Create better Out of Office auto replies in Entourage

Jul 28, '06 07:30:06AM

Contributed by: Demani

It's common for a user to want to set up an Out of the Office automatic reply this time of year. Unfortunately, this can often cause headaches when things like mailing lists, spam, and even other Out of Office replies get involved. You can end up with mail loops between two auto-replies, sending info out to a whole mailing list, or just a ton of 'sender not found' errors from forged spam addresses. With a little configuration and two fairly simple rules in Entourage, you can make this a relatively painless process.

I would also like to state for the record that server-side Out of Office messages tend to work better, since they usually offer better features (some will do the same things these filters do), and don't rely on a machine to be on all the time. But if that isn't an option, here's a workaround. First, create a Contact group called Out of Office. To this group, add any mailing lists you subscribe to (or use the Mailing List Manager to prevent rules from being applied), and any contacts whom you specificaly don't want to receive your auto-reply.

Next create a rule to that is set act on the messages. The critical rule condition is 'From' 'is not in' 'Group Out of Office'. I also usually add the 'Any To Recipient Contains "email address",' so that messages where the receiver is just CCd or BCCd don't prompt a reply. For IMAP accounts, I also add the restriction that it be in the Inbox, though that may not matter for some.

Set the Action to Reply using Reply Text, and add a second action to Add Sender to group Out of Office. That rule will make sure senders only receive the message once, so they aren't inundated and frustrated when you go leave for a long vacation.

This still leaves spammers. Since spam messages will almost always have a forged Reply-to: field, the auto-reply will get bounced back. Just create a second rule to move all messages that have the phrase "user unknown" to the Trash (or any other folder), so upon your return those messages are filtered out.

I also turn on Auto-login, Restart after a Power Failure, and Auto startup every day, as well as have Entourage started on login. This makes sure that, short of someone explicitly shutting down the machine and turning off the rules, the filter will run pretty regularly.

On return, clear out the Out of Office group so it's ready for the next trip. Mail.app doesn't seem to have a way to do this, because while it is possible to check a sender against a group, it doesn't appear possible to add a sender to a group afterward. Maybe it could be done using Smart Mailboxes, but I haven't sat down to figure it out yet.

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