I have setup an auto-reply rule in Outlook 2007. Basically any email coming to myaddress@mydomain.com, gets moved to a folder, gets marked as read and an auto-reply message is sent using a specific message template I have created.

When any outside user sends an email to this address the first time, everything works fantastic and they get the auto-reply message. After the first time, if that same user sends other emails to that address, they do not get the auto-reply. Looking at Outlook with the rule, I see their message arrive, get moved to the folder, marked as read, but no autoreply is generated. This will happen indefinitely for that sender unless I restart outlook. Then everything will work again as it should, but only the first time. Every subsequent time, it performs all of the rules tasks except sending the auto-reply.

Anybody have any ideas?