On Outlook, IMAP, and Malicious Intent

Over the past five years I have grown to grudgingly respect Outlook as a mail client. The way that it integrates schedules, tasks, and email together is really well done, when done properly.

(In particular, Ctrl-Shift-V is totally slick for clearing one’s inbox.)

And while I have a long list of gripes (contact and email searching are laughable, .pst archive size limits are a total hassle, and why must you hog all my bandwidth for mail?) I’ve never really thought that the flaws were malicious. Quirky, reflective of a bias towards all-things-Exchange, but never downright mean.

That is, until I tried to set my father up with an IMAP mail account today. Outlook’s support for IMAP is worse than you’ve heard. And you’ve probably heard how bad it is.

My father had set up his personal email account on his iPhone without a problem. I’m not a huge fan of IMAP, but the iPhone got me to switch from POP3 because that’s what the iPhone does. It does IMAP mail really well.

But after setting Dad’s Outlook up to use IMAP in addition to his Exchange account, any goodwill I felt towards Outlook is gone.

• Want to connect to the server? Restart your client.
• Want to store Sent mail on the server, and not locally? Create a custom rule. (You want a simple preference to do that? Dream on.)
• Want to delete your messages? Better expose a control buried several layers deep. (Instead of moving deleted messages to a separate folder and hiding messages marked for deletion, Outlook helpfully crosses them out… and leaves them there. This is actually representative of the actual server behavior, but not terribly useful.)
• Want to use SSL on your SMTP connection? Hope you remember that it’s port 465, because the port won’t change.
• Want to stay connected? Hope you like the IMAP timeout dialog popping up every few minutes, because it’s better to notify the user than it would be to simply reconnect when they need to use it again. Obviously.

Listen. I know that Outlook/Exchange helped Microsoft get where it is, and totally killed Lotus Notes. I don’t fault companies for making their products work really well together. Outlook is a good mail client, especially with Exchange.

But it sure looks like Microsoft went out of their way to make a really good mail client work really poorly with an open, competing mail standard, at the expense of their users.

And that turns what could have been a great thing into something really sad.