What I did when I first learned of thunderbird was download it, installed it, set up my 2 gmail accounts with a "Gmail" option already there when you click on "New Account". I received email fine and it went swell. I learned of webmail, and extension to be able to use hotmail/yahoo and whatever. I have a hotmail account and just wanted to add it for the novelty of multi-emails all in one. I'll get straight to the questions.. WEBMAIL, the thunderbird addon, is installed, was the first thing I installed. Next, I downloaded the hotmail addon. Ok, before I messed with that I downloaded the Gmail addon as well, I figured it'd help to prevent future problems if I have everything coming from the same source. I get my 2 gmail accounts up and running and my hotmail account works fine for a while. Long story short, I can't send emails from my hotmail account. I have updated to live and the whole deal, just like I found on the website (and after an hour of collectively googling for answers). It asks me for a password for the hotmail but when I enter it, the screen just keeps popping back up (Yes, it's the right password). Now with gmail, I send a message from one account and it appears as if it was sent from the other (sometimes, not all). One important question, which I think will help me out to understand better after I play around with it some more, if I have the hotmail and gmail addon installed, should I make the default server that it picks be the localhost webmail one? The way I had it was gmail accounts with the gmail option already provided in a stock install of thunderbird. If anybody has a similar setup I would greatly appreciate your input.