James's Weblog

When I left Sony, one of the little things that pleased me was that I no longer had to deal with Microsoft Outlook and a finicky Microsoft Exchange server.

Well, it turns out VMware also uses Outlook and Exchange, and I am reminded how much I hate them.

• Inflexible rules. The rules don’t allow boolean expressions, and what constructs they do allow are crippled. Want to match email that contains both “foo” and “bar” in the subject line? Forget it.

• Rules aren’t filters. Outlook’s rules don’t act as filters. In a sane system, each rule is applied in order to each received email message; if a message can be matched to multiple rules, the first rule gets precedence. Not so in Outlook. Outlook displays an error message informing the user of the rule conflict, and then silently disables the conflicting rule. A single message triggering a rule conflict warrants turning off the rule completely? How helpful.

  I’ve been told that I’m supposed to add a “Stop processing more rules” command to each of my Outlook rules to avoid this stupidity, but apparently Outlook 2000 has a bug where “Stop processing more rules” really means “stop processing rules for email, period.”

• User-friendly search gone awry. Microsoft tried to make Outlook’s Find function user-friendly by making it task-centered, but they made it too task-centered. They focused only on some common tasks and made the less common (but not rare!) tasks hard. The Find dialog box offers the ability to search for email from specific time periods, such as this week, last week, the past 7 days, this month, last month. Some of the “user-friendly” options require a bit of cognitive thought (does “this week” start on Monday or Sunday? does “last month” mean the past 30 days or since the first day of the previous month?), and if you want to search any other time periods (the past two weeks, the past two months, the month of March, from the last week of January through the first week of February, …), forget it, you have to use Outlook’s bewildering Advanced Find dialog. To specify a date range, you must use the freeform text field that provides no clues how the input should look. (Outlook actually is surprisingly intelligent about parsing the input into this field, but it’s still intimidating and error-prone. How can you really tell that Outlook parsed the input correctly?)

• Network and fault intolerant. Outlook is so poorly designed that if the Exchange server goes down (which seems to happen fairly frequently), its entire UI is unusable. You can’t even access mail stored on your local disk. Outlook eventually will figure out that the Exchange server isn’t responding—if you’re willing to wait 10 minutes. Even better, when the Exchange server comes online again, as far as I can tell, you can’t tell Outlook to reconnect; you must quit Outlook and restart it.

• No source for you! Outlook inexplicably makes it really hard to view the message headers to Internet email.

These are all issues I’ve had with Outlook 2000. In Microsoft’s defense, maybe they’ve fixed some or all of them in later versions. On the other hand, it’s sad that they were issues in the first place, because Microsoft’s free, light-weight (and independently-developed) email client—Outlook Express—has had friendlier search and filtering capabilities for years before!