E-mail Etiquette

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Just as the posted letter once replaced the smoke signal as a primary means of long-distance communication, e-mail is now displacing the letter. As it does so, many of us are moving into uncharted behavioral territory. But fear not -- our resident etiquette expert, Mac Manners, is on the case. So sit up straight, silence your cell phones, and follow along as we politely yet firmly offer advice on how to conduct yourself in e-mail.

Dear Mac Manners,

I recently sent a message about a political event to friends and family. Instead of the supportive reply I expected, an upstart relation chided me not only for putting the recipients' addresses in the message's To field but also for replying to the group. What terrible crime have I committed?

Offended in Oxnard

Dear Offended, My guess is that your relative was, as gently and respectfully as possible, alerting you to the fact that polite people do not plaster dozens of e-mail addresses into a message's To field.

People often pass messages like yours around, and when they do, all those addresses get passed as well, violating the privacy of anyone hoping to keep his or her e-mail address under wraps. What if your message gets sent to an Internet ne'er-do-well--one who might use the addresses in that message to spam or swindle your friends and relatives?

A packed To field can also be inconvenient for recipients. Reading a message with a long To field on an iPhone, for instance, is a bother when you have the Details field visible. You must either hide this field (and remember to display it again later) or scroll, and scroll, and scroll some more to finally get to the meat of the message.

To avoid this breach of etiquette in the future, use your e-mail client's BCC (Blind Carbon Copy) field--which isn't visible to recipients. Put one recipient in the To field (use your own e-mail address here to keep all other addresses private) and then put the other addresses in a BCC field. That way, everyone gets the message but no one can see the other recipients' addresses.

Dear Mac Manners,

I understand the advantage of using the BCC field, but I don't know how to find it in my e-mail client. Can you help?

Confused in Connecticut

Dear Confused, My pleasure. To expose the BCC field in Leopard's Mail, select View: BCC Address Field. This causes the BCC field to appear in all new messages. Alternatively, you can click on the Customize pop-up menu just to the left of a message's From area, and then choose BCC Address Field. This, too, exposes the BCC field. In Tiger's version of Mail, create a new e-mail message by choosing File: New Message, and then select View: BCC Address Field.

The versions of Mail that shipped with Jaguar and Panther let you use the BCC field, but the method for exposing the field may not be obvious. To display the field in Jaguar's Mail, open a new message and select Edit: Add BCC Header. In Panther's Mail, select View: BCC Header.

Microsoft Entourage always reveals the BCC field when you enter a new address. Just click on the To field in a new message, and a larger window that includes the option will pop up.

To expose the BCC field in MobileMe's Web-based e-mail client, locate the Composing tab in MobileMe's Preferences.

Web-based clients such as Yahoo Mail, Gmail, AOL, and MobileMe also include BCC options. When you're creating a new message in Yahoo Mail, look to the right of the To field. You'll see a Show BCC link. Click on it, and the BCC field appears. In Gmail, under the To field in a new message, you'll spy an Add BCC link. Click on it, and there's your BCC field. In AOL, click on the BCC link next to the To field in a new e-mail message. And when visiting MobileMe's mail client, choose Preferences from the Tools menu, click on the Composing tab, enable the Show BCC field option, and click on Save. All new messages you create will include a BCC field from now on.

Dear Mac Manners,

A friend often forwards messages to me, but more often than not I have to scroll through the message to find the text I want to read. Do you have any advice for avoiding this that I can pass along?

Perplexed in Poughkeepsie

Dear Perplexed, You might simply explain that there are two problems with forwarding messages in this manner. The first is that when you forward a message without editing it, you forward the sender's e-mail address (or, worse, multiple senders' addresses), too. Secondly, when a message has been forwarded a few times, the important material is often pushed to the bottom. No one really wants to read line after line of "Hey, check this out!" It's for this reason that we should edit out the dross before clicking on Send.

Dear Mac Manners,

A cousin sent me an unprintably uncouth reply to a message full of jokes I sent to family and friends. How should I behave when I next see her?

Irked in Irkutsk

Dear Irked, Apologetically. Before sending a chain letter, a list of your favorite cat jokes, a political or religious screed, or a link to a YouTube video of a toddler stuck in a sousaphone, be absolutely certain that the person you're sending it to will welcome it. And the best way to find out just how welcome these unsolicited messages are is simply to ask. A message along the lines of "I occasionally send tasteful jokes that I enjoy to my friends. Would you care to be included?" will help prevent a testy response.

Dear Mac Manners,

In order to avoid spam, I use my Internet Service Provider's challenge-response feature. Oddly, since I started using it, I receive very few replies to my e-mail messages. Have I done something to offend people?

Challenged in Chattanooga

Dear Challenged, Oh my, yes. Let's suppose that you sent this question to me via e-mail. I take the time to compose a thoughtful response, send it, and almost immediately receive an automated reply demanding that I verify my identity by visiting a Web page and entering a password before my message is delivered to your inbox. Even the most forbearing person could be forgiven for doing nothing more than tossing that automated demand into the trash. This, I suspect, is what's happening to you.

C-Command's $30 SpamSieve () is an immensely capable spam utility that lets you take responsibility for your own spam issues rather than foisting that responsibility on people you hope to correspond with. But if you'd rather keep your challenge-response system, at least have the courtesy to add the e-mail addresses of known correspondents to your whitelist (a list of accepted recipients who won't be subjected to a challenge) before sending a message to one of them. Ask your ISP how to do this.

Dear Mac Manners,

My e-mail client allows me to flag messages by importance (High, Normal, and Low). I've been reluctant to use this feature as, at one extreme, I don't want to alarm people and, on the other, don't want to dissuade them from reading my message. What's the proper use of these flags?

Flagging in Flagstaff

Dear Flagging, I see very little value in flagging a message as low priority. If your message is so unimportant that it earns this kind of disdain even from you, why would anyone be tempted to read it? However, I can imagine situations where you might make an exception--for instance, if you work in an office where you're constantly bombarded by high-pressure e-mails that are, for that workplace, "normal" (and marked that way), you may want to assign "when you get around to it" messages a low priority.

A high-priority flag can be useful in a couple of ways. Let's suppose you work in an environment where colleagues receive metric tons of e-mail each day. And because they do, many don't read their e-mail right away--there's just too much of the stuff to sift through. Flagging your message as high priority will likely cause others to read it sooner rather than later. A high-priority flag is also appropriate in situations when you're in a panic--you need something acted on right now.

The danger of high-priority flags is in their overuse. If you assign this flag capriciously, people you routinely correspond with will learn to ignore it--and, ultimately, your messages. To avoid becoming the Correspondent Who Cried Wolf, use that flag with care.

To avoid being ignored, don't become the person who flags every message as high priority.


Dear Mac Manners,

I've done a terrible thing. We have two Justins in our office--Justin G. and Justin K.--and I sent a catty message regarding Justin G.'s floral spats to Justin K. Or so I thought. Somehow my message went to Justin G. and not Justin K., and now I can't face Justin G. in the lunchroom. What have I done?

Shamefaced in Shiloh

Dear Shamefaced, You've been betrayed by your e-mail client's Autofill feature--which automatically fills in a recipient's address as you type a name into an e-mail message's To field. This is a wonderfully convenient feature--most of the time. But as you've discovered, it can cause a message to go to the wrong recipient if you're not careful.

Regrettably, today's popular e-mail clients don't provide a way to turn this feature off. It's therefore incumbent upon you to be careful. The easiest way to do so is to simply never say anything in e-mail that might offend someone, regardless of who reads it. But what fun is that?

Instead, you could make it a habit to always type the full e-mail address of recipients rather than relying on the Autofill feature, or you could let Autofill entries appear but deliberately click on a name in a list rather than pressing the return key to automatically enter an address. If you also look long and hard at every address in a message's To field before clicking on the Send button, you should avoid future embarrassment.

Another option is to assign nicknames to contacts you're likely to confuse. For example, if Justin G. works in the mailroom and Justin K. puts in his hours operating the office copying machine, assign the G.-man the nickname "mailroomjustin" and the other Justin, "copycat." To do this in Address Book, just select a contact's name, click on the Edit button at the bottom of the Address Book window, and then enter a name in the Nickname field. When you type the nickname in a message's To field, Mail will swap in the e-mail address associated with it.

Dear Mac Manners,


Cranky in Crawford

Dear Cranky, Thank you for providing such an excellent example of an unacceptably rude message. You've not only typed in all capital letters (which is considered shouting), but also used the exclamation point to excess. A message such as yours begs to be ignored, which I shall now do.

Senior Editor Christopher Breen is the author of The iPod and iTunes Pocket Guide, fourth edition, and The iPhone Pocket Guide, third edition (both Peachpit Press, 2008).

This story, "E-mail Etiquette" was originally published by Macworld.

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