First, the background: My company is providing the helpdesk for an event, and emails to the event email, help@example.net are forwarded to our helpdesk email, eventhelp@mycompany.com. The event organizer doesn't want replies to users to contain any hint of our company's name, so the sender address for our emails are spoofed to appear like they come from help@example.net. This is accomplished by our guys connecting to exchange using a pop3 client, and not MAPI. When our helpdesk replies to a request, the reply is sent to both the user and also to help@example.net (to be logged by the organizer's ticketing system, I assume). Now the problem: our helpdesk only works 9-5, so the organizer wants an autoreply to users stating that the helpdesk is out. I can't use out-of-office as the From: address has to be spoofed. I tried adding a new smtp address to our helpdesk email account, but that causes emails to help@example.net to be sent to our internal account and not to the actual help@example.net email address. I've run out of ideas. Our smarthost is running sendmail, but I would rather not touch that as it serves several companies throughout the region.

Hi, Try Exchange Server Address Rewrite Tool , you can download it from here. To install Address Rewrite Tool , referring the following link: http://www.msexchange.org/articles_tutorials/exchange-server-2007/compliance-policies-archiving/exchange-2007/2003-address-rewrite-feature.html

No, that won't work. The overview on the download page states "Use Address Rewrite to rewrite return e-mail addresses on outgoing messages sent from a third-party mail system to Exchange" it will only work if the 3rd party is sending out mails via our exchange system, which is not the case. My problem is that outgoing auto-reply emails originating from our exchange needs to have the address rewritten. Thanks for the reply though.