What’s the Worst E-Mail Mistake You Ever Made?

The other day, I received an e-mail that I shouldn’t have. While my name was indeed in the list of addressees, and while I knew some of the other addressees (as well as the sender), my name was plainly included by mistake. It took me about three seconds to figure this out, since the topic under discussion had nothing to do with me.

But not only did it have nothing to do with me: it was a confidential e-mail about an upcoming strategic move by a large American corporation, the news of which had the potential to move the market substantially.

The main purpose of this e-mail was to coordinate the announcement of this move without having any information leak to the public before the company could announce the move on its own.


In this case, the sender got lucky: I don’t plan to use the information against the company, or to profit from the confidential message (unless you consider this blog post a profitable maneuver). But it could have easily worked out differently. And perhaps the erroneous inclusion of my name on this e-mail was a good indicator that, alas, this company’s news will indeed leak to the public before it is ready.

I have long prided myself on not making any such disastrous e-mail mistakes. Sure, I’ve sent things to the wrong person now and again, but the stakes were always low. A few months ago, however, I messed up, royally.

Oddly enough, my mess-up was directly related to someone else’s mess-up. Let me explain.

There was a team of academics who had done some interesting research that Levitt and I hoped to write about. However, the member of this team with whom I communicated — let’s call him William — was rather brusque in response to my inquiries.

As time would reveal, William had a fairly complicated political agenda that he feared would be ill-served if his research appeared in a Freakonomics article — so, while the other members of his team wanted us to write about their research, William was evasive and a bit rude in his replies to me.

Then I received another e-mail — this one from another member of the research team (we’ll call him Zachary), which was intended for William and the others, but not for me. It said, in part:

INSERT DESCRIPTIONE-mail dramatization.

I thought the best thing to do in this situation was to write Zachary directly and let him know he’d inadvertently sent the e-mail to me. So here’s what I wrote:

INSERT DESCRIPTIONE-mail dramatization.

His reply:

INSERT DESCRIPTIONE-mail dramatization.

That seemed to break the ice, and communication got better. We were prepared to write about the team’s research, either on this blog or in our Times column. But then they got evasive again, and stopped communicating.

Then we got a surprise when a prominent article about their research suddenly turned up in a major publication. William had sandbagged us, and then Zachary had done the same.

It wasn’t a big deal — academics and journalists and politicians (and everyone else) are constantly competing over material — but if they had said from the outset that they were talking to another journalist, we would have happily left them alone.

Once I figured out what had happened, I dashed off an e-mail to Levitt:

INSERT DESCRIPTIONE-mail dramatization.

The only problem is, I sent the e-mail not only to Levitt but also to Zachary!

In the end, I believe Zachary thought I couldn’t have been so foolish as to mistakenly send him a critical e-mail after he’d inadvertently sent me one. Zachary seemed to think I sent him this last e-mail in order to directly insult him.

To date, that is my worst e-mail mistake that I am aware of. Perhaps I have made worse mistakes that people had the good heart to not tell me about. I recently heard about a family whose child is having some trouble in school, and in an e-mail to his parents that discussed psychological counseling, etc., the school inadvertently cc’d the entire class list. Ugh.

What are your worst e-mail mistakes?


The worst accidental e-mail I've received was addressed to a senior official of the Ministry of Finance (of Latvia) by some regular officer (probably a crony) and accidentally sent to all ministry addresses - including me, including the state secretary, including the minister.

It included a video of a soccer player taking a leak at the side of the football field, trying to look innocuous, and a message of "LOL, check this one out!" or some other words to that effect.

Needless to say, the mailing group (all@) was promptly disabled and the senior official certainly lost some credibility.


My story takes a different slant on this but, since it involves my dopey boss, I have to tell the world.

I received an e-mail from my boss about staff raises and bonuses that contained confidential salary information for each person. In a matrix was also each person's years of service, experience, education, degrees etc. used to calculate "value" and I was asked to verify the numbers.

I forwarded the email on to my department e-mail address, which includes my boss, after eliminating their salary information so they could verify their own information. My boss calls me into the office two minutes later chastising me for releasing confidential salary information and this was going to hurt moral. He went on and on for about 5 - 10 minutes as I stood in his doorway not saying a word. When he was all done I simply told him that he should actually read the e-mail.

And Stephen, we all await the day you slip and publish our e-mail addresses. Ooops.



An sms to a friend (A) of mine who knew another friend (B) who was visiting from interstate: "Is it bad that I'm still in love with (B)? I know it's been a long time, and I shouldn't be, but..."

Sent it to (B). Nice one.


Auto-complete hates me. I once sent an acceptance email for a job to Steve my current boss, instead of Steve my prospective boss.

Well at least I had another job to go to...


Not my mistake but it's a good story, nonetheless. At a previous employer an email came round to all staff one day asking if anyone knew about a cheque for ?XX,000 that had bent sent to the company without any reference to what it was for. Shortly afterwards a reply came from the company's DBA (who had a reputation for having the odd drink at lunchtime) saying something along the lines of "Is that my missing bonus cheque?". Problem was, in his slightly inebriated state he'd hit Reply All instead of Forward so it had gone to the entire company rather than the IT department.

He wasn't in the job for more than a few days after that.

Josh White

The worst email mistake I know of was something someone else did (well, many others). I was working at a US naval base as a file clerk, and some person sent off an email to the entirety of Defense Finance and Accounting Service (which does all the accounting for the DoD). The email was meant for about a dozen people, but ended up in the inbox of thousands across the US. To make it worse, people started replying to the email to tell the sender to "please remove them from the email list," and when replying, they also sent it to all of DFAS. This was followed by emails from people telling the first group of responders that they hit reply to all by accident . . . and the second group replied to all of DFAS, again. Nothing beats seeing "Ted, you just replied to everyone" sent to everyone. Eventually, the email system got overloaded and had to be shut down for an entire day.


Some time ago a non-important email was accidentally sent to the complete 300.000 plus corporate addresses. At first it was annoying when you got tons of replies like:

"Please get me of this mailing list"
"Please stop this chain"

Then it got funny:

"Hello from Singapore"
"Greetings from the Brazil team"

Then someone wrote:

"Probably even the CEO is copied on this"

To which an answer from the CEO address came:

"Yes I am"

It took two days to stop the massive amounts of mails and clean up the mess. The mail servers were frozen during that time, which also made it a very expensive mistake.


My twin sons get along very well but do enjoy teasing each other. One day one of them sent the other an email that said "You = Stink" or words to that effect. But thanks to autofill, the message went to one of his clients with the same first name as his brother.

When I heard the story, I suggested he send an all-points bulletin warning people to be wary of the Stink Virus that has recently been making the rounds. Fortunately his client was an understanding person and got a good laugh from the situation. And remains my son's client.


I once accidentally invited everyone in my entire Yahoo address book to be my facebook friend. I think that one went out to about 120 people. The best part was removing some desperate people's virtual friendships during the following weeks. I vowed from that day forward never to e-mail anyone ever again for the rest of my life. Then a week later, I e-mailed my stupid cat video to my friends.


When I was a summer intern at the Federal Reserve, I regularly emailed a group of coworkers via "auto-complete," inviting them to lunch and other activities. It wasn't until the end of summer when I received a reply from someone high-ranking from the Board of Governors saying that he can't come to Millenium Park on Friday because he lives in D.C. and does not know me. Oops.


Around the time of the 2001 anthrax attacks, I was at a major state university and was corresponding with a friend of mine at another university about the news of the attacks. I was making some predictions about people getting easily spooked by white powder, along the lines of, "get ready for all the campuses getting shut down whenever unidentified white powder is found." Soon after I wrote that message, a building at my university was shut down due to an unidentified white powder being found on the floor, and a vice president of the university sent out a message in an attempt to calm the campus and reassure the community that the incident was being taken very seriously. I immediately forwarded --- I thought --- the message to my friend, with a somewhat sharp comment to the effect of, "this is exactly the kind of idiocy I predicted in my last e-mail to you." A few minutes later, I got an e-mail from that vice president, saying, "James, I don't recall getting an earlier e-mail from you."

I was very embarrassed.



One key everyone seems to be overlooking:



Medical and psychological issues are good examples of things that should often NOT be discussed at all via e-mail.

I'm sure you can think of many other examples.


I work for a Fortune 20 company. Sent a very thoughtful idea to the CEO (who some consider to be one of the most power CEOs in the world). I misspelled his first name. Twice.

He was cool. I was mortified.


I work in a pretty specialized field. Just about everyone in this profession knows everyone else. And most of them are subscribe to this one listserv discussion for people in the field.

A while back someone sent a message to the listserv that was intended for their academic colleagues. It discussed one of the applicants to their graduate program in an unfavorable light and recommended not accepting the applicant into the program.


My email mishap was not an accident... BUT I was young (22) and didn't realize how much trouble I was about to be in.

I wrote an email to the entire school building where I was working dicouraging them from donating to the forced down our throats United Way campaign. The email was long and well researched but the premise was:

The United Way supports the Boy Scouts.
The Boy Scouts discriminate against gays.
We have gays that work and learn in this building.
Take a stand. Don't donate.

Our building contributions went south big time.
I was asked to resign a year later.

Don't regret it one bit.

Lazy Man and Money

I forwarded on my employee's salary information to about 1/10th the company. HR sent me an e-mail telling me to send an e-mail to an e-mail address to ensure the person's computer, office space, payroll, etc. all get set up. So I hit the forward button and put the e-mail address in. Turns out it was a mail-list instead of just going to HR like I thought.


An australian investment bank lost its contract with Australia's Department of Defence after an email containing classified information inadvertently got sent to the wrong people.

Once at my former work an IT worker sent a email replying to a notification email about a 1 hour system outage saying "my ass it was 1 hour" to over 1000 staff.


I'm an ordained minister working as a chaplain, happily married, with children. However, I got very close with a co-worker due to shared mutual professional and personal stress. In a rather bold move I sent an email sharing my personal lust for this individual. I didn't go into horrific detail or write anything lewd. I was rather drunk at the time and instead of "Delete", I hit "Sent". I was (and still am) mortified even though we have mended fences and have moved on. I still can't look at this individual the same and not remind myself of this rather embarrasing event. YIKES!


I'm a lawyer. I was having trouble with a bank while papering a ten million dollar deal so I sent an email detailing my situation with the loans officer. I included the lawyer for the bank as a recipient of the email. My client's high priced accountant did not notice the lawyer on the list and responded with an immediate Reply All that started: "You tell those a$$hole$ ..."


I once accidentally sent the message "I love you!" to a male colleague instead of my girlfriend. I had a red face for a day or two.

Once the corporation that accidentally sent you their confidential email makes their big announcement, I would like to see you publish the email. They don't deserve to have their inside information prematurely aired but they do deserve to be named and shamed after the fact for their indiscretion.