Since I’ve been playing around with Outlook (Outlook 2003 SP2, to be specific), I’ve come across various pet peeves and things that I’ve found annoying. I really like the way Thunderbird works for handling mail, for the most part, but I dislike its lack of integration with the Duke calendaring service. Since I’ve always liked Outlook’s interface, especially with the wide-screen view on a wide-screen notebook, I decided to see if I could find ways to resolve these issues. After poking around a bit and fiddling with things, here are workarounds and free add-ons I’ve found.

I’m not going to go into much detail in these because they’re largely here as notes to myself to remind me what I did to get something to work, but if you think these should include step-by-step instructions, or even more verbose information, please let me know either via email or a comment below.

Multiple Addresses, One Account

Outlook is smart enough to know that if you receive a message to a given account that when you reply to that message it should default to using that account’s address. However, I have multiple addresses — my primary one, a number of service-related ones, etc. — all being delivered to my main IMAP account. Regardless of what address the message was sent to, Outlook would reply using my main address for that account. I could allow myself the option to send out as another address by defining additional POP3 accounts with the address I wanted to use, a non-existent POP3 server host name, and then setting those not to receive (since I don’t actually have any POP3 accounts), but I’d have to remember to choose the right account manually when replying to a message originally sent to a different address.

Then, by chance, I came across someone’s mention of an add-in called RealAccount. This does the trick! I have my messages to these other addresses filtered off into other folders, one per address, and then I set up RealAccount to use the right fake-POP3 account for sending. It appears to work like a champ, so far!

Reply Quoting Format

While this is the subject of much debate (for a good overview of the parties involved check out the Wikipedia article on “Posting styles”) I tend to prefer inline-replying and bottom-posting for my messages. For one reason or another, however, Microsoft favors top-posting and makes it so you can’t really do anything else.

The solution to this: Outlook-Quotefix. It’s kinda weird the way it works — it runs in the Taskbar Notification Area, and dynamically reformats your replies — but it seems to do its job well.

GPG/PGP Encryption and Signing

We use Gnu Privacy Guard for signing and encrypting stuff amongst our group at work, and the Gpg4win distribution includes an Outlook add-on, as well as a whole host of other nice extensions and plug-ins for various tools.