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Create better Out of Office auto replies in Entourage Apps
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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Create better Out of Office auto replies in Entourage
Authored by: scooteristi on Jul 29, '06 04:38:59PM

<i>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.</i>

Except my Entourage requires I type my keychain password in at Login, else it cannot access my mail accounts.

And really malformed spam can jam up your Outbox.



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Create better Out of Office auto replies in Entourage
Authored by: snuff on Jul 30, '06 12:03:38PM

Having a rule that replies to anyone on the internet opens you up to start getting more spam; the out of office message becomes a verification to the sender that your e-mail address is valid, making it more valuable to the sender.

I like this hint because the idea would work with Mail.app also and gives you some good flexibility, but I don't like the potential of replying to senders that I don't know. In a larger business environment I personally prefer the following steps:

- The Exchange Server admin configures the server to not allow Out Of Office messages outside of the Exchange environment. This allows senders from within the company to receive the Out Of Office, but nobody on the outside.
- Its up to the individual to notify the people outside the company that they will be out. For me, when I recent went on vacation I changed my signature line a week in advance to include the information that I would be out, along with the appropriate alternate contacts while I was gone.

(Disclaimer: I cannot confirm that the feature I mentioned for blocking Out Of Office messages at the Exchange Server is available in Exchange 2003. I used to manage a large Exchange 5.5 environment where it was, but have since left the Exchange world and moved on to SMTP/Anti-spam/Anti-virus.)



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Create better Out of Office auto replies in Entourage
Authored by: Demani on Jul 31, '06 01:48:13PM

You could also add further filter conditions such as the message not being marked as Junk Mail (Entourage's filter does pretty well), or to only reply if the sender's email is in your address book already to cut down on the spam you reply to.

As for the Entourage Keychain thing- that is a setting you could change if you wanted to (leave the machine on and have the system require a password to exit the screensaver).



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