The Efficient Mac User

Making Mac Mail Work for You

- 2005.12.09 - Tip Jar

Two months ago I decided to move away from Microsoft's Entourage as my calendar, address book, and mail client and move to Apple's equivalent applications. I've been pleased with the move, and this will be the first of several articles for the Efficient Mac User that will look at the power and substance of Apple's offerings.

I know that Entourage is very popular - some will even argue that it is the best thing going for the Mac - and I'm not trying to dispute its merits or its power. My goal is to show how a Mac user can get as much out of the included applications as they can from the likes of Entourage - and maybe more.

In other words, Mac users don't have to pay for a mail client to get a good one.

Entourage Disclaimer

Let me make this disclaimer, lest my Efficient Mac User mailbag (and my Mail inbox) overflow with complaints and opposition: I don't think I have a clear picture of the power of Entourage. In fact, I'm quite certain there is more to it than I realize - and that I might not have switched if I knew all that it could do.

I do know this: Whatever power is there is buried too deeply in the "Microsoftism" of the application for me to discover it. Like so many Microsoft applications, there is such a steep learning curve to the program that I was simply daunted by it. (I read that a recent survey showed that something like 90% of the features that Microsoft Word for Windows users requested to be added were already there - they were just too hard to find. I suspect Entourage is like that, too.)

So I'm using Apple's Mail, and I love it. It has a clean, straightforward interface and an elegant design. Aesthetically, it doesn't stand out as eye-candy, but it certainly doesn't get in my way with ugliness either. It opens quickly, behaves well, and plays nicely with other applications.

Here are some aspects of Mail that make it work for me - and can work for you, too.

Essential Features in Mail 2.x

There are definitely some features that I consider essentials. They make my life easier and I wouldn't want to do without them. By the way, it so happens that two of these are unique to Mail (at least when compared to Entourage).

.mac integration

I like .mac. It works for me, because I don't like to bother with backing up as much as I should. .mac offers me a solution to this that is completely integrated into the system.

When it comes to Mail, I use .mac to sync everything that it can. This means that my account settings, rules, signatures, and smart mailboxes are all synchronized with my .mac account. If everything should crash today or if my iBook should be stolen, I could access all of my settings for Mail from any computer - all I would have to do is log into .mac and ask it to sync with Mail. (By the way, since I switched to Address Book, all of my contacts are also backed up to .mac.)

This is great, because I've lost my contacts before, so I know the dread that comes with restoring these manually. I've also spent the time that it takes restoring the settings for mail clients, and knowing I won't have to do it again is a comfort. I can't get that very easily with Entourage.

Spotlight

The reception for Spotlight has been (pardon me) spotty, but I find that it works pretty well for me. In fact, I use it often, and Entourage's lack of compatibility with Spotlight, though understandable, was one of the big reasons why I switched away from it.

Spotlight is fully functional with Mail, naturally. Spotlight in Mail was one of Steve Job's demonstrations of the benefits of Tiger. Smart Mailboxes, Smart Folders, desktop searches, and better searching within Mail are all benefits of Spotlight's deep integration with the Apple applications.

I haven't put Smart Mailboxes or Folders to use very much, but I do desktop searches and searches within Mail all the time. Spotlight is a great reason to give Mail a try.

Per-account Signatures

I manage multiple email accounts with Mail, which it handles flawlessly (so did Entourage). I've begun to use signatures more and more. Mail allows me to set up signatures specific to each account so that they are automatically there depending on the email account I've selected. (Entourage does this, too, and for me this has become an essential feature, so I was pleased I didn't have to sacrifice it in the switch.)

Tools I Couldn't (or Wouldn't Want to) Live Without

To get the most out of Mail, I've taken advantage of a few of the many plug-ins and integrated applications available for Mail. Here are some that I find really boost my Mail productivity - these are the true Efficient Mac User picks.

SpamSieve

Anyone out there like spam? With ten different email accounts, I certainly get my share. Mail's "Rules" settings are a good start, and Mail works well with mail servers to intercept spam (see below), but I found that I needed a little more protection.

Enter SpamSieve by C-Command. This gem of an application has gotten a lot of positive mention, even several times here on Low End Mac. Let me give it another plug: If you use email, you will want SpamSieve. It's simple to set up, it works very well with Mail (and Entourage, and just about every mail client I've heard of), and it's pretty close to foolproof.

SpamSieve uses Bayesian filtering, which means it determines the probability that an email is spam based on the content of the message itself. In essence it reads the mail for you, then determines if you will want to read it. To do this, it doesn't simply look at the content of that one message, it also compares that content to other messages, both good and bad (spam), to learn with a sort of artificial intelligence what kinds of messages are probably spam.

SpamSieve learns from your email with your input, so it customizes its filtering according to your mailbox contents. As a result, it's robust and very accurate. Since I installed it (over a month ago), I have had to deal with only one or two spam messages in my inbox. I also have only found three messages marked as spam that I wanted to keep, and SpamSieve lets me train it when it makes a mistake.

SpamSieve is shareware, and for only $25 you can have the same kind of freedom from spam that I now enjoy.

Mail.appetizer

Mail.appetizerOne of the things that I liked about Entourage was the notification of new messages, even when Entourage was minimized or behind other windows. I found the free plug-in Mail.appetizer to offer the same benefits in Mail.

In fact, Mail.appetizer gives me even better notification, because it's customizable (I can select how little or how much notification I have) and it allows me to exercise some control over the received messages without switching applications. For example, I can choose to delete the message, mark it as read, or open it in Mail from the notification box. Also, the box is "sticky" when my computer is inactive, so if I've stepped away from the computer, the notification lingers until I get back.

I used to use another free application, Growl, for Mail notification. Growl does a good job, and has a nice, basic notification box. I just like Mail.appetizer's rich features more.

MailTags

Spotlight is really good as is; when you combine it with some useful metadata, however, it really begins to shine. For example, if you invoke the "Information" window for any file in Finder, you'll see that there is a field for Spotlight comments. These improve Spotlight's accuracy drastically.

MailTags

MailTags offers the same function within Mail. You can insert preset or customized Keyword tags and Project tags, as well as notes, prioritization, and due dates, into metadata that is Spotlight-searchable. MailTags sets up easily in the Mail preferences window and utilizes a sidebar interface that is straightforward, doesn't obscure your regular mail usage, and hides easily. MailTags is donationware with a $20 recommended donation.

MailTags

Mail Act-On

I use a bunch of folders to sort and organize my mail. I've always done this, and it has typically meant the occasional hour or two of sorting a few hundred emails every month or so. Select, drag, drop. Over and over.

Mail Act-On offers a neat alternative, using a few keystrokes to take any selected messages and complete any set of predetermined rules and/or actions on them. You can sort them into a particular folder, mark them with a flag, and mark them as unread. You can specify that a particular rule will work only if the message was from a certain email address. You can use it to engage systems of organization, such as David Allen's popular "Getting Things Done" method. Use it to archive your messages to a back-up location, engage decision-based actions, or activate an AppleScript.

Mail Act-On

An added bonus: Mail Act-On works nicely with MailTags. For example, I have a Mail Act-On keystroke set up to mark a selected message with a flag, move it to my "Writing: Current Projects" folder, and mark its MailTags as keyword: Writing; project: Low End Mac column. With a mouse-click to select and two keystrokes, all of those actions are handled for me.

Mail Act-On is a great productivity-booster and efficiency-helper. And since it's open-source, it won't cost you anything to add it your system.

Mail Stamps & Uno

Mail Stamps

Interface matters. I like a clean, basic interface for all of my applications.

I admit it: I liked the old Mail 1.x buttons better than those that Tiger brought with it. This is fixed easily enough: Mail Stamps is a simple utility that changes the buttons to the old ones found in Mail 1.x. A couple of clicks, and you're done.

Uno GUI

You may have noticed that the Aqua interface design that graces Mail is absent in my screen shots. That's because I used Interacto's Uno GUI unifier to achieve a uniform interface in every application and window. Aqua, brushed metal, "burnt" brushed metal, and everything else - all have given way to a clean, straightforward interface design.

Features and Tools I Use Just a Little Bit (but I'm Glad They're There)

There is a lot of power in Mail that I don't use very often. Nevertheless, having it at my disposal when and if I should need it is a great comfort.

Parental Controls

Our three-year-old son is getting more interested in the computer every day. I love the fact that Mail has very good parental controls built-in. Our kids won't use my iBook very much, but they'll use Marcie's Mac mini a lot, and we'll take full advantage of Apple's thorough attention to parental controls, including good work with Mail's capabilities.

Spam-analysis Tool Leverage

Some of the mail servers that I access utilize server-based spam-analysis tools, like SpamAssassin and Brightmail. Mail leverages these for better spam reduction and filtering. Even though I use additional spam tools (see above), I'm glad that Mail has the strong spam-analysis features that it does.

iCal Invitations

Like Entourage, iCal can invite others to events through an email invitation. Mail is the conduit for iCal invitations, and they are usable by anyone else who runs iCal.

Fax Management

OS X allows any application to send a fax. What's more, the built-in modem can also receive faxes just like a standard fax machine, and here's a nice touch: Mail manages and organizes those faxes.

iPhoto Integration

Marcie handles most of the photo organization for our family using iPhoto, so I end up using iPhoto only occasionally. When I have used it, however, I've found Mail's easy integration with iPhoto to be a great feature - one-click adds any attached photo into your iPhoto library.

AppleScripts

AppleScript is a robust technology that not many of us utilize to anything close to its potential. While I don't use it very much myself, I have found that occasionally an AppleScript can accomplish something for me that would be a hassle otherwise. I've found Mail Scripts 2.7.8 to be a nice collection of scripts; you may also want to check out Mail2iCal and Mail2iCalToDo, which, as their names imply, allow you to easily transfer an email into iCal as an event or to-do item.

RuleBox

As your Mail Rules get more sophisticated for filtering emails, you may encounter the frustration of "broken rules" when a friend changes to a new email address. RuleBox offers a good solution: It will clean up the relationships between Mail Rules and Address Book entries.

GPGMail

I don't find it necessary to encrypt emails - or any other files - very often. (I think I can remember doing it about five times in as many years.) It would be a true waste of money, therefore, to pay for an encryption program. On the other hand, it's easy to keep GPGMail, an open-source encryption plug-in based on Mac GNU Privacy Guard, on hand for those few times when I will send or receive an encrypted email.

Features I Don't Use but Find Appealing

Mail has a few remaining features that appeal to me, not because I'll use them anytime soon but because I'm concerned about efficiency and functionality on the Mac.

Microsoft Exchange Compatibility

One of the big complaints I used to hear about Mail was that it wasn't compatible with Microsoft Exchange servers. Mail 2.x is compatible.

Integration with DayLite

I haven't used DayLite, but it gets great reviews, and many people use it to manage contacts and business networks. I understand that the Mail integration for DayLite is every bit as powerful as DayLite itself, which is to say that it's highly commendable.

MailPriority

This neat plug-in made functions like message priorities, message coloring, and return receipts easy to handle for pre-Tiger Mail users. Hopefully a Tiger-compatible version of MailPriority is on the way.

Features I Would Like to See in Mail

There are a few things that Mail doesn't offer (and neither do any third-party developers that I've found). Three features I would love to see in Mail:

Bulleted and Numbered Lists

I like to use bullets in my emails; they make things easier to read quickly, and that's good for efficiency. Numbered lists also help, but these are easy to do without a formatting option. Until Mail offers true bullets, I'll get by using a tab-indent and the tilde (that's the ~ symbol).

MailPriority for Tiger

Mail already has message priorities, so I'd settle for just return receipts, another feature that I use infrequently - but often enough to value it. Entourage had it, but you had to turn it on or off with a hard-to-reach dialog. Mail could offer this easily in a future update.

Address Book-specified Email Accounts

I may be the only one in the world who wants this feature, but here we go: What if I could specify in my Address Book what my default email account would be for a given contact? Since I manage ten different accounts, this would save me tons of time over the course of a week, a month, or a year. Just a few less clicks would boost my morale as well. (Any developers who want to take me up on this are welcome to use the idea.)

Mail is a powerful, elegant program, and a few third-party plug-ins and integrated applications gives it more power still. As I consider how much Mail has to offer, it seems clear that it offers features rich enough to accommodate my needs for some time to come.

Mail works for me, and it can work for you. LEM

If you find Ed's articles helpful, please consider making a donation to his tip jar.

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