Outlook Express was a very popular email application from Microsoft, for good reason. That good reason is that it has been free, but the catch is that it is only available for OS 9. Microsoft did not make an OS X version of Outlook Express, which is not a problem since Apple's Mail application for X works fine. Bottom line: if you still use OS 9, Outlook Express is great. If you use OS X, Mail is the way to go unless you need advanced features, in which case get Microsoft Entourage.

Unless you only use a web-based email account such as AOL or Yahoo!Mail, Outlook Express is a great way to receive, send and organize email. Outlook Express has multiple email account access, HotMail access (v5.0.3 required), powerful filtering/reply rules, and scheduled actions. The other OS 9 free email readers don't do it for me (Netscape, Eudora with ads, etc). Outlook Express for OS 9 is a free download from MS.

The fully-featured commercial version of Outlook Express is called Microsoft Entourage ($90, also available as part of the $350 Office X for OS X and Office 2001 for OS 9 packages), which improves email features and adds contact management, Palm-sync and calendar features.

Here are a bunch of crucial tips for Outlook Express and Entourage. I'll refer to them collectively as OE (aside from minor menu name differences, these should work with both):

You should occasionally compact and optimize your email message database. It can grow to huge proportions, because "deleted" files are not fully erased from the hard drive, even after you empty the "deleted items folder." They are partially still there, slowing down OE and taking up space on your hard drive (particularly the large messages with attachments). A few times a year, you should "clean house," and here's how :

1. Go through your folders and delete whatever you don't need to keep. Remember to check your "sent items" folder.
2. Save attachments to your hard drive, then remove them from your messages (Messages-->Remove All Attachments). To find the biggest attachments, sort columns by size and use the Advanced Find (Command-Option-F). Be sure to check the "Sent Items" folder this time too. See below for an automatic method which prevents attachments from accumulating in your sent items folder in the first place.
3. Empty the "Deleted Items" folder. This is found in "Tools-->Run Schedule-->Empty Deleted Items Folder" or just control-click on the "Deleted Items" folder. Much like the Mac OS's Trash, it needs to be emptied regularly.
4. Quit OE.
5. Now for the trick: hold down the "option" key when you relaunch OE, and it will ask if you want to compact the database. Click "Yes." Entourage gives you two options. Pick "Typical Rebuild." The "Advanced Rebuild" is rarely necessary and you would lose a few minor links.
6. This can take a while if you've never done it, and it ties up your Mac until it is done so be patient. Don't interrupt it! (One client of mine had 40-50 megabytes of undeleted data, and it took 30 minutes.)
7. After it is done it will tell you that it has created new files, and renamed the old files ("old database," "old messages" etc). You can find the old and new files in the folder "Documents--> Microsoft User Data --> Identities" (or possibly in the OE application's folder). Launch OE and make sure that everything is OK before trashing the 3 old files.
8. Now is a good time to back up the whole "Microsoft User Data" folder. What? You've never backed this up? DO IT NOW!

If you have DSL, cable or another "always-on" net connection, set up an automatic schedule to check your email periodically. This is found in the menu: "Tools-->Schedules". If you have multiple accounts, you can set varying frequencies depending on each account's priority.

OE has very powerful automatic actions that can be performed on incoming email. These can be created in the menu: "Tools-->Rules."

If you receive email newsletters, have OE automatically put them in a folder for you. In this example, I'll manage the many San Francisco event announcement emails that are sent each day from the popular SquidList.

If you use OE to access multiple accounts, try color-coding incoming mail to reflect where it came from (under THEN, select "change color"). Or have it color-code any incoming email with an attachment. Or try redirecting certain email to your pager.

Similar to the "Rules" description above, create a rule, but this time it is an "Outgoing" mail rule (the last tab in the rules window):

if "folder" "is" "sent items"
then "remove attachments"

This will save space and make OE run more efficiently. Besides, you most likely already have the file on your hard drive already.

"Groups" are lists of your address book contacts which will save you time and are easy to create. For example, you can make a separate list for personal and business email addresses. Open your address book, and click on "New Group." Then you can drag contacts into the new group. Check the box at the top which hides the list from the recipients (aka BCC). I like to name my groups with a leading asterisk (ie. "* Mac Tips Newsletter"), so that the groups are all listed together in my address book. Then when addressing an email intended for a group, just put the cursor in the "BCC:" field and type "*" (shift-8). A list will pop up to choose from all your groups. (For more on group email lists, see this tip. For more on BCC, see this tip.)

But there are a few group-management issues to watch out for:

First, you can't drag a contact from a group list to another list, or to an email which you are composing. If you only want to send a message to certain addresses in a list, address the new email to the whole group, and then click once on the group name in your email message's addressing window. You should see the group name listed in the "add/remove" sub-window. Now, "Control-Click" on the group name to bring up the contextual menu, and chose the menu option to "expand group." Now, individual members of the group can be deleted individually.

Also, be careful when updating contacts with multiple email addresses, as changes made to a contact may not be reflected in Group lists. If you add a second email address to a contact, and make that new address the "default" address (by moving the checkmark), the group may not reflect the change. Instead, "cut-and-paste" the new address over the old one in the same field. Otherwise the group will still show the old address. If you need to keep the old address, copy it into a new address field first. Finally, if a change in a group list doesn't "take," try adding a new contact to the list and then deleting it before saving changes.

For an even better way to ensure that your email lists don't look like SPAM to your recipients, try these scripts.

1. Keep an organized address book with people's names and addresses, because Entourage looks to that first for auto-fill.
2. Turn off this check box (X only): Entourage-->Mail and News Prefs-->Compose-->Display a list of recently used addresses. Also click the button "Clear List".
3. Delete old received emails and clear out your "sent items," particularly those from people you'll never email again. Empty the trash (and see the first tip above to compact the database).
4. Try turning off "automatically check names on outgoing messages". (In the Mail and News Prefs -->"Compose" tab.)
5. Make sure that there's no rule set up to automatically add addresses to your address book (Tools-->Rules).

These steps will decrease the incidence of this "feature"!

Outlook Express has a built-in spell checker, but it is not enabled unless you have Microsoft Office installed on your Mac. Entourage has it on by default, since it is part of the Office package. If you have Office but have not installed it, do so to enable the Outlook Express spell checker. For example, Office 98 puts the files in this folder: "Applications-->Microsoft Office 98- >Shared Applications-->Proofing Tools".

Once enabled, the settings for the spell checker can be adjusted in this menu: "Edit-->Preferences ->Spelling".

Outlook Express versions 5.02 and 5.03 and Entourage 2001 have a bug that forgets window positions. If you still have version Outlook Express 5.0 lying around, try this trick: Quit 5.02/03., then launch the old 5.0, reposition the windows as you like them, quit 5.0, and launch 5.02/03. Your windows will probably be where you told them to be while running 5.0.