Exchange 2003 auto replies...


We have a situation where we would like to setup an auto reply for one exchange 2003 mailbox to send to an external mail account. We configured server side rules in Outlook 2003 which works internally.

If we open up the allow automatic replies in system manager to allow external auto-replies, this would be for a global setting.

What solution can we use to prevent mail loops etc if we where to do this?

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evilrixSenior Software Engineer (Avast)Commented:
It's an all or nothing setting; you can't be granular in who can and cannot send auto-replies outside the organization.
Frankly, opening up auto-replies to external addresses does have potential to negatively impact your network, through email loops and so on. There is nothing you can do in Exchange to prevent such an email loop. Exchange does have a built-in "maximum hop count" figure which attempts to negate this issue, but that only works for messages with the same Message-ID. Chances are, an auto-reply from the other end will have a new Message-ID, so you'll get stuck in between nasty loops.
Have you considered using Outlook Out of Office for sending the reply message, because that will only reply once to an email address?
wk6838Author Commented:
Thanks for the reply... Can an out of office be used to send an attachment? We need to attach a pdf doc to the sender.
evilrixSenior Software Engineer (Avast)Commented:
To the best of my knowledge, that's not possible.
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evilrixSenior Software Engineer (Avast)Commented:
You CAN set Out of Office to do an auto reply with an attachment (using rules and a message template), but this doesn't follow the "true" nature of the feature since the reply is sent back to every message received. You'd therefore be back at square one with the possibility of it causing mail loops again.
So, in that respect, I'd have to say "no" based on what you are trying to do and the problems you're trying to avoid.
Ask any VBA developer he/she will do the attachment thing for you in a minute. Refer
Also, what do you mean by it does not work externally
Nitin Gupta (gupnit)
evilrixSenior Software Engineer (Avast)Commented:
Hi Nitin,
I was going to recommend that approach, but a quick test in an Exchange 2003 lab revealed the reply template will actually fire for every message received, rather than follow true Out of Office fashion by replying only once per sender email address. Thus, you'd be back at the point where it could potentially cause an email loop.
Clearly that is an option, but the potential for mail loops just makes it all a bit risky.

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