EDITOR’S NOTE: This article is an excerpt from
, by John Rizzo (2004; reprinted by permission of O’Reilly Media).
I can’t think of any technological innovation that has more potential for annoyance than e-mail: unreadable attachments, bucketloads of spam, and messages that blather on and on before getting to the point—all this and more, several times a day, every day.
But with a little know-how, you can work around the most annoying e-mail problems. Here, I look at fixes for the general problems with e-mail—ones that crop up regardless of which e-mail program you use.
Open the Unopenable
Sometimes I can’t read attachments that come with e-mail messages. I’m talking about attachments from colleagues who assure me that they’ve forwarded important Word files, spreadsheets, or images. Instead, the attachments either look like monkey-at-a-typewriter gibberish or won’t open at all.
The gibberish file you see is encoded in a format your e-mail software doesn’t understand. E-mail software encodes attachments into text to help the files survive the journey over the Internet. When you can’t open an attachment, it’s usually because your e-mail program doesn’t support the encoding standard used by the sender’s software. Encoding standards include BinHex (used almost exclusively by Macs), MIME/Base64 (a Windows favorite), UUencode (from the Unix world), and others.
Another possibility is that your e-mail software supports the encoding standard used but doesn’t recognize it. This can happen if the header or other parts of the message get mixed up with the encoded attachment. You have several options:
> Your first line of attack is StuffIt Expander (Applications/Utilities). Try dragging the attachment to the StuffIt Expander icon. This often doesn’t work, but it’s worth a try. If you own Allume Systems’ $50 (see
Best Current Price
) StuffIt Standard Edition or $80 (see
Best Current Price
StuffIt Deluxe, try opening the utility first and then dragging in the attachment.
> If no member of the StuffIt family can decode or recognize the file, try DataViz’s file-translation utility,
($70 — see
Best Current Price
). It generally does an excellent job of recognizing encoded files, filtering out any worthless text the encoding may have added, and then decoding the attachments.
> You can sometimes clean up an encoded attachment yourself in order to get StuffIt Expander to recognize it. Open the file in TextEdit or another word processor, and then delete everything above the line that begins with
(See screenshot). Save the file as text-only, and drag it on top of StuffIt Expander. This eliminates the e-mail message, headers, or other extraneous text that encoding may have added to the attachment and that may be confusing StuffIt Expander.
Open Winmail.dat Files
Sometimes I receive attachments with the name Winmail.dat that drive me crazy. I can never open them, not even with decoding software. When I ask the senders what Winmail.dat is, they tell me that they never sent such a file. Am I imagining things?
No, you’re just the victim of a Microsoft e-mail system that is making some wacky assumptions. These files come from users of Microsoft Outlook sending through a Microsoft Exchange server. Don’t blame Windows, though—Exchange server can cause this problem with people sending e-mail from Windows or Mac OS.
If certain configurations in Outlook are incorrect, the Exchange server assumes that all outgoing mail is headed for other Outlook users and encodes attachments in a scheme that only Outlook with Exchange understands. This file can be called Winmail.dat or can have a type called application/ms-tnef, which you can see in the file’s Get Info dialog box (press Command-I).
The cause is complex, but the fix is easy—just use TNEF’s Enough, a fabulous and free piece of software from
Josh Jacob. Just drag and drop the file on top of TNEF’s Enough, and the utility extracts the attachment.
If TNEF’s Enough can’t open the Winmail.dat file, it may also be encoded in another format, such as UUencode. If that’s the case, you must start over, running another decoding utility first before running TNEF’s Enough.
Send Windows-Friendly Attachments
When I send an attachment to colleagues who use Windows, they report back saying that they can’t open the files or that when they do, the files are full of gibberish. Of course, they blame it on the Mac and recommend that I join the rest of the world and buy a PC.
You’ve just touched on one of the most annoying things about most e-mail programs: they’re set by default to compress even the smallest attachments, as if we still lived in a world where everyone has a 28.8-Kbps modem. Windows users usually can’t decompress .sit (StuffIt) archives, and most Mac e-mail software defaults to .sit for compression.
To solve the problem, start by turning off that default compression. Most of your attachments don’t need it. Save it for when you really need it (for file sizes over a couple of megabytes). Apple Mail doesn’t use compression, but some other mail programs do. For example, in Entourage 2004, go to Entourage: Preferences and click on Compose. In the Attachments section, set Compression to None. (Menu items will have slightly different names if you’re using Entourage X.)
Hold on, though—you’re not done yet. The second reason Windows users can’t open your attachment is
that is, your Mac is encoding the file in a format the Windows e-mail software doesn’t understand. When sending files to Windows users, I find it best to use MIME/Base64 format. If your e-mail software doesn’t have MIME/Base64 as an option, try AppleDouble encoding.
Entourage, Bare Bones Software’s Mailsmith, and Qualcomm’s Eudora all let you select an encoding format directly from your message window, usually with a pop-up menu or a check box. The default format is often the Mac-centric BinHex. You can change the default encoding in the Preferences dialog box of these programs.
Mail lags behind other e-mail applications in this respect. Before Mac OS X 10.3, Mail was brain-dead in terms of encoding—there was no way to change the default encoding scheme. Your choices were AppleDouble or AppleDouble. But starting with Panther, Mail has the option of sending “Windows-friendly” attachments. To use it, make sure that you don’t have any message windows open and select Edit: Attachments: Always Send Windows Friendly Attachments. However, you can’t always count on this setting to deliver attachments Windows users can open. It’s one of the annoying weaknesses of Mail.
Keep Your ISP Mailbox Empty
E-mail messages don’t seem to like me. People keep telling me that their messages get bounced back. One friend told me that a message said my POP3 mailbox was full.
Whoever told you your box was full is a friend indeed for giving you the answer to your problem. Your mailbox probably
full, because you’re forgetting to delete mail from the POP3 e-mail server that holds your messages. Your ISP typically gives you 10MB on its server—when that fills up, further e-mail gets bounced back to the senders. If you have messages containing large attachments, your space on the server fills up even more quickly.
Most e-mail software lets you delete your messages on the server immediately or after a short period. To shorten the period of time that e-mail is stored on your POP3 server, do the following:
> In Mail, select Mail: Preferences. Select the account from the left column and then click on Advanced. Select Remove Copy From Server After Retrieving Message. Choose a new duration from the After One Week pop-up menu. Right Away or After One Day are good choices.
> In Entourage, go to the Tools menu and select Accounts. In the Mail tab, select the account. Go to the Options tab, find Server Options, and choose how long to keep messages on the server.
Copy Spam Training
I just spent several weeks training Apple Mail to filter junk mail like an obedient puppy. Now it works beautifully, and I no longer need to tell it what is junk and what isn’t. But my wife just got a new Mac, and we’d like to have spam filtering on it as well. Do we have to go through the whole training period again?
Fortunately, once you train one Mac to recognize junk mail, you can transfer its learning to any Mac you want; just copy one file from your Mac to the same location on the other Mac. In the Finder, select Go: Go To Folder and type
, then locate the file LSMmap. (It may also be called LSMMap2). Drop the LSMmap file into the new Mac’s Mail folder, and you’ve instantly trained Mail in the art of catching spam.
[A former editor at
magazine, John Rizzo publishes
, a Web site that helps Mac users get along in a Windows world.]
Do you get e-mail attachments that look like this? Delete everything above the line that begins with Content-Type:, and StuffIt Expander has a better chance of recognizing that the encoding used is MIME/Base64.