Section 12.1. Choosing an Email Program

12.1. Choosing an Email Program

Sending mail through the post office, dubbed "Snail Mail" by Internet veterans , requires several steps. You need to type or write a letter, stick it in an envelope, add an address and a stamp, and then drop it in the mailbox. Electronic mail works pretty much the same way: you type your letter into an email program, add the recipient's email address, and then click the Send button. You don't even need to pay any postagea perk long celebrated by spam traffickers worldwide.

All email programs, sometimes called email clients , handle the basic task of sending-and-receiving equally well. The difference lies in their frills: copying your address book to your iPod through iTunes, for instance, is a perk that's offered only by Outlook Express and Outlook. If you want a spell checker, you've got to turn to Mozilla's Thunderbird. And if you want a menu with emoticons (smiley faces, frowns, and so on) to inject into your email, Eudora's for you.

Sometimes the choice boils down to a program's "feel" rather than its features. To help you choose, here are some pros and cons for three popular programs that shuffle email across many electronic desktops today. The best part? They're all free.

12.1.1. Outlook Express

Many people look no further than Windows' Outlook Express (Start All Programs Outlook Express) to take care of their email needs. Legions have grown up with this freebie , tossed into every edition of Windows for the past decade ; its sixth version lives on your PC right now.

Outlook Express, shown in Figure 12-1, is not particularly fancy, but it handles the basics very well. It can send, receive, delete, print, forward, sort , and file your email; manage your address book; send and receive files; and even block email from people you've marked as spammers, enemies, or just plain annoying. It borrows Internet Explorer's Web-handling tools to display fancy emails that look like, well, Web pages.

Figure 12-1. Outlook Express lives on the Start menu of nearly every PC sold today, making it the world's most popular email program. Like most email programs, Outlook Express stores your mail in folders along its left edge. Incoming mail moves straight into your Inbox folder (Section 12.4.4) for you to read; your currently selected message appears in the Preview window. Your sent mail heads for the Outbox , ready for Outlook Express to send. After sending the mail, Outlook Express places a copy of the message in your Sent Items folder for reference. Deleted mail goes into your Deleted Items folder. And Drafts contains mail you've started, but haven't quite found the time to finish.

• Pros . The huge popularity of Outlook Express forces many other programs to stay compatible with it. Rest assured that if you ever upgrade to a more powerful email program, your old email isn't trapped: Nearly every email program will import Outlook Express's messages and contacts. iPods even offer to carry your contacts from Outlook Express or Outlook. Outlook Express is fairly easy to use, free, and already living on your PC. Many people fire it up and never turn back.

• Cons . Since it's used so widely, Outlook Express is a big target for viruses, worms, spammers, spyware, and other dark forces in computer-dom. The program shares Internet Explorer's vulnerabilities as well, since it borrows Internet Explorer's code for displaying messages. And many viruses peek into Outlook Express's address book, emailing a disguised copy of themselves to all your listed friends or coworkers.

  You can nullify most of these threats by installing Windows XP's Service Pack 2 (Section 15.4) and setting Windows Update to Automatic (Section 15.3), which lets Microsoft automatically patch newly discovered security problems. Add an antivirus program (Section 15.6.3), and Outlook Express stays reasonably safe.

  Despite its flaws, zillions of people find no reason to switch from Outlook Express. In fact, the biggest gripe probably boils down to its lack of a spell checker. That's Microsoft's subtle way of prodding you to buy Outlook, the full featured email program included with the pricey Microsoft Office. It's also a way to push you into buying Microsoft Wordwhen you install Word, Outlook Express sneaks over and borrows Word's spell checker, giving you an easy way to proofread your outgoing email.

12.1.2. Eudora

Eudora (www.eudora.com), shown in Figure 12-2, has a small, but devoted, following, most of whom are determined to cut down on the number of Microsoft products on their PCs. If that quest appeals to you, your biggest challenge will be deciding which version is for you:

• Paid Mode . The $50 version, used mainly by businesses, includes 12 months of free upgrades, 6 free calls to tech support (within a 12-month period), and a spam filter.

• Sponsored Mode . This free version drops two features from the pay version: the spam filter and the free tech support. This version of the program also displays a small ad in the screen's bottom corner, as well as two ad buttons on the top menu.

• Light Mode . If you find ads so offensive that you're willing to sacrifice the program's spell checker to rid yourself of them, choose this option.

All three versions of Eudora handle the same email basics as Outlook Express. Installation is easy, too: the program visits Outlook Express to import your email account settings as well as your previously received messages. (It copies your messages only; your originals remain safe with Outlook Express.) When the program finishes installing itself, it presents itself on the screen with all your old email waiting for you. To check for new mail, you need only enter your email account's password.

Figure 12-2. Eudora looks very similar to Outlook Express, with a row of toolbar buttons along the top and a row of folders along its left edge that contain your mail. Eudora's "adsupported" version, shown here, contains most of the features of the paid version, but continually displays an ad in its lower-left corner.

• Pros . Eudora comes in both PC and Mac versions, a plus if you find yourself computing on both types of computers. To help keep your different email conversations separate, you can assign different colors to different conversations. The program also makes extensive use of tabslittle clickable protrusions for quickly changing views. Click a tab on your Mailboxes window, for instance, and the window switches from a row of In and Out boxes to a file browser, a handy way to drag a file into an outgoing email. Click the Mailboxes tab to bring back your Inbox, Outbox, and other mailboxes.

• Cons . Many people find Eudora to be overkill, yet, frustratingly, it lacks some of the details of Outlook Express. For example, it doesn't show how many unread messages are waiting in each folder, nor does it let you create and nestle subfolders inside your Inbox to track different projects. And although the ads try to be unobtrusive , it's annoying when a misplaced click on your part interrupts your work flow with a word from the sponsor.

12.1.3. Thunderbird

Thunderbird (www.mozilla.org/thunderbird), shown in Figure 12-3, flies to us from the Mozilla Foundation, the nonprofit organization that also unleashed the popular Firefox Web browser (Section 13.1.2). Both programs are open source , meaning the programs' code sits on the Internet, freely available for any programmer to inspect or modify (open source programs often get customized to fit the needs of particular user groups). With everything on the drawing board, some miscreants can look for weak spots to unleash viruses. But this open approach also lets other programmers find potential flaws and fix them before the attacks occur.

Figure 12-3. Thunderbird looks and feels a lot like Outlook Express. One big difference: its open source programming lets anybody examine the application's internal structure. Most folks are content to work with its existing menus , but creative types are free to add bells and whistles. Some people create and share add-ons to enhance Thunderbird. Others translate the program into their own language or just pitch into the communal bugfixing that contributes to the health and well-being of all open source programs.

So far, open source seems to be working, as Thunderbird contains far fewer security problems than Outlook Express.

• Pros . Thunderbird's open source underpinnings let programmers offer small add-on programs called extensions spam killers, address book enhancers , duplicate message removers, and so on. By downloading only the extensions you need from inside the program (Tools Extensions Get More Extensions), you can keep the program small, speedy, and free of long menus with unused features.

  Like most competing email programs, Thunderbird automatically imports your information from Outlook Express (as well as from Outlook, or Eudora), keeping your originals safe inside Outlook Express. Thunderbird looks and feels like Outlook Express, but with a few more featuresa built-in Real Simple Syndication (RSS) reader (Section 13.5), for instance, alerts you to updates on your favorite Web sites. New features appear almost daily as programmers release more extensions.

• Cons . Although Mozilla's Web site is well written, with Frequently Asked Questions areas and a searchable support database, it doesn't offer person-to person tech support. Instead, Thunderbird fans need to seek help on the community forums (go to mozilla.org/support/ and, under the Thunderbird header, click Community Support Forums); if that fails, a third-party company, InfoSpan (1-888-586-4539), offers tech support for a $39.95-perincident fee.

12.1.4. Web-based Email

Some people don't want an email program that lives on their PC. Instead, they prefer to log onto the Internet with their Web browser and read their email online, using what's known as a Web-based email service. These folks can always copy mail to their PC for reference, if they wish, but for the most part, everything stays on the Web.

Some people find both types of systems too attractive to pass up. They'll sign up for a Web-based service to keep in touch while traveling, and keep their standard, PCbased email program for use at home or work. There's nothing wrong with having several email addresses from different types of email systems.

To help you decide which system's best for you, here's a look at the advantages and disadvantages of Web-based email.

• Pros . Since your messages live on the Internet itself, you can read your mail from any Internet-connected PCa big plus for travelers. Web-based mail programs keep your address book online, too, making your contact info accessible from anywhere .

  Another big plus: your email address never changes (unless you want it to, of course). When people move or switch ISPs, they typically have to give up their old email address (for example, [e-mail] has to tell everyone that he's now [e-mail]). A Web-based email address, in contrast, never changes. You can move to a new city, state, or even a different country; or you can fire AOL as your ISP and hire Earthlinkthe point is, it doesn't matter who provides your Internet connection. With a Web-based email account, you never have to change your address.

  Web-based mail also works better when sending mail from certain WiFi hotspots (Section 11.1.1). An increasing number of WiFi providers block traditional, PC-based mail services to keep spammers from parking down the block and flooding the network with spam. That doesn't affect Web-based email, which handles mail differently.

  Some people find Web-based mail easier to set up, because they're spared the chore of configuring the most confusing part of a PC-based mail program's settings: those annoying acronyms called SMTP, POP3, and/or IMAP (see the box on Section 12.1.4). Most Web-based email sites offer ways to send copies of your mail to Outlook Express, if you wish, giving you the best of both worlds : you can read and respond to email while on the road, and have that same mail waiting for you in your PC's inbox when you return home. That lets you store a master record of all your mail on your PC for reference.

  Best of all, the three Web-based email services described in the next sections are free, although two offer more features when you pony up some cash.

  UP TO SPEED
  The DIRT on POP, IMAP, and SMTP

  Few things break a person's confidence like being asked to choose between POP3 or IMAP while setting up a new email account. Each acronym describes a different email protocol a particular way of sending, storing, and retrieving messages so every computer along the delivery chain knows what to expect.

  Fortunately, this humbling moment occurs only once: when you first set up Outlook Express or any other PC-based email program. Neither POP3 or IMAP is better than the other; instead, you simply choose the one your ISP uses to send your mail. Here's how both POP3 and IMAP work:

  • POP3 (Post Office Protocol, version 3) . By far the most common way of receiving email. POP (also known as POP3) lets your PC fetch mail from another, centrally located, mail-serving computer. POP works like this: your email program knocks on your ISP's mail server the huge computer responsible for storing incoming emailand asks for any waiting email. The mail server sends any new email to your PC's email program, and then deletes its own copies to make room for more messages. Most POP3 mail servers store about 10 MB of new email for each person, so if somebody sends you a huge file, it could fill your mailbox. Any other incoming mail might bounce : the embarrassing situation where your ISP decides you've exceed your storage space and returns your incoming mail to its sender. After you download the huge message to clear out your mail server's mailbox, your incoming messages stop bouncing. If you want a Web-based email service to forward its mail to your PC's email program, the service must support POP3 forwarding.

  • IMAP (Internet Message Access Protocol) . A newer , less common way of receiving mail. IMAP stores your mail permanently on a large network, usually a mail system inside a corporation or a university. The system works especially well for folks with portable email-reading devices, like Blackberries, since IMAP seamlessly updates your inbox and outbox, regardless of what kind of machine (portable or PC) you're using to view your email. You need to be connected to the network when reading your mail; you don't actually download the mail into a mail program as with POP3. Instead, you use your email program as a kind of browser, from which you can read and send messages. Since you're connected the entire time you're in your email program, you don't need to click a Get Mail button: New messages automatically show up.

  The upshot of all this is that you need to know whether your ISP's mail service supports POP3 or IMAP. Once you learn the answer (it's almost always listed on your ISP's Customer Service or Support section of its Web site), choose that option for your email program's incoming mail server. Choose SMTP (Simple Mail Transfer Protocol) for your outgoing mail server. It's the only way Outlook Express, or any other mail program, can send email.

  Once you enter these settings into your mail program, you'll never have to deal with these terms again.

  
  

• Cons . Some people think it's creepyand possibly a security riskto store their email on any computer other than their own. But this shouldn't be particularly frightening; after all, your PC-based email travels through dozens of other computers, each with its own potential security problems, before safely arriving in your Outlook Express inbox. There's nothing inherently insecure about Web-based email.

  Perhaps a bigger problem is that you always need Internet access to see any of your email, or to locate that recipe Aunt Maria sent last weekunless you've set up Outlook Express to grab a copy of all your Web-based mail, too.

The next three sections describe the three most popular Web-based email providers: Gmail, Hotmail, and Yahoo.

12.1.4.1. Gmail

Before Google entered the Web-based email wars with its Gmail service (http://mail.google.com), its competitors offered free email accounts with thimble- sized storage. More ominously, your account evaporated if you didn't log on after a few weeks. The competitors hoped people would grow tired of these limitations and fork over the annual subscription fee for a "real" account with larger storage and shelf life.

Google shook up the industry by offering free accounts with a whopping 2 GB of storage. And the accounts remain active even if you don't log in for 9 months (after that, Google shuts down your account). Instead of annoying customers into purchasing accounts, Google makes money selling targeted ads alongside your email; if you're discussing carpentry with a friend, for instance, small text ads for routers and chisels appear along your screen's right side. Don't worry. Nobody's reading your email. Google's computers do all the matching and ad placing. Since your email already runs through dozens of computers, checking it for viruses or spam, what's one more computer in the chain?

In addition to the mammoth storage and long-lived accounts, Google includes innovations like letting you apply labels to certain emails to make them easier to find later. For instance, if you find yourself planning a trip to Vermont with your pals, select all the related emails (via the checkboxes next to every message) and then assign them a label like "Vermont Trip" (click the Edit Labels link on the left side of the window to create new labels). To retrieve all the messages pronto, click "Vermont Trip" from the Label menu; Gmail then retrieves all those messages, no matter what subject they use. Gmail also groups messages with the same subject into one thread. Click a subject name , and all the messages with that same subject appear. A built-in spell checker helps catch typos before you hit the Send button.

You can read your Gmail on the Web, or have Google send the incoming email to your PC-based email program like Outlook Express, Thunderbird, or Eudoraan easy way to back up your Gmail to your PC.

Google's Gmail easily outclasses the competition, leaving them wondering how to fight back.

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Note: At the time of this writing, you can receive a Gmail account in only one of two ways: through an invitation from an existing account holder or by visiting the Web site with your PC and entering your cell phone number. Google then sends your cell phone a text message with an invitation code that you enter at the Gmail site to complete the sign-up process.

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12.1.4.2. Hotmail

Hotmail (www.hotmail.com), Microsoft's salvo in the free Web-based email wars, comes with ads next to your messages, like Google. But to make even more money, Microsoft burdens its free account holders with other restrictions, in an attempt to annoy you into upgrading to the $19.95-per-year, restriction-free account.

For instance, Microsoft bumped its storage from a paltry 2 MB to a slightly-less-paltry 25 MB when Google arrived, and plans to increase it to 250 MB. But that's still only one tenth of Gmail's storage capacity. Hotmail's free email account's shelf life still remains low: if you don't check your mail for 30 days, Microsoft erases it all, leaving you with nothing to read when you return from that month-long, email-free, yoga retreat.

You're also limited to sending 100 messages a day, and you can't send mail to more than 50 email addresses, which hampers Hotmail's effectiveness as an emailer for groups. On a positive note, Hotmail also offers a calendar for tracking your appointments online. However, Microsoft automatically deletes every appointment older than 90 daysa good thing for people seeking to clean up their paper trail, perhaps, but a downer for folks who want to save their old appointments for later reference.

Finally, your emails remain stuck online. Unlike Gmail, Hotmail's free accounts won't forward mail to your PC's email programuntil you fork over the $19.95 a year, of course, Microsoft's cure-all for all these annoying restrictions.

12.1.4.3. Yahoo

Before Gmail arrived, Yahoo (http://mail.yahoo.com) offered 4 MB of storage. They've since bumped it up to 1 GB, and are making serious efforts to compete with Google. Like Gmail, Yahoo's free mail account also sends mail to your PC's mail program, if you wish.

You can even set up Yahoo to grab mail from other mail servers the computers holding mail from your other email addresses. The reason that's a good thing? It means you can log onto Yahoo to read mail from your ISP's mail account, your Gmail account, and your Yahoo' email address. It's a great way for globetrotters to merge all their email addresses into a single spot, accessible from any Internetconnected PC.

Like Gmail and Hotmail, Yahoo displays some advertising as you read your mail. If you don't log in for four months, Yahoo deletes all your email, an inconvenience you can avoid by upgrading to a paid version of the service, the Yahoo Plus account, which costs $19.99 a year.

Although Yahoo's great at retrieving mail from other accounts you may already have, it drags its feet when it comes to exporting mail. Yahoo forwards email only to Outlook Express, and only if you upgrade to Yahoo's Plus account.

POWER USERS' CLINIC
Accessing Web-based Mail in a PC-based Program

Although having both a Web-based mail account and a PC-based account has its advantages, the system is like storing your shoes in two closets: you can never find the pair you want when you need it.

Luckily, it's a lot easier to copy mail than shoes. Tell your PC-based email program to pick up a copy of every message that gets sent to your Web-based accountautomatically.

Most email programs, including Outlook Express, can receive email from a wide variety of email accounts, including those you've set up on a Web-based service like Gmail. If a Web-based service says it offers POP3 or IMAP support, those magic terms mean it can send mail to nearly any PC-based mail program.

Before Outlook Express or any other email program can fetch your email from a Web-based mail service, you need to know the same three things required by any email account: your user name, your password, and the mail server names . Here's where to find step-by-step instructions for setting up any PC-based email program to work with Gmail, AOL, or paid accounts from Yahoo or Microsoft's Hotmail.

• Gmail; see the page http://support.email2pop.com/Gmail_Outlook_Express.html

• AOL; see the page http:// postmaster .info.aol.com/imap/express.html)

• Yahoo's paid "Plus Account"; see the page http://help.yahoo.com/help/us/mail/pop/pop-06.html

• Hotmail's paid "Plus Account"; see the page http://support.msn.com

To retrieve mail from a Web-based account in Outlook Express, summon the Internet Connection wizard (Tools Accounts Add Mail), slip on a pair of comfortable shoes, and walk through the steps of creating a new account as described in the next section.