October 27th, 1999

Outlook Express 5.0
Contact and Other Information
Manufacturer: Microsoft
Product Home Page: Outlook Express 5.0
Description: E-mail and newsgroup client
Address: Microsoft Corporation
One Microsoft Way
Redmond, WA 98052-6399
Price: Free
Telephone: 1-800-936-5600
Requirements PowerPC processor
Mac OS 8.1 or later
6 MB available RAM
15 MB available disk space
Open Transport 1.1.1 or later

System Used For Testing G3 All-in-one 233MHz
Mac OS 8.6
Outlook Express 5.0, So Many Improvements, It's Hard To Believe

Outlook Express 5.0
Michael Munger

Recently, Microsoft announced a major upgrade to its e-mail and news application Outlook Express. Now in version 5, this release made the news pretty much everywhere in the Mac community on the Internet, and it is time to take a look at it. As e-mail is the backbone of everybody's Internet connection, we have to consider all the options, even from Microsoft.


The download file is a self-mounting Disk Copy image taking up about 9 MB in MacBinary and 12.5 MB in BinHex. When you launch OE for the first time, Microsoft's auto-repair feature dumps several required extensions and libraries in your system folder - this is a pain considering most e-mail packages do not need to do that - and takes you to the setup assistant.


As Outlook Express comes only on the Internet, there is no written documentation, so it is difficult to whack the Microsoft boys for it. Rest assured: the online help system is complete, holding pretty much all the information you want.

The looks

For this reviewer, this is an important aspect. The new Outlook Express looks great. Its interface is Appearance-savvy under Mac OS 8.5 or later. It is thus compatible with Kaleidoscope for those who really want to customize their Mac's interface. There are some quirks for people who use dark schemes in Kaleidoscope, which the OE team is reportedly aware of. By the way, the icons come from the folks at Iconfactory!

Main Window For
Outlook Express 5.0
(Click for larger view)
OE's interface looks a lot like the old Emailer, as the screen screen shot below shows:

On the left, you can see the folder list. Clicking once on any item will display a list of messages on the right. On the screen shot, the preview pane was taken away as a personal preference, but there is one by default. One of the advantages of this product is that you can customize your main window by choosing if you want the preview pane, the folder list, toolbars, and even what columns you want. These options serve the power user well.

A big plus is the ability to grab anything from a window. You can choose when you will send the message, the signature that goes with it, which account you use to send, and if you want to rewrap the text. You can attach files, then select compression and encoding. The options button lets you decide whether to format in HTML or not (I would recommend plain text only, and OE has this selected for you), to select a priority, a character set, and where you want to move the message after sending. Here is a screen shot to explain:

Composing Window For
Outlook Express 5.0
(Click for larger view)
This is the composing window. A cool feature is the ability to choose your signature on the fly, if you have several of them and prefer to use a particular one in the circumstances. This is one of the perks offered by the toolbar. Very handy.

Day-to-day with Outlook Express

This software is powerful. Buckle up if you use Eudora 4.2... Outlook Express 5.0 offers more power than Eudora (no joke). OE offers more options and features. Moreover, it is fast, though it was not tested to see if it was faster than Eudora. It is multi-threaded. It downloads messages and sorts them quickly. It supports IMAP and HTML.

Some additions are neat. The address autocomplete (finally!) recognizes addresses from your address book and completes them. Hotmail support was added. Now you can handle your Hotmail account from OE 5.0 just as if it was a POP3 account. This is useful for someone who wants to have both the Web and a client to use e-mail. During testing, receiving and sending mail through the account worked as well as with a normal POP account, though checking requires a few more operations for OE to handle. When you use your Hotmail account, an icon will be added in your folder list to access your downloaded mail. Palm synchronization - sharing contacts with OE! - still needs some polishing, but this feature represents a step in the right direction for everybody who wants to keep everything updated both in e-mail and the Palm device without the manual changes hassle.

How about a rewrap when you compose, especially if there are quotes? Just click on a toolbar button and it is done for you. Really handy, many users appreciate this. What it does is to adjust the wrap to make sure that no other client will mess it and end up creating lines filled with only a couple of words, and then much longer lines. It allows you to (somehow) justify your text. You can see the status of your message (flagged, replied to) just under the toolbar. You can even click on a link to read your reply from the Sent Mail folder. You can create your own sound sets to hear your favorite sounds after sending mail, when launching OE, when getting mail, etc.

The contextual menus are surprising. They look exactly like the ones in the Finder, with the little menu icon appearing if you hold the Control key on your keyboard. They draw as well as Apple's default contextual menus, which is rather rare in software that takes advantage of this technology. How come? It is the way they align when you click near the monitor's border. Try it with Netscape Communicator and then in OE. You will notice the difference. The items available in the menus are great too.

Now try this. Drop a file on the Outlook Express icon and see what it does. OE will launch (if not already open) and create a composing window with the attachment ready.

Had enough SPAM lately? Go into the Tools menu and play with your Junk Mail filter's sensitivity. Don't forget to activate it. By default, it will display possible SPAM messages in yellow. Funny thing... the welcome message from Hotmail showed up in yellow :-) Do other clients offer this built-in feature? Not as far as I know.

Do you subscribe to several mailing lists? Then you have to look at the Mailing List Manager. This killer feature will do all your organizational work for you. Its advanced options let you place all the list addresses (including the admin's), will filter it and will even burst a digest into individual messages. This means once you downloaded the huge digest that patched the day's messages together for one download only, OE will separate the messages individually to make your life easier when replying to other people's postings.

Misc. features

If you like to customize everything you should be happy with OE's options. You can check several accounts, set each one up differently, use schedules to check them at your favorite intervals, have different signatures to choose in your composing windows... and then use different Rules to filter mail as desired.

Although there is a progress window, you can see most of what you need at the bottom of the main window (see the very first screen shot). The Find feature was improved. Handling attachments is easy... for images, Outlook Express will preview them inside your message window or treat them just as a file, depending on what you chose in the preferences.

All the mail is now stored in one big mail database. This is less annoying for someone who wants to back up without copying zillions of files, but can create a delay when you navigate in the e-mail client.

A good thing about priorities is that you have options. You can use flags, colors, or simple priorities, from lower to higher. So no matter what you do to sort your mail, you have the tools to do it. Then, there are "Emailer features" like the colored quotes in the messages. There are a lot of other features, and several new ones, but reviewing each of them would take... the day.


Outlook Express is mostly an e-mail application, so it shouldn't be too much af a surprise that the newsgroup part is so weak. It is usable, but far from perfect. For example, the message window allows threading, but does not allow you to sort threads by date. So if you want to see what the latest thread is... good luck. You will have to click on Date and see all the messages separated individually. Normally, the date should be the second key to sort the threads, but rather, it is done alphabetically! Eeeek! It does not offer a tab with news related preferences, nor does it sort threads and replies with references. Oh well... MT-Newswatcher is far ahead in news reading.

Switching to Outlook Express

With all the new features, this improved interface and all the power behind it, you want to test-drive this software or even switch to it? Well, you cannot run this race without hurdles. Switching from Emailer 2.0v3 proved difficult.

The import took 27 minutes and 13 seconds for a 4.7 MB mail database. With the normal RAM allocation, Outlook Express was not stable while importing data from Emailer and it also made Emailer crash (Type 1 error). After trying time and again and finally succeeding, I discovered that all the attempts duplicated the contacts in the address book. OE also does not import accounts and filters from Emailer.

General problems

The address book cannot hide recipients from a group. It leaves you with an endless contact list if you have several different groups. You cannot hide them. Deleting them from the address book will delete them from the group itself.

Outlook Express hogs your RAM. The default setting requires 11.2 MB. Ouch! You better have more than 32 MB of RAM if you plan on making this your day-to-day e-mail and news application.

MacFixIt has a deeper report on problems related to Outlook Express.


While not perfect, Outlook Express 5.0 is a huge step forward and it is hard not to like it. It has come a long way since it was the puny "MS Mail & News." Though there are still holes to patch, I think it's well worth trying out.

Final Score (Maximum Score is 5 Gadgies)
3 1/2 Gadgies
Pros Great interface
Powerful mail handling
Palm synchonization
Hotmail support
Help system
Cons Devours RAM for breakfast
Weak for newsgroups
Importing is not easy for everyone
Address book needs some work
Appearance quirks with Kaleidoscope