Email blunders, messaging mishaps and more: Your stories...

Many people have fallen foul of the ‘email quarantine trap’, or have mistakenly sent the wrong email to the wrong person. Well, we asked for your stories - and you certainly had plenty of blunders to share!

Email disasters? You've had them. And you've been sharing your messaging madness with us, in our 'email that got away' competition, brought to you in association with Mimecast, SaaS provider of unified email management.

The four best entries will win a fantastic prize as a reward for your honesty. We just hope you've learned your lesson... Winners will be announced soon.

Read on for our favourite email blunders - no (real) names are revealed, in order to protect the not-so-innocent!

Don't tell the client!

While working for an FM outsourcing company on project for a firm of tax advisors, I was using a database provided by my employer and noticed that a field which had been requested some time earlier had not yet been added by one of the developers at our FM company. I wrote an email to the developer setting out the problem and the resulting inefficiency. I used a joint email account accessible to both my employer and the client company - one that I was in the habit of using because my FM company colleagues would be automatically copied in. What I hadn't factored in was that the FM manager of the client company would also be able to read it...

No sooner had I pressed the send button than my error became apparent. The boss of the client firm's FM section phoned the operations manager of our FM company asking what was going on. My immediate supervisor then put me on the carpet for disclosing problems directly to our client... I immediately wrote an apology to my supervisor asking it to be forwarded to my employers' area and operational managers explaining my mistake - I had wanted only to copy in my supervisor and colleagues and had chosen the joint email account out of habit, resulting in the error. Thankfully, I have not heard any more about this matter and hope that it is now closed!

The day I brought down the Internet

In 1999, I was just about to go on holiday. It was Friday afternoon and I was desperate to leave on time. My last task before logging off was to put on my Out-of-Office (OO) assistant. I'd never done this before: we were new to Outlook in our company back then. Without knowing exactly what I was doing I found the relevant menus and set up the outgoing message. In this early version of Outlook there was a tick-box that enabled you to send an OO message to all the contacts in your address book. Unfortunately I ticked this box as I turned the OO assistant on. To my horror, I saw my Sent Items Folder filling up with messages and my inbox filling up with messages from colleagues' OO systems too. And every time my computer received their inbound OO message, my computer would respond to it and so on... Pretty soon my inbox and sent items folders were filling uncontrollably. My response was simple: I pulled out the network cable and turned off the computer -(I didn't understand mail server technology back then) - and rushed out of the office, pausing only briefly to tell my boss of the impending doom and asking him to contact the helpdesk to warn them and ask them to please, make it stop. Not the most relaxing start to my holiday.

The next morning, after an evening spent in the pub calming my nerves, imagine my horror, when on entering the newsagent I read on the front page of nearly every newspaper the headline 'Rogue Email Brings Down the Internet'. With some trepidation I read the story - I was probably the only person in the world relieved to hear that it was in fact the Melissa virus, which had been spreading uncontrollably over the previous few days, and not my OO assistant, that had overwhelmed the internet!

Who's got your goat?

As part of some testing on a text messaging product we were developing at work, I set a rule on Exchange that would poll and auto route incoming text messages containing a particular keyword in the SMS message to a specific folder in the product manager's email inbox. The chosen word, for amusement, was 'goat'. So, I duly sent a text message from my phone with 'goat' as the first word. The Exchange rule did its job and routed the message to the correct folder. We left the rule there for future testing and forgot about it.

Now, at that time, I was chasing the very cute receptionist for some 'extra-curricular activity'. Things were progressing nicely via email (can you see where this goes yet?) and I was getting close to a result when, after a long weekend of late nights on the booze, having neglected to shave properly I had come into work with a goatee beard - saving vital recovery time. So, 'Oooh i love your goatee!' appeared at the top of a very long ongoing conversation that was full of rather interesting suggestions and arrangements to meet up the following week. Well, the Exchange rule still did its job, checked the incoming message for 'goat', found it inside 'goatee' and forwarded the whole dodgy conversation to the product manager. Much ribbing ensued... and still does, years later!

Refusal often offends (but a refund might appease)

I used to be an Operations Manager for a distance learning company. One particular student was starting to annoy me with his inability to grasp the concept of NO REFUNDS WHEN YOU'VE BEEN ON THE COURSE OVER FOR A YEAR! Eventually I decided to escalate it to a different department. I added to the top of the email chain, "Please can you sort this retard out as he is getting on my nerves." Unfortunately I sent it back to the student in question as a reply, rather than forwarding it. The chap got on the phone. He was, unsurprisingly, not very happy. But on the bright side, at least after that I gave him his refund!

The first rule of business: delegate (but do it selectively)

Shortly after Outlook had been rolled out at my workplace I incorrectly added a distribution list containing all employees to my 'delegates'. I had thought this would enable people to view my calendar. However, the next time I sent out a meeting request to one of my colleagues it also sent out a meeting request to all my delegates - every employee at work – over 1,500 people.

My phone didn't stop ringing with people querying if they needed to attend my meeting. In fact, the Facilities department helpfully rang up to ask me just how many chairs I wanted! Eventually the error brought down the company email system because of all the traffic I had caused on the network... It took a very long time to live that down...

Temporary glitch

I had the unfortunate experience of sending the right email to the wrong person just a couple of weeks ago. We've recently employed someone internally to fill the space left by a colleague who emigrated a few months back. Temporarily, we had a contractor fill the position, whom I neither like, nor get on with. One day, while sending an email intended for the internal applicant one day, I decided to let them know that the contractor expected his contract to be extended and possibly even to be transferred within the company to another department, but that he was mistaken and his contract would be terminated. Unfortunately, I sent it to the contractor, and my attempts to recall the message didn't succeed. It took me 10 minutes to talk my way out of the email! Luckily he is only here temporarily after all!

Typographical error

Some time ago, as Head of Technical sales, I reported to the Sales Director, someone with whom I'd worked closely on many large sales, so we were on friendly terms. The business was growing from its beginning as a start-up and with the expanding workload the Sales Director had decided to hire a new personal assistant. On her first day in the office, I sent an email to the Sales Director commenting on his choice of candidates and received a prompt reply to the message, as follows:

"Thanks for the email.

As PA to the Sales Director part of my role is to read and redirect all correspondence, including email, to the appropriate staff members or department.

With regards to your email titled "but can she type?", I think it should probably be redirected so that HR can look into it.

Awaiting your response, PA to sales Director"

Certainly put me in my place!

A brief history of MIME

I was working as a permanent technician on a newly installed SAP R/3 system for an engineering company in Bedfordshire in the 1990s and was heavily involved in applying patches to the application late most evenings, as this was the only time we could get downtime. It was an onerous task at best but we were very wary of suffering any major disruption in service, so each evening we took a full offline backup of the application environment and data, before applying the latest patches just in case anything went wrong.

This meant we worked late into the evening almost every day. What made it all the worse was that the weather during that time was glorious and we were all very keen to get away as quickly as possible to enjoy what little of the day remained. Around that time we'd also installed our first Microsoft Exchange server and although we were all very new to e-mail, it was proving to be an invaluable tool for communicating all sorts of messages... In my spare time, (what little of it there was) I'd been reading a book called "A Brief History Of Time" by Professor Stephen Hawking. I spotted what I thought was a flaw in the book so I duly sent off an e-mail to Professor Hawking explaining where I thought he was going wrong.

A few days later I was particularly keen to get home at the end of a long hard day at work. We just had the latest SAP patch to apply before we could finish for the day. We'd brought the system down as usual but I could see that no backup had been fired off so I sent a fiery e-mail off to our Basis Operator with a view to speeding things along a bit. The operator was located just next door in our machine room but it no longer seemed necessary to walk around and talk anymore now we had this fabulous new e-mail system. The e-mail message was something along the lines of, "Come on get your finger out, I haven't got time to be sitting here all day waiting for you, get on with it!" You get the idea.

Unfortunately the operator was called Stephen Hawkin and yes you guessed it - I sent the message to the wrong contact...

Five minutes later an e-mail arrived back from Cambridge University. It said something along the lines of, "Whilst we are certain that Professor Hawking would no doubt find the contents of your e-mail fascinating we regret that on this occasion he is unable to respond in person." I never did hear back from the Professor about my hypothesis. They say "no news is good news" but after waiting for more than twelve years I'm beginning to have my doubts.

Dodgy geezer

From the early 1990's till the late 1990's, a guy - we'll call him Geezer - was working as a contract instructor for a number of high-profile computer companies. One of these companies had a world-wide email alias that all instructors could sign up to. Geezer was on the alias and regularly received and responded to emails from other instructors, especially in the USA, who would ask questions about technical matters or ideas regarding how to teach a particular topic.

One such email arrived in his In-box and, on reading it, Geezer was quite taken aback at the apparent stupidity and lack of knowledge shown by the sender - a young female instructor, based in the USA, who'd only taught this course a handful of times. For a laugh, Geezer replied to the original email and added a UK-based alias-name (of his closest and most open-minded colleagues in the UK) as a CC recipient.

He'd intended to tweak the original sender & alias name so that it wouldn't actually get sent to the original sender or world-wide alias but, alas, in his haste to send out his "joke" to his colleagues, he forgot to doctor those addresses as planned.

His response was very crude in its language and, to an American, would obviously cause great offence (especially the bits about what would be done to her to help her learn the things she'd asked about).

Unfortunately for Geezer, she read his response as soon as it arrived in her In-box. The resultant uproar reached her manager's, manager's manager and within 40 minutes of sending the email, Geezer was being smartly ejected from the training centre by two burly security guards.

Suffice to say, Geezer did no more contracting for that client again!

The morals of this tale: 1) Always check the email addresses you're sending to 2) If you're going to be offensive, be so to people you know can take it and who won't mind receiving such emails from you 3) Never use email to shock an American with details of a sexual nature 4) Think before pressing 'Send' 5) What's funny to you may not be to someone else.

The truth is out there

This is a story about an IT Manager, a Business Analyst and a Software Development Manager. OK so it sounds like a Englishman, Irishman & Scotsman joke, but hey, bear with me...

We have two main sites to our business, located just 10 minutes walk from each other. One site was growing rapidly, so it was decided by the echelons of power that they needed a new IT Manager to cover the infrastructure side of things. OK so far.

Now, this new manager wanted to get involved in the software development side of things as well - thinking that she could be a conduit between the users and us developers, a bit like a Babel fish if you like. Converting "user speak" into "geek speak" (not that over the last 7 years we had had any problems with translations - hell, we have a business analyst for that). Anyways, after a few months it became apparent that things were, to coin a phrase, lost in translation. After a few more months of hair tearing and badly translated user requirements an email landed that proved the straw to break our business analyst's back. She just couldn't take anymore.

Now, our BA isn't one for mincing words when needs be. So she quickly forwarded the email request to the development manager asking the poignant question, "Is she f***ing joking?" (only without the asterisks). Sadly for her, our spam filters only work on incoming email or email going outside the business. Internal email doesn't, or should I say rarely, gets checked for such language.

Upon sending the email, she asked our DM if he'd received it and, sanguinely, he said, "No." Our BA's face drained of all colour. The memory of the sound of her jaw hitting the desk still sends shudders down my spine.

You've probably guessed the rest of the story now... Yes, the email had gone not to the intended recipient, but to the IT Manager who was its subject! Ouch. That's got to hurt? Right?

Everyone in the team ducked for cover, tin hats at the ready and pitchforks at hand. Surely the IT Manager would blow her top and rain terror upon us? But the sound of the IT Manager's wrath did not appear. No missiles, bombs or broadsides. Nothing. Nada. Diddly Squat. Zilch. Just the sound of petrified developers and monitors murmuring their incandescent hum.

To this day nothing has been mentioned. The IT manager is as nice as pie to everyone. No digs or snide comments. Only one thing happened, and it proved something of a bonus (for us) out of this mêlée. The IT Manager ceased translating the user requests! Speaking the truth sometimes generates the required results...

Reply all

Years ago, I chaired a committee that had a couple of big-wigs as members, one of whom (X) had just written a very influential book on the Internet. Periodically, I would have to send nagging emails to members to ensure assigned tasks were completed and, after one such request to someone who was a good friend, I received back an email from him, telling me humorously that he wouldn't do his task. Without blinking, I fired off an email to him, explaining that unless he carried out his task I would lock him in a room with X who would "bore him to death about the Internet". Very satisfied with myself, I saw that I had received an almost instantaneous response. I opened it to read a warning from my friend: "next time you send something to me, try not to click on 'reply to all'"…

To my horror, I had emailed the entire committee including X. Sweating profusely, I decided to tough it out and three days passed with silence from X.

Eventually I received a response saying simply, "Ha ha ha. Very funny. Well, my wife thought so".

Leading by example?

A long while ago, I worked for an organisation which found itself appearing on the front pages of national newspapers after a member of staff sent a spectacularly ill-intentioned email which caught the national interest. In the wake of the event, I was charged with putting together a roadshow for all staff to explain appropriate and inappropriate usage of email. The talk covered both legal and moral aspects and concluded that, prior to sending something, one should first consider (a) how your mother might react to reading it and (b) how you would feel if the email were to be featured in a newspaper. The Senior Partner took me to one side after his session to congratulate me on a really useful briefing session and I returned to my desk, happy that I had done well.

Two days later he phoned me to complain that an email he was sending kept being bounced back. I offered to look into it for him, and asked him to forward the email to me. The bounceback, it turned out, was caused by a bad email address but what caught my eye was the opening line: "A blind man walks into a lesbian bar…."

Mr Right?

This week I received the following email from someone who appears to work at CBS (truly):

"Not sure if I have the right person - but I’m looking for a Mxxx Sxxxxxt of Ypsilanti, who competes in the World Rock Paper Scissors Championships, for a feature story. If this is the right Mxxx, I’d like some contact info so I can talk with you sometime in the next week or so about your training. If not, sorry for the intrusion. Scott R."

I am still considering my response.

Honesty is the best policy

I was at work and someone copied me into an email to my boss after I had FUBAR'd a database. Keen to minimise any damage, I immediately went up and explained about the database problems to my boss, although I did notice she had a somewhat quizzical look on her face throughout my confession.It wasn't until I got back to my desk that I realised the sender of the email had deliberately spelled my boss' name wrong in the email, so it would bounce. I'd just gone and admitted all my failings to my boss, when I could have got away with it. I'm sure there is a moral here, just not sure what it is!

And fnally, here's one with a happy ending...

My Dad, who was a semi-pro musician in their 60's, retired to central Spain five years ago. To keep in touch, he has, for the first time in his life, been learning his way around a computer. I was visiting once and as usual, his PC was 'playing up' - a result of him clicking and downloading everything in sight. He'd already managed to flood his Hotmail address with spam in the past, so I'd set up a pretty draconian spam filter. Taking a look in my Dad's Junk Mail folder, I noticed that amongst all the Viagra ads, there were also several emails from "Sanctuary Records" that somehow looked far too official to be spam. He said he'd started getting them every day about three weeks previously and had just marked them as spam without reading them. I checked the emails out. It turned out Sanctuary Records - a UK label - were looking to release a CD of my Dad's old band from the 60's and had sent the urgent emails requesting my Dad's permission! He ended up getting in touch with Sanctuary, and with his permission, the CD release went ahead – he even ended up writing a liner notes for it!

Update: More entries...


About 8 years ago, I worked in IT for my local council and was about to leave for a new job in Knutsford, Cheshire. Staying late one night in the office to dash off an 'all users' email invite to the customary farewell drinks in the local pub, I quickly typed a vaguely funny message, skipped through the spell check, pressed send, and went home. Over the next few days, so many people complimented me on my “funny mail” that I was beginning to think I was a new comedy genius. It took the Director of Finance to bring me down to earth with a bump.

Catching me in the corridor he laughed and remarked “Great email by the way, I don’t like Knutsford that much either”. I walked back to my desk, mystified, and decided to check my sent messages. Only to find I had told everyone in the council that I was going to work in “leafy Kuntsford”...

Some people just don't get IT...

In my last job, over the extended Xmas holiday (when the premises were closed) I had been logging in remotely to check that the email server was receiving emails and to make sure the host server did not get overloaded. Halfway through the holiday period the email server was not responding and the host server was building up large numbers of emails. Given no one was working in the building and the customers and suppliers were all on holiday too, these emails were 99.9% spam. So I went on the host server via the web browser and bulk deleted them. As you know these set-ups are often not particularly easy to use and can only deal with about 20 emails at a time. I was pleased with myself that I had spotted one or two genuine emails (mainly Xmas messages) amongst them, and even one very important order from a large customer. These were saved.

Getting back to work I told the MD what had happened, and how I had spent an hour or two of each day of my holiday deleting these spam emails - I estimated about ten thousand of them in all (we had no spam filter) - in order to keep everything running. I also pointed out that I had spotted one good order amongst them, and forwarded it to him. Feeling pleased with myself I was sure the MD would be happy too - even if he did not know much about technology and thought it all a waste of company time and money.

My self satisfaction, however, lasted for only about an hour, until someone came up to me having overheard the MD telling a member of the sales team "Joe has just gone and lost us ten thousand emails!" Well, it's nice to know you're appreciated!

IT's no joke...

A few years ago we ran an online joke shop and decided to branch out into a bricks and mortar business to, selling jokes, costumes and everything else you would expect from a joke shop. As you can expect we had to employ some people to help us with the business as we couldn't do it single handedly. One of our employees was a girl called Gem. Gem wasn't what you could describe as a model employee. She tried to avoid work whenever she could and would pretend to be busy even when she had nothing to do, just so that no one could assign her any work. And boy, could she talk! Her favourite topic for discussion was her fellow workers, her neighbours, relatives, friends; anyone she could paint in a negative light.

One day she was sitting in the office doing some clerical work when she decided to use the computer to send an email to a friend. I can only guess that she was bored, or inquisitive; because she didn't even claim to know how to use a computer. But she managed to turn it on, log into Windows, open Outlook and tap out an email to her friend. It was actually a pretty nasty email about her job and her boss, using derogatory terms and bad language, and wishing all sorts of bad things on her employer. What she didn't realise was that Outlook keeps a copy of the email you send in its Sent folder...

So the next time my wife used her computer she found a copy of the email in her Sent Items folder and realised exactly what sort of employee she had on her hands. Needless to say she wasn't very happy and that was the last day Gem worked for her.



This competition has been sponsored by Mimecast, SaaS provider of unified email management. Mimecast provides email security, continuity and archiving delievered as a Software-as-a-Service, which integrates seamlessly with in-house email servers. Every day Mimecast takes care of millions of emails and documents for thousands of companies around the world.

What’s more since Mimecast stops spam before it reaches your network, the problem of lost email is a thing of the past.

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