Remove attachments in Mail

I am a Mail plug-in developer and several users have already reported this problem to me. It does not seem to depend on account settings and happens with some incoming messages as well. It is a specific message structure that triggers the problem, and the same messages are handled OK on Mac OS X Snow Leopard. Moving to another folder helps because Mail changes the internal structure of the message (structuring of the mime parts, header order, etc.), but it may not help always.

The problem can be replicated reliably by saving a message as raw source, converting it to the mbox format (by prefixing it with a From line) and then importing it on a different computer.

I have reported the problem to Apple (it is also present in the current developer preview of 10.7.2):

http://openradar.appspot.com/radar?id=1313404

The more reports Apple gets the more likely they are to fix it. So please report the problem too if you have experienced it. You can do so even without a developer account:

http://developer.apple.com/bugreporter/bugrptform.html

(In that case, I recommend saving a message from which attachments cannot be removed as raw source, uploading it to a web server and including a link in the bug report. Feel free to reuse the text fo my bug report.)

iBiD created a rule in order to mark send emails as read which made paperclips re-appear and finally I am able to remove attachments from my sent mail! 🙂

see:

https://discussions.apple.com/thread/3226400?start=0&tstart=0

The only thing that has worked for me (and solved the problem) is the one with creating the rule and then clicking on "Apply rules" to the messages sent. This brings back the paperclip for all messages with attachments and allows to use "Remove attachments".

The process is described in iBiM's post here: https://discussions.apple.com/thread/3226400?start=0&tstart=0 (scroll to the bottom of page 1)

Tonden

I found an answer on lifehacker.com

1. Open up Apple Mail and create a new Smart Folder. You can do this by clicking the + sign in the bottom left corner of your Mail window, or by going to the Mailbox menu and choosing New Smart Mailbox.
2. From there, make sure to specify that this Smart Mailbox's rules apply to all. (This should be the default.)
3. Now all you have to do is set one simple rule: "Contains Attachments". You may also want to specify that the smart mailbox should include messages from your junk and trash folders, just so you're covering all your bases. When you're done, just click OK and Mail will create the smart mailbox.
4. If Mail doesn't do it for you automatically, select the new smart mailbox you just created and watch the messages roll in. There will be a little indicator next to the mailbox in the sidebar to let you know Mail is still working. When it's done and all the messages with attachments have appeared, press Command+A to select every one of them (or go to the Edit menu and choose Select All).
5. Go to the Message menu and choose the Remove Attachments option. (It should be toward the bottom.) It may take awhile for Mail to perform this task on every message if you have many, but go grab some lunch and check back in about an hour. By then, you should have attachment-free mailboxes.

I'm new to the Mac as of Lion and find it very difficult to manage the attachments in Mail. PDFs are displayed inline in the email message and the only way I can figure out how to save them is to right click on the PDF. I am having the same problem with photos too. I can also double click them and they open in Preview.

When you click the "Remove Attachments" in the drop down, where do they go?

It also took me forever to figure out how to add the address book icon to the New Message window!

Same problem here as the original poster. Removing attachments for emails in the inbox works fine so far, but attachments from mails in the sent folder cannot be removed. Yet, for somer older sent emails (sent before installing lion) removing attachments works, for all lately sent mails (since lion) remove attachments is grayed out. What's going on here?

Just tried it out a little bit more: The problem is related only to mails sent from Mail.app 5.0 in Lion. Mails sent through the mobile me web interface for example behave normally after being synced back to Mail.app. Attachments can be removed from those mails within Mail.app.

Another thing I noticed: The mails that do have the problem do not show the paper-clip symbol in the list of mails on the left side. The paper-clip should appear next to the addressee's name. The mail preview on the right, however, correctly shows that the mail has an attachment and it can be opnened by clicking. I also created a smart mailbox to show only mails that do have an attachment and are in the sent folder: Only the mails sent before installing lion are listed (attachements can be removed) – all lately sent mails are nout found: Obviously something makes Mail.app "forget" that there is an attachment when sending mails in Lion, thus graying out the command to remove the attachment from the specific mail.

Regarding file types of the unremovable attachments there doesn't seem to be a pattern. I have the problem with both word documents and PDF files. The number of attachments neither seems to make a difference.

Temporary solution: Do not send mails with attachments you want to potentially remove later on from within Mail.app in Lion at the moment. Instead, use an iOS device or your mail provider's web interface for sending those mails. Apple, please fix it!

Message was edited by: FabeRox

Thanks for pointing this out!

I can second that only attachments in mails in the Sent folder are affected and cannot be removed

Thus there is an easy workaround until the issue is fixed: just move the mail from the Sent folder into another mailbox and then you can remove the attachment.

We are referring to moving an email message (that was sent from within Mail.app in Lion) from the sent folder it was placed in when sending it to any other folder, for example the trash folder or a created archive folder or even across mail accounts, for example from your mobile me account to a microsoft exchange account. The idea here is that potentially this would enable the command to delete the attachments again. However, remove attachements – at least for me – is still grayed out.

With regards to the missing paper clip symbol, please refer to my longer post earlier:

Quote: "The mails that do have the problem do not show the paper-clip symbol in the list of mails on the left side. The paper-clip should appear next to the addressee's name. The mail preview on the right, however, correctly shows that the mail has an attachment and it can be opnened by clicking."

Cheers

FabeRox

Okay, this is what I do with Mail.app in Lion (latest public version 10.7.0)

- I compose a message, attach a file by drag & drop at the end of the mail (e.g. a screenshot.png)

- I send it with Mail.app in Lion

- If I change the view to the sent box and select the just sent E-Mail, the menu item "E-Mail > Remove Attachments"* is greyed out and there is no way to remove the attachment.

- However, when I move the sent E-Mail from the sent folder to another folder of my IMAP-Account (e.g. INBOX), the menu item becomes available and I can remove the attachment.

I'm running the latest public Lion and only have IMAP accounts. To me, it was really helpful to learn that only the Sent folder seems to be affected.

Hope this helps.

* I have a german menu, so the name might be slightly different.

Thanks for the clarifications. I am not challenging anything you said, but simply being exacting so I can replicate. I just tried Copy To using an On My Mac mailbox, and likewise found the Remove Attachment command unavailable.

Ernie

Glad that it works for you Zeichensprecher and thanks for your advice. Unfortunately, it doesn't work for me. I have a mobile me account and a microsoft exchange 2010 account. No matter where I move the mails to (including inbox) – removing attachments remains impossible for emails sent since installing lion. I have also tried attaching file in various ways, including drag and drop or via the paper-clip button.

So far the best advice for new readers following this thread appears to be:

1) Try to move the the affected mail to another folder and see whether the remove attachment commands is available again.

2) If that doesn't help, use you email provider's web interface for sending emails with attachments you might want to remove later on and let those mails sync back to mail.app.

Jamooche wrote:

I'm new to the Mac as of Lion and find it very difficult to manage the attachments in Mail. PDFs are displayed inline in the email message and the only way I can figure out how to save them is to right click on the PDF. I am having the same problem with photos too. I can also double click them and they open in Preview.

When you click the "Remove Attachments" in the drop down, where do they go?

It also took me forever to figure out how to add the address book icon to the New Message window!

"the only way i can figure out how to save them is to right-click on the PDF."

sounds like mission accomplished. no? 🙂 you can also drag them to your desktop, to your dock, or to a folder in the finder, desktop, or dock. does that help?

"When you click the "Remove Attachments" in the drop down, where do they go?"

as far as i know, they're deleted. isn't that the goal of "removing"?

Thanks. The main problem I was having was that I wasn't clicking on "detais" (or even seeing the item to click) on the top right of the email message. Keeping that turned on gives you the full hearder, quick look, and info on the attachment.

It's a bit of a pain but I've found that rebuilding the mailbox seems to do the trick to make the attachment icon appear and therefore allow you to remove attachments. Hopefully this gets fixed with an update.