Tutorial/How-to: E-mail survival guide

Tutorial/How-to: E-mail survival guide

Do you dread opening your e-mail program in the morning? Are you overwhelmed by the endless busywork of checking, sorting, and replying to a constant onslaught of mail? Do you practically need a private detective to track down legitimate correspondence lost amidst the offers for hair tonics and weight-loss pills? Hey, email was supposed to make your life easier. Here's what MacWorld's writers have to say...

Do you dread opening your e-mail program in the morning? Are you overwhelmed by the endless busywork of checking, sorting, and replying to a constant onslaught of mail? Do you practically need a private detective to track down legitimate correspondence lost amidst the offers for hair tonics and weight-loss pills? Hey, e-mail was supposed to make your life easier.

Macworld’s E-mail Survival Guide will put you back in control of your in-box. We'll help you find an e-mail client that can better handle the load. We'll show you how to develop a strategy for staying organized. And then we’ll address e-mail’s biggest time waster: spam. We’ve got the latest tricks and tips for eliminating junk mail before it hits your in-box.

Change e-mail clients

Do you find it increasingly difficult to deal with the daily flood of e-mail? Do you wish your e-mail client could share information with other Mac programs? If so, it may be time for you to choose a new e-mail program.

E-mail management is no place for nostalgia -- you shouldn’t stick with a client simply because you’ve used it since the first Bush administration. You’re better off basing your choice on the volume of e-mail you receive, the control you need over your e-mail program, and how well the app fits into your workflow.

Changing e-mail clients doesn’t have to be painful. I’ll help you find a program that fits the way you use e-mail, and then I’ll show you how to take your messages and contacts with you to their new home.

Create an e-mail wish list

Before you can find the perfect fit, you need to understand what features are most important to the way you use e-mail. To help you sort it all out, first consider some of the big issues.

Money matters If price is your primary concern, you can’t go wrong by choosing an application you already have -- Apple Mail. Likewise, if you’ve shelled out money for the Microsoft Office 2004 suite, you already own Entourage.

Spam protection If you have an e-mail account, you will get spam. Many ISPs and company networks try to filter out the obvious spam before it reaches you. But if yours don’t do that -- or if you’re still overrun with the stuff -- you’ll want an e-mail client that can take on the task. All the programs we recommend here offer spam filters that learn how to correctly identify incoming spam and that remove it from your in-box. If you receive a lot of spam, you’ll further benefit from a program with sophisticated mail filters, such as those included with Entourage or Bare Bones Software Inc.’s Mailsmith. These filters can help you isolate the spam that circumvents your other barriers.

Simplicity Completing day-to-day e-mail tasks shouldn’t require excessive brain activity. If you often receive or create HTML-formatted messages, for example, you should think twice about adopting an

e-mail client such as Mailsmith, which makes you jump through hoops to do either. You should also consider the accessibility of the information you need. If you routinely use OS X’s Address Book or iCal, you’ll be happier if your e-mail client does, too.

Manageability Some people keep every message they’ve ever received in one in-box. And that’s fine for very light e-mail users or people who don’t mind weeding through an endless list of messages. But if you receive a lot of mail, you’ll benefit greatly from a program with sophisticated mail filters that can automatically sort and prioritize your incoming messages.

You also may want a client that offers flexible scheduling. Although all e-mail clients can download mail every couple of minutes, only high-end programs such as Entourage and Mailsmith let you create more-complicated schedules -- for example, to access a rarely used account only on Tuesdays and Thursdays.

Advanced control If you regularly receive or send high volumes of mail, you may need something that goes above and beyond the normal call of duty. You might want to use AppleScript, Apple’s native scripting language, to automate some of your e-mail client’s tiresome tasks. Or you may want to be able to add mail headers to your outgoing e-mail messages -- a PGP fingerprint header, for example.

Proper access E-mail is hosted on one of two kinds of servers -- POP (Post Office Protocol) or IMAP (Internet Message Access Protocol). POP accounts, which download messages to your computer, are more common than IMAP accounts, which store mail on your ISP’s server. However, many Web-based e-mail services -- including Apple Computer Inc.’s .Mac and America Online Inc.’s AOL -- require an IMAP connection. If you use an IMAP account and your client doesn’t support it, the client is useless to you.

Find the right fit

OS X users have several options when it comes to choosing an e-mail client. But three programs stand out from the rest in terms of features, reliability, and performance -- Apple Mail, Microsoft Entourage 2004, and Bare Bones Software’s Mailsmith 2.1. The kind of e-mail user you are will determine your choice.

The casual e-mailer

You receive a light to moderate amount of e-mail and don’t spend much time trying to keep it organized, beyond dividing it into folders. You already use (or would like to use) Apple’s Address Book and iCal programs, and you want an e-mail program that can take advantage of them.

Our recommendation: Apple Mail 1.3.

Why: Apple’s e-mail client has evolved into a reasonably mature application. Mail is accessible enough for beginners and complete enough for people who need to manage a moderate amount of e-mail.

Mail includes all the basic rules necessary to capably route messages to different mailboxes (although the list of rules isn’t as extensive as that of Entourage or Mailsmith). Users who collaborate with others via e-mail will particularly appreciate Mail’s Thread view, which groups messages that are part of an ongoing exchange. But Mail’s scheduling options are extremely limited compared with those in Entourage -- you can’t create multiple schedules, and you can’t ask Mail to check your mail less often than once an hour. There is potential for adding more-advanced features; Mail offers solid support for AppleScript and lets you trigger an AppleScript from a mail rule.

Of course, Mail’s greatest advantage is its integration with other Apple applications. You can configure iCal to send announcements of upcoming events through Mail. And you can add contacts to Address Book with the click of a button.

The Office e-mailer

You rely on Microsoft Office to get your job done, and you want an e-mail program that seamlessly integrates into your workflow. You get a moderate to heavy amount of e-mail and you need a way to quickly sort through your incoming messages, pick out the important messages from the not-so-important notes, and file them away in the appropriate folders.

Our recommendation: Microsoft Entourage 2004.

Why: Entourage offers nearly every feature found in Mail (except integration with other Apple programs and message threading) and many more.

Entourage’s greatest strengths lie in its management features. Its mail rules can filter messages in ways not possible in Mail -- for example, you can create rules that apply only to messages formatted as HTML. And its Mailing List Manager greatly simplifies the process of sorting mailing-list e-mail. The program’s Project Center, which allows you to organize contacts, events, mail, and documents by project, is unmatched in any other e-mail client.

Entourage can schedule more tasks than Mail can. It’s also the only e-mail client in this roundup that can trigger an AppleScript from a schedule -- for example, to archive messages when you quit the program.

Entourage doesn’t share information with Address Book or iCal. Instead, it offers its own tools for managing contacts, calendars, notes, and more. If you work in a cross-platform office, you’ll appreciate the program’s superior support for Microsoft Exchange Server -- server-based software that lets Entourage and Outlook users share contacts and calendars over a network. Entourage is also the only Mac e-mail client that can send and receive messages by default.

Entourage’s weakest link is its single database. A bloated database can slow down performance, and if it becomes corrupt, you could lose everything. If you choose Entourage as your e-mail client, you should regularly back up Entourage’s Database file (located in your user folder at Documents: Microsoft User Data: Office 2004 Identities: Main Identity).

The e-mail commander

You’re no e-mail novice. You use e-mail for advanced tasks, such as running a newsletter or managing multiple accounts, and you need to have full access to your e-mail settings. You also want a no-nonsense program that can quickly search and manipulate a high volume of e-mail.

Our Recommendation: Bare Bones Software’s Mailsmith 2.1.

Why: Although Mailsmith is approachable enough for typical Mac users, it tends to appeal to a highly technical -- and proudly geeky -- audience.

If you’re accustomed to other e-mail clients, you may be thrown off by Mailsmith’s spartan interface and its lack of amenities common in other e-mail programs -- for example, support for HTML messages (though you can view such messages in your default browser at the click of a button), support for IMAP e-mail accounts, and an in-line spelling checker.

But for exercising complete control over your e-mail client, Mailsmith’s list of features is hard to beat. Although the program doesn’t search mounds of messages as quickly as Qualcomm Inc.’s Eudora -- one of Macworld’s past favorites for advanced users -- Mailsmith does a better job of pinpointing the messages you’re after, thanks to its highly configurable search feature. For example, you can search for words that begin or end a text string, or use special grep characters to identify loose patterns of text. And the options for creating mail filters are just as expansive.

Mailsmith offers built-in support for PGP encryption and Michael Tsai’s powerful SpamSieve software -- which is superior in many ways to what you’ll find in Mail or Entourage. And if you’re handy with AppleScript, you can automate nearly all of the program’s functions.

Make the switch

Regrettably, there’s more to switching e-mail clients than just deciding which one suits you. There’s also the sometimes-messy business of moving e-mail and addresses to a new home.

Most e-mail programs have an Import command that automates the process of moving your e-mail, contacts, and other data. But if the Import option doesn’t support your client -- or if it doesn’t do a sufficient job -- there’s still hope. You can almost always get the job done with a third-party utility or by manually converting your files into the standard mbox or vCard formats.

Here are some guidelines for bringing your old messages and contacts into your new program.

Moving to mail


If you’re moving to Mail from Entourage, Outlook Express, Netscape/Mozilla, or Claris

E-mailer, open Mail’s Import Mailboxes command (File: Import Mailboxes) and select the appropriate import option. You can also import mbox files that you created in another application. In the Import window, select Other, click on the right-arrow button, and navigate to the location of the mbox files.

Although Mail offers to automatically import e-mail from Eudora, the process is far from ideal -- it ignores attachments and removes HTML and rich-text formatting from your messages. Instead, use Andreas Amann’s free Eudora Mailbox Cleaner (find This utility correctly transfers messages, as well as filters and nickname files.


Mail stores its contacts in Apple’s Address Book. You can import addresses from Entourage, Outlook Express, Palm Desktop, Eudora, Claris E-mailer, or Netscape/Mozilla by using the Import Addresses AppleScript.

If you haven’t already installed OS X’s Script Menu (look for a tiny scroll that appears in the

Finder’s menu bar), go to your Applications: AppleScript folder and double-click on the Install Script Menu item. Then, from the Finder, click on the newly installed Script Menu and choose Address Book Scripts: Import Addresses.

Moving to Entourage 2004

E-mail Entourage’s Import command (File: Import) will transfer e-mail messages and addresses from Entourage, Outlook Express, Eudora, Mail, Netscape Communicator, and Claris E-mailer. If you’re coming from a different e-mail client or from a different computer, first export your messages as an mbox file, and then drag this file onto the Folders On My Computer entry in Entourage’s Folders pane.


If you have contacts, calendars, notes, and other bits of data stored in Microsoft Outlook or a personal information manager such as Palm Desktop, you can easily bring them to Entourage 2004 with the help of Paul Berkowitz’s US$20 collection of AppleScripts, Export-Import Entourage X (find This collection includes more than 50 scripts for moving almost anything into and out of Entourage X and 2004.

If you have vCard files that you exported from another application, you can also import these by dragging them into Entourage’s Address Book window.

Moving to Mailsmith


When you launch Mailsmith for the first time, it offers to import mail and contact information from a variety of programs, including Eudora, Claris E-mailer, and Mail. If you need to import mail from other clients or want to add messages after the initial import process, you can do so by dragging mbox files into the Mailsmith window.


You can also import contacts from Eudora and other vCard-compatible applications by exporting them as vCard files and dragging them into Mailsmith’s Address Book window. (Mailsmith uses OS X’s Address Book, so you don’t need to import these contacts.)

Message received

For many of us, e-mail has become an integral part of the workday and a primary means of keeping in touch with others. Given the variety of e-mail clients out there, you have no excuse for sticking with a program that can’t meet your needs. If it’s time to switch to a better client, this guide will point you in the right direction. But only you can get the ball rolling.

What about Eudora?

Sharp-eyed readers will notice that Qualcomm’s Eudora 6.1 doesn’t appear on our list of recommended e-mail clients. Although Eudora has been a past favorite -- particularly for users who need nearly infinite control over their e-mail settings -- the e-mail landscape has changed and, regrettably, Eudora has been slow to change with it.

It’s true that Eudora makes quick work of searching massive mailboxes and offers almost limitless ways to customize your mail settings (for example, you can designate which headers will appear in messages sent from a particular account). But for most advanced users, these perks won’t make up for the program’s aging features, including limited filtering options -- Eudora provides just two If conditions and four Then actions for sorting messages.

It also does a poor job of displaying complex HTML messages. And although Eudora is scriptable, its scripting dictionary is out of date, so the program is more difficult to script than Mail, Entourage, and Mailsmith.

If Eudora suits you, by all means stick with it. But if the program no longer fits the bill and if you need absolute control over your e-mail, I recommend switching to Mailsmith.

Exporting to standard file formats

In a computing world rife with incompatible standards, the mbox and vCard file formats offer a rare sliver of sanity. By converting your data into these two cross-platform standards -- mbox for e-mail messages and vCard for contacts -- you can quickly and easily move much of the information in your e-mail client and address book to other applications, or even to the same application on a different computer.

Here’s how to access mbox and vCard files from Mail, Entourage, Mailsmith, and Eudora.

Creating mbox files To generate an mbox file from Entourage, Mail, or Mailsmith, just click on one of the program’s mail folders and drag it to your desktop. Repeat this for each folder you want to move. Note that in Entourage, the newly generated mbox file won’t include any of the folder’s subfolders. You’ll have to drag these to the desktop separately.

When you drag Mailsmith’s mailboxes to the desktop, they become text documents by default. To import these files into Mail or Entourage, you must first append the .mbox extension to them.

Eudora doesn’t support this drag-and-drop method. To access its mbox files, open your user folder and go to Documents: Eudora Folder: Mail Folder.

Creating vCards In most cases, creating vCards is also a drag-and-drop affair. To export vCards from Apple’s Address Book -- which both Mail and Mailsmith use -- just select the contacts you want and drag them to the desktop. You’ll end up with a single file with all the selected contacts.

Unlike Address Book, Entourage won’t export multiple contacts as a single vCard file. So if you plan to export multiple contacts, it’s a good idea to first create a folder to hold all of the resulting vCards.

To export Eudora’s nicknames as vCard files that can be imported into Apple’s Address Book, Entourage, or Mailsmith, use Andreas Amann’s free Eudora vCard Export (

Import mail from Microsoft Outlook for Windows When contemplating a move to the Mac, one of the first questions many Windows users ask is “Will I be able to access my old e-mail, contacts, and calendars on my new computer?” Thanks to Outlook2Mac, a $10 program from Little Machines (, the answer is yes.

Outlook2Mac painlessly converts Outlook mail to a form that you can import into Mail, Entourage, or Mailsmith. It will also export contact and calendar data to any program that supports the vCard and iCalendar (.ics) file format standards -- including Address Book, iCal, and Palm Desktop.

Outlook2Mac is remarkably easy to use. Simply purchase an appropriate version of the program (separate versions are available for Outlook 2002/2003/XP, Outlook 2000, and Outlook 97/98) and launch it. The software then walks you through the process of exporting the needed data. You can select specific mailboxes, a range of calendar dates, and the most appropriate file format for the data export. If you’re moving to Address Book or Palm Desktop, you’ll need to export your Outlook contacts as a single vCard file. Likewise, iCal requires a single .ics file for calendar data. If you’re moving to Entourage, you’ll need to export your data as individual vCard and .ics files. You should also instruct the program to filter out any attachments that won’t work with your Mac -- files ending with an .exe extension, for example.

Get organized

E-mail was supposed to be a time-saver. But hand-sorting an in-box overflowing with personal messages, business correspondence, mailing-list deliveries, and jokes from clueless cousins (not to mention the load of unsolicited e-mail you receive each day) can take a substantial bite out of an already busy day.

What you need is an e-mail strategy. I’ll show you seven ways to take control of your jammed in-box.

1. Establish rules

One of the easiest ways to automate filing duties is to create a mail rule -- a set of criteria that tell your e-mail client how to sort and file your messages when they arrive. This not only makes your in-box more manageable, but also helps you quickly prioritize your incoming messages. For example, you can use rules to assign colors to different types of mail, so you can quickly distinguish work assignments from family gossip.

To access rules in Entourage, go to Tools: Rules and click on New. In Mail, go to Mail: Preferences: Rules. In Eudora and Mailsmith, go to Window: Filters.

Regardless of the program you use, the basics of setting up a mail rule are essentially the same. You use If statements to tell your e-mail program how to identify the messages you want to control, and Then statements to specify what to do with those messages.

For example, if you have two e-mail addresses -- one for personal mail and one for business mail -- you might find it useful to separate these messages into two different mailbox folders. Such a filter would look like this:

If: Any Recipient is

Then: Move Message to Personal E-mail Folder

For more-powerful filters, you can combine multiple If and Then statements. For example, to make sure you give prompt attention to messages from your company’s bigwigs, you might want to move their incoming messages to a From The Boss folder and play a suitably ominous sound.

2. Take control of mailing lists

Using rules is also vital if you subscribe to mailing lists -- particularly ones that don’t offer digests, but rather copy you on every message sent to the list.

Entourage has a handy Mailing List Manager feature (in the Tools menu) that automates the most laborious aspects of managing such lists. For example, it can move incoming list e-mails to a designated folder, break list digests into individual messages, and delete duplicate copies of messages you send to the list. If you don’t use Entourage, you can set up something similar -- but much more basic -- by creating a mail rule that picks out any message with the list’s e-mail address in the From field and moves it to a dedicated mailing-list mailbox.

3. Follow a conversation

Some e-mail exchanges can span weeks and include half a dozen people. You can often get a quick overview of the back-and-forth by sorting your mail by Subject, but this method is far from perfect: I can’t tell you how many of my message threads have started with the subject lines “A quick question” and “Hello.”

With Entourage, you have only the sorting method. Mail and Eudora offer more-efficient solutions. In Mail, go to View: Organize By Thread. Mail then groups all your related e-mails -- and only the e-mails relevant to this specific thread -- under a single heading highlighted in blue. You can view all of the messages in a thread by clicking on the arrow to the left of the highlighted message. To group messages by thread in Eudora, go to Special: Sort: Group Subjects (or just option-click on the message’s subject line).

4. Get a better view

Most e-mail programs offer basic sorting options -- such as Message Status, Subject, and To. Entourage 2004, however, lets you further arrange your messages into groups -- larger categories of sorted messages that you can then quickly collapse or expand.

For example, you could use the Groups feature to quickly slim down your Entourage database by eliminating large files from your in-box. Turn on Groups by going to View: Arrange By: Show In Groups. Now when you sort your messages by Size (View: Arrange By: Size), Entourage groups them into categories such as Small, Medium, Large, Huge, and Enormous. To quickly eliminate all of your Enormous, Huge, and Large files, click on the Group header (which selects all messages in the group) and press delete.

To further control your messages, you can define how they are sorted within individual groups. For example, you may want to eliminate only some large files: those that are older than a week or that are

from certain individuals. To do this, create a new custom arrangement (View: Arrange By: Edit Custom Arrangement) that groups items by size and then arranges items within the group by Sent or by From. Click on OK to save your new arrangement. To apply this view to your in-box, go to View: Arrange By and select the saved custom arrangement.

5. Find anything fast

Most e-mail clients offer an advanced search option that uses multiple criteria to scan all your stored

e-mail. Entourage’s advanced search option even lets you include contacts, notes, and calendar options in the hunt.

Apple Mail won’t let you search by more than one criterion. But there is a workaround. Create a rule that uses multiple criteria to identify messages and then copies those messages to a special folder.

For instance, if you wanted to find all your business-related messages older than seven days that CC’d your coworker Fred, you’d create a rule that looked like this:

If: CC contains Fred

Date Received Is Greater Than 7 Days Old

Account Is

Then: Copy Message To Mailbox Fred

To apply the rule to a selection of messages, go to Message: Apply Rule. Everything that meets these requirements will appear in your Fred mailbox, which you can delete once you’re done.

6. Create e-mail archives

Any good e-mail maintenance plan should include a backup strategy. That way, if a question comes up months or even years from now, you’ll have an intact, searchable record of the correspondence. But archiving all of your messages at once can be unwieldy. A better approach is to create separate archives of related messages. This way, you can conserve space by backing up only the messages

you need.

One easy way to create these archives is to filter messages as you normally would while also filing away a copy in a separate, archived mailbox. For example, if you employ freelance workers, you might create a rule that filters their messages to a mailbox for whatever project they are currently working on and sends copies to a mailbox called Quarterly Projects, which you archive four times a year.

When you’re ready to back up your archive file, just drag the mailbox from your e-mail client (if you’re using Mail, Entourage, or Mailsmith) to the desktop to create an mbox file that you can then burn onto a CD. To locate Eudora’s mbox files, open your user folder and go to Documents: Eudora Folder: Mail Folder. Later, if you need to access the information in an archived mbox file, just open it in a text editor or drag it back into your e-mail client.

7. Archive Entourage projects

If you use Entourage 2004’s Project Center to group related e-mails, tasks, and documents, you can archive projects via the Export command. In the Export window, enable the Items That Are In The Project option and choose a project from the pop-up menu. To save space, tell Entourage to delete messages once they’re archived. Entourage will create an .rge file. To restore the data in this file, select File: Import: Import Information From An Entourage Archive. If you don’t want to permanently return the messages to your mailbox, import them into a new identity (Entourage: Switch Identity) and delete the identity when you’re done.

Manage your Web mail

Free Web-based mail services such as Yahoo Mail and Hotmail are great for checking your mail when you’re on-the-go. But when you’re sitting at your desk with your favorite e-mail client in front you, having to open a Web browser to check your messages is frustrating. It also makes archiving a challenge. But there are ways to access your Web mail from a desktop client.

The paying way Both Yahoo Mail and Hotmail offer extended mail plans that let you download messages via a POP mail account, for $20 a year. With POP access you also get greater e-mail storage capacity, spam filtering, and no advertising. For a rundown of Web mail options and applicable fees, see “Web Mail Supersizes” (Mac Beat, August 2004) or go to

The built-in way Some e-mail programs offer tools for accessing specific Web-based mail accounts. For example, you can access Hotmail messages from within Entourage. Just run the Account Setup Assistant (Tools: Accounts: New), and enter your Hotmail address in the E-mail Address field to get started.

The third-party way Several utilities let you forward e-mail from a Web-based service to an e-mail account you maintain with another ISP.

You can download Hotmail messages to Mail with the help of Daniel Parnell’s free HTTP Mail Plugin ( After you install the program, open Mail’s Accounts preferences, click on the Account Information button, and click on the plus sign (+) button to create a new account. An httpmail option should now appear in the Account Type pop-up menu. Choose it; then enter your Hotmail settings in the appropriate fields. Your messages will now download to a newly created Hotmail mailbox.

Yahoo Mail users can forward their mail to any POP account with the help of System Support Products’ $15 Mail Forward ( This application, which can also forward AOL and Hotmail messages, logs on to your account and forwards your messages to another e-mail account via your ISP’s SMTP server.

Organize your rules 

The order in which mail rules appear is important. E-mail programs apply rules in the order they’re listed. So if you’ve created a filter that moves all messages sent by Jane Doe to one mailbox and another filter that transfers all messages that came from the Taffy Lovers mailing list to another mailbox, Jane’s message expressing her love for taffy will be filtered by whichever rule appears first. If one of your rules doesn’t work, check to see whether another rule higher in the list conflicts with it.

Win the spam war

Imagine going to your mailbox every day, pulling out hundreds of flyers, and then sorting through them to find the one bill or personal letter you were expecting. For many of us, this is exactly what the spam epidemic has become: a frustrating and time-consuming daily ritual of weeding out offensive and irritating offers so we can get to the messages we actually want and need. To make matters worse, spammers’ tactics are constantly changing -- rendering spam-proofing strategies that worked a year ago all but useless today.

Even by conservative estimates, spam now accounts for well over half the e-mail sent worldwide. But you can fight back -- in many cases by using tools you already have. Stopping spam involves much more than just clicking on a check box. A good spam-fighting strategy includes keeping your e-mail address away from spammers, using common sense about reading and replying to spam, and fine-tuning your built-in filter for optimum accuracy.

I’ll focus on optimizing the spam-fighting tools built into Apple Mail and Microsoft Entourage, two of the most popular e-mail clients for Mac OS X. However, many of the strategies I discuss apply to all e-mail users, regardless of what software they use.

Don’t let the spammers find you

So who exactly are these spammers, and what do they want with you? Although some spammers are hoping you’ll give away personal information so they can steal your money, most just want to sell you something. Clever hackers write programs that gather potentially valid e-mail addresses, and then they sell these addresses by the hundreds of millions to spammers -- often ordinary people hoping to make a quick buck. Spammers know that most of their messages will be deleted or ignored, but they make up for this in volume. If even a tiny fraction of their messages results in a sale, spammers can make a considerable sum.

Your first line of defense, then, is to stay off the radar of spammers and their address-gathering programs.

Guard your address The easier it is for someone to find your e-mail address, the more likely you’ll be the target of junk mail. So avoid publicizing your e-mail address on Web pages or in newsgroup postings. If you really must post your address online, turn it into a graphic with no mailto link. If you need to enter an address in Web forms for online purchases, contest entries, and the like, consider getting a second address, such as a account, just for this purpose. This will let you to keep your primary address private and relatively spam-free.

Practice the silent treatment Resist the temptation to reply to spam messages -- even to unsubscribe from them. In most cases, no one will read your reply. And if it does get through, it simply confirms that your address is valid. In general, you can safely unsubscribe from newsletters and other mailings from legitimate companies with which you’ve done business -- but if you’ve never heard of the mailer, chances are any Remove Me links are bogus.

The same is true of bouncing messages -- returning a spam to its sender in hopes of tricking the spammer into thinking that your address is invalid. Savvy spammers can still tell that a message reached its destination. Besides, since spam messages are sent out by the millions, spammers aren’t likely to bother removing invalid addresses from their lists.

Turn off HTML Spammers can tell that you’ve read their messages by using a Web bug, a small graphic that your e-mail client downloads when you display a message with HTML formatting. The graphic’s URL contains a unique identifier tied to your e-mail address, so merely displaying the message tells the spammer’s server that you’ve read it.

To thwart Web bugs, turn off the display of HTML graphics in your e-mail client. By default, Entourage 2004 doesn’t download images unless the sender is in your address book. In Mail, open your Viewing preferences and deselect the Display Images And Embedded Objects In HTML Messages option. If you receive a legitimate HTML-formatted message, you can easily download the images by clicking on the Load Images button in Mail or the Download Pictures link in Entourage 2004.

Take advantage of spam filters

Of course, it’s almost impossible to elude spammers completely. This is where your e-mail program’s built-in spam filters come into play. Spam filters function as e-mail gatekeepers, separating invited guests from the riffraff.

Apple Mail 1.3 (included with Panther) and Entourage 2004 both offer significantly better spam-fighting tools than their predecessors. In fact, if you’re using earlier versions of Mail or Entourage, I recommend upgrading for the spam improvements alone. But to really put these built-in filters to work, you need to train them to recognize the type of company you like to keep -- and the type that should be left on the curb.

Practice makes perfect Mail and Entourage use statistical junk-mail filters -- programs that try to learn which words and message attributes distinguish spam from legitimate mail. When you identify an incoming message as junk, the filters add information about that message to a database, making it easier for them to identify similar messages in the future. Likewise, the filters track the attributes of valid messages to avoid marking them as spam. By constantly updating their databases, these junk-mail filters get smarter as you use them and are able to better adapt to the latest spamming tactics.

But for statistical filters to be effective, you must diligently correct their mistakes. If your e-mail client fails to identify a spam message, take the time to mark it as junk. In Mail, select the message and choose Message: Mark: As Junk Mail. In Entourage, choose Message: Mark As Junk (or press 1-shift-J in either program).

Similarly, if your e-mail client mistakes a legitimate message for spam (called a false positive), correct that mistake by marking the message as Not Junk.

Introduce it to your friends Because legitimate messages sometimes include the same words and phrases as spam, the best way to prevent false positives is to create a white list -- a list of people whose messages should never be marked as junk.

Entourage’s spam filter automatically exempts messages from anyone listed in the Entourage Address Book. Similarly, you can have Mail exempt anyone in the OS X Address Book by opening Mail’s Junk Mail preferences and selecting the Sender Of Message Is In My Address Book option. Then be sure to keep your address book up-to-date with the names and e-mail addresses of everyone who regularly sends you mail. To add the sender of a selected Mail message to the OS X Address Book, choose Message: Add Sender

To Address Book (or press 1-Y). To add a sender to Entourage’s Address Book, go to Tools: Add To Address Book (or press 1-= [equals sign]).

Optimize mail’s settings

Mail’s default spam settings offer a good start to fighting junk mail, but they should be considered just that -- a start. There’s plenty more you can -- and should -- do to optimize Mail’s spam sensitivity.

Go Automatic Mail provides two modes for filtering junk mail. The default -- Training mode -- simply uses color to distinguish suspected spam from legitimate mail. This lets you easily monitor whether Mail is flagging spam correctly. But once you become comfortable with Mail’s choices, you should switch to Automatic mode.

In Automatic mode, Mail moves all suspected spam to a Junk mailbox, letting you largely ignore its existence. And despite the confusing names, switching from Training to Automatic mode doesn’t interfere with the training process at all; the Junk Mail filter continues to learn new spam-fighting skills as you correct its mistakes.

To put the filter in Automatic mode, open Mail’s Junk Mail preferences, make sure Enable Junk Mail Filtering is selected, and then select the Move It To The Junk Mailbox (Automatic) option.

Tweak your preferences While you have your Junk Mail preferences open, I recommend making a

couple of other changes to further heighten your spam security.

Because spam frequently includes the recipient’s full name, deselect the Message Is Addressed Using My Full Name option. Next, turn on the Trust Junk Mail Headers Set By Your Internet Service Provider option. Some ISPs add a special header (called the X-Spam-Flag header) to incoming messages their servers suspect are spam. By telling Mail to look for this clue, you can increase the Junk Mail filter’s accuracy. Even if your ISP doesn’t currently offer this feature, there’s no harm in leaving this setting turned on.

Preempt other rules If you use mail rules to file your incoming e-mail, you may find that Mail misses a considerable amount of spam. That’s because Mail’s built-in Junk Mail rule affects only the messages left in your in-box after all other rules have been applied. So, if you have a rule that filters all of the mail sent to your personal account into a special mailbox, the Junk Mail filter will never look at any of those messages. In this case, consider overriding the built-in Junk Mail rule with one of your own.

To create a new rule that mimics Mail’s built-in filter, go to Mail: Preferences, click on Rules, and then choose Add Rule (see “Priority Filtering”). When you’re done, move the new rule to the top of the list so it runs before any others.

Thin out your VIP list You should also keep an eye on Mail’s Previous Recipients list. Mail assumes that if you send someone an e-mail, you want to receive the reply. So every time you hit Send -- even if it’s only to unsubscribe from a mailing list—Mail adds the person to its Previous Recipients list. Because the Junk Mail filter ignores messages from anyone on this list, you could accidentally give approval to any number of unwanted guests. In fact, in previous versions of Mail, just moving a message to any mailbox other than Junk could add its sender to the approved list.

To remove spurious addresses from this list, choose Window: Previous Recipients. Click on any suspicious addresses and select Remove From List. If you find the process of pruning your Previous Recipients list too tedious, or if it results in too many false negatives, you can instruct Mail to ignore this list when filtering. Just open your Junk Mail preferences and deselect the Sender Of Message Is In My Previous Recipients option.

Optimize Entourage’s settings

Entourage 2004 also lets you customize your spam filter to determine how aggressively it filters your e-mail.

Become Less Tolerant Entourage offers three levels of spam filtering -- Low, High, and Exclusive. You can access these settings by selecting Junk E-mail Protection from the Tools menu. Although Entourage uses the Low setting by default, High is appropriate for almost everyone. You should choose Low only if the High setting results in too many false positives -- and if you can’t correct the problem by adding the senders to Entourage’s Address Book. Avoid using the Exclusive setting, which filters out all mail from anyone not on your white list. While this is certain to keep your in-box free of spam, it’s also likely to clutter your Junk folder with legitimate messages.

Approve large groups Adding recipients to your Address Book is a great way to exempt them from your Junk Mail filter. But trying to add everyone with whom you work can be tedious. A simpler solution is to add an entire domain -- that of your employer or school, for example -- to your white list. To do this, open the Junk E-mail Protection window (under Tools), click on the Safe Domains button, and enter all approved domains, separated by commas.

If you subscribe to mailing lists, you can guarantee that mail from these lists isn’t considered spam by using the Mailing List Manager (in the Tools menu). The Mailing List Manager not only helps you filter any related messages into a dedicated folder, but also ensures that any messages other members sent to the list make it through -- regardless of whether the senders are in your Entourage Address Book.

Look for outside help

What if you’ve diligently trained your junk-mail filters and fully optimized your settings, but you’re still getting a steady influx of spam? Your built-in filters simply may not be accurate enough to handle the problem -- especially if you receive hundreds or thousands of spam messages every day. What you need is some external help.

Third-Party Software One of our favorite add-on spam filters is Michael Tsai’s $25 SpamSieve, a powerful, accurate, and highly configurable statistical filter that works with Mail, Entourage, and other OS X e-mail clients. (It’s also included with Bare Bones Software’s Mailsmith). Whereas Mail and Entourage let you optimize a few basic settings on their spam filters, SpamSieve provides almost endless opportunities for customization.

Mail users should also consider Benjamin Han’s JunkMatcher software (http://junkmatcher.source JunkMatcher is a free Mail plug-in that lets users define wildcard patterns called regular expressions to identify spam characteristics that Mail’s built-in filters could otherwise miss -- such as intentionally misspelled words.

A better ISP Another option is to switch to an ISP that can take on some of the heavy spam filtering for you. Many ISPs use expensive server-based spam filters that are much more sophisticated than what’s available in desktop e-mail clients. Some of these filters tag suspected spam messages so that your e-mail client can take whatever action you choose, while others block spam from reaching you at all. For example, if you own a paid FastMail account (, you can choose what action FastMail takes -- to delete, move, or just mark suspected spam -- based on the message’s spam score, a numerical measure of how similar the message is to confirmed spam. Apple’s own .Mac e-mail service also offers excellent spam filtering. Other good choices include Tuffmail ( and Runbox (\

If switching to a new e-mail provider is out of the question, consider subscribing to a spam-filtering proxy service. A proxy service checks your existing e-mail account for you and runs its own high-powered spam filters on it. You can then set up Mail or Entourage to retrieve your (freshly filtered) mail from the proxy server, rather than your original mail server. This lets you keep your existing e-mail account while benefiting from the superior spam filtering of a much larger service. Examples of such services are Spam Zapper ( and SaferSurf’s Spam Guard ( english/safersurf).

Keep spam in the can

Spam is on the rise. But with a bit of effort and the right tools, you can prevent it from taking over your in-box. If you use your built-in tools wisely, remain diligent, and know when to ask for help, you’ll remain ahead of the game. 

Essential spam-fighting rules

Although statistical filters are much better at catching spam than manual rules, there are a few cases where adding your own rules can help catch spam your built-in filters might otherwise miss. (For instructions, see “Get Organized.”)

Here are three rules that all spam-fighting warriors should have in their arsenals.

1. Look for spam headers Some ISPs insert a hidden header—most often the X-Spam-Flag header -- into messages they suspect are spam. To view these headers in Mail, choose View: Message: Long Headers; in Entourage, choose View: Internet Headers.

Although Mail knows to use these headers to help filter your mail, Entourage doesn’t. But you can add this capability with the help of a new Entourage rule (Tools: Rules: New). Choose Specific Header from the first If pop-up menu, type X-Spam-Flag into the text field that follows, and then select Exists from the second pop-up menu. (If your ISP uses a different flag, enter that header in place of X-Spam-Flag.) Under the Then section, specify where such messages should be moved to.

2. Dump suspicious sttachments Attached files with extensions such as .exe, .pif, .scr, .bat, .com, .lnk, or .js are often Windows viruses or spyware programs. They may not harm your Mac (unless you’re using Virtual PC), but they certainly won’t do you any good. Mail’s rules ignore attachments, but you can set up an Entourage rule to automatically remove these attachments from incoming messages to a POP account (IMAP accounts don’t offer this option).

In Entourage, create a new rule; then choose Attachment from the first If pop-up menu and Name Ends With from the second. Enter the first extension (.exe, for example) and then click on Add Criterion and repeat the process for each extension you want to exclude. From the Execute pop-up menu, select If Any Criteria Are Met. In the Then section, choose Remove Attachments, add a second action, and choose Change Status from the first pop-up menu and Junk E-Mail from the second.

3. Stick to English Sometimes messages that use non-Latin character sets, such as those written in Russian or Chinese, trip up statistical spam filters. If you don’t read these languages, it’s a safe bet that such messages are spam. To identify these messages, you need a rule that looks at the messages’ Content-Type headers.

When creating this rule in Mail, choose Edit Header List from the If section. In the resulting dialog box, type Content-Type in the Header field, click on Add Header, and then click on OK. Change the Edit Header List pop-up menu to Content-Type, select Contains from the middle menu, and then enter the appropriate header in the text field. In Entourage, your If statement should read as follows: Specific Header Content-Type Contains appropriate Content Type header.

Improve Eudora’s spam IQ 

Like Mail and Entourage, Qualcomm’s Eudora 6 uses a statistical spam filter. You can use the Junk Threshold slider (Preferences: Junk Mail) to make the program less tolerant. To determine how low you should go, first open the Mailbox Display panel and activate the Junk option under the Columns heading. A new mail column will appear, showing each message’s assigned spam score. Note the scores of any spam Eudora misses and then adjust the Junk Threshold slider to catch them. -- Adam C. Engst

Spammers versus the law

Everyone hates spam. It’s a drain on your time, bandwidth, and patience. E-mail filters can reduce the time you spend scrolling through your in-box every day, but they can only do so much -- and they do nothing to reduce the amount of messages being sent.

But voter outcry has spurred lawmakers to try to find a solution. CAN-SPAM (Controlling the Assault of Non-Solicited Pornography and Marketing Act of 2003) is the result of three years of work by Democratic senator Ron Wyden of Oregon and Republican senator Conrad Burns of Montana. The law, which took effect on January 1, 2004, prohibits many of the worst spam tactics, including the use of false or misleading header information. The law also requires that all commercial mail include a valid mailing address, a clear demarcation that the e-mail is an advertisement, and a way for recipients to opt out of future mailings.

So how does CAN-SPAM measure up so far?

“CAN-SPAM made a lot of things illegal that already were illegal, and increased the penalties for criminals who weren’t being caught anyway,” says Cindy Cohn, Legal Director of San Francisco’s Electronic Frontier Foundation, a group dedicated to protecting technology-related civil liberties.

Cohen points out that fraud and deceptive advertising practices are already crimes. For example, the Buffalo Spammer case, hailed by many as a victory in the war on spam, had nothing to do with CAN-SPAM. Last April, Howard Carmack was tried and convicted under New York’s identity-theft law for stealing the identity of two Buffalo-area residents and sending out hundreds of millions of spam messages in their names.

“Spam is a difficult problem to address through legislation,” says Cohen. The positive side of the new law, she admits, is that it “spurred law enforcement to go after these people.” So far, four of the largest ISPs (AOL, EarthLink Inc., Microsoft Corp., and Yahoo Inc.) have filed more than 200 lawsuits against alleged spammers. And in late June, the federal government charged an AOL employee under CAN-SPAM with stealing 92 million AOL e-mail addresses and selling them to spammers.

Under current law, only ISPs and the government can sue spammers.

So what can you do to help the fight? If you have the time, you can report spammers to a higher authority. Although this won’t reduce the amount of spam you receive, it can help larger organizations build cases against the most flagrant abusers.

You can report spam to the U.S. Federal Trade Commission by forwarding the messages to Many ISPs also offer an address for spam complaints -- often at Since the sender information in most spam messages is fraudulent, you should examine the message’s header to see from where the message actually originated. (Earthlink offers a tutorial of what to look for. Go to 0046 to view it). Many ISPs will terminate the accounts of confirmed spammers. Others may use the information you send to improve their spam filters. -- Jonathan Seff -- Macworld (US)

Join the CIO New Zealand group on LinkedIn. The group is open to CIOs, IT Directors, COOs, CTOs and senior IT managers.

Join the newsletter!


Sign up to gain exclusive access to email subscriptions, event invitations, competitions, giveaways, and much more.

Membership is free, and your security and privacy remain protected. View our privacy policy before signing up.

Error: Please check your email address.
Show Comments