The Rules Wizard rule to "reply using a specific template" is designed to send the reply only one time to each sender during a session. This prevents Outlook from sending repetitive replies to a sender from whom you receive multiple messages.
During a session, Outlook remembers the list of users to whom it has responded. When you restart Outlook, this list is deleted and the rule is reset to start again for each sender.
NOTE: Outlook must be running for the Rules Wizard to automatically reply. Additionally, Outlook 2007 must be running and configured to check periodically for new messages.
For additional information about how to emulate the Out of Office Assistant in Outlook Express, click the following article number to view the article in the Microsoft Knowledge Base: