I have a bunch of rules set up for Exchange (they filter messages directly to certain folders and such). I like my rules: they do what I want them to do which fundamentally is keep out of my Inbox stuff that isn't addressed directly to me. The stuff in the Inbox is the stuff I really care about. Today I needed to set up an Out of Office message. Guess for what messages I wanted it to fire? Only those that actually make it to the Inbox of course! It turns out that this is FAR from a trivial matter. It apparently used to be that the Out of Office "rule" fired, it fired only AFTER all the other rules. This is exactly what I wanted but it seems that back in 2006, Microsoft deemed this a bug and "fixed" it. I can certainly understand that some would want their Out of Office rule to fire first and therefore be applicable to all incoming messages--but can't Microsoft understand that some of us wouldn't want that? Didn't they design the feature the initial way intentionally? Even if not, couldn't they find some users happy with it? What I'm driving at is this: it's not a bad idea to accommodate users who didn't like the initial behavior but it is, however, a terrible idea to stop accommodating users who do like the initial behavior! And it didn't have to be an either/or thing: if they would have just provided a simple flag (checkbox) in the Out of Office Assistant that allows us to choose to apply our regular rules prior to the Out of Office rule if that's how we want it or to apply our regular rules after the Out of Office rule, I'd be in fine shape right now. Come on, Microsoft!!!

But since I don't have such a flag, I had to come up with a system for beating Exchange at the Out of Office game. There are two main approaches you can take if you're in this situation (and neither is anywhere near perfect):

2011-04-21 UPDATE: you actually can't beat Exchange at the Out of Office game. You're stuck. You can read what I originally wrote below this paragraph but, for reasons I will give in a moment, I don't recommend following those approaches. The best thing to do is just set the external Out of Office message and hope it doesn't cause problems. Of course the actual best thing would be for Microsoft to make it such that your regular rules can be applied before your Out of Office rule. But until they do that, you need to set the external Out of Office message and live with the results--and if you can't live with the results then don't set an Out of Office message. But definitely do not use a regular rule that replies to every message you receive--if you do this, you run the risk of completely filling up your mailbox. The reason is that some irresponsible senders (I'm talking about you E*Trade!) will send you messages that, when replied to, generate another message to you (perhaps, as was the case with my E*Trade situation, it will tell you that the email box to which you sent your message is not monitored). If such a message were generated only once per incoming sender (which is the way that Out of Office messages work), this would not be irresponsible--it would in that case be informative and helpful. But when the message is sent out in response to every single message then it's irresponsible because what it creates is the possibility of filling up a recipient's email box because it creates an infinite loop of the recipient's rule sending a message and the irresponsible sender's server responding back with a message which causes the recipient's rule to send another message which causes the irresponsible sender's server to respond back with another message and so on and so forth. Fortunately, I happened to check my email and see this happening fairly soon after it started and then, by marking the offending E*Trade sender as a Junk Mail sender, I was able to terminate the loop after a "mere" 498 messages were sent to me. But it could have been a lot worse and if the point is to be able to not have to monitor your email box (as it was for me--I just got lucky in my timing) then it's not a risk to which you want to expose yourself. So anyway, all that said, read on if you want to but unfortunately, you won't find any info that's really practical to use as long as there are irresponsible senders in the world.

1. Do not use Out of Office at all; use a regular rule instead. Instead, add a regular rule after all your others that sends out a template that, while not an actual Out of Office message, at least conveys the same info. Out of Office is specifically designed to fire only 1 time for every sender (that too should be configurable) and this approach cannot emulate that: it sends the reply every time the rule's conditions are met and if that's a problem for you then this approach won't work.

2. Use Out of Office plus a regular rule. Remember, my ideal is that my Out of Office message fires only on those message that have already made it past my other rules. And this means that in my ideal approach, my Out of Office would never be sent to an internal distribution list or an external mailing list because my rules handle all mail sent to internal distribution lists and external mailing lists. But if I turn on Out of Office, it's going to fire off prior to my regular rules--and that means it's going to send Out of Office messages to internal distribution lists and external mailing lists, right? The answer to both parts is not necessarily. On the first part, internal distribution lists: when you turn on the Out of Office assistant, it will send Out of Office messages to senders from within your organization and so yes, messages could be sent to internal distribution lists. However, if your Exchange administrator sets the SuppressOOFsToDistributionLists flag on the Exchange Server, such messages won't be sent. In my case, I figured if the Exchange admins don't have that flag set, it must not be too big of a deal if my Out of Office messages go to internal distribution lists. If that is a big deal to you then you really have no choice but to use a regular rule as described in option 1 (you can use 2 rules, 1 for internal people and 1 for external people; keep reading to see how I set my rule to not fire for internal people; you could do that on the first rule with "stop processing more rules" then create basically the same rule again, but with different content for the internal people, and put it after the first rule). So what about external mailing lists? I don't believe setting that flag prevents the sending of Out of Office messages to external mailing lists so you have to take a different approach. It turns out that you can turn off/on the sending of Out of Office messages to senders outside your organization even when you've turned your Out of Office message on (so you can send to just those inside your organization or to both those inside and outside your organization; however, you can't send to just those outside your organization; this too makes utterly no sense to me) and if you do this then you have the opportunity to set up either a regular rule as in the manner described in approach 1 or you can set up a special Out of Office rule in the Out of Office Assistant: it turns out these rules fire AFTER your regular rules, the net of which is that they're like setting a regular rule at the bottom of your other rules, it's just that these rules are turned off/on with your Out of Office, which is nice. The problem with the special Out of Office rules, however, is that they aren't as sophisticated as regular rules. So what I had to do was set up a regular rule as described in option 1 plus I added one condition to the rule: it doesn't fire for any message with "adobe.com" in the sender's address. Thus, the result of all this is that internal people get the internal Out of Office message (and because it's a normal Out of Office message, they get it only 1 time, not every time they send me a message) and external people get a template that conveys the same info as an Out of Office message, but they get it every time they send me a message. I'm actually fine with external people getting the message every time they send me one as that will remind them I'm out in cases where there's a gap of time between their emails and they might have forgotten--and I'm okay with holding internal people to a higher standard of remembering that I'm out after being notified once! Note that in my case, I needed the internal people at the external people to receive different content anyway but of course the content of both messages could be the same if that's what you want in your situation.