Apple Mail not downloading attachments

Based on the page http://lifehacker.com/5841097/how-to-delete-or-archive-attachments-in-apple-mail-and-free-up-disk-space I used the steps bellow.

** Method recommended only for those who feel comfortable using the Terminal **

• open the terminal app (Applications > Utilities > Terminal)

• change to the directory/folder with the emails typing in the terminal window

  $ cd ~/Library/Mail/V2
  

• list the folders you have

  $ ls
  

  or

  $ ls -1
  

• you will obtain something like:

  $ ls -1
  IMAP-info@furia.com.br@pop.furia.com.br
  IMAP-infofuria@imap.gmail.com
  MailData
  Mailboxes
  

• go to the folder of the account you want to clean, list the files and the result shows one or more mbox

  $ cd IMAP-info@furia.com.br@pop.furia.com.br
  $ ls -1
  INBOX.mbox
  

  or

  $ ls -1
  INBOX.mbox
  INBOX0.mbox
  INBOX1014.mbox
  

• if you have only one mbox, go to this folder, list it and you will see

  $ cd INBOX.mbox
  $ ls
  CE7AE9-C83C-410A-9406-4DEFB7034
  Archive.mbox
  Deleted Messages.mbox
  Drafts.mbox
  Info.plist
  Junk.mbox
  Sent Messages.mbox
  Trash.mbox
  

• change to the folder of the messages sent (note the backslash before the space) and list to see the files

  $ cd Sent\ Messages.mbox
  $ ls 
  CE7AE9-C83C-410A-9406-4DEFB7034
  Info.plist
  

• the first file is a folder and contains all the messages and attachments in a series of subfolders. Now you will use the powerful unix find command to find all the files to be deleted and delete them.

• the find command can recursively descends the directory tree to search files by name and by size (among other options), so if you know that the attachmentes to be deleted are PDF files with more than 200k you can use the first command to find and list the files. Then if it's ok, delete them with the second command. The second example will find and delete zip files with more than 1 MB.

  $ find . -iname "*.pdf" -size +200k
  ./77CE7AE9-C83C-410A-94/Data/Attachments/303/2/abc.pdf
  ./77CE7AE9-C83C-410A-94/Data/Attachments/305/2/xyz.pdf
  $ find . -iname "*.pdf" -size +200k -delete
  $ find . -iname "*.zip" -size +1M -delete
  

• and if you want to delete all attachments bellow the present folder, you can use one simple command. To confirm that you are at the correct folder verify first printing the working directory. Then, remove every Attachments folders bellow it.

  $ pwd
  /Users/user/Library/Mail/v2/IMAP-info@furia.com.br@pop.furia.com.br/INBOX.mbox/Sent Messages.mbox
  $ find . -iname Attachments -exec rm -R {} +
  

• repeat these operations on all mbox of the account

Do you see these strange attachments in some version of Outlook?

In my own testing it seems to be that if there is anything after an attachment then Outlook interprets it as another unnamed attachment and generates an ATT0001.txt file (I'm assuming different versions of Exchange or Outlook might result in different names for the attachments).

If you make sure that the attached PDF is the last thing in the email then Outlook seems to parse the emails okay.

About the Insert attachments at End of Message option on the Edit -> Attachments menu in Mail. By default if you drag an attachment onto a Mail message window it'll place the attachment wherever you drop the attachment. But if you select the Insert attachments at End of Message option, then when you try to attach a file Mail will automatically drop it at the end of the message no matter where you actually position the cursor as you drag the attachment over the window. However it won't prevent you subsequently typing text after the attachment, which results in the ATTxxxx.txt file.

Long story short, make sure the PDF attachment is at the very end of the email and Outlook should parse the email okay.

Let us know how you get on.