I’ve been using the combination of Microsoft Exchange and Microsoft Outlook for my work e-mail for over a decade. It hasn’t been an unhappy experience, so I kept using Outlook at my current job over the past two years even though we don’t use an Exchange server. That’s changing this weekend. I’m starting a trial separation from Microsoft Outlook, and it may lead me to divorce Microsoft products all together.

Up until this point, I’ve had Outlook connect to my mailserver using POP3 because it’s only really been important for me to be able to handle my mail from my laptop. Now though, I’d like to be able to check and reply to mail from my iPhone, and so POP isn’t going to work very well.

With POP, all your mail is supposed to be collected by the computer running your e-mail client and deleted from the server. There are ways to leave mail on the server so it can be checked from multiple machines/devices, but it doesn’t work very well, and it’s no help if you want to be able to do anything with folders other than your inbox. So, for example, if I stick with POP, I can’t refer to a copy of a message I sent from my laptop from my iPhone.

IMAP solves this problem by letting you manage folders on the server and keeping them in sync with a local copy on your laptop in case you want to do something when you don’t have a network connection. Unfortunately, Outlook is a horrible, horrible IMAP client.

Microsoft has crippled the IMAP user experience in both Outlook and Outlook Express in order to provide incentive to use Exchange server. For example, if you delete a message on a POP or exchange account, it moves the message to a Trash folder. If you delete a message on an IMAP server it leaves it in the folder and just draws a line through it, cluttering up the mailbox. Beyond that, it won’t let you set up rules for mail received via IMAP, so you can’t use it to automatically sort mail for you. I’d hoped they would have changed their stance in Outlook 2007, but from the reading I’ve done, the IMAP support just as bad as it’s always been.

I’ve been irritated by this customer-hostile crap for a long time now, but it is finally come to a head for me. For the most part, they could get away with this behavior to extract more money from customers when they were still able to leverage their monopoly position to squash competitors. Now though, this tying together of products by making customers lives more difficult is working to drive customers away. I don’t have Exchange server, I’m not going to start using Exchange server and now, I may be ditching Outlook. Even before this, I was becoming more and more convinced that I could do my job just as well with a Mac. I’d probably have to use some Microsoft applications, either via XP running in a virtual machine, or by using Mac Office, but it would certainly be another step away from Redmond.