Take Control of Apple Mail

Take Control of Apple Mail


183 Pages


Master Mail in Yosemite and iOS 8!

Email is a necessary evil in today's world, but you can work more effectively in Apple Mail with the hard-won advice in this book, written by email expert Joe Kissell. You'll learn how to make Mail serve your needs with essential setup, usage, and troubleshooting instructions, whether you use Gmail, iCloud, Exchange, IMAP, or POP -- or more than one -- in both 10.10 Yosemite on your Mac and iOS 8 on your iPad, iPhone, or iPod touch.

Joe explains core concepts like special IMAP mailboxes and email archiving, reveals Mail's hidden interface elements, helps with common tasks like addressing and adding attachments, and offers tips on customizing Mail to your preferences. You'll also learn how to find that message in the haystack, figure out how digital signatures and encryption work in Mail, and uncover solutions to numerous common problems. Perhaps most important, Joe shares his strategy for avoiding email overload; the article where he first introduced it won American Business Media's Neal Award for Best How-To Article.

Mavericks and iOS 7? After you download this ebook, you can follow its Ebook Extras link to download the first edition, which focuses on Mavericks and iOS 7.

Using the fully linked table of contents, Quick Start page, or other hot links in the ebook, you'll quickly find the essential information that's most important to you, including:

  • Key changes in Mail for Yosemite and iOS 8
  • The whys and hows of sending attachments with Mail Drop
  • How to sign, annotate, and otherwise modify outgoing attachments (such as permission forms or contracts) within Mail
  • Setting Mail's Junk Mail filter correctly and other tips for defeating spam
  • Understanding special mailboxes like Sent, Drafts, and Junk
  • Using notifications to manage incoming messages
  • Turning on the much-loved classic window arrangement
  • Using search tokens AND understanding Boolean searches
  • Taking charge of email organization with rules and other measures
  • 14 things everyone should know about iOS Mail
  • Deciding whether you should encrypt your email, plus detailed, real-world steps for signing and encrypting email
  • Fixing problems: receiving, sending, logging in, bad mailboxes, and more
  • Managing Mail's new "Automatically detect and maintain account settings" checkbox -- especially if it's causing a connection problem



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10.10 Yosemite & iOS 8Table of Contents
..................................................................Read Me First 3

Introduction ....................................................................5

Apple Mail Quick Start ......................................................7

Learn What’s New in Yosemite and iOS 8 Mail .....................8

Learn about Email Protocols ............................................12

Master Mail Concepts ..................................................... 24

Customize Mail .............................................................. 51

Use Gmail with Mail ....................................................... 64

Find Your Messages ........................................................ 76

Take Control of Your Inbox ..............................................87

Become a Better Correspondent .................................... 103

Sign and Encrypt Messages ...........................................115

Fix Mail Problems .........................................................134

Use Mail in iOS 8 .......................................................... 150

About This Book 180

Copyright and Fine Print ............................................... 183

2 Read Me First
Welcome to Take Control of Apple Mail, Second Edition, version 2. 0,
published in December 2014 by TidBITS Publishing Inc. This book was
written by Joe Kissell and edited by Dan Frakes.
This book helps you understand the most effective ways to use Apple’s
Mail app in OS X 10.10 Yosemite and iOS 8, including customization
and troubleshooting. It also helps you manage your incoming and
outgoing email efficiently.
If you want to share this ebook with a friend, we ask that you do so
as you would with a physical book: “lend” it for a quick look, but ask
your friend to buy a copy for careful reading or reference. Discounted
classroom and Mac user group copies are available.
Copyright © 2014, alt concepts inc. All rights reserved.
Updates and Mo re

You can access extras related to this ebook on the Web (use the link
in Ebook Extras, near the end; it’s available only to purchasers). On
the ebook’s Take Control Extras page, you can:
• Download any available new version of the ebook for free, or buy
any subsequent edition at a discount.
• Download various formats, including PDF, EPUB, and Mobipocket.
(Learn about reading on mobile devices on our Device Advice page.)
• Read the ebook’s blog. You may find new tips or information, links
to author interviews, and update plans for the ebook.
If you bought this ebook from the Take Control Web site, it has been
added to your account, where you can download it in other formats
and access any future updates. However, if you bought this ebook
elsewhere, you can add it to your account manually; see Ebook Extras.
3 Basics

To review background information that might help you understand
this book better, such as finding System Preferences and working with
files in the Finder, read Tonya Engst’s free Read Me First: A Take
Control Crash Course, available on the Web or as a standalone ebook
in PDF, EPUB, and the Kindle’s Mobipocket format.
What’s New in the Seco nd Editio n

This fully revised second edition brings the book up to date with the
numerous changes in Mail running under OS X 10.10 Yosemite and
iOS 8. As a result, most of the new material is referenced in the chapter
Learn What’s New in Yosemite and iOS 8 Mail .
Note: For help with Mail in Mavericks and iOS 7, you can download
the first edition of this book. To find it, visit Ebook Extras and look on
the Blog tab.
4 Introduction
If Apple Mail is your email client of choice under OS X 10.10 Yosemite
or iOS 8, as it is for me, this book will help you get more out of it. You’ll
understand the app better, learn useful tricks and techniques, and
even become a more effective correspondent. I hope and expect that by
the time you finish this book, you’ll be a much happier Mail user than
when you started. (Encouragingly, early updates to Yosemite have
fixed a few Mail problems, so be sure to install the latest version if you
haven’t done so already. )
I say this to start on a positive note, because Mail is by no means a
perfect app. As much as I wish I could offer solutions to every short -
coming, bug, and missing feature, there will always be issues that
only Apple can address. However, I can at least identify the major
trouble spots, which may enable you to avoid them. I can guide you
to fixes when they do exist. And I can tell you what I’ve done to make
Mail work better for me. (Of course, this book isn’t only about dealing
with Mail problems. Far from it; I also help you get more out of Mail,
enhance your email workflow, and much more. )
It’s also worth noting that even though I’ve written books about Mail,
I have no particular allegiance to it as an app. I just want the best
email tool I can find for my particular needs. So I’ve tried quite a few
alternatives—with an open mind and a complete willingness to jump
ship if I found something better. The thing is, even at its worst, I still
liked Apple Mail the best. Given the way I’ve customized my settings,
and the third-party plug-ins I’ve added, I haven’t found another app
that gives me all the capabilities I’ve come to depend on in Mail. It’s
like that favorite pair of jeans that you still wear despite the odd tear
or stain. I hope you’ll feel the same way after reading about the many
ways you can improve on Mail’s out-of-the-box state.
As for the iOS 8 version of Mail, the story is even more encouraging.
Mail under iOS 8, while not perfect, is remarkably good. The biggest
issue with iOS Mail is that, like most mobile email clients, it still lacks
5 many of the useful features found in the desktop version, which means
iOS 8 users will need to develop a strategy that takes those differences
into account.
Regardless of whether you use Yosemite, iOS 8, or both, this book
is about how to do useful things with Mail—how to bend Mail to your
will (to the extent possible) and feel as though you are genuinely in
control of your email. Along the way, I’ll show you how to do more
with the parts of Mail that work, and I’ll identify and tell you how to
deal with as many problems as I can. But this isn’t a comprehensive
reference guide: I’ll largely ignore basic tasks that you either know
how to do already or can figure out easily by consulting the Help menu.
I’m assuming you already know your way around an email client and
mainly want guidance with less-than-obvious tasks and features.
Several chapters apply equally to Mail in Yosemite and iOS 8, but
most of the book focuses on the Yosemite version of Mail, which
is only right, since it has far more features (and problems) than the
iOS version. The final chapter, Use Mail in iOS 8 , covers the
differences between the two platforms as well as the special strengths,
weaknesses, and idiosyncrasies in the iOS 8 version of Mail.
6 Apple Mail Quick Start
Although you can jump directly to any topic of interest, I suggest
starting with the first few chapters to get a solid foundation. Chapters
are marked with [OS X] and/or [iOS] to show the platforms they cover.
Understand what you’re dealing with:
• Discover Mail’s new features and design changes. Read Learn
What’s New in Yosemite and iOS 8 Mail . [OS X/iOS]
• Get a grip on POP, IMAP, SMTP, Exchange, and more as you Learn
about Email Protocols . [OS X/iOS]
• Make sure you understand account-setup details and how Mail
deals with common tasks. See Master Mail Concepts . [OS X]
Find the ideal Mail setup for your needs:
• Tailor Mail to your needs and tastes with settings, shortcuts, plug-
ins, and more as you Customize Mail. [OS X]
• Gmail user? You’re in for some weirdness, so there’s a whole
chapter just for you: Use Gmail with Mail . [OS X]
Become a better Mail user:
• Search like a pro. Read Find Your Messages . [OS X]
• Manage incoming and saved messages as you Take Control of Your
Inbox, and then learn the best ways of sending and replying to email
in Become a Better Correspondent. [OS X/iOS]
Handle exceptional tasks:
• When privacy is a priority, Sign and Encrypt Messages . [OS X/iOS]
• Perplexed by an error message or other misbehavior in the Mac
version of Mail? Read Fix Mail Problems . [OS X]
• Make the most of Mail on your iPhone, iPad, or iPod touch. See Use
Mail in iOS 8 . [iOS]
7 Learn What’s New in
Yosemite and iOS 8 Mail
The Yosemite and iOS 8 versions of Mail contain useful new features
and design changes. Skim over this chapter to see which of these
changes may be important to you.
Mail Changes in Yo semite

The Yosemite version of Mail looks almost identical to its OS X 10.9
Mavericks predecessor at first glance, but it’s much different under -
neath. Here are the changes I think you should be aware of:
• Mail Drop: Mail Drop takes the pain out of sending large
attachments. Drag a file into a message—up to 5 GB in size—and Mail
uploads the file to iCloud in the background, and then includes a
download link in the message rather than sending the whole file as
an attachment. Mail Drop eliminates multiple problems, including
bounced messages when either your server or the recipient’s server
can’t handle large files. And, although it’s an iCloud feature, it
works even with non-iCloud email accounts. See Mail Drop .
• Markup: If you ever need to annotate or sign a graphical email
attachment, Mail’s new Markup feature enables you to do so with-
out opening a separate app such as Preview or PDFpen. (This is
a built-in example of a new feature in Yosemite called Extensions;
other apps can also make extra capabilities available within Mail
in much the same way.) See Markup.
• Handoff: Start composing a message on one of your devices (Mac
or iOS) and continue it on another with a click or a tap—at least
under ideal conditions. See Handoff.
• Show nicknames and short names: A new setting gives you the
option to show nicknames when available, or to use a short version
8 of a name (such as first name only, or first initial and last name);
the setting applies to both Mail and the Contacts app. Open the
Contacts app, go to Contacts > Preferences > General, choose an
option from the Short Name Format pop-up menu, and optionally
check Prefer Nicknames. Both Contacts and Mail reflect the change.
• Aperture export: Previously, Mail offered a shortcut to export
images from any message directly to iPhoto. Now you can also save
to Aperture. See Hidden Interface Elements.
• Automatic setting detection: A new preference for both
incoming and outgoing servers claims to detect and maintain your
account settings automatically, but its actual operation is somewhat
mysterious and problematic. See the sidebar Automatic Setting
Detection (for incoming mail) and Fix the “Incorrect Settings”
Problem (for outgoing mail).
9 Noteworthy Changes in Mavericks
If you skipped 10.9 Mavericks and upgraded from an earlier version
of Mac OS X to Yosemite, or if you didn’t use Mail much in Mavericks,
you may be unaware of the many changes Apple made to Mail in
Mavericks. I won’t detail them all here, but a few are worth knowing
✦ iCloud acco unt syncing: If you have an iCloud account set up
on your Mac, with Documents & Data (in Mavericks) or iCloud
Drive (in Yosemite) enabled in System Preferences > iCloud, the
settings for all your email accounts (not just your iCloud account)
will sync automatically with all your other Macs—as long as those
other Macs are also signed in to the same iCloud account, with
that same preference enabled. Although rules sync as part of this
process, their enabled status doesn’t sync, because you might not
want the same rules enabled on each Mac. And, sorry, but synced
account settings don’t sync with iOS devices.
✦ No more fo rcing plain-text incoming messages: In previous
versions of Mail, a secret “defaults write” command in Terminal
forced all incoming or saved messages to display in plain text,
if available; you could toggle between different formats using
commands on the View > Message submenu. Unfortunately for
lovers of plain text (like me), that Terminal command no longer
works, and the options to switch among message formats are
✦ Gmail changes: Starting with Mavericks, Mail attempts to meet
Gmail on its own terms, with mixed success. You may have to
undo any changes you made previously to Mail or Gmail settings
to make them work better together, because the assumptions on
both sides have changed.
✦ IMAP caching: In previous versions of Mail, you could choose,
for IMAP accounts, whether to download and cache full messages
including attachments, only message text, only read messages, or
none of the above. Starting in Mavericks, downloading the full text
of every message is mandatory for IMAP accounts. You can opt to
skip attachments, but that’s it.
10 Mail Changes in iOS 8

The iOS 8 version of Mail also contains several important new
• Expanded swi pe controls: iOS 8 adds new options (and a degree
of configurability) to Swipe Left and Swipe Right gestures in the
message list, including a distinction between short and long swipes.
See Use Swipe Gestures.
• Minimize new messages: It’s now possible to minimize the
message you’re composing to the bottom of the screen (and you
can even do so to multiple messages) to make it easier to switch
between what you’re typing and other messages. See Minimize
Inprogress Messages.
• Thread noti fications: You can now request to be notified when a
new message arrives in a specific thread. See Manage Notifications.
• Contacts and Calendar shortcuts: Banners sometimes appear
at the tops of incoming messages with shortcuts for adding the
sender to Contacts or events to Calendar. See Use Calendar and
Contact Shortcuts .
• Show ni cknames and short names: As in Yosemite, a new
setting gives you the option to show nicknames when available, or
to use a short version of a name (such as first name only, or first
initial and last name); the setting applies to both Mail and the
Contacts app. You can make any desired adjustments in Settings >
Mail, Contacts, Calendars > Short Name (in the Contacts section).
Besides these major changes, Mail handles signed and encrypted
messages slightly differently (see Sign and Encrypt Messages in iOS 8),
supports Zip archives (see Incoming Attachments), and includes other
small changes, as I’ve indicated throughout the book.
11 Learn about Email Protocols
The word “protocol” may sound complicated, but it’s just a way of
describing how your email program (in this case, Mail) talks to a mail
server. If you know a few basics about email protocols, you’ll have an
easier time understanding Mail’s interface and solving problems.
Although you may not be aware of it, most email accounts involve two
separate systems—one for receiving and another for sending—and
these often use entirely different servers. You probably use the same
username and password for each, but behind the scenes, each account
may function as two separate accounts:
• Your incoming account fetches email from your mail server and
delivers it to you using a mail delivery protocol—such as POP (Post
Office Protocol) or IMAP (Internet Message Access Protocol). Just
ahead, I explain more about POP and IMAP, I discuss common
IMAP and POP Misconceptions , and I offer guidance if you’re still
using POP and want to Switch from POP to IMAP (you probably
do). I also mention a few important points about iCloud and Gmail
accounts, both of which also use IMAP.
• Your outgoing account uses a mail transfer protocol called SMTP
(Simple Mail Transfer Protocol) to send email from your machine
to your mail server, and then (usually through a number of interme -
diate steps) to the recipient’s mail server.
Microsoft Exchange accounts are a bit different. They act like IMAP
accounts in many ways, but use a single—and an entirely different—
protocol for receiving and sending mail, as well as calendar items,
contacts, and other information.
Note: In this book I refer to IMAP (including iCloud and Gmail)
accounts and Exchange accounts, which manage and work with
messages on the mail server, as server-based accounts to distinguish
them from POP accounts, which store all retrieved messages locally.
12 In this chapter I also discuss the concepts Fetch, Push, and IMAP
IDLE, which apply to multiple account types and affect how rapidly
your email client can find out about new messages.

A POP account works like this:
• First, your client (that is, your email program) asks the server for
the list of messages in your Inbox.
• Then, depending on your client’s capabilities and settings, it down -
loads either all the messages, just the messages you select, or all
messages under a specified size, to your local device.
• Finally (and optionally), your client instructs the server to delete
the server copy of some or all of the messages.
The server doesn’t keep track of whether a message has been down-
loaded, read, or deleted; only your client knows this, and the assump-
tion underlying the protocol is that you want to read, organize, and
store your mail on a single device, using the server only as a conduit to
receive your mail. If you want to store any messages in mailboxes other
than your Inbox, when you create those mailboxes in your email client,
they’re stored locally (not on the server); the messages you move to
these mailboxes are thus also stored locally.
You can usually set your client to leave messages on the server (rather
than delete them immediately after retrieving them) and then check
your email with a different client (or on a different device), but all
those messages will appear to be “new” and unread on every other
client or device. This, among other reasons, makes POP a poor option
if you work with email on multiple computers and devices.
In addition, although iOS supports POP, iOS Mail doesn’t let you
create new mailboxes to file messages locally. That means an iOS
device doesn’t work well as the sole device used with a POP account,
and because POP works best when used with a single device, this
mismatch of capabilities makes POP less than ideal for an iOS device.

From a user’s point of view, the main distinction between POP and
IMAP is that by default in an IMAP account, messages stay on the mail
server even after you’ve downloaded and read them. You can create
mailboxes on the server for filing messages, and those mailboxes are
mirrored in all your client(s), on all your devices. (Nothing prevents
you from moving messages off the server and into mailboxes that are
stored only locally, if that’s your preference—but by doing so you lose
most of the IMAP advantages for those messages since they’ll no
longer sync to your other clients and devices. )
In addition, the server—not your local client—keeps track of which
messages you’ve read, forwarded, or replied to, so you see the correct
status indicators even if you check your email from another client
or device. You can, of course, delete messages you no longer want
in order to free up space on the server; doing so deletes the message
from all devices. Although each client and provider handles deletions
somewhat differently, deleting a message typically means moving it
to a Trash or Deleted Messages mailbox, which you can then empty
manually or have your email client empty on a preset schedule.
The biggest advantage of IMAP is that you can view your email using
any client, on any device, and you will always see exactly the same
thing. So, you can access a single email account on your iPad, your
iPhone, your Mac (using, say, Apple Mail) and your PC (using, say,
Microsoft Outlook), and all your mailboxes, sent and saved messages,
read/unread status, and so on will look exactly the same, all the time,
in all those places. (Many IMAP accounts also provide a Web-based
client.) In other words, unlike POP, IMAP imposes no penalty for
checking your mail from more than one device.
14 Mail and IMAP Subscriptio ns
Most IMAP clients let you select which of the stored mailboxes

on the server you want to see in your local mailbox list, a process

known as subscribing. But Mail in Yosemite does not, for the most

part, understand the concept of subscriptions—with one exception,

it simply shows you all the mailboxes that are on the server, all

the time.

If you choose Get Account Info from the pop-up Action menu

at the bottom of Mail’s sidebar, and then click Subscription List in

the Account Info window, you’ll see a list of mailboxes to which you

can subscribe or unsubscribe—use the pop-up Accounts menu at

the top to switch between accounts. (Don’t see the sidebar? Choose

View > Show Mailbox List.) B ut usually this list is blank; it shows

only mailboxes in “Public” or “Shared” folders on the server, if such

folders exist (which is rarely the case).

iCloud, AOL , and Yahoo (among other providers) use IMAP by default
for incoming email, although they may do some additional sneaky
things in the background that aren’t entirely standard. (I say a bit more
about this in Fetch, Push, and IMAP IDL E, later in this chapter. ) Gmail
(see Gmail, ahead) uses a specially wacky version of IMAP.
Microsoft Exchange servers can be configured to support IMAP,
though for various reasons, many Exchange-server administrators
choose not to enable IMAP support. The much better, and more
common, way to access an Exchange server on a Mac or iOS device
is to use Exchange Web Services (in OS X) or Exchange ActiveSync
(in iOS), both of which I describe next.
Note: iCloud and Exchange accounts handle not only email but

also other data, such as contacts and calendars (and, in the case

of iCloud, bookmarks, documents, and several other types of data).

However, you’re not required to use all the services together. If

you want to use an Exchange account only for calendars, an iCloud

account only for email, or whatever, you can turn off the features

you don’t want to use.


For each POP or IMAP account you set up in Mail, an associated SMTP
(Simple Mail Transfer Protocol) server, for sending outgoing mail,
must be specified. (Exchange, by contrast, uses the same server for
sending and receiving email. ) In most cases, you can simply enter the
server information provided by your email provider and not have to
think about it again. However, if you encounter errors when sending
email, you may have an SMTP-related problem; see Fix Outgoing Mail
(SMTP) Problems.
IMAP and POP Misco nceptions

Over the years that I’ve been writing about and evangelizing IMAP, I’ve
had countless people tell me that IMAP is a nonstarter for them or that
POP was the only protocol they’d ever use, based on what turned out to
be complete misunderstandings.
In an attempt to clear up some of this confusion, I wrote an article for
TidBITS called FlippedBITS: IMAP Misconce ptions, and I think you’ll
find it interesting reading. L et me briefly summarize a few of the points
I make there:
• IMAP isn’t a new protocol by any means—it’s been around since
1986 (making it just two years younger than POP).
• The fact that IMAP stores messages on the server doesn’t mean you
can read or process your email only when you’re online. It’s always
an option to keep local copies of all your messages—and, in fact,
most modern email clients keep those offline copies.
• “Stored on the server” doesn’t mean “impossible to delete. ” You can
delete messages from both your client and the server if you like.
• Just as with POP, you can store any or all of your messages locally
and not on the IMAP server if you prefer.
16 • POP permits only one connection at a time per account, while IMAP
lets more than one device connect simultaneously, making IMAP
much better if you frequently use multiple devices—say, your Mac,
an iPhone, and an iPad—to work with your email.
• Even if your ISP or other email provider doesn’t offer IMAP, you
can almost certainly set up an IMAP account with another provider
and then forward email from your old address to the IMAP account.
The fact that an ISP doesn’t “support” IMAP doesn’t prevent you
from using IMAP from another provider.
I find it a bit bewildering that anyone still uses POP these days, but
lots of people do, largely out of habit. IMAP is a bit “chattier” and
uses slightly more bandwidth, but in my own experience IMAP has
performed well even on slow dial-up and cellular connections. Some
IMAP servers limit the amount of data you can store on the server,
but if you run into such a limit, it’s usually possible to have it raised; to
switch to another provider; or to archive some of your messages locally
by creating a local (“On My Mac”) mailbox, dragging messages or
entire mailboxes into that local mailbox in Mail’s sidebar, and then
deleting the server-based copies.
The only argument for POP that I find vaguely persuasive is that it
may reduce your susceptibility to hacking or eavesdropping, because
incoming messages stay on the server only until you retrieve them.
Of course, your email provider may keep indefinite backups of all
incoming messages, and a government agency could monitor and
capture all messages as they come in, so I think this supposed advan -
tage is largely illusory.
I can’t think of any compelling reason to keep using POP in this day
and age, especially with so many robust IMAP servers and clients to
choose from. IMAP gives you much more convenience and flexibility,
while still enabling you to have a complete local copy of all your mes -
sages for offline access.
In short: If you’re still using POP, I suggest switching to IMAP (or
Exchange)—especially if you use multiple devices to check your email.
17 Switch from POP to IMAP

Many mail servers allow both POP and IMAP to be used for retrieving
email from the same account, which can make it easy to switch from
POP to IMAP. If you currently use POP, try adding a second account
to Mail with identical settings, except for an account type of IMAP (see
Account Setup for a tip on doing this):
• If i t works: Look for any messages in your POP Inbox that aren’t
also in your IMAP Inbox, and copy them there; also, if you have
mailboxes that you created to file your POP mail locally, copy those
mailboxes to the IMAP server. Finally, if you wish, delete the POP
account from Mail.
Tip: I go into more detail about why and how to switch from POP to

IMAP in my Macworld article The IMAP advantage.

• If i t doesn’t work: Contact your email provider to see if it can
enable IMAP for you. In some cases, you may need to set up an
entirely new email account. If your provider doesn’t offer IMAP
and you’re interested in switching to one that does, consult this
(somewhat dated, but still useful) list of providers.
Tip: My current IMAP provider is easyMail from easyDNS. To learn
more about why I made that choice, see my Macworld article Why
(and how) I’m saying goodbye to Gmail.

For the most part, everything I said earlier in this chapter about IMAP
accounts is also true of iCloud accounts. In fact, you can use any IMAP
client—not just Mail—to connect to your iCloud account. But unlike
other clients, Mail can use any iCloud email aliases you’ve set up (for
details, read Use iCloud Aliases )—they appear automatically as options
in the Account pop-up menu in the New Message window. In addition,
as long as you’re signed in to your iCloud account with iCloud Drive