lawman

Usually mail that is not able to be sent from the OUTBOX goes back to the DRAFT box. I was able to send to most email addresses but not to my wife's work email address. When it fails to send from the OUTBOX, it sends the email back to the DRAFT box.

Ok, I just found out why. Make sure that under Messaging/Tools/Options - Address TAB, that you do not have the ISP name checked. This checkbox is for comparing names using address book from your ISP. It shoudl not be checked as you want it to compare against your Outlook database itself not against your ISP unless your ISP email addresses are up to date.

Hope that works for you.