailbox folders themselves were created by a previous version of Mail.
I can reproduce this too, by moving e-mails to a mailbox folder created BEFORE I upgraded to Lion/Mail 5!
The reason Apple seems to have a hard time reproducing the problem (although they are obviously not trying very hard, based on the number of reports here) might be that there is something problematic with the way Mail 5 indexes mailboxes, and it only occurs in certain combinations of circumstances.
Thanks for the new information.
Pierre Igot---LATEXT: Literature, music, and visuals / Littérature, musique et graphisme
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Can't edit my post anymore. Something about the URLs in my signature that Apple didn't like .
Sadly, I was mistaken. The workaround does NOT work for me. It might still be something about the Mail version that created the mailbox folder. But it does not fix the problem for me. Do you have a POP or IMAP account?
Hi Pierre Igot,
here is some more new info. I can now remove the attachments, if I mark ALL messages in the folder 2012 but I cant remove after marking a single message that has an attachment.
And second, somewhere deep in the subdirectory, Mail creates a folder "Attachments". If you remove that it wont re-appear but you can still send mails with attachments. I have no idea where the attachments are stored then, maybe they are incorportated in the mails.
The file structure has change dramatically after the upgrade, could cause the problem.
Kind regards, Tino
I have not had a chance to further investigate this, as I must primarily work in Snow Leopard for my work flow.
However, I can confirm that attachments are stored with the message content, and anything in an Attachments folder is redundant. In versions of Mail prior to SL, only IMAP accounts generated the Attachments folder, but then it became part of POP accounts as well -- but again a redundant storage location.
In earlier tests, I established that any message sent from Mail in Snow Leopard on an IMAP account, would in Lion be amenable to removing the attachments in a single message. Very curious behavior.
tinoberlin FabeRox and others, just a support mail. Glad I found this discussion and to know I ‘m not the only one with this very annoying problem of not being able to remove attachments from sent messages since using Lion.
I also came across the ‘solution’ of Bulchand BCCing myself and remove the attachment from the incoming mail.
Hope Apple will fix this soon!
Yesterday I did a clean install of OSX Lion (10.7.2) on one of my MacPro's internal hard drives where there had never been any other OSX installed previously. Booted from this drive and more or less "for fun" set up Mail (two IMAP accounts - MobileMe and Macbay [German provider]) and let the application fetch all messages (received AND sent) from the corresponding servers (more than 2,000 messages in total). Believe it or not: "Remove attachments" was not greyed out after this and I am able to delete attachments from any sent mail now - no matter which account, no matter if message had been sent in 2012, 2011 or 2010 (or even 2009 in my case).
Not sure if this information will be helpful for all you guys suffering from this weird problem. Hope it will.
Regards from Germany.