Outlook Express Tips and Tricks 
by Richard O. Johnson 
Revised July 21, 2010
Microsoft Outlook Express, which came bundled with Internet Explorer version 4 through 6, is except for its feeble spam filtering an excellent email client. (Although sharing many features and sometimes confused with Microsoft Outlook, it's an entirely different program.) The purpose of this article is to help you get the very most out of Outlook Express. The suggestions are directed at Windows users of OE 6, although most will apply to other versions, or even other email clients (like Outlook).
Use Keyboard Shortcuts
While "point and click" has an intuitive appeal, power users will when possible eschew the mouse in favor of the keyboard. Using the keyboard not only saves time, but it will allow you to clean up your display and enjoy more work space.
Nearly everything for which you use your mouse can be done more efficiently with the keyboard. Chances are you're already using this first group of shortcuts, whose applicability extends well beyond Outlook Express. See http://snipurl.com/bs3j for a more complete list.
  • Use Ctrl-C to copy selected text to the Windows clipboard.
  • Use Ctrl-X to "cut" a selection to the Windows clipboard. (This is a combination of copy and delete.)
  • Use Ctrl-V to paste a selection from the Windows clipboard. (Think of V as an insert carat.)
  • Use Ctrl-Right or Ctrl-Left to highlight a word.
  • Hold down Shift to make your actions cumulative. Shift-Home and Shift-End will respectively highlight text to the start and to the end of the line of text.
  • Use Ctrl-A to select all.
  • Use Ctrl-Z to undo an edit.
  • Use Ctrl-Y to reverse the undo.
  • Use Ctrl-S to save.
  • To emphasize text in formatted messages, use Ctrl-B for boldface and Ctrl-I for italics.
  • Use Alt-space followed by X to expand any window to full size. This can be particularly useful for email messages. See "Other" Tip #2.
Following are my favorite OE keyboard shortcuts. For more, see OE Help (press F1).
  • Use Ctrl-M to receive incoming mail (and send any mail in the Outbox).
  • Use Ctrl-N to compose a new message.
  • Use Ctrl-I to return to the Inbox.
  • Use the Delete key to delete a message.
  • Use Ctrl-R to reply to a message.
  • Use Ctrl-F to forward a message.
  • Use Alt-S to send a message.
  • Use Enter to open a message, after moving to it with the up or down key.
  • Use Esc to close a message.
  • Use F3 to find a word or phrase within a message.
  • Use Ctrl-Y to open another folder. (Think of Y as a tree with two branches as folders.) Press the letter-key of the folder name's initial -- as, b for Business Items, f for family, etc. If necessary, press again.
  • Use Shift-Ctrl-F to open the Advanced Find menu, with which you can locate any message with ease. (Then use Alt-B to browse to the folder of your choice) See "Other" Tip #3.
Organize Your Messages
Users who save messages in the Inbox are asking for trouble. Filing them in folders you create not only markedly eases message retrieval, but it minimizes the risk of corruption of the Inbox (which could result in your losing access to all those messages).
Like a politician with flexible opinions, your Inbox is highly corruptible, since it changes so much. Try to keep no more messages there than you can view without scrolling. Doing this will not only be safer but will help considerably with message handling.
To create a new folder you'll have to open the Folder List, and then right-click on the folder that's the parent of the new one.
Tip: Creating a hierarchical folder structure (with sub-folders) will ease the task of finding a message later, since (unless you uncheck the relevant box) a search will apply to the designated folder and its sub-folders. Drag and drop sub-folders within the folder list, as necessary.
If you regularly receive predictable messages that don't require your immediate attention, you may wish to use OE's Message Rules to force those messages to bypass the Inbox entirely. In the OE toolbar, go to Tools and then Options. You can also use Message Rules as an easy way to move en masse messages already received, with the "Apply Now" instruction.
The corruption danger to the Sent Items folder stems from its size. Exceeding about 2,000 messages in any folder is hazardous. A good plan is to set up (as a sub-folder under Sent Items) a separate folder for each previous year's sent messages, to hold messages you've moved from Sent Items. Or you might be able to speed up OE by archiving older messages in a different location; for instructions on doing that, go to http://snipurl.com/fule.
Optimize the Interface
You customize the Outlook Express interface via the Layout dialog box under View in the OE toolbar. Proceeding from top to bottom, here are my suggestions:
  • Contacts. You'll probably want this checked. This will permit you to have a narrow column on the side listing your address book contacts, and to initiate an outgoing message to any of them by double-clicking the name.

  • Folder Bar. This should be unchecked. A pure waste of space, it serves only to duplicate in larger type the current folder's title.

  • Folder List. If you frequently add, rename, or remove folders, and you don't have your Contacts List displayed by default, you might want to check this option. Otherwise, leave it unchecked. (You can always toggle it on by clicking the folder icon.)

    Tip: If you do leave it unchecked, open it now (by clicking on the icon), and drag your Contacts down to the very bottom. (Then close the Folder List.) That way, when you have occasion to open your Folder List, your Contacts won't get in the way.

  • Outlook Bar. This enables point-and-click navigation to folders. If you have the Folder List enabled, the Outlook Bar is superfluous. If you don't have the Folder List enabled, it's still superfluous, since you can more easily switch folders with Ctrl-Y. Leave it unchecked.

  • Status Bar. Useful. Check it.

  • Toolbar. Can be useful. Check it.

  • Views Bar. Rarely useful. Leave it unchecked.

  • Preview Pane. It's really important to leave this unchecked. Enabling the preview pane invites computer infections that may accompany HTML messages. Displaying a message "preview" has the same security implications as opening the message. (If you've configured OE to receive all messages unformatted, the preview pane may be enabled without a problem.)

    Tip: When you're uncertain about opening a message, you can read it safely via its source code, by pressing Alt-Enter while highlighting the message.
The Layout dialog box will also invite you to customize the OE toolbar. To save space you'll want to choose "No text labels," and display no more icons on your toolbar than will fit on the same line with the text links like File, Edit, View, etc. (which can't be hidden). On my system I've hidden all the icons except those for Address Book and Folders. You can eliminate the Address Book icon if you use the Shift-Ctrl-B shortcut.
Perform Necessary Maintenance
Just as you maintain your car to keep it performing well, you need to properly maintain your email client.
To keep OE working as efficiently as possible and to prevent folder corruption, compact your folders every two or three weeks. But you should not be compacting while you're online or doing other work, or (ironically) the compacting process itself may cause corruption!

If your Windows operating system predates XP, Windows will by default, unfortunately, enable just that. That is, it will schedule compacting to be performed in the background. So the first thing for you to do is reverse that setting, which you can get to via the OE toolbar [Tools>Options>Maintenance].

To compact safely and efficiently, follow these steps in order:
  1. Clear Deleted Items [toolbar Edit menu].
  2. Go offline [File menu].
  3. Move to the OE mother folder ("Outlook Express") with Ctrl-Y.
  4. Make sure your Folder List is not displayed.
  5. Start compacting [File>Folder>Compact All Folders].
  6. During the compaction, refrain from using your computer.
Filter Spam
Out of the box, OE's spam filtering depends entirely on your creation of Message Rules. (OE toolbar-->Tools-->Options) Your rules will tell OE when to divert an incoming message from your Inbox, generally on the basis of trigger words, of which a good starter list is here. You can also create rules that will not divert messages but color-code them. This is handy when you think an incoming message might be spam, but you still want to see it before deleting it. See "Other" Tip #6.
If some of your rules might conflict with each other, bear in mind these two points:
  • OE processes the rules according to the order in which they appear. The last rule triggered is the one OE uses.
  • Each rule will give you the option to "stop processing more rules" upon its execution.
Whitelist selected senders. It's a simple matter to override all other rules and route selected senders' messages to your Inbox. Create a rule specifying the senders, with the action, "Stop processing more rules." Then use the "Move Up" button (just above the Rule Description). Your whitelist rule should be ahead of all rules diverting messages, but behind any rules color-coding messages.

Don't bother with the Block Sender instruction, as it cannot be overridden by your whitelist, and these instructions are generally ineffective against spammers anyway.
Hint 1: If you're going to create a rule on the basis of an objectionable message, don't delete the message first, but use the Apply Now option, and then note whether the message is gone. Following this procedure will weed out typos that could defeat your rule.
Hint 2: Although OE's message rules as spam filters are fine as far as they go, they're effective only against a small portion of spam. For more sophisticated spam filtering, consider either of the following:
  • Gizmo Richards recommends SPAMfighter, specifically designed for Outlook Express and Outlook. Richards tested SPAMfighter on 1100 emails, of which 69% were spam, and found a detection rate of 93.9%. Even better, he found zero emails falsely classified as spam. The program will work on Windows ME and later.
  • An entirely free solution is to open a Gmail account, have your incoming mail sent to that account, and instruct Gmail to forward a copy of such mail to your primary account (for which you use Outlook Express). Gmail's spam filtering is first-rate. This method has the additional advantage of giving you an automatic backup of all your sent and received messages. More about Gmail here.
Other Tips and Tricks
  1. Take full advantage of the Signature option [Tools>Options>Signatures]. Along with your phone number and the URL of your website (if you have one), it's a good idea to include your email address, since it's not always appropriate for correspondents to use the Reply function.

    You can save emailing time by including in your Signature your salutation! Just start the closing 4 lines below the salutation, and for each message, fill in the message body (after skipping a line) in the blank space. For example, your salutation might be "Hello xxx," with the name of the recipient to be filled in later. The signature proper or closing (perhaps starting with "Best wishes," or whatever you choose) should begin 4 lines down. 

    Hint: OE makes it easy to alter your signature depending on the time of year. For example, you could change "Best wishes" to "Best holiday wishes" by copying and pasting your original signature as your "Signature #2," inserting the word, "holiday," and selecting the altered signature to be your new default (until the holiday season passes).

  2. Use a good width for your messages. If you leave your messages at full screen or anything close to it, reading them will be difficult. On the other hand, many HTML messages will be partially hidden if your message window is too narrow. A good compromise is to use about 60% to 65% of your screen width, which you can implement by dragging the side borders. (Windows will adjust to your preference.*) Expect to have to maximize the message screen on occasion; use Alt-Space + x for that purpose.

    *To lock in your new borders at once, open a blank new message and immediately close it after dragging the borders to your preference.

  3. Use the Advanced Find dialog [Shift-Ctrl-F] to locate messages quickly, but don't be confused by OE's quirky terminology. Microsoft uses "before" to mean "on or before," and "after" to mean "on or after." Thus, a message received "before" 12/5 and also "after" 12/5 will have been received on...12/5.

    If you don't know in which folder to look, choose the "Outlook Express" folder using your Home key. All other folders will then be included in your search, since by default sub-folders are searched.

  4. Use the message subject line as it was intended. Few things are more annoying than a subject line that reads "From Joe," or is otherwise unhelpful. Properly crafted subject lines will moreover increase the likelihood that your messages will (a) pass through spam filters and (b) be opened by the recipients.

    Liberally change the default subject line in your reply messages, when appropriate, to a completely new subject line. This will be useful to the perhaps clueless recipient, and especially to you, both in getting your message the proper attention and in enabling you to locate it easily in the future.

    Use pre-tags like REQ, FYI, or URGENT. Use a subject followed by [eom] as the entire message, to save the recipient from opening a message only to find just a few words from you in the body. (This technique is especially handy for thank-yous.)

    If you reply twice to the same message, some email programs will proliferate the Re: (as Re: Re: xxx). If that's not the case, add (2) to the more recent subject line, so the recipient won't discard it as a duplicate.

  5. You're no doubt familiar with the use of the Bcc: field to send mail to multiple recipients without revealing their identities to each other. But what do you enter in the To: field? Just add to your address book a suitably named new contact with your own email address. For example, if you want to send a message to certain members of the ABC club, the contact name (with your email address) could be "Certain ABC club members," and you'd fill the To: field accordingly. A side benefit is that you'd get an immediate confirmation that the message was properly sent, usually in your Inbox (depending on your ISP) and always in your Sent Items.

  6. Use OE as a simple reminder system. Create a message with the subject, "To Do" (or any other subject you choose), and type each entry on a separate line, with a blank line in between. Leave the "To" field empty. Then save the message, and move it from Drafts to your Inbox with right click + V.

    The list will then stay in your Inbox even after you've made and saved changes. It may move up or down depending on what other messages appear, but you can if you like use OE's flag function to set it apart. Or instead of flagging, you can apply a color for that purpose with OE's Message Rules (under Tools>Options), using "Apply Now."

    (Re-saving the message will necessitate reapplying the flag or the color. On the upside, re-saving will move the message to the bottom, unless you've enabled a different sort order.)

    To be reminded later, use a free Web app like Time Cave [www.timecave.com], which will send you a message you compose on the date you specify.

  7. With the current aggressiveness of spam filters, it's a good idea to send your messages in plain text in most cases. Spam filters will rarely block plain-text (unformatted) mail. In OE, go to Tools>Options>Send>Mail Sending Format, and check "Plain Text." To format the text in a particular message, click "Format" or press Alt-O, and choose Rich Text.

  8. If by default you send formatted (HTML or "rich text") messages, you'll want to allow for those few recipients who cannot easily read formatted text. These may include users of very old AOL versions (before v. 6), and users of MSN TV or Web TV. In OE it's very easy to remove such recipients from the default, if your access to them is via the Windows Address Book. Just right-click the contact name to go to Properties, and then go to Edit. A check box on the Edit screen can force plain-text emails to that person.

  9. Don't risk sending a message before you're ready. It might not be polished to your satisfaction, or you might not be sure you want to send it at all! It's all too easy to press Alt-S (or click Send) too soon. To minimize the risk, fill in the subject line last. OE will require confirmation before sending a message without a subject line.

  10. Use OE drafts as templates (boilerplates), for messages you need to send repeatedly with only slight variation. Once they're saved, OE will store these in the Drafts folder, but you can move them to folders you create (right click + V), optionally as sub-folders of Drafts.

    Hint 1: Assign each boilerplate message two subjects. Type the normal subject--what the recipient will see--in the subject filed as usual. The other subject will be what you'll use to distinguish one boilerplate from another, and you'd type that in the To: field (to be later replaced, of course, by the recipient's email address). If you need to associate notes with a particular template, post those notes in the Cc: or Bcc: field. (OE won't let you forget to erase them before sending.)

    Hint 2: In place of the recipient's name in a boilerplate, instead of a real word like NAME, use a made-up word like firstname or xxx. Then, before sending, your spellcheck program will remind you to substitute the name. (Be sure to use lower-case, in case your spellcheck program ignores uppercase.) If you don't have a spellcheck program installed, a good free one is available at www.geocities.com/vampirefo.

  11. Don't open attachments, unless you're expecting the attachment and need to view it. Attachments from well-meaning friends and associates can carry computer infections. And attachments are by far the most common means of spreading those infections. You can't rely on your anti-virus program, which cannot catch newer viruses not yet analyzed. In most cases attachments are entirely unnecessary, as the information can be included in the body of the message.

    (If you feel you must open attachments even occasionally, I recommend you instead use a viewer program that will allow you to view attachments without opening them.)

  12. Don't send attachments, unless you absolutely have to, for the reasons outlined above, and also because opening an attachment unnecessarily is simply annoying. In nearly all cases an attachment's contents can instead be included in, or appended to, the body of the email. If an attachment is truly necessary, it's a good practice to first get the recipient's okay.

    Violating this rule by sending your resume as an attachment (when not so requested) will almost guarantee that it won't be seen.

Richard Johnson is a writer and editor, and founder/administrator of NotBarter.com, The Los Angeles Skills Pool. The author provides Outlook Express support at no charge to NotBarter.com members.
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