Why can't I remove attachments from mail in Apple Mail 5

There are some messages in sent, that to mail don't seem to have attachment even if you did attach something and on these "remove attachments" does not work.

You can spot those messages by creating a smart mailbox with the rules

contains messages that match all of the following condition:

• Contains attachments
• Message is in Mailbox (here select your Sent mailbox)

I noticed that quite a few of messages in the Sent-Mailbox were not detected by these rules, but their header did show up to 8 attachments! And those are exactly the messages where it seems to be impossible to remove the attachment.

I suspect it to be the new scheme how Lion incorporates attachments in mails. Does anyone know more about the changes with respect to attachment?

Will there be a fix?

I don't know about Apples plans ...

Curious as to why there hasn’t been more dialogue about this and why Apple isn’t answering our very basic question of why attachments can no longer be removed from sent messages. I archive all messages sent to clients and alwayts remove attachments so I’m not wasting space with duplucate files. Someone? Anyone?

I have the same problem. I can't delete attachments from sent messages. The option is greyed out - why? Does it have something to do with Versions or whatever it's called, the built-in function that is supposed to let me step back to earlier versions of my work? I am totally uninterested in that, since I'm perfectly able to keep order myself.

I have been waiting for Mail 5.1 to address this problem ever since Mail 5 appeared. Now it's out, but the problem remains. Why, Apple? And how do I clear my sent messages from attachments?

There's a parallel discussion on <https://discussions.apple.com/thread/3219700?answerId=15847942022#15847942022>.

Edit: corrected wrong URL.

I have now created a smart mailbox as described above (good idea), and although I have some 50 messages in my Sent box, all with attachments (waiting to be removed so I can store the messages in the proper mailboxes), the smart mailbox is empty. So, Mail doesn't recognise these messages as containing attachments.

This led me to think that maybe Mail has been redesigned to work the way you would expect it to, at last; to contain a link to attachments instead of including them in all their bits and bytes. That would mean that the messages in my Sent box - with attachments - could be stored in local (or server-side) mailboxes without taking up extensive space.

But then I checked the size of my Sent Messages folder inside the Mail Folder in Finder, and - whoops - it's 50+ MB. So the sent messages do contain attachments all right. And Mail doesn't recognise these, since a) the smart mailbox trick says that the messages are free from attachments, and b) the Remove Attachments menu option is disabled.

I will have to wait for the next Mail update, and my Sent box will grow accordingly ...

I had the same problem after upgrading to Lion. Called Apple Care about this. The rep promised to look into it and call me the next day. He did. Seems to be a problem with indexing mail during the Lion upgrade. Fix (we think): Select the Sent mailbox, and then choose Mailbox > Rebuild. So far, so good.

Rebuild did not fix it here, both for older emails and for anything sent after the rebuild.

Weird that you get no 'paperclip' for the individual emails, but in the message viewer window it will indicate "2 Attachments, 168KB".

Same situation here.

BUT: Today I did a fresh install of OSX Lion (10.7.2, didn't update to 10.7.3 yet) on one of the internal hard drives of my MacPro where there had never been any other OSX installed before. Booted from this drive and more or less "for fun" set up Mail (two mail accounts - MobileMe and Macbay [German provider]) and let the IMAP routine import all mails (received AND sent) from the corresponding servers. Believe it or not: I am able to delete attachments from sent mails - no matter which account, no matter if mail had been sent in 2012, 2011 or 2010 (or even 2009 in my case).

Not sure if this information might be helpful for all you guys suffering from this weird problem. Hope it is.

Regards from Germany.

10.7.3 Combo Updater does not resolve this issue.

I have tried archiving the emails to the Desktop as mbox files then reimporting, but that did not help.

I have noticed a few sent emails I've sent do get the 'paperclip' in list view and are treated properly with attachments, but 99 out of 100 do not. I'm not sure what triggered the proper handling.

Does it make a difference if you had added the attachment per drag and drop from, say your desktop to the message pane rather than attach them via the corresponding command in Mail?

Not here.

Also, auto-sent items like iCal invites are not handled properly either.

The behavior isn't specifically tied to Sent Items. It is a global issue where Mail is inconsistent in recognizing (fully) attachments for the purpose of removing them. I had the same problem with a PDF attachment someone just sent me. Remove Attachments was grayed out. I did a Rebuild on my inbox and after that, I could remove the attachment before filing in another folder.

So the real problem appears to be highly foundational, which is surprising for Apple. Outlook for Mac does not have this problem and never has. I remove attachments all the time and I never have to "Rebuild" anything. The very fact that such a corrective command exists is troubling. I want to use Mail instead of Outlook due to its integration with the other Apple apps (iCal, etc) and I don't need all of Outlook's other features, and with $100 billion in the bank, you would think Apple would really have their e-mail client (read: computers 101) completely dialed in by now. The luster will wear off quickly if simple stuff like this that is being reported doesn't get fixed. Apple, I love you, but don't pull an Intuit or that love will die.