Take Control of Apple Mail (1.0) (2014)

Become a Better Correspondent

In the previous chapter, Take Control of Your Inbox, I looked at the ways you can improve your management of incoming email. In this chapter we look at the flip side: handling outgoing email. I felt it was important to spend a few pages on this topic, because anyone who doesn’t exercise care in sending email becomes part of the problem for other people dealing with their incoming mail.

Lots of people are bad at email—you can probably think of a few examples immediately—and I want to make sure you’re not one of them. But even if you’re fantastic at sending email, I hope the points I make in this chapter help you to set a good example and teach other people how to improve their email skills.

Don’t Be Part of the Problem

The most common mistakes people make when sending email aren’t premeditated or malicious; they’re simply a matter of not thinking things through—of not looking at email from the recipient’s point of view. If your guiding principle is to send only email messages you’d be happy receiving yourself, you’re already well on your way to being a better correspondent.

But what counts as email courtesy isn’t always obvious, so let me offer several specific tips:

· Use Bcc for lists: A few times a month, I receive an email message sent to all the parents of my child’s preschool by a member of the parents’ association. And all 108 addresses are in the To field, which means I have to scroll past them when viewing the messages on my iPhone before I get to the message body. It also means I know the email address of every other recipient, which not everyone is comfortable sharing publicly.

When sending a message to multiple people—especially a long list, and even more especially when they don’t know each other—put your own address in the To or Cc field, and put all the recipient addresses in the Bcc (blind carbon copy) field (see Message Header). That way, each recipient’s address is hidden from the other recipients. And they’ll thank you for it.

· Be careful with Reply All and Cc: Suppose you’re the recipient of a message sent to multiple people, and their addresses are in the To or Cc fields. You might be tempted to click Reply All out of habit, but please think before you do. Does everyone else on that list really need to hear what you have to say, or just the sender? Or perhaps a subset of the recipients? You can individually delete email addresses when replying to all, and more often than not, replying to everyone on a long list amounts to unwanted clutter for most of them.

Similarly, think before adding someone as a Cc recipient. People regularly Cc me on complaints, bug reports, and other matters that vaguely involve a book or article I’ve written, but really: I don’t need to be involved, and I assure you that putting my name on a message you send to Apple (or whomever) won’t lend it any more weight. Ask yourself whether the potential Cc recipient truly needs to be involved in a discussion.

· Don’t forward nonsense: Jokes, funny animal pictures, political screeds, and other such stuff that gets endlessly forwarded is nearly as bad as spam. You can’t stop someone from sending this material to you (although you can ask politely), but you can certainly make sure you’re the last link in the chain. Seriously, no matter how funny or apt you find one of these generic messages, your friends and family don’t need to read it.

Tip: A subspecies of “nonsense” is the urban myth, a breathless story about some supposed tragedy, scandal, or other atrocity that sounds plausible, but is in fact false. Sometimes it’s hard to know whether a story is fact or fiction, and if in doubt, a good place to check is the Web site Snopes.com.

· Use good subjects: When you’re scanning an Inbox full of messages to decide what requires your most urgent attention, it helps to have some clue what a message is about before you open it. And later, if you’re searching for a message, you’ll find it more quickly if the subject is descriptive. So, “Hi Joe” (an actual subject on a recent message to me) is not helpful, whereas “Question about shipping company” (the actual message topic) would have been. You don’t have to agonize over the subject, just give the recipient some idea about the topic.

· Reply promptly: If I had a nickel for every time someone expressed amazement at how quickly I’d replied to them (even if the person was a complete stranger), I could retire today. But this practice doesn’t seem unusually virtuous to me; it’s merely a natural byproduct of wanting to keep my Inbox empty. Not everyone checks their email constantly, and sometimes a proper, thoughtful reply requires hours or days go compose. But I can’t overstate the amount of good karma you generate with timely replies. If a response requires more time than you can invest at the moment, say so right away—something like “I need a bit of time to think about this, but I’ll get back to you in the next day or two” goes a long way.

· Avoid pointless replies: The canonical example of a pointless reply is “Me too,” where multiple people are discussing some topic and the only contribution of your message is that you agree. Once again, the question to ask yourself is whether the recipient(s)need to know what you’re saying—whether it will help them. If not, don’t send the message.

· Respect the recipient’s time: Although I’ve written some epic email messages in my time, email as a medium works best for relatively short messages—especially when you’re composing or reading on a mobile device. Messages that go on and on with needless details or elaborate stories are more likely to be ignored—or to have delayed replies. So, do your best to be concise but also include all essential information, because a series of back-and-forth “Wait, what did you mean by x?” messages wastes everyone’s time.

And remember: even though you may have all the time in the world, the person you’re writing to may be extremely busy. Messages that cover a single topic, and do so in a compact and straightforward way, are the most likely to merit someone’s attention.

It seems kind of crazy to me that I should be giving a “do unto others” speech like this in 2014, but judging by the email I get every day, far too many people still haven’t got the message (so to speak) that politeness in email is a virtue. So, practice and preach all these things, and it’ll raise the level of email interaction for all of us.

Those major points out of the way, I want to turn to a few issues that are a bit more mechanical in nature, such as choosing the best format for your message, being smart with message attachments, and quoting effectively.

Choose Formatting Wisely

When composing an email message, there are two potential formats you can use:

· Plain text: Plain text includes text only, without custom fonts, styles, or other formatting. Plain text is ideal when readability is paramount.

· Rich text: Rich text, which is Apple’s way of referring to HTML (the system of tags used to create Web pages), gives you formatting options such as font, size, style, color, bulleted and numbered lists, and adjustable indentation. You cannot, however, manually edit the HTML code in your outgoing email messages.

In most cases, the simplicity and universality of plain text outweigh the creative control of HTML.

In iOS Mail, there’s no explicit switch; messages use rich text automatically if you add bold, italics, or other formatting—and plain text otherwise. Even so, incoming messages almost invariably look fine, because the formatting options are so limited.

In Mavericks Mail, I generally suggest sticking with plain text, because that way your recipient gets to decide which font, size, and style to display your message in. Every time I get a message written entirely in, say, green, 18-point Marker Felt—and believe me, it happens—I cringe. I know what fonts, styles, and sizes are easiest to read on my Mac, and I dislike messages that override those choices. If you want do your correspondents a favor, stick with plain text. However, if you include any graphics or photos as attachments in a message (see the next topic), I recommend that you use rich text for that message, because the images are more likely to show up correctly for your recipient.

To switch between plain text and rich text for the current message, choose Format > Make Rich Text or Format > Make Plain Text. To set a default for all new messages, go to Mail > Preferences > Composing and choose either Rich Text or Plain Text from the Message Format pop-up menu.

Avoid Attachments

Please stop attaching files to email messages. Thanks.

Wait, what? All right, let me give that suggestion a bit more nuance.

You have a file that you need to get to someone else in a hurry. A photo, a PDF, a word-processing document, or whatever. What most of us do reflexively in these cases is to drag it into an email message and send it. And don’t misunderstand, there’s nothing wrongwith that, per se. It works (most of the time), and (pretty much) everyone knows how to deal with it.

But I’ve soured on email attachments as a general-purpose file-transfer method, for several reasons:

· Each email program (and user) does things a bit differently. Mail assumes that the program receiving the messages it sends will be at least as intelligent and capable as Mail is, but that may not be the case. Mail also assumes you always want attachments to appear in what it deems the “prettiest” manner, and your idea (or the recipient’s idea) of “pretty” may not match Mail’s.

· The experience of downloading and viewing attachments on a mobile device is often poor, especially when you’re on a cellular network (as opposed to Wi-Fi). Attachments count against your monthly data transfer limits and chew up valuable storage on your device, and while iOS can display many file types natively, many others can be displayed only on a computer.

· One or two smallish attachments may be fine, but when attachments get up in the multi-megabyte range or higher, that uses a lot of storage space on my devices and eats into my IMAP storage quota.

· Most email servers have strict limits on the sizes of attachments (iCloud’s limit, for example, is 20 MB). If you happen to go over that size, Mail tries to send the message but fails, eventually displaying an error message.

· Larger messages take longer for you to send and the recipient to download.

· As a recipient, I generally dislike having to deal with attachments, so I try to extend my recipients the courtesy of not having to either.

Now then. The world will not come to an end if you email a friend of yours a 100 KB PDF document. However, if you’re in the habit of emailing files frequently, emailing large files, or emailing lots of files in a single message, I’d like to suggest that you stop doing that and adopt an alternative approach that’s better for you—and better for your recipients.

What I recommend is putting the files you want to send in a cloud-based storage system such as Dropbox, Box, or Microsoft OneDrive (née SkyDrive)—which is normally as simple as dragging the file to another folder on your Mac—sharing a link to that file, and emailing your recipient the link. All that is simpler and quicker to do than it is to write about, but if you want an even faster and more automatic approach, pick up CargoLifter, a Mail plug-in that automates the entire process. With CargoLifter, you drag a file into a Mail message and send it as usual, but behind the scenes, the file is moved into your Dropbox (or any of numerous other cloud services) and a link to the file inserted in the message. Easy.

All that said, if for any reason you can’t or aren’t willing to email links instead of actual files, at least meet your recipient halfway by following these tips.

On a Mac:

· Always include file extensions: Extensions at the end of a file’s name (like .doc or .pdf) never hurt, and they often help (especially when sending to someone on another computing platform, but even when your recipient is a Mac user). To make sure a file has an extension before you attach it, select it in the Finder, choose File > Get Info, and look in the Name & Extension section. It doesn’t matter if a particular file has Hide Extension checked; as long as the extension exists, it comes through on the recipient’s end.

To save yourself the bother of checking each file (at the expense of slightly less beautiful file names), choose Finder > Preferences, click the Advanced button on the toolbar, and select the Show All Filename Extensions checkbox. This tells the Finder to always display filename extensions on the Desktop, in folders, and so on, so you can see those extensions at a glance. (This can also be useful when you have multiple documents in a folder with the same name but different extensions and want to be sure you attach the right one.)

· Always use Windows-friendly attachments: Sending attachments in “Windows friendly” format (which omits resource forks, if they exist) usually makes them friendlier for Macs too. To tell Mail to use Windows-friendly encoding for all new messages, choose Edit > Attachments > Always Send Windows-Friendly Attachments (the default setting).

Curiously, although this command appears on a menu, it’s saved as a preference. Equally oddly, the command is disabled when you compose a new message, although it appears as a checkbox at the bottom of the file selection dialog when you click the Attach button on the toolbar. But as long as you have that menu command checked, you’ll prevent the problem of Windows seeing certain single files as two separate files.

· Forget what you see on the screen: In an outgoing message, you can right-click (Control-click) a graphical attachment and choose Show As Icon to display an icon in place of the full graphic. However, this does not affect how Mail sends the message. Even though a file appears as an icon on your screen, it may appear inline on the recipient’s screen. The opposite can also happen: You set a graphic to appear inline but it doesn’t on the other end. That’s typically because the recipient’s email client does not support inline graphics display (many, but not all, do)—or because the recipient has turned off the inline display option.

You can solve many of Mail’s icon-versus-inline graphic problems with Lokiware’s Attachment Tamer. For incoming and outgoing messages, this plug-in lets you choose whether to display graphics, PDF documents, text attachments, and HTML files inline—always, never, or only under a given size. Because it changes the way Mail sends and processes messages, it greatly increases the probability that the sender and recipient will see attachments in the same way.

A Place for Everything

By default, Mail places attachments at the spot in the message where you drop them. To force them to go to the bottom of the message:

· For a single message, with that message window open: choose Edit > Attachments > Insert Attachments at End of Message.

· For all messages, with no message window open: Choose Edit > Attachments > Always Insert Attachments at End of Message.

This does not affect whether an attachment appears as an icon.

· Use rich text format for graphics: Although it’s no guarantee of what will show up on the other end, you’ll improve your odds of having graphics show up correctly if you use rich text (Format > Make Rich Text) rather than plain text for such messages.

· Scale down large graphics: Mail can reduce the size of outgoing graphics—which your recipients may appreciate, because the email message will download faster. If you attach graphics (except for very small ones), a status bar appears at the top of the window showing the total message size, including all attachments, on the left and a pop-up Image Size menu on the right. When you choose a size from the Image Size menu, Mail scales all the images in the message accordingly.

On an iOS device:

Because iOS doesn’t have a browsable file system, you’re more limited in what kinds of files you can attach and in what ways—which is probably a good thing.

For photos and videos, the easiest approach is to move the insertion point to the spot in your message where you want a photo or video to appear, and then tap the insertion point (just as you would if you were going to paste text). In the popover that appears, tap Insert Photo or Video. (In some cases, you may need to tap the right arrow to get to the Insert Photo or Video button.) Navigate to the photo or video you want to use, tap it to select it, and then tap Use.

If you attach large photos, you usually have the option to resize them (depending on the format and starting size):

· On an iPhone or iPod touch, when you tap Send, Mail displays a list of resizing options.

· On an iPad, the right side of the Cc/Bcc, From header shows the total size of the attachments. Tap that header and you’ll see a series of buttons for changing the image size. Tap Small, Medium, or Large (the exact resulting file size is shown on each button) to resize the image, or tap Actual Size to send the original, full-size image.

If you want to share links to items in your Dropbox or similar cloud storage systems, there’s usually a way to generate links from within each service’s iOS app—consult its documentation for instructions.

Quote Effectively

The final pointer I want to offer involves quoting the text of a previous message when replying to or forwarding a message.

Broadly speaking, there are two models for quoting previous text:

· Top-posting (or bottom-quoting) is the default in Mail and most other modern email clients. You hit Reply, and the entire text of the previous message (along with any earlier messages in the thread) is quoted. Your reply goes at the very top, and the earlier portion of the conversation is below, for the recipients’ reference.

· Bottom-posting (or top-quoting) is the reverse. The original message (or, more often, a brief excerpt from it) goes first, and the response goes underneath. If the message contained several questions or points, there may be alternating blocks of quoted text and replies.

I get why people tend to prefer top-posting: it’s much easier—for the sender. It requires no thought or effort; you simply type your response and put the burden of reading the context on the recipient. And that’s an entirely reasonable approach if, and only if, the response is brief and it’s entirely obvious to the recipient(s) what you’re responding to. But beyond that, please be kind to your recipients and go to the tiny extra effort to put your replies after their questions or comments.

Note: In incoming messages, Mavericks Mail very kindly hides bottom-quoted text by default to give you a nice, uncluttered view. (Click See More to display the quoted text.) But other email clients aren’t so considerate—and even iOS Mail hides quoted text only in certain situations—so you shouldn’t use that feature as an excuse to quote everything.

In Mavericks Mail, first go to Mail > Preferences > Composing and make sure the “Include selected text, if any; otherwise include all text” radio button at the bottom is selected.

Now, whenever you reply to a message, select just the text you want to quote—I suggest including just enough of the original text to provide context for your reply—and click Reply. Then type your reply after the quoted text.

Tip: To make quoting easier still, I use the free QuoteFix plug-in, which alters the way that Mail handles replies. QuoteFix puts your insertion point beneath the original message (or the portion you’ve quoted) and removes extraneous blank lines, signatures, and older nested quotes to make your replies as clean as possible.

In iOS Mail, bottom-posting is more awkward, but here’s how you can do it (and think how much pain you’ll save the recipient):

1. While viewing the message you want to reply to, double-tap and hold over the portion of the message you want to quote. Adjust the selection handles to select the desired text.

2. Tap the Reply icon. Mail opens a new message, addressed for a reply, but with only the selected text quoted.

3. Delete the extra return(s) at the beginning of the message, move the insertion point after the quoted text, and begin entering your reply.

iOS Mail always puts your signature at the top, above any quoted text, even if you quote only a selection. One way to avoid this is to cut and paste your signature from the top of the message to the bottom—admittedly a bit awkward. Or, you can turn off Mail’s automatic signature (see Change Account Settings); then use the iOS Shortcuts feature (Settings > General > Keyboard > Add New Shortcut) to quickly insert a one-line signature wherever you want it to go. Or, if you don’t mind switching apps in order to compose email messages, use a third-party tool, such as TextExpander touch, to type replies, entering custom signatures on the fly.