A Beginner's Guide to Effective Email


Kaitlin Duck Sherwood
The underlying rules governing email transmission are highly standardized, but there are a large number of different software programs that can be used to read email. It's quite possible that the message you send won't look at all the same when displayed on your correspondent's screen. You therefore have to be careful about how you present your text. This section will discuss the problems that may arise from a mismatch between the sending and receiving software, and show how to avoid them.

Fancy Text

Some email reading software only understands plain text. Italics, bold, and color changes will show up as control sequences in the text. You might send something like:
Hiya! Hey, I loved the presentation you gave to Jack this morning. Great Job!
but if your correspondent's software can't handle formatting, the message could show up as:
	Hiya!  Hey, I <I>loved<I> the presentation you gave to
	Jack this morning.  <B>Great Job!<B>

Web documents are particularly difficult to read with older email programs. You may have a choice of sending the web page as text or as HTML; keep your correspondent's capabilities in mind when you make that choice.

Extended Character Sets

Back in the dark ages of 1982, when the email specs were being written, the decision was made to encode email in such a way that only 128 different characters - letters, numbers, punctuation, and so on - could be transmitted from one computer to another. This allowed some free space for error correction - something important when computers were calling each other with modems.

However, the net is a different place now. Characters like ä, ç, and Ø are now important for large numbers of email users. So now there is a way of encoding data so that 256 different characters can be represented, called "quoted-printable".

Unfortunately, the underlying transport is still limited to 128 different characters, so the email gets converted to the more limited set, transmitted, then (hopefully) converted back on the other end. If the receiving software doesn't know how to do quoted-printable (or if something gets munged somewhere), the extended characters will show up as an equals-sign and two letter/digit code:

	La premi=E8re journe=E9 de nos deux voyageurs fut assez agr=E9able.  
	Ils =E9=taient encourag=E9s par l'id=E9e de se voir  
	possesseurs de plus de tr=E9sors que l'Asie, l'Europe, et 
	l'Afrique n'en pouvaient rassembler.  Candide,
	transport=E9, =E9crivit le nom de Cun=E9gonde sur les arbres.

So why do you care? After all, you might not ever use umlauts. You care because there are "special" characters that you probably will encounter, that are NOT part of the standard extended character set, but which some software will allow you to insert. Even if your correspondent's software knows how to convert codes back to extended characters, different computers have different symbols for the same codes. For example, the trademark symbol, bullet, and "curly" quotation marks are all legal characters in both Windows95 and MacOS, but are in different places in the character set. For example, Windows thinks that character number 241 is a ñ, while the Mac thinks that character number 241 is a Ò. Thus you have yet another reason to worry about what your correspondent's email software is capable of.

Web Links

Some email reading software will recognize URLs (Uniform Resource Locators, or web addresses) in the text and make them "live". While some software recognizes URLs from the "www.", most software recognizes URLs by the http:// at the front. Thus, if there is a URL in your email, it is much safer to include the http://!

You should also be careful about punctuation - especially periods - right after a URL. For example, take the message

	Hi - The URL is http://www.webfoot.com/writings.html.  See 
	if you like it!
The software on the receiving end may think that that last period after the URL is part of the URL. Or, if the software doesn't recognize links, the reader may cut-and-paste too much. Either has the potential to lead to an ugly email exchange, with your correspondent insisting that the page doesn't exist and you insisting that it does. I will admit that it looks ugly, but it causes less confusion if there is at least a space after the URL:
	Hi - The URL is http://www.webfoot.com/writings.html .  See 
	if you like it!
People who are cutting and pasting might also select too little. Since HTML files can have either the extension .html or .htm, this can also be a difficult mistake for your reader to catch. To make cut-and-paste mindlessly easy for people, I try to always put URLs on a separate line:
	Hi - The URL is
	See if you like it!
Yes, the period after the URL is now missing. Yes, this is ungrammatical, but I sure don't want to put it on the next line! I have found it worthwhile to trade grammatical perfection for easier cut-and-paste.

Some URLs are so long that they will get split into two lines:

	Hi - The URL is
	See if you like it!
If your correspondent's email software makes links live, it is probably not capable of realizing that formality.html belongs with the rest of the URL.
	Hi - The URL is
	See if you like it!
If your correspondent is cutting and pasting, he or she may not see the last bit. What you can do is put angle brackets around the URL. Some (but not all) email software will recognize that stuff inside angle brackets should be kept together:
	Hi - The URL is
	See if you like it!

Punctuation and Quotation Marks

Another grammatical rule that I usually break is the placement of punctuation. American grammar rules say that punctuation belongs inside quotation marks, for example the period in the next sentence:
	Bob said, "I love you madly."
That's fine when the stuff in quotes is normal speech, but can cause problems when discussing computer input. Consider:
	When you get to the password box, type "smiley."
Is the period something that goes in the password box or not? I prefer to use British grammar rules and say
	When you get to the password box, type "smiley".
This makes it clear that the period does not go in the password box.

I could switch back and forth between the two styles, depending on whether the thing in quotes was to be typed or not, but I would rather be consistent so that if the period is supposed to be in the password box, that will be clear.

If you can't bear to do such gyrations, modify the sentence so that there isn't punctuation there:

	When you get to the password box, type "smiley" and hit return.
or if you want to make it absolutely clear:
	When you get to the password box, type
	and hit return.


Some mailers support "attachments", where you can specify a document to send through email. This allows people to share essentially any file in any format. GIF-encoded images, JPEG-encoded images, Word documents, WordPerfect documents, Photoshop files, Excel spreadsheets, and executable files are just a few of the types of documents that can be sent.

If your correspondent has a mail reader that can handle attachments, this can work very well: a long attachment can be looked at later. However, if your correspondent's email software doesn't understand attachments and you send a non-text file (like a Word document, a binary, a picture, or even compressed text), be advised that it will appear as lots of garbage. Pages and pages of garbage, usually.

Even if your correspondent has email software that understands what attachments are, they still have to have software to read the document. Think of it this way: somebody can use the Post Office to send you any kind of document. But if you send someone microfilm, they probably won't be able to read it. Even executable programs can't always be useful to your correspondent. Macintosh programs won't run on Microsoft Windows machines; Windows95 programs will not run on machines that only have DOS installed.

Furthermore, even if your correspondents can receive and view the attachment you send them, if they are low on disk space or dial in from home to get their email, they will not be happy to receive a 200MB video, no matter how funny it is.

It almost always better to post large documents on the Web and email the URL instead of the file. If you don't have that option, please email your correspondents first and ask them if they can handle a large attachment of that format.


If you don't know what email reader your correspondent has, play it safe. Also bear in mind that punctuation doesn't mix well with URLs or quotations of things people should type.
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Created 30 Oct 1998
Tweaked 7 Dec 1998
Added angle brackets to URLs (to help the client make URLs hot) 9 Nov 1999
Beautified page 23 May 2001

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