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I had a very similar scenario working a while back where the message was sent to the user's INBOX and then to another mailbox where a pipe would send the vacation message. It would do it once per day and for the first message from the sender. You can get a sample from the Postfix State-of-the-Art Book (google it). However, this way is very clumpsy and slow, but it's the fastest alternative with virtual accounts and Dovecot. You can use procmail with system accounts, but I don't like system accounts; I'd rather have a blackbox setup. Other MDA's have built in filtering, such as Courier, I think Qmail also. But the best one is Cyrus SIEVE - that's what I use now. It is truly the best mail filtering server out there. However, setting up Cyrus has a very steep learning curve; it's not as easy to setup as Dovecot and others; but the flexibility you get is tremendous - many commercial and non-commercial Email systems are based on Cyrus.