Sending and Receiving Files with E-Mail

One of the most valuable uses of e-mail is to send and receive attachments. Again, Mail handles file attachments similarly to other e-mail applications you might be accustomed to.

Attaching Files to Your E-Mail

Attaching files to messages you send can be done in the following ways:

  • In the message to which you want to attach files, choose Edit, Attach File (Shift+graphics/symbol.gif+A). Then, use the Choose File sheet to select the files you want to attach.

  • Click the Attach button on the New Message window's toolbar.

  • Drag the files onto the New Message window.

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If the contents of the file are being displayed and you would rather see just an icon, open the file's contextual menu and choose View as icon. The file will be displayed as an icon instead. To view the file's content again, open the menu and choose View in place.


When you place a file in a new message window, you will see a thumbnail preview of the file in its icon, the filename, and its size in parentheses. If the file type is one that can be displayed in the message, such as a TIFF image or a PDF file, you will actually see the contents of the file in the body of the message.

File attachments must be encoded before they can be sent; when a file is encoded, it is translated into a string of text. The application that receives the message must then decode that message so that the files become usable. Mail encodes all files using the AppleDouble format, which can be decoded by most modern e-mail applications on any platform (such as Macs and Windows PCs). Encoding and decoding is handled automatically, and you can't choose the encoding method that is used.

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If recipients of your file attachments have trouble with them, see "Recipients of My Attachments Are Seeing Odd Things" in the Troubleshooting section at the end of this chapter.

AppleDouble Encoding

Forcing you to use AppleDouble to encode all file attachments is not a good thing in my opinion. While most modern e-mail applications are supposed to be able to handle AppleDouble-encoded files, this doesn't work as well as it is supposed to. I regularly send files to people who use Windows computers. Using Mail to send files to these people makes them have to deal with multiple copies of the same file, unexpected messages, and so on. At the best, this is a hassle for them and reflects poorly on the Mac. At the worst, this makes the files unusable. In other Mac e-mail applications, you can choose the encoding scheme to use, such as Base64/MIME, to match the platform that your recipient uses so that the recipient can more easily deal with your files. Hopefully, the way Mail handles the encoding of file attachments will be improved in future versions.

You should also compress files you attach to e-mail messages. Unlike some other Mac e-mail applications, compression is not built into Mail, so you have to use a different application to compress the files before you send them. One of the best tools for compressing files is Aladdin's DropStuff application.

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You can download a copy of DropStuff from www.aladdinsys.com.


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Aladdin's StuffIt Expander application uncompresses files that are compressed in many different formats. StuffIt Expander is used by default to uncompress files you download from the Web.


To learn more about uncompressing files, see "Downloading and Preparing Files," p. 345.

After you have downloaded and installed DropStuff, simply drop the files you want to compress onto the DropStuff icon. The files are compressed; attach the compressed version of the files to your message.

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Make sure that you open Drop Stuff and explore its preferences. You can set the default compression used, where the compressed files are stored, and so on.


Using Files Attached to E-Mail You Receive

When you receive a message that has files attached to it, you will see the files in the body of the message. As when you send files in a message, you will see the file's icon, name, and size. If the file can be displayed in the body, such as a TIFF or PDF, the contents of the file will be displayed in the message. You can use the file attachments in the following ways:

  • You can open a file attachment directly by pointing to the filename (the pointer changes to a hand) and clicking.

  • You can open the attachment's contextual menu and choose one of the listed actions, such as Save Attachment or Save to downloads, where downloads is the name of the folder you have set as your download folder in the Internet pane of the System Preferences utility. You can also open the file with its default application or use the Open With command to select the application you want to open the file with.

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    If the contents of the file are being displayed and you would rather see just an icon, open the file's contextual menu and choose View as icon. The file will be displayed as an icon instead. To view the file's content again, open the menu and choose View in place.


  • You can save an attachment message by dragging it from the message to the folder on your Mac in which you want to store it.

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If you have trouble viewing a message and the folder into which you want to store the file attachments, double-click the message to open it in its own window. Then you can resize the window so that you can more easily see the folder into which you want to drag it.


If the files you receive are compressed, you will need to uncompress them before you can open them.

To learn more about uncompressing files, see "Downloading and Preparing Files," p. 345.