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E-mail with confusion attached

More and more computer users are finding that attachments they get via e-mail won't open properly.

©New York Times

© St. Petersburg Times, published August 16, 1999

The situations may sound far-fetched in the physical world, but for e-mail users they are frustratingly common. As more and more people use e-mail to send photographs or word processing documents as attachments to their messages, tech support managers say, more and more people are faced with attachments that won't open.

Simply put, attachments are computer files that use e-mail messages for transport over the Net. Just as e-mail messages carry text from one computer to another, attachments carry files of many sorts, including word processing documents, images and software. People usually use attachments when they are sending a file that contains something more than simple text, such as a memo on special letterhead or a spreadsheet.

Attachments are supposed to make life easier. They can enable scientific collaborators to send one another graphs showing research results. They allow friends and relatives to send photographs over the Internet. With a few clicks of the mouse, they can eliminate the cumbersome job of sending floppy disks through regular mail or the intimidating prospect of sending something via FTP, a file transfer protocol favored by more sophisticated Internet users.

That is the theory. The reality is often much different.

"There are so many things that can go wrong," said Greg Smith, a computer-support consultant at Stanford University. "It's not as easy as it is supposed to be."

Even experienced computer users become frustrated. John Mainwaring, a longtime technology professional at Nortel Networks, said that when he and his colleagues first tried to share information via attachments, "it was a very hit-or-miss affair."

Michael Day, an English professor at Northern Illinois University, has been using e-mail in his classes for years, but said in an e-mail interview, "There are still attachments that defy my efforts, such as WordPerfect files converted to MS Word that arrived the other day and completely crashed the two computers on which I tried to open them."

Attachments usually show up in e-mail messages as icons. E-mail programs such as Eudora, or those that come with Microsoft Office, America Online or Lotus Notes, are designed to enable people to click on those icons, triggering the file to open in a separate window. Click on a file that was created using a word processor such as Microsoft Word, and if you have Word on your computer, the file should open immediately.

But in many cases, that click opens nothing but the door to confusion. Sometimes the file does not open at all. Sometimes a dialog box opens on the computer screen, asking the user which program should be used to open the file.

Once in a while, a message appears asking for the file to be decompressed, or unzipped. And then there is the gobbledygook response -- the file opens but displays a useless jumble of symbols, looking like a series of profanities written comic-book style.

Frustrated users should take comfort in one fact: Recipients are almost never to blame for attachment problems.

"Usually it is the sender's fault, whether the problem is intentional or unintentional," said Kenneth Breshears, manager of technical support for Eudora.

Typically, e-mail experts say, the problems can be traced to three technological glitches: The file may be incompatible with the software on your computer; the file may not have been encoded or decoded properly as it journeyed across the Internet; or the file has been compressed and requires decompressing before it can be read.

In most cases of attachment aggravation, incompatibility is the culprit. Consider the exchange of files via floppy disks. If you were to give someone a disk containing a document created in Microsoft Word, but that person used WordPerfect, the file would probably show up as a page with gibberish or not open at all. The same goes for attachments.

"The real challenge here is that we have an unlimited amount of software developers that have an unlimited amount of file formats," said Jeffrey Belk, Eudora's president and general manager. His suggestion: Senders should check whether the recipient has software that will open the file.

To avoid incompatibility problems, some technology experts recommend purchasing software that lets you view attached files of myriad types without having to open them.

Ben Gottesman, technical director of software for PC Magazine, suggests trying Keyview, created by Verity (, or Quick View Plus, by Jasc Software ( Each program, which displays the file but does not allow you to edit or otherwise alter it, sells for $59.

"These programs are quicker to use than launching a big application," Gottesman said, "and they can avoid the spread of worms, like Melissa," which cannot be activated when a file is merely viewed without actually being opened.

Encoding also can wreak havoc, though most e-mail programs are sophisticated enough to eliminate the need for users to know what encoding means. To encode a file is to repackage it as a text file so it can travel across the Net as quickly and easily as a regular e-mail message.

Most attachments are wrapped up using one of three encoding standards -- MIME, BinHex or Uuencode -- which are recognized by most e-mail programs.

Most programs automatically decode encoded files before they arrive in e-mail in boxes. But some users may come across an attachment that they must decode themselves.

If a user of America Online's e-mail program receives a message with three attached photographs from someone using a different e-mail program, for example, those files will be in the form of a MIME package that must be decoded. To do that, users need to have decoding software. AOL's e-mail help pages tell users to download Winzip (

In rarer cases, files will arrive that were not packaged correctly by the sender's e-mail program. Gibberish or a message about corrupted files results. "That's where people bail and say, "Just fax it to me,' " said Smith, who regularly conducts a clinic on e-mail attachments at Stanford.

An attachment may need to be decompressed as well as decoded. Compression is a method of squeezing computer files into tiny packages so they can move over the Net and be downloaded as quickly as possible.

Some e-mail programs will decompress files automatically. Others will show you an icon with the extension .zip (common on Windows-based files) or .sit (common on Macintosh files).

As with decoding, decompressing files requires special software. Several decompression programs have decoding mechanisms. Tech-support experts suggest using PKZip ( or Winzip for Windows users and Stuffit Expander ( or ZipIt ( for Macintosh users. Typically these measures are taken by experienced computer users.

"People who are clever enough to use compression are usually clever enough not to send it to someone who doesn't know how to deal with it," Smith said.

But even computer gurus will admit that sometimes e-mail attachments can create more work than they are worth. Day at Northern Illinois University tells his students and colleagues to send attachments only if absolutely necessary.

"Let's remember that the Internet lines are getting crowded," Day said. "Plain text e-mail messages take up a lot less space and bandwidth than e-mail messages with fancy attachments."

Avoiding aggravation

Here are a tips for avoiding attachment aggravation:

KNOW YOUR SENDER. Do not open an attachment if you don't recognize the sender. Some of the most dangerous computer viruses have been spread by e-mail attachments, which are activated upon opening.

BE DISCREET. Do not send an attachment to a large number of people simultaneously. A 1-megabyte file sent to a 500-person mailing list creates 500 copies of that. That many megabytes moving through the e-mail system at one time could clog or even cripple the mail server.

TALK IT OVER. Let recipients know that an attachment is coming. You may want to determine whether a package of compressed photographs, for example, can easily be decompressed or whether the pictures should be sent individually.

LEND A HAND. Let recipients know what they need to do to open the attachment. They may need to know what word processing program, for example, was used.

WARN OF WHOPPERS. Indicate the file's size. People with slow Internet connections can then decide whether to download the file later, instead of clicking on the file and discovering that they have started a 15-minute download. And some e-mail programs are designed to filter out files over a certain size.

AVOID EMBARRASSMENT. If you get an attachment with an .exe extension, be prepared -- especially if you are at the office. The file might be an animated program or video, complete with sound. You may want to turn down your speaker volume or wait until the office is empty.

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