I have six email accounts I use regularly – four for my Web sites, one for my corporate email (my hosted Exchange account), and one for my personal email. All are IMAP accounts, other than the Exchange account. There are certain people, such as my wife and friends, that I tend to email strictly from my personal (jasondunn.com) email account. And when it comes to sending emails to business contacts, I use one of my business accounts. I imagine I’m quite typical in that regard, and that anyone using Outlook with both a personal and a business acount probably works the same way. So why then do I have to manually select the account I want to send the email from every time I send a new message?
I want Outlook to be smarter. I want it to recognize that if I’m sending an email to my wife, it should be sent from the personal email account. If I’m emailing a contact at Microsoft, it should come from my Exchange account. I could override this behavious if I wanted to, but once it learned which email accounts were used to email each person, I doubt I’d never need to…