Mail.app- 'Remove Attachments' corrupting mails

I have a weird issue that I've not seen mentioned anywhere. Wondering if anyone can give me any debugging tips.
I'm using Mail 5.0 in Lion 10.6.1 (issue was occurring in 10.6.0 as well).
I have Mail connected to Exchange Server 2010.
I have a fairly tight restriction on mailbox sizes so I have to remove attachments from emails before I file them.
My problem is this; about 1 in 3 times I remove an attachment the 'replacement' e-mail is full of gibberish characters.
Typically if I look at the raw source of the e-mail then the text version of the mail is retained correctly- it seems to be the Base64 encoded version that is corrupted.
Any idea what I can do to debug this? I have tried removing the envelope files and removing/adding the account back in and re-syncing it but the issue has reappeared.
I've reported this to Apple on http://bugreports.apple.com but have not had a response.
Thanks in advance.

Edward- do you mean Entourage mailbox or Exchange mailbox? i.e. are you using mail.app or Entourage/outlook as your mail client?
Assuming you meant Exchange mailbox on mail.app, the steps you would take are simple;
1- Save attachments
In the mail, click the 'Save' button (next to the 'Quicklook' button) to save all attachments to your normal folder (this folder is changeable in the settings- the default is to save to your 'Downloads' folder).
2- Move the mail to a local mailbox.
If you don't already have a local mailbox then select Menu: Mailbox/New Mailbox... and in the dialog box select 'On my Mac' to save the mailbox locally instead of on the Exchange server.
To move the message you select menu: Message/Move to... and select the local mailbox
3- Remove attachments
View the local mailbox, select the message you moved in there and do menu: Message/Remove Attachhments
(I have added a keyboard shortcut for this as I do it a lot)
Because it's a local mailbox the message should be stripped of its attachments without corruption.
4- File the message
Now that the message has been stripped of the attachments, file the message in whatever mailbox you want with menu: Message/Move to...
Hope this helps.

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Remove attachments in Mail

"Remove attachments" in Mail (Lion) is disabled and I cant remove the files from the emails I have sent. it worked fine before I switched to Lion and kept my Mail folder in Libary small. Anybody else having this problem?

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

Remove attachments in Mail fails

Since I first installed Yosemite, I am no longer able to remove attachments in Mail. I use a POP account to download my email from a Microsoft Exchange Server and store the mail with attachment(s) on my iMac. The email plus attachments(s) are now physically in a folder - not the Inbox - on the hard disk of my iMac. They are no longer on the server. I drag (or save) the attachment (no problem) to the desktop or an OS X folder. But now when I try "Remove Attachments" within Mail to discard the attachment, leaving only the email text, the menu choice Messages->Remove Attachments is grey not black and thus unavailable. What is going on? Why does this no longer work? I also have tried dragging the file to one of my iCloud email folder - not the Inbox - but that does not work either. This used to work under Mavericks but no longer. But it should be there because the menu choice still exists. I get this behavior on my iMac at work and also on my iMac at home. Both iMacs are running OS X 10.10.1.
Many thanks to anyone who can help solve this problem.

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

Mac Mail - Cannot Remove Attachments

I have an intermittent problem in that I often cannot remove attachments from mail messages. It is very inconsistent, and I cannot find a pattern.
Oftentimes, when I send an email with a large attachment, I want to keep the email text, but don't need/want the attachment (as I have it on my hard drive anyhow). But when I select the message, Remove Attachments on the Messages menu is greyed out. Again, it is intermittent as I sometimes can delete the attachments.
I am using Maverics and the latest software updates. My mail server is Exchange.
Any ideas how to solve?
Thanks.

I have the same problem (and same configuration). Either of the following works for me:
1) rebuild the mailbox - sometimes I have to rebuild multiple times but eventually it works
2) find another message where the system will let you remove attachments - select both that message and the problematic message and remove attachments - it seems that if the system is able to remove messages from at least one of all the selecte messages, it will remove the attachments from all of the selected messages
I'm getting a new laptop soon and have decided that I will give up on Apple Mail and switch back to Outlook with the new computer. I'd had more problems with Apple Mail than I have ever had with Outlook. (cannot remove attachments - entire message is corrupted when an attachment is removed - messages are not visible in the mailbox until after the mailbox is rebuilt - intentionally deleted messages reappear after the mailbox is rebuilt - custom stationary only produces the subject line and not the content of the message when applied to a new message - multiple copies of a single draft e-mails which cannot be deleted until I rebuild the mailbox to clean up the clutter)
I'm now rebuilding my mailbox at least 10 times a week just to simply manage the mail, and I'm just an average user - not trying to do anything special. It's not worth the trouble.

Why does "remove attachments" in Mail now remove entire e-mail?

This is just one of numerous problems with Lion after installing it on MacBook Pro. Every time I choose "remove attachments" in Mail, it deletes the entire e-mail and I can't bring it back. Additionally:
1.     I-Cal entries take forever (delayed entry) and assume I have an all-day event so I now have to enter the event and then open and edit it - additional steps.
2.     Airport (Wi-Fi) now shuts off without warning and cannot, under any circumstances, be restarted from any of the several screens and buttons that supposedly offer that option. Therefore, when I switch from Wi-Fi to Ethernet and then back, I have to do a restart.
3.     The Address Book now has a stylistic but non-functional interface that requires several additional steps to look at anything and there is no longer an option in Mail to "Open in Address Book" without first opening the v-card, once again complicating my life.
4.     The removal of arows on scroll bars means that I can no longer gradually look at a large file line by line but, rather, have to use the trackpad (which is also jumpy) try to focus in on the area I want by trila and error. I hate the trackpad for these reasons and now that I have lost the arrows, I have essentially the same problem with the mouse - very cumbersome for anyone doing production type work, rather than just playing.
5.     My Carbonite no longer works and I see there are compatibility issues with all kinds of other software. Worse some of my favorite old programs (e.g. Fetch) no longer work in Lion.
6.     The conversation function in Mail now groups things I don't want grouped (e.g., totally unconnected e-mails with the same words in the subject). I had to turn that off for this reason.
Overall, Lion is a huge disappointment. It's all bells and whistles with actual losses in functionality for basic work - style over substance. This is the same thing I've seen happen with Microsoft Excel as basic issues that needed addressing have been ignored while all sorts of pretty stuff that is pretty much useless has been added.
Even more frustrating is the message I got from Apple Support, which was to re-nstall Lion. That took 6 hours and resulted in not one correction of any of these issues. What has Apple done? This OS was not ready for primetime.

The "feature" I experience is that the message disappears, just as shown in Herbert's video (good work), and that it comes back after a quick mailbox switch. It has nothing to do with message sorting or anything. All my Mail settings are the same as in Mail 4.x, and everything worked fine there. Must be a bug in Mail 5. (Yes, I have reported it.)
The "explanation" that Mail creates a copy without the attachment, instead of keeping the old message without the attachment, doesn't really solve the problem. (Sorry for my extensive use of smileys, it's not my style but sometimes convenient.) The copy should come up without the mailbox switch either way.
Edit: spelling.

Selectively removing attachments in mail to send

If I am sending a bunch of files as attachments, and then decide I want to remove just 1 of them before I send the e-mail, how do I do that? Clicking on Remove Attachments removes them all, and selecting one and dragging it to the trash does nothing.
Thanks,
Richard

Place the cursor after or before the one you want to remove, and either use the backward delete key or forward delete key to remove just that one.
Ernie

Removing attachments in Mail

When I select the command "remove attachments" I end up with a message that has the initial attachment removed, but with a new attachment, small in size, named Mail Attachment.txt that says that the iniital attachment was removed (used to be just text in the previous Mail versions).
As I select a command that promises to get rid of attachments, I exchange it with a new one. Very irritating. How can I have it really removed all the way, and rather have the remove confirmation in text again?

Similar problem, and this seems to be common among users of this forum.
The "Remove Attachments" command does not work with sent files. This is true whether I drag a photo to the message, or use the paper-clip attachment button.
I can remove attachments from received messages. Just not sent ones.
This is a bug, methinks.

Remove Attachments from Leopard Mail does not remove attachment from .emix

Every day I back up my mail (and other items) to an external hard drive using an Automator workflow, in order that I can synchronize mail on my work and home Macs. In order to make this process as quick as possible, I routinely remove attachments from all mail messages once I have saved them to where they need to go on my hard drive.
I have noticed that since upgrading to Leopard (archive and install), the size of the mail folder which I back up (user>library>mail) is getting significantly bigger every day, despite removing all attachments. Upon investigation it seems that although the attachment has been removed from the mail message, the attachment is still in it's associated .emix file (e.g. user>library>mail>POP???mailaccountfolder>INBOX.mbox>messages>?????.emix - if this email contained a 5mb attachment which was removed using mail>message>remove attachments, the .emix file will still be 5mb).
Anyone else experiencing this problem? know a workaround? It didn't happen with mail in 10.4!

I am not sure when I will get the chance to test this -- maybe this afternoon. But I had not understood that what you called original continued to have the attachments. If so, this strongly suggests to me that it indeed may be the way Gmail maintains the All Mail folder that is causing this. See:
http://mail.google.com/support/bin/answer.py?hl=en&answer=6581
If there is a setting to help this, it will have to be one that is selected in the Settings webpage of Gmail, I suspect.
Ernie

How can I automatically open Mail.app message attachments after downloading

The subject says it all, I think.
My wish #1
Automatically Opening Mail.app message attachments after downloading
My Wish #2
At least having the Finder automatically default to the folder I just downloaded to after completing the download.
Is this an option in Leopard, at least?

Very clever. But unfortunately that doesn't seem to work in Tiger.
Then again, I stil presume that when you do that, a ile is still downloaded and appears somewhere on your hard drive. If you "save as" the file opened by preview, you probably still need to go back to the place where the file was saved and delete it.
Then again again, if Preview is peeking into a Word or Excel attachment, it may not actually be "downloading it" first?? Strange. If it was a jpg file attachment, on the other hand, it seems more likely that some sort of file would be downloaded to the hard drive as a result of that drag and drop of the paper clip.
I did find that drag and drop capability interesting, though. Even in Tiger.
Oh well. I have to start looking at scripts.
When I downloaded that Automator application that was supposed to "close all open applications", I was surprised that it didn't work. Says it works with TIger. ???
http://www.apple.com/downloads/macosx/automator/
Was I supposed to import it into Automator as an "action" and save it as an Automator application and then open Automator and click "run" for that action each time I wanted to use it? Seams a bit cumbersome.

How to remove Attachments part in Send Mail UI.

Hi All,
Is its possible to remove the Add button in Send Mail option?.
If Add button is not possible, then is it possible to remove the whole Attachments part of the Send Mail component?
How can we remove these components?
Regards
George

Hi George,
we use an SMTP Proxy called "eWall". With this 3rd Party Component you are able to modify the Portal Mails to your needs. e.g. remove attachments.
You can download a testversion and try for about 30 days.
good luck
joerg

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

I'm sure I used to be able to do this in SL?
I can do it on some messages, but not all, and not quite sure of a rhyme or reason (I've noted others think it doesn't work on Sent mail, but SOME of my sent messages let me delete attachments??)
Has there been a change?
Will there be a fix?

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 ...

Issue with removing attachments in mail

Since my update to Yosemite i have been experiencing a problem when removing attachments from email messages. At random a few seconds after removing the attachment the rest of the message becomes unreadable - just a bunch of random symbols and letters. This is also affecting older emails that have had the attachments removed. This happens randomly and i cant identify any one thing or file format that maybe the cause - any help would be appreciated.

Similar problem, and this seems to be common among users of this forum.
The "Remove Attachments" command does not work with sent files. This is true whether I drag a photo to the message, or use the paper-clip attachment button.
I can remove attachments from received messages. Just not sent ones.
This is a bug, methinks.

How to remove a corrupt games app. Cannot get into mcBook Pro as soon as I reboot the app appears.

HOw do I remove a corrupt game app from my McBook Pro. As soon as I reboot the app appears preventing me from doing anything. Also the game does not open it is just the main screen of the game.

Hi Shirpat,
Welcome to the Apple Support Communities!
What I would recommend in this situation would be trying to Force Quit the application. I know that you said the application opens as soon as the computer display comes on and you cannot access anything else. You can use the key command Command-Option-Escape to bring up the force quit menu and quit the game causing the issue. Please use the following article for more information.
OS X: How to quit an unresponsive application using Force Quit
http://support.apple.com/kb/HT3411
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Mailbox size increased after removing attachments

Doing a little clean-up on my mail, I noticed my sent mailbox was 1.23 gigs. So, I went in saved several hundred attachments and then tried to remove attachments. It would only let me remove attachments about 5 messages at a time, so I moved over 300 messages that all had attachments to a new folder. After moving them I was able to remove all the attachments at one time.
But after moving and removing attachments the size of my sent mailbox did not decrease it actually increased by over 400 megs to 1.7 gigs. And the new folder was also very large, at almost 700 megs (even after removing attachments).
Any ideas how/why this happens? and what can I do to reduce the size of that mailbox?
I have had the overflow issue before and have been trying to keep and eye on the mailbox sizes and keep them under 1 gig, but this one got by me. My only complaint is mail does not tell you the size of a mailbox in the application, if I was able to check the mailbox size right from the app it would be an easier thing to keep an eye on an everyday basis.
Any help would be great.. thanks!
G4 400 Mac OS X (10.3.9)

For each mailbox, Mail 1.x stores messages sequentially in an mbox file within the *.mbox package associated with the mailbox -- you can see the files contained in an *.mbox package by ctrl-cliking on it in the Finder and choosing Show Package Contents from the contextual menu.
When a message is removed from a mailbox in Mail 1.x, the actual message may be completely erased from the mbox file, or it may remain there just marked for deletion in one of the other supporting files within the *.mbox package. In order to reduce the mailbox size when a message is deleted from the middle, the entire mailbox would have to be rewritten to disk every time, which is clearly not practical.
When attachments are removed from a message, the attachments aren’t actually removed from anywhere. What really happens is that Mail creates a new message without the attachments and deletes the original message... and now you know what it really is that actually happens when a message buried in the middle of the mailbox is deleted...
My only complaint is mail does not tell you the size of a
mailbox in the application
Mail 1.3 sure does. The size of the selected mailbox is displayed in the status bar (View > Show Status Bar). Interestingly enough, that feature is no longer available in Mail 2.x.

Remove Attachments also removes Gmail labels?

Whenever I "remove attachments" from a message in my inbox, the message disappears from my inbox. However, the message is still in my Gmail "All Mail" folder. So, I'm thinking that "remove attachments" is also removing the inbox label from the message.
I also found that if I first move the message to a project folder, an then use the "remove attachements" command, the message disappears from the project folder.
Does anyone have a fix for this?

I am not sure when I will get the chance to test this -- maybe this afternoon. But I had not understood that what you called original continued to have the attachments. If so, this strongly suggests to me that it indeed may be the way Gmail maintains the All Mail folder that is causing this. See:
http://mail.google.com/support/bin/answer.py?hl=en&answer=6581
If there is a setting to help this, it will have to be one that is selected in the Settings webpage of Gmail, I suspect.
Ernie

Mail.app- 'Remove Attachments' corrupting mails

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