You might ask yourself how come I kept doing this. Very simple, I just could not find the right setting under the Preferences pane that would change the behavior. There is also no setting related to the positioning of the signature under the “Signatures”window to address this.

I finally found the time and did some online research and was able find the answer. I figured others could benefit from this tip as well. So, here it is. To get Entourage automatically add the signature at the top of the reply/forward, make sure you have the setting as in the screenshot below.

Alternatively, you could upgrade to Outlook which is a much better email client for Mac and is part of the new Office 2011, or use a webmail like Gmail.