'He is the laughing stock of everybody he ever respected': IT worker in charge of CEO's email triggers an email apocalypse

Author image for Remy Millisky
Remy Millisky • Writer and Editor
Feb 21, 2023 3:00 PM EST

When the CEO of this IT company demanded changes to his email system, he totally miscalculated the consequences. U/dingdongdelongwong shared this story of malicious compliance, which was all brought on because of this bigwig's inane ideas. 

The OP shared that they were tasked with helping the CEO, "Mr. Bigwig," set up an auto reply feature on his email while he went on a vacation. The CEO seemed to not understand why he couldn't send someone an out of office email every single time they emailed him. Apparently he just wanted limitless reminders of how much fun he was having on holiday while his employees continued on with their workweeks. This smug CEO thought he knew exactly what he was doing, but he didn't expect the OP to comply with his demands specifically as he said. 

After you read about this excellent case of malicious compliance, read this story of a teacher who decided to follow their administration's stupid new rules exactly as written. 

Add as a preferred
source on Google
Advertisement
  • 01
    Purple - MAT s 190CY 'I get a phone call. From Mr. Bigwig... He is not happy because he is blacklisted on about every blacklist in existence.
    via Austin Distel
  • 02
    Font - r/MaliciousCompliance Posted by u/Dingdongdelongwong 2 S "Everybody must know when I am out of office."
    via r/MaliciousCompliance
  • 03
    Font - So yeah, a couple of years ago I was working for an IT company which also provided server management and general domain and E-Mail services. We had some really big companies as clients, so we were used to some really idiotic demands, but most of the time we could convince the people whose main job seemingly was "to be in charge" to listen to our expertise. Not so Mr. Bigwig. Mr. Bigwig was the CEO of a large automobile sales company. He also was the type of guy wh prided himself with bein
    via r/MaliciousCompliance
  • 04
    Font - Mr. Bigwig went on a holiday once and set up an automatic out of office reply in his mail account, but - as is the technical standard - everybody who wrote him during that time only received the reply just one single time. When Mr. Bigwig returned from his vacation this infuriated him a lot so he called our support line and yelled and cussed his way up our hierarchy until he had me on the phone. I tried to tell him that this was working as intended and tried to explain why, but Mr. Bigwig
    via r/MaliciousCompliance
  • 05
    Font - Now let us jump to December the 29th of the same year. I get a phone call. From Mr. Bigwig. He is not happy. He is not happy because he is blacklisted on about every blacklist in existence. He is also not happy because he can't receive or send any email. And he is not happy because he can't find any mail he received during the Christmas holidays or near them. He can't find them because the nice number in brackets besides his inbox folder, that indicates the amount of unread mails he has,
    via r/MaliciousCompliance
  • 06
    Handwriting - He is also not happy because he is the laughing stock of everybody he ever respected.
    via r/MaliciousCompliance
  • 07
    Font - Now let me guide you as the reader to the bottom of this. What you don't know and we also did not know at the time is: Mr. Bigwig was member of a very exclusive group of business owners, CEOs and high ranking politicians around the globe. The kind of people you would imagine sitting around a large oak table, smoking cigars, drinking 200€ whiskey and discussing world dominance.
    via r/MaliciousCompliance
  • 08
    Font - This group had a mailing list. A s ty, basic mailing list. It went something like this:
    via r/MaliciousCompliance
  • 09
    Font - Bigwig: (Out of Office Reply) Hey, thank you for you mail, but I am on holiday! I will reply later. Somerandomdude @mailinglist: Merry Christmas! Mailinglist @everybody: Hey guys, Somerandomdude is wishing you Merry Christmas. Bigwig @mailinglist: Thanks for telling me, but I am on holiday! I will reply later. Mailinglist @everybody: Hey guys, Mr. Bigwig is on holiday, he will reply later. Bigwig @mailinglist: Thanks for telling me, but I am on holiday! I will reply later. Mailinglist @F
    via r/MaliciousCompliance
  • 10
    Font - Bigwig @mailinglist: Thanks for telling me, but I am on holiday! I will reply later. Mailinglist @FING EVERYBODY: Hey guys, Mr. Bigwig is on holiday, he will reply later. ...repeat until the servers give out.
    via r/MaliciousCompliance
  • 11
    Font - So B-Diddy was not the only one who had thousands and thousands of mails in his folder. All his fancy pants networking contacts had too. Mr. Bigwig raged hard at everyone who was brave enough to get on the phone with him, threatened to sue us for millions of Euros and to "end us as a business". We finally put him through to our founder, who listened to his rant and told him he would send him a solution within the next ten minutes.
    via r/MaliciousCompliance
  • 12
    Font - He sent two documents: A scan of the signed waiver, in which the consequences of disabling the out of office message restriction were outlined in detail, and a service contract, allowing us to fix the problem to our abilities without any financial budget limitations, but with a really nice (read: enormous) estimated budget.
    via r/MaliciousCompliance
  • 13
    Human body - It was a good year for the company, with an unexpected spike in revenue, just before new years eve.
    via r/MaliciousCompliance
  • 14
    Font - or foobar 75 Yeah. I got to do this once. It was an automated monitoring system that had pretty extensive logs and would send out a summary email every 30 minutes. New boss shows up and after a minor issue demands that we send an email every time we write something to the logs. We go back and forth trying to explain that sending 5 GB of log entries split into god knows how many emails isn't going to work until the new boss just says, "Do it because I said so and I'm in charge." So we all
    via r/MaliciousCompliance
  • 15
    Font - 5 minutes after we start the program up, new bosses email account is disabled and we get the call to roll back the changes from the heads of IT and Software Development. After that, every change new boss would propose had to get approved by the head of Software Development.
    via r/MaliciousCompliance
  • 16
    Font - LaserGuided Polar Bear When I was running the Exchange environment for a largish company, some guy somewhere insisted on all EVENTS for some monitoring system somewhere be mailed to his team's DL. Not alerts, not warnings. All events. Events are logged every couple seconds. I make them go through change board which meets every week. I say this is a bad idea, you don't want to do this. The guy says no we need this, this is critical. I argue you shouldn't generate a mail unless there is som
    via r/MaliciousCompliance
  • 17
    Font - Okkkkaaayyyyy. They finally push it through change board, which BTW meets once a week. I walk over to their area and say okay, here you go, and light things up for them to push mail. Some of the people on that team had mail set to actually beep on their phones, and they just start blowing up. I kinda chuckle and say okay, looks like it is all working and walk back to my office. By the time I am back at my office they are calling me on the phone to ask for larger mailboxes because their ne
    via r/MaliciousCompliance
  • 18
    Mammal - So they basically spent the next week constantly deleting their incredibly necessary email alerts just so they could use mail.
    via r/MaliciousCompliance
  • 19
    Human body - + [deleted] Replyallpocalypse!
    via r/MaliciousCompliance
  • 20
    Rectangle - ls952 Mm-mm. I love a good story of "Big man is an as-de and wants it his way. We give him exactly what he wants and now he's in shambles."
    via r/MaliciousCompliance
  • 21
    Font - Geminii27 Founder and CTO reeled that one in. High fin' five to them. 564 Reply Share Dingdongdelongwong OP Technically they were also the ones who got the bonuses. Great guys to work with and definitely quick on their mental feet. Well deserved I say.
    via r/MaliciousCompliance
  • 22
    Font - now_you_see I thought it was going to be that, another 'out of office' response kept replying to his and it just went on and on. But this is SO much better! Not only has he lost his s and all the companies communications. But he's fed up the main form of communicate for the top 20 City CEO's (or whatever they are) as well. Right round That critical end of year period. Your founders way of dealing with this is perfection
    via r/MaliciousCompliance
  • 23
    Font - zawata Holy h I have a relevant story So in my last job as an T2 email support we have enabled a feature to allow people to send as public folders. Some of the public folders also had auto-replies.... Someone at some point decided to send as a public folder with an auto- reply, to a public folder with an auto-reply. We had gotten these types of tickets before. Turn off auto-replies, delete the few hundred emails(max) wait like an hour and turn auto-replies back on. Not this ticket. Becaus
    via r/MaliciousCompliance
  • 24
    Font - So we got a ticket to go stop and auto-reply loop and delete the emails. We mounted the public folder to find 2.1 million emails. Turns out they hadn't been checking the public folder for like 3 months. Best part of that was our maanager didn't let us send the ticket to the server team for batch deletion and at the time we weren't given access to powershell....so it was deleted all by hand. 500 emails at a time. Took about 4 hours. Not fun.
    via r/MaliciousCompliance
  • 25
    Font - squiggyfm I was a contractor for NASA a few years ago and a someone made the mistake of replying all to an agency wide email. NASA has about 80,000 highly educated civil servants and contractors. You can see where this is going. Then some clever people though it would be funny if they too replied all. Then some people were upset at their quickly mounting unread emails so they replied all to tell everyone else to stop. This in turn caused people replying to all about how it was ironic. Thi
    via r/MaliciousCompliance
  • 26
    Human body - showmedogvideos Listen to the people who know what the f they are talking about!
    via r/MaliciousCompliance
  • 27
    Font - Pikalika Bröther may I have some lööps
    via r/MaliciousCompliance
  • 28
    Font - Austin Bennett Writer Glorious! You gave him what he wanted and he was too dumb to know the consequences. Wonderful! Bravo! 41 Reply Share tzenrick They gave him what he wanted after they warned him of the consequences.
    via r/MaliciousCompliance

Want More? Follow Us and Add Us as a Preferred Source on Google.

Tags

boss email holidays vacation management Office computers
Scroll Down For The Next Article