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?

Hi albracco,

I am not sure if this issue is still live, but anyway are you speaking about the out of office auto reply? Because if this is the case, then it really should be sent once for each sender. I am CCing my manager in almost every email I send, and it would be really annoying to be informed about him/her being out of the office each time.

Rgds,
Wries

Good thought, but no, it's not the out-of-office. It's a custom auto-reply rule.

I have set this same scenario up in testing for something we may implement soon, and my tests always sent the auto reply template each time. The only thing I can think of is if both the auto reply and move are in the same rule, maybe seperate them into 2 rules, the auto reply running first before the move. It's just a thought.

I just checked my test setup and the way I got it to work is this:
Open the out of office assistant and add a rule. Enter criteria at top. Check Reply with Template and type the template message and save it. If you check "currently our of office" and check the rule the auto reply template should go each time a message is received. I think this is what you want.