The Two Email Rule For Out of Office Replies

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I avoid mailing lists the same way I avoid fun activities like meetings and pouring lemon juice into bloody scrapes. Even so, I still somehow end up subscribed to one or two. Even worse, once in a while, despite my better judgment, I send an email to such a list and am quickly punished for my transgression with an onslaught of out of office auto replies. You know the type:

Hey there friend! Thanks for your email! No seriously, I’m thanking you even though I haven’t read it. I’m sure it’s important because I’m important.

Unfortunately (for you), I’m off to some island paradise drinking one too many Mai Tais and probably making an ass of myself.

If you need to reach me, you can’t, LOL! You can contact this list of people you don’t know in my absence. Good luck with that!

punishment Wait till you see the punishment for sending an email during the holidays! Photo by: Tomas Alexsiejunas license: CC BY 2.0

If you have such a rule set up, let me humbly offer you a friendly constructive tip:


The universe has gone on for around 14 billion years before you were born just fine. And chances are, it’ll continue to survive after your death for another 100 googol years until the entropy death of the last proton, or another universe inflates to take its place. Whichever comes first.

So in the grand scheme of things, nobody cares that you’re out of the office, on vacation, or worse, too busy to respond to email so you automatically send me one as if I have all the time in the world to deal with more email.

Ok, that might have come across as a eensy weensy bit ranty. I’ll try to tone it down and offer something more constructive. After all, I’ve probably been guilty of this in my past and I apologize and have paid my penance (see photo above).

Maybe there’s a tiny bit of a purpose

The first time I experienced widespread use of out-of-office replies is during my time at Microsoft. And to be fair, it does serve a small purpose. While 99.999999% of the world doesn’t care if you’re out of the office (that’s science folks), sometimes someone has a legitimate need to know who they should contact instead of you. For example, at Microsoft, I had an internal reply set up that directed emails to my manager. The lucky guy.

Fortunately for those using Outlook with Exchange, you can choose a different reply for internal emails than external emails. So definitely go and do that.

The two email rule of out-of-office replies

But what about the rest of us who really don’t care? I offer the following simple idea:

If you must have an out-of-office auto reply, create a rule to only send it when you receive two direct emails without a response. The idea here is that if I send you one email directly, I can probably wait for you to get back to respond. If I can’t, I’ll send you another “hey, bump!” email and then receive auto notice. After all, if I send you two emails, sending me one is fair game.

Also, make sure you never ever ever send an auto-reply when you are not in the TO list. That rule alone will cut out billions of email list out-of-office spam. Ideally, the auto-reply should only occur if you’re the only one in the TO list. Chances are someone else in the TO list will know you’re gone and can reply to the others if necessary. Again, the two email rule could come into play here.

In the meanwhile, I think I’m going to switch tactics. Spam me, I spam you. So I may respond to those auto-replies with something like:

Dear So-and-so,

Hey dude, thanks for letting me know that you’re not in your office. I bet you’re on a really important business trip and/or vacation! I bet you have such important things to do there!

Me? Not so much. I wish I was on an important business trip and/or vacation.

It turns out, I have nothing better to do than respond to your automatically generated email to me! Thank you so much for that. The fact that it had your name at the bottom of the email and my email address in the TO: list was a nice personal touch. It really felt like you took the time to lovingly craft that email just for me.

So I thought it would be rude not to respond in kind with a thoughtful response of my own.

Sincerely and without regret,


p.s. I left you a little surprise in your office, but since you’re not there, I hope it doesn’t die before you get back. If it smells bad when you get back, you’ll know.

Hopefully email clients take this up and just implement it automatically because I don’t expect people to take the time to do this right.

What do you think? Are auto-replies more important than I give credit or do we live in a world with a lot of narcissists who must be stopped? Tell me how I’m right or wrong in the comments. Thanks!